The 7 Cheapest Places to Fly from Chicago in 2025

625

If you’re looking to explore new destinations without breaking the bank, flying from Chicago has some great options for 2025. With years of experience visiting 45 U.S. states and 66 countries around the globe, I dove into over 100 flight routes from Chicago’s primary airports—O’Hare International (ORD) and Midway (MDW)—to find the most budget-friendly places to visit next year. This analysis considers average fares, flight availability, popular airlines, and seasonal demand, making sure you get the best options for stretching your travel dollars.

From quick domestic getaways to stunning international escapes, these seven destinations combine affordability with a wealth of experiences. Whether you’re craving a beach escape, a cultural city, or a nature retreat, there’s something on this list for every budget-conscious traveler departing from this Midwestern city.

Let’s jump into the most wallet-friendly places to fly from Chicago in 2025, so you can plan your next adventure without the high costs!

#1 tip for finding cheap flights out of Chicago

Looking for the cheapest places to fly out of Chicago O’Hare? Here’s my favorite way to find the best flight deals.

For 4+ 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 Jon20 to save 20% when you join Going!

Other considerations when finding cheap flight deals from Chicago 

For this roundup of the cheapest places to fly from Chicago, I primarily focused on North America and Europe. However, you can find cheap flights from Chicago, IL, to just about anywhere via O’Hare. Chicago O’Hare International Airport is the fourth busiest airport in the world and hosts more than 40 airlines. What does this mean for a wannabe jet setter? It’s easy to find a great deal no matter where in the world you want to go. 

When looking for cheap flight deals from Chicago, remember that when you travel is often as important as where you travel. For instance, certain times of the year are always busier for certain destinations. In that case, you’re less likely to find an amazing flight deal (although it’s always possible!). With that said, if you have a specific vacation spot in mind, it’s important to plan ahead of time. Research the peak season for your destination and try to schedule your trip when things are less busy. This will help you avoid the crowds and find the best deal possible on a cheap vacation from Chicago.

Finding flight deals isn’t always as easy as we’d like. If you’re having trouble finding cheap flight deals to your dream destination, don’t give up! Booking a trip far in advance is a great way to score discounted airfare, but it’s not the only way. As the date of the trip gets closer, you might score last-minute deals thanks to other people canceling their flights. Most airlines would prefer to sell a seat reduced than to send out an airplane with empty seats. In this case, you can score a great last-minute getaway from Chicago for cheap.

Cheapest places to fly from Chicago in 2025: 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:

1. 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.

Frequently asked questions (FAQ) about cheap flights from Chicago

Before you start planning your vacation and book your flight, there are some things you should know. Here are some common questions and answers about how to get cheap plane tickets from Chicago:

What is the cheapest month to fly from Chicago?

While finding the cheapest airfare will also depend on your destination, generally, the cheapest month to fly from Chicago is January. The summer (specifically June and July) are high season in Chicago, and airfare prices are likely to be higher. 

To get below-average airfare, you will probably have the best luck booking at least two weeks in advance. However, it’s important to keep in mind that it is possible to score last-minute flight deals regardless of the season. 

What is the cheapest airport to fly out of Chicago?

While the larger and newer Chicago O’Hare International Airport is the more popular airport in and out of Chicago, the Midway International Airport (MDW) is a more budget-friendly option. Midway is Chicago’s second-biggest airport and is mostly controlled by low-cost carrier Southwest Airlines. 

Because most of the flights are controlled by Southwest, which offers cheap flights from Chicago to many domestic destinations, you can find many cheap flights. However, keep in mind that budget airline carriers are not for everyone. When looking for the cheapest flight deals out of Chicago, compare the costs of departing from both airports before you make your final decision. For comfortable international flights, you might be better off with the larger O’Hare. 

What are the cheapest flights from Chicago?

Thanks to its central location and large major airports, it’s easy to find cheap flights from Chicago. While you can find cheap places to fly from Chicago across the globe, the cheapest places to fly from Chicago tend to be domestic destinations. You can fly to major cities such as Savannah, Tampa, and New Orleans for well under $100 roundtrip.

It’s even possible to find affordable flights to international destinations, too. You can fly roundtrip to  Canada and the Bahamas for only a few hundred dollars. Even flights to some European destinations aren’t too expensive, such as Ireland and Sweden.

What airlines offer flights from Chicago O’Hare International Airport?

Chicago O’Hare is one of the busiest airports in the world, with more than 500 flights daily to international and domestic destinations. This major airport hosts over 40 different airlines across four different terminals. If you have a favorite airline, chances are you can catch a flight out of O’Hare. 

Here is a complete list of commercial airlines offering flights out of Chicago O’Hare: 

• Aer Lingus
• AeroMexico
• Air Canada
• Air France
• Air India
• Air New Zealand
• Alaska Airlines
• All Nippon
• American Airlines
• Austrian Airlines
• British Airways
• Cape Air
• Cathay Pacific Airways
• Copa Airlines
• Delta
• Denver Air Connection
• EVA Air
• Emirates
• Ethiopian Airlines
• Etihad Airways
• Finnair
• Frontier Airlines
• Iberia Airlines
• Icelandair
• Japan Airlines
• JetBlue
• KLM Royal Dutch
• Korean Air
• LOT Polish Airlines
• Lufthansa 
• Qatar Airways
• Royal Jordanian
• SWISS
• Scandinavian Airlines
• Southern Airways Express
• Southwest Airlines
• Spirit Airlines
• Sun Country
• TAP Air Portugal 
• Turkish Airlines
• United Airlines
• VivaAerobus
• Volaris Airlines
• Westjet Airlines