7 Cheapest Places to Fly from Chicago (Right Now)

by Jon Miksis
cheapest destinations from Chicago, Illinois
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Looking for the cheapest places to fly from Chicago? Maybe you want to leave the Windy City for warmer weather or an international destination. No matter where you’re headed, you can find cheap flights from Chicago to anywhere with great flight deals!

Chicago, Illinois, is a vibrant midwestern city known for its architecture, iconic food, and stunning views of Lake Michigan. There’s so much to enjoy about Chicago it’s hard to imagine anyone would want to leave the Windy City. Where else can you enjoy a Chicago-style hot dog at a Cub’s game or a slice of deep-dish pizza?

As a frequent flyer, I know that sometimes the travel bug bites, and you just have to get on a plane and go. If you’re a Chicago native looking to take a hike (or a swim), I can help you find some of the cheapest places to fly from Chicago. 

When it comes to travel, Chicago is a great departure point. And with two main airports, it’s easy to find a great deal on flights to anywhere from Chicago. You have infinite options, ranging from North America and South America to Europe, Asia, and everywhere in between. 

Now, finding cheap flights from Chicago may not be the easiest thing you do this week, especially if you’re not an avid traveler. But Chicago’s busiest airport – O’Hare (ORD) – is home to some of the best flight deals in the midwest. You just need to know how to find them. To help, I have rounded up some of the most popular cheap flights out of Chicago. 

Here are the cheapest places to fly from Chicago in 2023. 

Cheapest places to fly from Chicago text overlay on a photo of Millennium Park
This round-up of the cheapest places to fly from Chicago contains affiliate links, where I may receive a commission at no extra cost to you.

#1 tip for finding cheap flights out of Chicago

Looking for the cheapest places to fly out of Chicago O’Hare? Before we get to the cheapest destinations from Chicago, I want to tell you about my favorite way to find the best flight deals. This is the key to saving money on airfare, no matter where you travel. 

For 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 $500 roundtrip on selected flight routes. 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.

Mesmerizing Tunnel at Chicago O'Hare Airport
Mesmerizing Tunnel at Chicago O’Hare Airport.

Cheapest places to fly from Chicago in 2023: 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, Georgia ($54) 

Looking for a unique and affordable vacation destination from Chicago? Visit Savannah, Georgia! This charming southern city is a perfect getaway spot for anyone looking for a combination of history, culture, and natural beauty. 

Savannah, Georgia, is one of the cheapest places to fly from Chicago
Savannah has many beautiful neighborhoods to explore.

Flying from Chicago to Savannah is easier and cheaper than you might think. The best airport to fly into is Savannah/Hilton Head International Airport (SAV), located just 15 minutes from the city center. This airport is served by major airlines like Delta, American, and United and always has affordable flight options. 

Once you arrive in Savannah, there are plenty of attractions to explore. One of the most popular is the Historic District. You can take a stroll or a horse-drawn carriage down the cobblestone and admire the stunning architecture of the city’s historic buildings. For more of Savannah’s history and culture, the Telfair Museums is a must-visit. The museum has three locations featuring a variety of art and artifacts.

Another must-see attraction in Savannah is Forsyth Park, a 30-acre public park located in the heart of the city. The park is home to beautiful fountains, lush greenery, and a variety of events throughout the year, such as concerts and farmers’ markets.

a walking path through the Savannah marshlands
Savannah marshlands.

Finally, no trip to Savannah is complete without trying some of the city’s famous southern cuisine. Savannah has many dining options, from casual seafood restaurants to upscale fine dining establishments. You can try local favorites like shrimp and grits, fried green tomatoes, and pecan pie. Two restaurants you must try before leaving are The Grey and Mrs. Wilkes Dining Room

2. Chicago to Tampa, Florida ($73) 

Looking for cheap places to fly from Chicago where you can soak up the sunshine? Add Tampa, Florida, to your bucket list! This vibrant city offers a variety of attractions and activities that make it a perfect vacation spot for everyone. Moreover, with so many affordable flight options, it is easy to find a cheap trip to Tampa from Chicago.  

Tampa, Florida, is one of the cheapest places to fly from Chicago
Downtown Tampa

Tampa is known for its beautiful beaches, warm weather, and bustling nightlife. The most affordable airport to fly into is Tampa International Airport (TPA), conveniently located just 6 miles west of downtown Tampa. Airlines like Southwest, United, and American offer frequent flights from Chicago to TPA, making it easy to plan your trip. 

Once you arrive in Tampa, there are several popular attractions you can visit. One of the most famous attractions is Busch Gardens Tampa Bay, a theme park with thrilling rides, exotic animals, and live shows. Another popular attraction is the Florida Aquarium, which features more than 20,000 aquatic animals, interactive exhibits, and a 4D theater.

Tampa also offers plenty of dining options for food lovers. One of the most famous restaurants is Bern’s Steak House, which has been serving high-quality steaks since 1956. Another popular restaurant is Columbia Restaurant, which serves Spanish and Cuban cuisine and has been in business since 1905.

Clearwater Beach near Tampa, Florida
Clearwater Beach near Tampa, Florida.

Of course, you can’t leave Tampa without checking out some of its many beautiful beaches! Clearwater Beach and St. Pete Beach are two of the most popular beaches in Florida for soaking up that beautiful sunshine. You can also enjoy swimming, surfing, and paddleboarding. 

