Let’s be real: Chicago is the greatest city in the world, but the winters? They can be brutal. However, living in the Windy City comes with a massive travel perk: you have unmatched flight connectivity.
Between O’Hare (ORD)—a global mega-hub for United and American—and Midway (MDW), the fortress for Southwest, the competition for your ticket is fierce. I’ve spent years navigating these two airports, flying to over 73 countries, and I’ve learned that you rarely need to pay full price if you know where to look. By leveraging the competition between these two hubs, I’ve found that escaping the Midwest is often cheaper than a night out in River North.
In this guide, I’m sharing 7 of the most affordable (and exciting) destinations you can fly to from Chicago in 2026. From Caribbean beaches perfect for thawing out to European capitals rich in history, these are the high-value routes that offer the perfect escape for every budget.
My Selection Criteria: Why These 7?
I didn’t just pick random spots on a globe. To build this list for 2026, I analyzed routes out of Chicago based on three specific factors:
- 📉 The ORD vs. MDW Effect: I specifically looked for destinations where Southwest (at Midway) competes directly with the legacy carriers (at O’Hare). This cross-town rivalry is the secret sauce that drives prices down for Chicago travelers.
- ✈️ Non-Stop Convenience: Cheap is good, but efficient is better. Chicago offers direct flights to almost everywhere, so I prioritized destinations where you can get straight to the fun without wasting hours on a layover.
- 💰 Total Trip Value: A $80 flight isn’t a “deal” if the destination is overpriced. I selected spots where your dollar stretches further, whether that’s affordable seafood in Savannah or free museums in Dublin.
The Chicago Flight “Cheat Sheet” (2026 Edition)
Need a quick getaway? Here is the breakdown of the best deals from Chicago this year, organized by price estimates so you can find a trip that fits your budget instantly.
| Destination | Est. Price* | Flight Time | Best For… |
| 🇺🇸 Savannah, GA | $54 – $120 | 2h 00m | History & Food |
| 🇺🇸 Tampa, FL | $73 – $150 | 2h 30m | Beaches & Theme Parks |
| 🇺🇸 New Orleans, LA | $84 – $160 | 2h 30m | Music & Nightlife |
| 🇨🇦 Calgary, Canada | $229 – $350 | 4h 00m | Mountains & Nature |
| 🇧🇸 Nassau, Bahamas | $351 – $480 | 3h 40m | Beaches & Sun |
| 🇮🇪 Dublin, Ireland | $404 – $550 | 7h 30m | History & Pubs |
| 🇸🇪 Stockholm, Sweden | $441 – $600 | 8h 30m | Design & Culture |
*Estimated roundtrip fares from ORD or MDW for 2026.
My #1 tip for finding cheap flights out of Chicago
Looking for the cheapest places to fly out of Chicago O’Hare? For 5+ years, I have been using this amazing site called Going (formerly Scott’s Cheap Flights) to find the best travel deals on domestic and international flights. It’s simple yet incredibly comprehensive. And the best part? They have a free version you can try out to see if you like it (spoiler alert: you will love it). When you create an account, you enter your home airport (such as ORD) and where you’d like to go. Going will send you mistake fares and other incredible flight deals right to your inbox.
Personally, I’ve saved thousands of dollars on flights thanks to their email alerts. With Going, I save on average between $300 and $400 roundtrip on each flight I take. If you’re a frequent flyer like me, you’ll find the most benefit with their premium membership. For $49 a year, you get access to even better flight deals. The membership will pay for itself in no time.
Use my discount code Jon25 to save 25% when you join Going!
3 Insider Rules for Finding Cheap Flights from Chicago
Finding a deal from the Windy City isn’t just about luck; it’s about strategy. Here are the three rules I live by when booking flights out of Chicago.
1. Play the “Two Airport” Game
Most cities are stuck with one expensive hub, but we are spoiled with two. O’Hare (ORD) is your gateway to the world, where United and American constantly undercut each other on international fares. Midway (MDW) is the Southwest fortress.
- The Hack: Always check both. Even if you live next to O’Hare, a $40 Uber to Midway might save you $200 on a ticket. Plus, remember that Southwest (at MDW) allows two free checked bags, whereas budget carriers at O’Hare (like Spirit or Frontier) will charge you for everything but the air you breathe.
2. Follow the “Goldilocks Window”
Forget the myth that “last-minute deals” are the way to go—in 2026, waiting until the last minute usually means paying double. On the flip side, booking too early (11 months out) is also expensive. You need to hit the sweet spot:
- Domestic Flights: Book 1 to 3 months in advance.
- International Flights: Book 2 to 8 months in advance.
- Pro Tip: Use the “Explore” feature on Google Flights. Set your origin to “Chicago” and leave the destination blank. It will literally show you a map of the cheapest places you can fly to on your dates.
3. Factor in the “CTA Discount”
A cheap flight isn’t cheap if it costs you $100 to get to the airport. Unlike New Yorkers who often pay a fortune to get to JFK, we have the Blue Line (to O’Hare) and the Orange Line (to Midway).
- Taking the train costs $2.50. Taking an Uber from the Loop during rush hour can cost $70+.
