Chicago has always been a standout on the food map, and after visiting three times, I can say it’s a city that holds its own against the best in the world. With a dining scene that’s as diverse as it is bold, Chicago offers everything from iconic deep-dish pizza to gourmet tasting menus that push culinary boundaries. Whether you’re grabbing a classic Chicago dog at a local joint, dining at a sleek rooftop with skyline views, or enjoying a meal by the river, this city knows how to impress.
The mix of historic neighborhoods and modern hotspots makes it a dream for foodies. Think vibrant Mexican restaurants in Pilsen, trendy brunch spots in West Loop, and hidden cocktail bars in River North. As a travel blogger who’s explored 70+ countries, I can honestly say Chicago’s food scene is as cool and unique as it gets. Here are 23 of the city’s most exciting restaurants that you absolutely need to try!
- 👉 Pro Tip: I HIGHLY recommend doing this ultimate food and walking tour. It takes you past downtown landmarks like Millennium Park, the Riverwalk, and Michigan Avenue while you taste deep-dish pizza, a Chicago-style hot dog, Italian beef, popcorn, and the original Chicago brownie. This tour is an absolute must-do on a Chicago itinerary in my opinion.
23 Most Unique Restaurants in Chicago at a Glance
The table below gives you a quick, at-a-glance look at the 10 most unique restaurants in Chicago, including the neighborhoods they’re in and the standout details that make each one worth a visit. It’s a simple way to compare your options and decide which spots fit your vibe before diving into the full guide.
| Restaurant | Best For | What Makes It Unique | Neighborhood |
|---|---|---|---|
| 1. Alinea | Culinary Theater | Two Michelin stars, theatrical tasting menus, and an edible green apple helium balloon | Lincoln Park |
| 2. Kumiko | Japanese Cocktails | 2025 James Beard Award for Outstanding Bar, a full spiritfree menu, and a Japanese whisky bar downstairs | West Loop |
| 3. The Drifter | Hidden Speakeasy | An original Prohibition-era room with a nightly tarot card cocktail menu and short burlesque acts | River North |
| 4. EL ideas | Interactive Tasting Menu | Michelin-starred dinner party where guests can walk into the open kitchen, plus no-corkage BYOB | Douglas Park |
| 5. Schwa | Rebel Fine Dining | Michelin-starred and BYOB, with no servers, as chefs bring out each course to a rap soundtrack | Wicker Park |
| 6. Chicago Magic Lounge | Dinner and a Show | A secret laundromat entrance, close-up magic at your table, and free bar magic nightly | Andersonville |
| 7. Three Dots and a Dash | Tiki Escape | A hidden alley entrance leading to a basement tiki bar with shareable group drinks | River North |
| 8. Galit | Modern Middle Eastern | Michelin-starred four-course menu where you choose a dish for each course | Lincoln Park |
| 9. The Wiener’s Circle | Late-Night Legend | Char-grilled Chicago dogs since 1983, with insult comedy at the counter until 4 AM on weekends | Lincoln Park |
| 10. Cindy’s Rooftop | Skyline Views | Time Out’s No. 1 Chicago rooftop restaurant in 2025, overlooking Millennium Park and Lake Michigan | The Loop |
The quick-reference details in this table give you a small taste of the city’s incredible variety. For the full backstories, reservation tips, and deeper dives into the menus of all 23 spots, check out the complete guide below.
1. The Drifter
- 📍 Location: 676 N Orleans Street, Chicago
- 💲 Price range: $15.50 per tarot card cocktail plus an $8 cover per person
- 🍽️ Cuisine Style: Speakeasy / Craft Cocktails / Small Bites
- 🔥 Standout Features: Original Prohibition-era speakeasy room, nightly tarot card cocktail menu, short burlesque and variety acts
- 🎯 Perfect For: Date nights and cocktail fans who want a hidden bar with a show
The Drifter is my top pick for a speakeasy in Chicago, and it hides beneath Green Door Tavern in River North. The basement room operated as a speakeasy during Prohibition, and the bar says it’s the only one from that era still open in the city. To find it, head through the tavern and down the back stairs, then look for the disguised door.
There’s no printed menu, which is my favorite part of the night. Each evening, bartenders pull a handful of cards from a deck of more than 100 tarot cards, and each card lists a different cocktail. Every tarot cocktail costs $15.50, and I like asking the bartender to choose when two cards sound equally good.
Short pop-up performances happen about every 45 minutes from Wednesday to Saturday, and each one lasts around five minutes. You might catch a burlesque dancer one round and a jazz singer the next. For food, I’d order the Devils on Horseback, which are bacon-wrapped dates with chorizo and tomato fondue.
The Drifter doesn’t take reservations, and weekend waits can get long. I recommend a Wednesday or Thursday visit, or arriving between 5 and 7 PM on Friday or Saturday. Expect an $8 cover per person on your bill, and keep your phone flash off because the bar doesn’t allow flash photos or flashlights.
2. Kumiko
- 📍 Location: 630 W Lake Street, Chicago
- 💲 Price range: $16 to $50 per cocktail, $15 to $16 per spiritfree drink
- 🍽️ Cuisine Style: Japanese Dining Bar / Craft Cocktails / Japanese Whisky
- 🔥 Standout Features: 2025 James Beard Award for Outstanding Bar, full spiritfree menu, Japanese whisky bar downstairs
- 🎯 Perfect For: Date nights and anyone curious about Japanese spirits
Kumiko is my favorite cocktail bar in Chicago, and you’ll find it on Lake Street in the West Loop. Julia Momosé opened it in 2018, and it won the James Beard Award for Outstanding Bar in 2025. It also made The World’s 50 Best Bars list in 2025.
The drink menu centers on Japanese spirits, and signature cocktails start at $21. I’d start with the Cloud Hopper, a fruity mix of rice shōchū, mezcal, passionfruit, and oat milk. If you’re not drinking, Kumiko has eight spiritfree cocktails for $15 to $16, made with the same care as the boozy list.
Momosé also became executive chef in December 2024, and the food is now a big reason to book. Order the Truffle Milk Toast ($15), Japanese milk bread with fermented honey ice cream and shaved truffle. For sharing, I’d add the yuzu koshō karaage and the A5 wagyu gyoza, both $15.
Kumiko is open Wednesday to Sunday from 5 PM to midnight, and I’d book ahead on the website for weekend tables. Expect a 20% service charge on your bill, which the restaurant shares across the whole team. Downstairs, a Japanese whisky bar pours highballs and rare shōchū, while Café Kumiko serves coffee and daytime food on weekends from 11 AM to 3 PM.
3. Alinea
- 📍 Location: 1723 N Halsted Street, Chicago
- 💲 Price range: $450 to $594 per person, prepaid
- 🍽️ Cuisine Style: Modernist / Avant-Garde Tasting Menu
- 🔥 Standout Features: Two Michelin stars, Chef Grant Achatz, three dining formats, edible helium balloon dessert
- 🎯 Perfect For: Milestone celebrations and diners who want a once-in-a-lifetime tasting menu
Alinea is Chef Grant Achatz’s modernist tasting menu restaurant in Lincoln Park, open nightly from 5 to 10 PM. Michelin cut it from three stars to two Michelin stars in late 2025. Its run at three began with Chicago’s first Michelin guide in 2011, and Achatz has led the kitchen since Alinea opened in 2005.
I haven’t found a more theatrical dinner in Chicago, and the menu changes through the year with new courses. Alinea sells prepaid tickets for three experiences, and you’ll pick one when you book. The Salon starts at $450 per person with individual tables for one to six guests, while The Gallery and the private Kitchen Table both cost $594 per person.
I’d pick the Gallery for a big celebration, the Kitchen Table for a private room with the chefs, and the Salon for a first visit on a tighter budget. Many meals end with Alinea’s famous edible helium balloon, made from green apple taffy. I’d list any allergies or dietary needs when you book, because every ticket is prepaid.
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👉 Send me cheap 2026 flightsAlinea is moving reservations from Tock to OpenTable, which handles all bookings from November 1, 2026. I recommend joining the mailing list on Alinea’s website for news on ticket releases, especially if you’re planning a winter or spring 2027 visit. Valet parking is available, and the restaurant is a short walk from the North/Clybourn Red Line stop.
4. EL ideas
- 📍 Location: 2419 W 14th Street, Chicago
- 💲 Price range: $195 per person plus tax and service charge
- 🍽️ Cuisine Style: Contemporary American Tasting Menu / BYOB
- 🔥 Standout Features: One Michelin star, 2026 James Beard semifinalist, open kitchen, no-corkage BYOB
- 🎯 Perfect For: Special occasions and diners who want Michelin-level food in a relaxed setting
EL ideas is a Michelin-starred tasting menu restaurant from Chef Phillip Foss, tucked on a dead-end street in Chicago’s Douglas Park neighborhood. It holds one Michelin star for 2026 and was a 2026 James Beard semifinalist for Outstanding Restaurant. I love it because the whole room feels like a dinner party, with no wall between the dining area and the open kitchen.
Dinner is a nine-course tasting menu for $195 per person, plus tax and service charge. The menu changes often, but the French fries and Frosty course, inspired by Foss’s kids, never leaves it. You’re welcome to walk into the kitchen during the meal, and I’d take them up on it to chat with the cooks.
EL ideas is BYOB with no corkage fee, which keeps the bill lower than at other Michelin-starred spots in Chicago. The team suggests starting with sparkling wine and moving to a light white or light red, and beer pairs well too. If you’re coming from out of town, Perman Wines works closely with the restaurant and can deliver.
Booking works differently here, since you send a reservation request on OpenTable and pay an emailed invoice to confirm. The kitchen handles almost all dietary restrictions, including vegan, and solo diners are welcome. Street parking is free, with a lot on the north side of the street, and the restaurant is about 15 minutes from the Loop.