- If you find a flight that is $30 more expensive but leaves at a time when the trains are running (vs. a 5 AM flight requiring an expensive Uber), take the slightly more expensive flight. You’ll still save money in the total trip cost.
Cheapest places to fly from Chicago in 2026: The best flight deals from Chicago
Do you dream about a tropical escape to the Bahamas? How about taking a haunted tour of New Orleans? Or experience the rolling green hills of Ireland? With the low price of airfare on flights from Chicago, there’s no reason you can’t do all this and more.
Ready to plan your escape from the Windy City? Here are seven of the cheapest places to fly from Chicago right now:
✈️ My #1 Hack for Cheap 2026 Flights:
It’s January, so flight prices are climbing fast—but you don't have to pay them. I’m currently seeing roundtrips to Europe for under $300 (deals you won’t find on Google Flights).
Step 1: Join Going.com's Free Plan here. It takes 10 seconds and requires no credit card.
Step 2: If you're doing a big trip this year, grab the 14-day free trial of Premium. You can even use my code JON25 for 25% off.
Seriously, this is the single best money-saving tool I’ve used in 8+ years.
👉 Send me cheap 2026 flights1. Chicago to Savannah ($54-$120 roundtrip)
- ✈️ Flight Time: 2 hours
- 🛫 Airlines: American Airlines, United, Delta (8+ daily direct flights, with American offering the most frequent service)
- 📅 Best Time to Visit: March to May 🌸 and September to November 🍂 for perfect weather and fewer tourists
- 🏆 Perfect for: History buffs 🏛️, food lovers 🍽️, romantic getaways 💑
Savannah feels like stepping into another world, where life moves at its own sweet pace just a 2-hour flight from the Windy City.
Take a walk through the Historic District‘s 22 gorgeous squares, where massive oak trees drip with Spanish moss and frame some of America’s most beautiful old homes. You’ll want to peek inside the Mercer-Williams House that starred in “Midnight in the Garden of Good and Evil,” and don’t even think about leaving without sitting down to a meal at Mrs. Wilkes Dining Room, where you’ll share a table with strangers and pass platters of the best fried chicken and Southern sides you’ve ever tasted.
Spring is magical here. March through May brings perfect weather and flowers blooming everywhere you look. For getting there without breaking the bank, keep an eye on United Airlines’ deals from O’Hare, which sometimes drop below $175 roundtrip midweek. Grab a morning flight and you’ll be wandering along the riverfront by lunch, wondering why you didn’t visit sooner.
2. Chicago to Tampa ($73-$150 roundtrip)
- ✈️ Flight Time: 2 hours 30 minutes
- 🛫 Airlines: Southwest, American Airlines, United, Frontier (12+ daily direct flights, with Southwest offering the most budget-friendly options)
- 📅 Best Time to Visit: February to May 🌊 and October to December 🌴 for perfect beach weather without the summer humidity
- 🏆 Perfect for: Beach enthusiasts 🏖️, theme park adventurers 🎢, water sports lovers 🏄♂️
When Chicago’s winter feels never-ending, Tampa Bay offers the perfect warm-weather getaway just a 2.5-hour flight south.
Soak up Florida sunshine at Clearwater Beach with its powder-white sand consistently ranked among America’s best beaches. Thrill-seekers can experience world-class coasters at Busch Gardens Tampa Bay, while nature lovers might spot manatees drifting through the crystal-clear waters at Weeki Wachee Springs. The historic Ybor City neighborhood reveals Tampa’s Cuban heritage with hand-rolled cigar shops, colorful architecture, and authentic restaurants serving mojo-marinated pork and Cuban sandwiches pressed to perfection.
February through April delivers ideal temperatures before summer humidity arrives, with average highs in the mid-70s while Chicago shivers. For the best flight deals, watch Southwest Airlines’ frequent Tampa sales, which often drop Chicago-Tampa fares below $140 roundtrip during their Tuesday promotions. Their direct flights from Midway provide the quickest escape from Midwest winter blues to Florida sunshine.
3. Chicago to New Orleans ($84-$160 roundtrip)
- ✈️ Flight time: 2 hours 30 minutes
- 🛫 Airlines: American Airlines, United, Spirit (12+ daily flights)
- 🌸 Best time to visit: February to May, September to November
- 📍 Perfect for: Music lovers, foodies, history buffs
New Orleans is a feast for the senses, blending jazz rhythms, Creole flavors, and centuries of history into one unforgettable experience. Wander through the French Quarter, where every street corner hums with live music. Dive into a bowl of gumbo at a local eatery or grab beignets at Café du Monde. For a deeper look at the city’s past, explore the Garden District or take a ghost tour through the city’s famous cemeteries.
To score the best deals, visit in early fall or late spring when crowds thin out and hotel prices drop. Watch out for Southwest Airlines’ flash sales between Chicago and New Orleans, which sometimes dip below $100 roundtrip midweek.
A morning flight from Midway gets you to the Crescent City in time for lunch and an afternoon exploring this one-of-a-kind American treasure.