5. The Wiener’s Circle
- 📍 Location: 2622 N Clark Street, Chicago
- 💲 Price range: $7 to $14 per item
- 🍽️ Cuisine Style: Chicago Hot Dogs / Burgers / Late-Night Eats
- 🔥 Standout Features: Late-night insult comedy at the counter, char-grilled Chicago dogs since 1983, outdoor patio
- 🎯 Perfect For: Post-bar food and anyone who can take a joke
The Wiener’s Circle has served char-grilled hot dogs on Clark Street in Lincoln Park since 1983, and it’s my favorite late-night food stop in Chicago. Daytime visits are pretty calm, but after the bars close, staff and customers trade loud, profane insults across the counter. I love the show, and I’d only go late if you can laugh at yourself.
Order a Char Dog ($7) with everything, which means yellow mustard, relish, onion, tomato, a pickle spear, sport peppers, and celery salt. Don’t ask for ketchup unless you want the whole line to hear about it. I’d add large fries ($4.50) with cheddar for $2 more, or a Char Burger ($9.50) if you’re hungry.
The stand opens daily at 11 AM and closes at 2 AM Sunday through Thursday and 4 AM on Friday and Saturday. For the full experience, I’d arrive between 1 and 2 AM on a weekend and grab a seat on the outdoor patio. The closest train is the Diversey stop on the Brown Line.
Follow the stand on Instagram during the 2026 Bears season, since it has given away free hot dogs after big Bears wins. You can order delivery on DoorDash, but the roast only happens in person. For a group celebration, you can book the patio or a karaoke party through the website.
6. Virtue Restaurant
- 📍 Location: 1462 E 53rd Street, Chicago
- 💲 Price range: $50 to $90 per person
- 🍽️ Cuisine Style: Southern American / Soul Food
- 🔥 Standout Features: 2022 James Beard Award-winning chef, Michelin Bib Gourmand, Tom Bullock cocktail menu
- 🎯 Perfect For: Date nights and Southern food fans exploring the South Side
Virtue is Chef Erick Williams’s Southern restaurant on 53rd Street in Hyde Park, and it’s my top pick for dinner on Chicago’s South Side. Williams won the 2022 James Beard Award for Best Chef in the Great Lakes region, and Virtue holds a Michelin Bib Gourmand for great value. The dining room feels warm and personal, with china plates and art inspired by his great-grandmother’s home.
Start with the gumbo ($16), made with chicken, andouille sausage, and Carolina Gold rice, plus cornbread with honey butter ($12). For a main, I’d order the blackened catfish ($30) or the short rib ($42) with caramelized onion gravy. Save room for Millie’s Puddin’, the house banana pudding with Nilla wafers ($15).
Virtue opens at 4 PM Tuesday through Sunday, closing at 10 PM on Friday and Saturday and 9 PM on other nights. I’d book ahead on weekends, since every table is held for 90 minutes. The restaurant is cashless and adds a 3.5% surcharge to each bill to help fund health insurance for the team.
For a cheaper visit, grab a bar seat at happy hour, Tuesday to Friday from 4 to 5:30 PM, when a cup of gumbo is $8 and cocktails are $10. The cocktail list honors Tom Bullock, the first African American to publish a cocktail book, in 1917. Pair dinner with an afternoon at the free Smart Museum of Art on the nearby University of Chicago campus.
7. Three Dots and a Dash
- 📍 Location: 435 N Clark Street, Chicago
- 💲 Price range: $16 to $22 per cocktail, $60 to $250 for group drinks
- 🍽️ Cuisine Style: Tiki Bar / Rum Cocktails / Polynesian-Inspired Small Plates
- 🔥 Standout Features: Hidden alley entrance, shareable group drinks, The Bamboo Room rum bar inside
- 🎯 Perfect For: Group nights out and rum lovers
Three Dots and a Dash is the tiki bar I send friends to first in Chicago, hidden down an alley behind 435 N Clark Street in River North. Follow the alley stairs down to a basement filled with bamboo and tiki decor. It’s part of the Lettuce Entertain You group and admits guests 21 and over.
Order the namesake Three Dots and a Dash ($16), made with rhum agricole, aged rum, falernum, and allspice. Don the Beachcomber created it to celebrate the end of World War II, and its garnish spells V for victory in Morse code. Skull icons on the menu flag the strongest drinks, and the Nuclear Shark Bite has a limit of one per person.
For a group, I’d order the Zombie, which serves four for $75. Pair it with the Pu Pu Platter ($65) or the Thai curry crab rangoon dip ($22). Non-drinkers can order the Royal Hawaiian ($14), an Earl Grey and pineapple mocktail.
Three Dots opens at 4 PM, or 2 PM on Saturday, and stays open until 1 AM Thursday through Saturday. I’d book on OpenTable, which takes a deposit, for weekend nights. For a calmer night, reserve The Bamboo Room inside, an intimate rum bar that Esquire named one of the best bars in America.
8. Gotham Bagels – Gold Coast
- 📍 Location: 1212 N Dearborn Street, Chicago
- 💲 Price range: $3.15 per bagel, $13 to $17 per sandwich
- 🍽️ Cuisine Style: New York-Style Bagels / Breakfast Sandwiches / Deli
- 🔥 Standout Features: Hand-rolled kettle-boiled bagels, 13-bagel New York Dozen, covered and heated patio
- 🎯 Perfect For: Breakfast before exploring the Gold Coast and grab-and-go mornings
Gotham Bagels makes hand-rolled, kettle-boiled New York bagels, and its Gold Coast shop is my go-to breakfast stop on the Near North Side. The shop started in Madison, Wisconsin, and opened here in 2020, sharing a space with Eduardo’s Enoteca at 1212 N Dearborn Street. Look for the Hot Bagels neon below the Eduardo’s sign.
I’d order the Brighton Beach ($16.95), with cold-smoked salmon, cream cheese, tomato, red onion, arugula, and capers. If you want something heartier, the OMFG ($16.75) stacks Nashville fried chicken, bacon, a fried egg, and cheddar. A plain bagel with cream cheese is $5.65 if you want a lighter breakfast before a day of sightseeing.
The shop is open daily from 7 AM to 2 PM, and it has about 30 seats inside plus a covered, heated patio out front. I recommend ordering ahead online on weekend mornings, since your bag is ready when you walk in. The Clark/Division Red Line stop is a two-minute walk away.
If you’re taking bagels back to your hotel, a New York Dozen gets you 13 for $28.25. After breakfast, walk 12 minutes to Oak Street Beach or seven minutes to Washington Square Park and the Newberry Library. Gotham also has Chicago shops in Lakeview, the South Loop, and Streeterville off Michigan Avenue.
9. Carnivale
- 📍 Location: 702 W Fulton Market, Chicago
- 💲 Price range: $50 to $90 per person
- 🍽️ Cuisine Style: Nuevo Latino / Latin Fusion
- 🔥 Standout Features: 35,000-square-foot space with 400+ original artworks, free samba shows on Thursday and Friday, half-price happy hour drinks
- 🎯 Perfect For: Group dinners, birthdays, and celebrations
Carnivale has filled a converted Fulton Market warehouse with color since 2005, and it’s my top pick in the West Loop for a big group dinner. The space covers 35,000 square feet and holds more than 400 pieces of original art, plus murals you can spot from the Kennedy Expressway. On Thursday and Friday nights, samba dancers perform in the Rumba Lounge, and the show is free.
The Latin fusion menu pulls from across Latin America, and I’d start with the ropa vieja ($14), braised beef with sweet plantains and queso fresco. The ceviche tasting ($34) brings all four ceviches, including a Yucatán-style hamachi with dragon fruit. For two people, the Argentinian Parrillada ($89) piles on churrasco, short rib, chorizo, and bone marrow.
Carnivale opens Tuesday through Sunday from 4 or 4:30 PM, staying open until 11 PM on Friday and Saturday. I’d book on Tock for weekends, and note that tables of five or more get a 20% service charge. Every check also includes a 3% surcharge, which the restaurant adds instead of raising menu prices.
On a budget, come for happy hour, Tuesday to Friday from 4:30 to 6:30 PM, when beer, wine, and cocktails are half off. Save room for the 20 Years of Chocolate Cake ($15), made with 20 layers of dark chocolate ganache. Carnivale offered a prix fixe menu during Chicago Restaurant Week 2026, and the 2027 edition takes place January 22 to February 7.
10. Daisies
- 📍 Location: 2375 N Milwaukee Avenue, Chicago
- 💲 Price range: $21 to $32 per pasta, 25% service charge included
- 🍽️ Cuisine Style: Midwest Italian / Handmade Pasta / Bakery Café
- 🔥 Standout Features: Michelin Green Star, produce from the chef’s family farm, all-day bakery café
- 🎯 Perfect For: Pasta lovers and date nights in Logan Square
Daisies is my favorite pasta spot in Chicago, a Midwest Italian restaurant on Milwaukee Avenue in Logan Square. Chef Joe Frillman sources much of the produce from his brother’s farm outside the city, and Daisies holds a Michelin Green Star for sustainability. The restaurant moved into a larger space in 2023, and it now includes an all-day bakery café.
Handmade pastas cost $21 to $32 and change with the seasons. I’d order the pappardelle with mushroom ragu ($21) and the rigatoni with nduja and lemon breadcrumbs ($24) to share. Start with the onion dip and house-made chips ($10), and add caviar if you want to splurge.
Dinner is served Tuesday through Sunday from 5 PM, and I’d book on OpenTable for weekends. Every dine-in check includes a 25% service charge, which covers the tip, and no extra gratuity is expected. For a cheaper visit, come for happy hour from Tuesday to Saturday between 3 and 5 PM.
The café opens daily from 7 AM to 3 PM, with pastries from partner and pastry chef Leigh Omilinsky. Lunch is first come, first served from Monday to Saturday, and Sunday brunch starts at 10 AM. If you’re in Chicago for Thanksgiving 2026, Daisies sells a to-go dinner kit for up to four people through Tock.
11. Chicago Magic Lounge
- 📍 Location: 5050 N Clark Street, Chicago
- 💲 Price range: $60 to $103 per Signature Show ticket, free entry to the Performance Bar
- 🍽️ Cuisine Style: Magic Speakeasy / Craft Cocktails / Small Plates
- 🔥 Standout Features: Hidden laundromat entrance, close-up magic at your table, free bar magic nightly
- 🎯 Perfect For: Date nights and groups who want dinner and a show in one stop
Chicago Magic Lounge hides behind a laundromat storefront on Clark Street in Andersonville, and it’s my top pick for a night out on the North Side. Inside is an Art Deco lounge built around Chicago-style magic, the close-up sleight of hand born in the city’s bars. It’s 21+, though guests aged 16 to 20 can attend shows with a guardian.