4. Chicago to Calgary ($229-$350 roundtrip)
- ✈️ Flight Time: 4 hours
- 🛫 Airlines: WestJet, United, American Airlines, Air Canada (6+ daily flights with WestJet offering the best value)
- 📅 Best Time to Visit: June to September 🏔️ for hiking and December to February ❄️ for world-class skiing
- 🏆 Perfect for: Mountain adventurers 🧗♀️, wildlife photographers 📸, outdoor enthusiasts 🏞️
Calgary delivers big city perks with Rocky Mountain adventure just up the road. You’ll get both urban fun and outdoor thrills all in one trip.
Visitors love Stephen Avenue’s cool historic buildings and shops, the wild Calgary Stampede in July with its rodeos and citywide pancake breakfasts, and Heritage Park where frontier life comes alive. The real magic happens just an hour away at Banff National Park with its stunning mountain views and impossibly turquoise lakes.
Summer brings long days, perfect for hiking and outdoor fun. If you’re looking for the best rates, Air Canada often has sales for fares under $350 roundtrip. United also offers good options through Denver, with early morning flights leaving plenty of daylight for exploring.
5. Chicago to Nassau ($351-$480 roundtrip)
- ✈️ Flight Time: 3 hours 40 minutes
- 🛫 Airlines: American Airlines, United, Delta (5+ daily connections)
- 📅 Best Time to Visit: December to April 🌴 for sunny days and minimal rain
- 🏆 Perfect for: Beach enthusiasts 🏝️, water adventurers 🤿, relaxation seekers 🍹
Swap Chicago’s winter for Nassau’s endless summer. Crystal waters, powdery beaches, and Bahamian rhythms await just 3 hours away.
Downtown Nassau bursts with pastel colonial buildings and local markets worth exploring before hitting the sand. While Paradise Island draws crowds to its mega-resort Atlantis, locals prefer the more laid-back vibe at Junkanoo Beach. Don’t miss snorkeling at Clifton Heritage Park, where underwater sculptures create an eerie artificial reef.
American Airlines runs frequent Chicago-Nassau flights, with January-April fares sometimes below $350 roundtrip. United occasionally beats these prices by $50-100 during flash sales. Book 6-8 weeks ahead for best deals.
Perfect weather? February through April. Fewer crowds? September and October still offer sunshine with occasional brief showers and significant savings.
6. Chicago to Dublin ($404-$550 roundtrip)
- ✈️ Flight Time: 7 hours 30 minutes
- 🛫 Airlines: Aer Lingus, American Airlines, United (4+ daily direct flights)
- 📅 Best Time to Visit: April to June 🌷 and September to October 🍂 for mild temperatures and fewer crowds
- 🏆 Perfect for: History buffs 🏰, pub hoppers 🍺, first-time Europe travelers ✈️
Guinness, literary giants, and emerald landscapes. Dublin packs Irish charm into a compact, walkable city just 7 hours from Chicago.
Forget the tourist traps. Start in the cobblestone alleys of Temple Bar for live music, then wander to Trinity College where the 1,200-year-old Book of Kells rests. History buffs should tour Kilmainham Gaol, where Ireland’s revolutionary past comes alive. Nights? Duck into a traditional pub like The Brazen Head (Ireland’s oldest) for proper pints and spontaneous folk sessions.
May and September offer ideal weather without summer crowds. Aer Lingus flies direct from O’Hare with shoulder season fares sometimes dipping below $600 roundtrip. American Airlines occasionally runs competitive deals through their partners. Tuesday departures typically save $50-100 over weekend flights.
Day trips? Stunning Howth cliffs or historic Malahide Castle are just 30 minutes from city center by train.
- Read Next: Cheap Places to Fly Into in Europe
7. Chicago to Stockholm ($441-$600 roundtrip)
- ✈️ Flight Time: 8 hours 30 minutes
- 🛫 Airlines: Scandinavian Airlines (SAS), Finnair, United (3+ daily flights with connections)
- 📅 Best Time to Visit: May to September ☀️ for long daylight hours and outdoor festivals
- 🏆 Perfect for: Design lovers 🪑, photography buffs 📸, outdoor explorers 🌲
Ancient meets ultramodern in Scandinavia’s trendiest capital. Stockholm spreads across 14 islands connected by 57 bridges, creating a unique maritime playground.
The medieval Gamla Stan (Old Town) feels frozen in time with narrow, cobbled streets and ocher-colored buildings. Must-see spots include the imposing Royal Palace and Nobel Prize Museum. Design geeks love the sleek Fotografiska photography museum with its killer rooftop views and the ABBA Museum where dancing is practically mandatory.
Food scene? Phenomenal. Try traditional Swedish meatballs at Pelikan or hit the buzzing Östermalms Saluhall food hall for everything from smoked salmon to cinnamon buns.
Chicago travelers find the best deals May-June when days stretch incredibly long. SAS offers connecting flights with summer fares around $700-900 roundtrip. Finnair sometimes beats these prices with Helsinki connections. Book 3-4 months ahead for best rates, especially during the magical Swedish midsummer celebrations.
- Read Next: How to Find Cheap Flights
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.