For a first visit, I’d book The Signature Show, Thursday through Sunday. Magicians perform at your table before a 60-minute stage show, and tickets cost $60 to $103 plus a $4.99 fee. Friday and Saturday 7 PM shows sell out more than a week ahead, and main-floor seats add a bonus set in the 654 Club.
On a budget, skip the tickets and head to the free Performance Bar, which opens at 5 PM, or 3 PM on Sunday. A magician performs 20-minute close-up sets there all night. I’d order the Smoke and Mirrors cocktail, prepared with a burst of fire, and the pork belly sliders.
Monday through Wednesday, the Bewitching Hour offers bar drink specials from 8 to 10 PM. Extra Signature Shows are scheduled December 26 to 30, plus a New Year’s Eve show. There’s no parking lot, and I’d take the Red Line to Argyle, a 10-minute walk away.
12. Galit
- 📍 Location: 2429 N Lincoln Avenue, Chicago
- 💲 Price range: About $115 per person for the four-course menu
- 🍽️ Cuisine Style: Middle Eastern / Seasonal Prix Fixe
- 🔥 Standout Features: One Michelin star, James Beard Award-winning chef, walk-in à la carte communal table
- 🎯 Perfect For: Group dinners and special occasions in Lincoln Park
Galit is a Michelin-starred Middle Eastern restaurant on Lincoln Avenue in Lincoln Park, and it’s the first place I recommend for hummus in Chicago. James Beard Award-winning chef Zachary Engel owns it with partner Andrés Clavero, and the menu follows the seasons. The wine list includes bottles from Palestine and Armenia that rarely show up on Chicago menus.
Dinner is a four-course, choose-your-own-adventure menu for about $115 per person, and every reservation requires it. You pick a dish for each course, and I’d bring a group to share and taste more of the menu. Ask about the rotating wine accompaniment if you want pairings without studying the list.
Galit is open Tuesday through Sunday from 5 PM, and I’d join the Resy notify list for prime weekend times. From Tuesday to Thursday, the communal table takes walk-ins and serves an à la carte menu. Happy hour also takes place Tuesday through Thursday from 5 to 6 PM at the bar and communal table.
For breakfast or lunch, the same team opened Cafe Yaya right next door at 2431 N Lincoln Avenue. It serves pastries and Mediterranean dishes from 7:30 AM Tuesday through Friday and 8 AM on weekends. Galit sits steps from the historic Biograph Theater, where FBI agents shot gangster John Dillinger in 1934.
13. Schwa
- 📍 Location: 1466 N Ashland Avenue, Chicago
- 💲 Price range: $205 to $245 per person
- 🍽️ Cuisine Style: Creative Modern American / Tasting Menu
- 🔥 Standout Features: One Michelin star, chefs serve every course, BYOB, rap soundtrack
- 🎯 Perfect For: Adventurous diners who want a fun Michelin splurge
Schwa is Chef Michael Carlson’s tasting menu restaurant on Ashland Avenue in Wicker Park, and it’s my pick for Michelin-starred food without the formality. There are no servers here, and the chefs bring out each course themselves while rap music plays. Carlson was a Food & Wine Best New Chef in 2006, and Schwa holds one Michelin star for 2026.
The current menu lists 15 courses, and it changes often. The quail egg raviolo with truffle and ricotta is a Schwa classic, and I’d also look for the cornbread with leche de tigre and roe. You can check the full menu on Schwa’s website before you go and plan your drinks around it.
Schwa is BYOB, and bringing your own wine keeps the total bill down. It’s good form to bring a six-pack or bottle for the kitchen crew too. Don’t be surprised if the chefs offer you a shot of whiskey at the end of the meal.
Schwa is open Wednesday through Saturday by reservation only, with seatings from about 6 to 9 PM. Expect to pay $205 to $245 per person, and book on OpenTable as early as you can. The plain storefront is easy to miss, and the Division Blue Line stop is about a five-minute walk away.
14. Beatnik West Town
- 📍 Location: 1604 W Chicago Avenue, Chicago
- 💲 Price range: $15 to $42 per dish, $17 cocktails
- 🍽️ Cuisine Style: Mediterranean / North African / Mexican-Inspired Small Plates
- 🔥 Standout Features: 400+ living plants, salvaged antiques and chandeliers, Andalusian-style courtyard
- 🎯 Perfect For: Date nights and weekend brunch with friends
Beatnik West Town is the restaurant I recommend when you want a room that feels like a trip abroad, and it sits on Chicago Avenue in West Town. The 200-seat space holds more than 400 living plants, a 40-foot carved teak façade from Bali, and 15 crystal chandeliers salvaged from a Los Angeles hotel ballroom. I’d ask for a table in the Andalusian-style courtyard, which is the prettiest spot in the house.
The menu travels from the Eastern Mediterranean across North Africa to Mexico. I’d share the hummus with octopus ($19) and the halloumi fries ($16), then order the short rib tagine ($41) with apricot and chickpea stew. For a showpiece drink, the Piña Colada ($28) arrives in a young Thai coconut.
Beatnik serves dinner Wednesday through Sunday from 4 PM, and weekend brunch starts at 10 AM on Saturday and Sunday. In 2026, happy hour takes 26% off everything on the menu from Wednesday to Friday between 4 and 7 PM. Every dine-in check includes an 18% service charge, and paying by debit or cash avoids the 3% card fee.
I’d book on OpenTable for Friday and Saturday nights. The #66 Chicago bus stops near the door, at the corner of Chicago and Ashland avenues. If you’re celebrating with a group, Beatnik also has semi-private dining rooms and a private event space.
15. The Waterfront Café
- 📍 Location: 6219 N Sheridan Road, Chicago
- 💲 Price range: Casual counter-service pricing
- 🍽️ Cuisine Style: Seafood Rolls / Salads / Cocktails
- 🔥 Standout Features: Lake Michigan patio with skyline views, nightly live music, dog-friendly seating
- 🎯 Perfect For: Summer sunsets and casual lakeside dinners
The Waterfront Café sits in the coach house of the Berger Park Cultural Center in Edgewater, steps from Lake Michigan. It’s where I’d go in Chicago for a summer sunset dinner with lake and skyline views. Frank Pullen opened it in 2007 as a hot dog stand, and it has grown into a full café with cocktails and nightly live music.
Order the lobster roll or the brown butter crab roll, two of the café’s best sellers. The jerk chicken nachos are a good pick for sharing, and the drink list includes tropical cocktails, beer, and wine. Local jazz, blues, and classical guitar players perform on the patio in the evenings.
The café is counter service only, and it doesn’t take reservations. Order inside, then grab any open seat on the patio, and I’d arrive before sunset on summer weekends to get a table by the water. Well-behaved dogs on a leash are welcome, and groups of 12 to 36 can arrange a gathering ahead of time.
The Waterfront Café is seasonal, and it closes each winter. It reopens on Friday, May 28, 2027, and it also closes on days with bad weather. Take the Red Line to Granville and walk east about 10 minutes to the park.
16. Ina Mae
- 📍 Location: 1415 N Wood Street, Chicago
- 💲 Price range: $14 to $31 per dish, $14 cocktails
- 🍽️ Cuisine Style: New Orleans / Creole / Southern
- 🔥 Standout Features: Chef Brian Jupiter’s family recipes, char-grilled oysters, live music and weekly events
- 🎯 Perfect For: Group dinners and weekend brunch in Wicker Park
Ina Mae Tavern brings New Orleans cooking to a corner of Wood Street in Wicker Park, and it’s my go-to for Creole food in Chicago. New Orleans native Brian Jupiter named it after his great-grandmother, and he was a James Beard semifinalist for Best Chef in the Great Lakes in 2019 and 2020. Ina Mae has also earned a Michelin Bib Gourmand three times.
Start with the Gumbo Ya-Ya ($14), Jupiter’s family recipe with chicken, shrimp, andouille, and crawfish. The shrimp po’boy ($19) comes on Leidenheimer French bread from New Orleans, and the char-grilled oysters ($18) are a must. Finish with a plate of warm beignets ($12) dusted in powdered sugar.
Ina Mae is open Tuesday through Sunday from 11 AM, with brunch on Saturday and Sunday until 3:30 PM. Happy hour takes place Tuesday to Friday from 4 to 6 PM, and a Hurricane pitcher ($49) serves up to five people. I’d book on OpenTable for weekend dinners and grab a patio table when the weather is warm.
The tavern hosts live music, bingo, and trivia nights, plus LSU football watch parties during the 2026 season. Upstairs, the team rents out an Airbnb apartment if you want to stay above the bar. The 606 trail is about a 10-minute walk north for an easy pre-dinner stroll.
17. Big Star
- 📍 Location: 1531 N Damen Avenue, Chicago
- 💲 Price range: $4 to $7 per taco, $14 margaritas
- 🍽️ Cuisine Style: Mexican Street Food / Tacos / Whiskey Bar
- 🔥 Standout Features: Big Wicker Park patio, handmade corn tortillas, 20 exclusive house barrel bourbons
- 🎯 Perfect For: Patio days and pre-game tacos near Wrigley Field
Big Star is a taco and whiskey bar from Chef Paul Kahan, and its Wicker Park patio on Damen Avenue is where I’d spend a summer afternoon. The bar pays homage to the honky-tonks of Bakersfield, California, with classic country and 70s rock on the speakers. A second location sits across from Wrigley Field at 3640 N Clark Street.
The corn tortillas are handmade in-house every day, and I’d order the al pastor ($4.95) with grilled pineapple and the panza ($5.95) with braised pork belly. The pescado ($6.95) brings beer-battered tilapia with chipotle mayo. Whiskey fans should ask about the 20 exclusive house barrel bourbons, and a margarita pitcher ($56) works well for groups.
On Taco Tuesday, al pastor, pollo, panza, and papas tacos drop to $2.95, with $3 Tecate. Happy hour from Monday to Thursday, 4 to 6 PM, brings half-off nachos and $12 margaritas. If the patio is packed, the to-go window serves tacos from 4 PM on weekdays and from 9 AM on weekends.
The Wicker Park location opens at 11:30 AM on weekdays and 11 AM on weekends, with brunch on Saturday and Sunday until 2 PM. If you’re catching a Cubs game in 2027, the Wrigleyville location is the easiest pre-game stop, though happy hour skips home game days. Every bill includes a 3.5% supplement that funds staff health insurance.
18. Avli on The Park
- 📍 Location: 180 N Field Boulevard, Chicago
- 💲 Price range: $31 to $50 per person
- 🍽️ Cuisine Style: Contemporary Greek / Mediterranean
- 🔥 Standout Features: Michelin Guide recommended, rooftop patio with heated cabanas and firepits, free valet at dinner
- 🎯 Perfect For: Brunch with friends and dinners near Millennium Park
Avli on the Park serves contemporary Greek food in Lakeshore East, right beside the neighborhood’s five-acre park. It’s a Michelin Guide recommended restaurant, and it’s my pick for a Greek meal downtown near Millennium Park. The rooftop patio has heated cabanas and firepits, and I’d book a table up there on a cool fall evening.
Start with the saganaki ($14) and the tirokafteri ($14), a spicy feta spread with roasted red peppers. The grilled octopus ($26) comes over Greek fava with roasted beets and orange. For a splurge, the lamb chops ($52) arrive with broccolini and potatoes.
Avli on the Park opens daily for lunch and dinner, with weekend brunch on Saturday and Sunday from 10:30 AM to 4 PM. Happy hour takes place Monday to Friday from 3 to 6 PM, and a three-course lunch special is available on weekdays. Dinner guests get free valet parking, and I’d book on OpenTable for weekend nights.
After dinner, walk a few minutes to Maggie Daley Park, then continue to Millennium Park and Cloud Gate. Groups of more than 12 book through Avli’s events team, and the restaurant has two private rooms. Avli also has locations in Lincoln Park, River North, and Winnetka if you want a second Greek meal on your trip.
19. Piccolo Sogno
- 📍 Location: 464 N Halsted Street, Chicago
- 💲 Price range: $19 to $55 per dish at dinner, lower prices at lunch
- 🍽️ Cuisine Style: Regional Italian / Handmade Pasta / Wood-Fired Pizza
- 🔥 Standout Features: Hidden garden patio, all-Italian wine list, pasta made in house daily
- 🎯 Perfect For: Romantic patio dinners and Italian wine lovers
Piccolo Sogno, which means “little dream” in Italian, has served regional Italian food on Halsted Street in River West since 2008. Chef Tony Priolo and wine specialist Ciro Longobardo opened it together, and the hidden garden patio is one of the prettiest in Chicago. I’d request a patio table when you book on OpenTable for a warm evening.
The kitchen makes its pasta in house every day. I’d order the Ravioli “Piccolo Sogno” ($27), four-cheese ravioli with a Marsala glaze, or the pappardelle con cinghiale ($30) with wild boar ragù. Wood-fired pizzas cost $19 to $22, and they’re a good pick for sharing at the table.
The wine list is all Italian, with bottles from $36 to a $600 Sassicaia. Wines by the glass start at $12, and the restaurant pours its own house-label Prosecco. On weekdays, lunch is a cheaper way to visit, with the same ravioli for $22.
Piccolo Sogno serves lunch Monday to Friday from 11 AM to 2:30 PM, and dinner nightly from 5 PM, or 4 PM on weekends. The patio is open when the weather allows, and I’d plan a visit from late spring through early fall. You can also buy the restaurant’s pastas, sauces, and olive oil at Mariano’s grocery stores.
20. The Whale
- 📍 Location: 2427 N Milwaukee Avenue, Chicago
- 💲 Price range: Mid-range neighborhood pricing
- 🍽️ Cuisine Style: Upscale American / Cocktail Bar / Sports Bar
- 🔥 Standout Features: 1940s and ’50s casino-inspired decor, booths with their own TVs, rotating boozy slushies
- 🎯 Perfect For: Brunch with friends and dressed-up game nights
The Whale is a Logan Square bar and restaurant on Milwaukee Avenue built around 1940s and ’50s high-roller casino culture. In casino slang, a whale is a gambler with a million-dollar bankroll who gets every perk the house can offer. Inside, you’ll find chandeliers, plush booths, gold accents, and vintage photos, and it’s my pick for a dressed-up night out in the neighborhood.
The menu sticks to upscale American comfort food, from handhelds to entree salads. I’d order the Whale burger or the fried chicken sandwich, the two dishes regulars recommend first. The bar mixes craft cocktails and keeps at least one boozy slushie on rotation.
It’s also a sports bar in disguise, with flat-screen TVs throughout and two screens in each front booth. I’d book a front booth for a big Bears game, and the room seats about 200 people inside, plus an outdoor patio. The Whale also serves weekend brunch, plus happy hour and Wine Wednesday specials.
I’d reserve ahead for Friday and Saturday nights and for weekend brunch, when it gets busy. After dinner, walk under 10 minutes up Milwaukee Avenue to the Illinois Centennial Monument in the center of Logan Square. The California Blue Line stop is about a five-minute walk away.
21. Ed Debevic’s
- 📍 Location: 159 E Ohio Street, Chicago
- 💲 Price range: $15 to $22 per main dish
- 🍽️ Cuisine Style: American Diner / Burgers / All-Day Breakfast
- 🔥 Standout Features: Sassy servers, dance routines on the counters, World’s Smallest Sundae, bottomless mimosas
- 🎯 Perfect For: Families with kids and groups who can take a joke
Ed Debevic’s is a 1950s-style diner in Streeterville near the Magnificent Mile, and it’s my top pick for a family meal downtown. The servers are famous for their snark and break into dance routines on the soda counters. Ed’s opened in River North in 1984 and moved here after the original building was torn down.
Order a cheeseburger ($19.95) or the Route 66 Burger ($21.95) with bacon and guacamole. The My Kinda Dog ($14.95) is a proper Chicago-style hot dog with neon relish and sport peppers. Finish with a thick shake ($10.95) or the World’s Smallest Sundae ($4.95), and add $2.50 to keep the glass.
Ed’s is open daily from 8 AM to 9 PM and serves breakfast all day. Bottomless mimosas cost $25 from 8 AM to 2 PM, a fun brunch perk for adults. I’d book on Tock for weekends, and parties of six or more pay an 18% gratuity.
The kitchen has no tree nuts, peanuts, or sesame, which helps families with food allergies. There’s stroller parking inside, and the Grand Red Line stop is about a 10-minute walk away. Fans of The Bear may know the name, since the show credits Ed’s with inspiring Carmy’s dad to open his restaurant.
22. Lost Larson (Andersonville)
- 📍 Location: 5318 N Clark Street, Chicago
- 💲 Price range: Casual bakery-café pricing
- 🍽️ Cuisine Style: Scandinavian-Inspired Bakery / Café
- 🔥 Standout Features: Grains stone-milled in house, signature cardamom buns, second location in Wicker Park
- 🎯 Perfect For: Morning coffee and pastry runs in Andersonville
Lost Larson is a Scandinavian-inspired bakery on Clark Street in Andersonville, the historically Swedish neighborhood on Chicago’s North Side. Siblings Bobby and Bree Schaffer opened it in 2018, naming it after the Larson surname their grandfather gave up in his 30s. Mashed named it the best bakery in Illinois, and it’s my first stop for breakfast in this part of the city.
The bakery mills its own grains on a stone mill and uses long fermentation for its breads. Order the cardamom bun, its best-known pastry, and grab a loaf of rye sourdough to take home. For lunch, I’d try one of the open-faced Scandinavian sandwiches with an espresso.
Lost Larson is a morning bakery, and I’d arrive early on weekends for the full pastry selection. There’s no Wi-Fi on purpose, since the owners want guests to slow down for fika, the Swedish coffee break. A second shop at 2140 W Division Street makes it easy to visit if you’re staying near Wicker Park.
If you’re visiting in February or March 2027, look for the semla, a cardamom brioche filled with almond cream and whipped cream that the bakery makes for Lent. They often sell out, and you can preorder them online for pickup at either shop. Afterward, walk a block south on Clark Street to Women & Children First, an independent bookstore open since 1979.
23. Cindy’s Rooftop
- 📍 Location: 12 S Michigan Avenue, Chicago
- 💲 Price range: Upscale rooftop pricing
- 🍽️ Cuisine Style: Seasonal American / Rooftop Bar / Shared Plates
- 🔥 Standout Features: Millennium Park and Lake Michigan views, glass atrium, year-round terrace
- 🎯 Perfect For: Brunch with a view and sunset cocktails
Cindy’s Rooftop sits on the 13th floor of the Chicago Athletic Association hotel, looking straight over Millennium Park and Lake Michigan. Time Out Chicago named it the city’s No. 1 rooftop restaurant in 2025, and it’s where I take first-time visitors for the view. The rooftop is named for Marian “Cindy” Pritzker, a Chicago philanthropist, and it’s part of Boka Restaurant Group.
The dining room sits under a glass atrium, and the all-season terrace adds fire pits in colder months. At dinner, I’d order the duck pot pie with muscovy duck confit, plus the crispy truffle fries. The smashburger with two patties, aged cheddar, and house pickles is my pick at lunch.
Cindy’s opens at 11 AM on weekdays and 10 AM on weekends, with brunch on Saturday and Sunday until 2 PM. Reservations open 14 days ahead, and walk-ins are welcome, though sunset tables on weekends book up fast. Cindy’s sometimes closes early for private events, and I’d check the hours on its website before you go.
The website also has a live terrace camera, which helps you check the weather and the view before heading up. Cloud Gate and the rest of Millennium Park are right across Michigan Avenue. I’d pair a late lunch here with an afternoon at the Art Institute of Chicago, one block south.
- Visit the Cindy’s Rooftop website
- Read reviews of Cindy’s Rooftop
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Global Viewpoint is a personal blog. All content is for informational and entertainment purposes only and does not constitute professional financial, medical, or legal advice.