3. Chicago to New Orleans, Louisiana ($84) 

When looking for cheap cities to fly from Chicago, it’s hard to do better than New Orleans. This vibrant Louisiana city offers a unique blend of history, culture, music, and cuisine. It is, frankly, one of the best vacation destinations for just about anyone. The best part? A flight from Chicago to Louis Armstrong New Orleans International Airport (MSY) is only about 2.5 hours. 

New Orleans, Louisiana, is one of the cheapest places to fly from Chicago
Downtown NOLA.

Once you arrive in NOLA, there is so much to see and do. One of the most famous attractions is the French Quarter, a historic district that features stunning architecture, live music, and some of the best restaurants in the city. New Orleans also has beautiful parks and outdoor spaces, like City Park and Audubon Park.  Here, you can stroll along the walking paths, rent a bike, or have a picnic and enjoy the natural beauty of the city.

If you’re interested in history and culture, add the New Orleans Museum of Art to your bucket list. The museum showcases more than 40,000 objects, including paintings, sculptures, and photographs from around the world. Another popular attraction is the National World War II Museum, which tells the story of the war through exhibits, films, and personal stories.

New Orleans is synonymous with delicious food. You can sample some of the city’s famous dishes, such as gumbo, jambalaya, and beignets, at popular restaurants like Commander’s Palace, Cafe Du Monde, and Galatoire’s

a stone bridge and bench in City Park, New Orleans
City Park is one of New Orleans’ best outdoor spaces.

In the evening, you can enjoy live performances happening all over town. Hear live jazz, blues, and other genres at iconic venues like Preservation Hall, Tipitina’s, and the Maple Leaf Bar. Day or night, there is so much to do and see in this wonderful city! 

4. Chicago to Calgary, Alberta, Canada ($229)

When looking for the cheapest places to fly from Chicago, don’t forget to look to Canada! Specifically, the city of Calgary. This Alberta city is full of natural beauty, cultural attractions, and delicious cuisine that will make your trip unforgettable.

Calgary is one of the cheapest places to fly from Chicago
Calgary is Alberta’s largest city.

If you love spending time in nature, you will love visiting Calgary. The city is near Banff National Park, which is known for its stunning natural beauty and outdoor activities like hiking, skiing, and snowboarding. In the city, you can visit Prince’s Island Park, a beautiful urban park with hiking trails, picnic areas, and stunning views of the Bow River

One of Calgary’s most popular attractions, though, is the Calgary Stampede, a ten-day festival celebrating western heritage and culture. You can experience everything from rodeos and chuckwagon races to live music and delicious food during this exciting event. If you visit during the month of July, you must add this to your itinerary! 

To take your taste buds on an adventure, Calgary has no shortage of delicious options. One popular restaurant is Charcut Roast House, which serves up delicious local meats and farm-fresh vegetables in a cozy atmosphere. Another favorite spot is Pigeonhole, a trendy restaurant that offers inventive dishes and an impressive wine list.

a scenic view of Banff National Park, Alberta
Banff National Park is not far from Calgary.

The cheapest airport to fly into Calgary from Chicago is typically Calgary International Airport (YYC), which is serviced by several major airlines. With so much to see and do in Calgary, it’s no wonder this city is quickly becoming a top cheap travel destination from Chicago!

5. Chicago to Nassau, Bahamas ($351)  

Looking for a cheap tropical getaway? Nassau in the Bahamas is an excellent choice! This bustling city on New Providence Island offers a range of attractions for visitors, including some of the world’s most beautiful beaches, a rich history, delicious cuisine, and endless opportunities for outdoor adventure.

Nassau, Bahamas, is one of the cheapest places to fly from Chicago
Atlantis Hotel in Nassau.

One of the biggest draws of Nassau is the crystal-clear water and soft, white sand beaches surrounding this Caribbean island. The most popular beach is Cable Beach, with its luxurious resorts, water sports, and vibrant nightlife. Other top beaches include Cabbage Beach, Love Beach, and Saunders Beach

Aside from beaches, Nassau has plenty of other attractions to offer. History buffs can visit the famous Pirates of Nassau Museum to learn about the island’s swashbuckling past or take a tour of Fort Charlotte, which dates back to the late 18th century. The National Art Gallery of the Bahamas is another must-see for culture lovers, while the Straw Market is the perfect spot to pick up souvenirs and local crafts.

When it comes to dining, Nassau has something for every palate. The Fish Fry at Arawak Cay is a popular spot for traditional Bahamian cuisine, such as conch fritters and fried fish. For a more upscale experience, Sapodilla Estate offers a refined take on Caribbean cuisine, with stunning sea views.

Cabbage Beach Nassau, Bahamas
Nassau is known for its beautiful beaches.

The cheapest airport to fly into Nassau from Chicago is Lynden Pindling International Airport (NAS), which is served by several major airlines, including American Airlines, Delta, and United. Not only is it easy to find a cheap flight, but travel time should take you less than four hours. 

6. Chicago to Dublin, Ireland ($404)

If you’re looking for a charming and historic European destination, you’re in luck!  Dublin, Ireland, is a perfect choice for a cheap trip from Chicago. This capital city is filled with fascinating museums, stunning architecture, lively pubs, and beautiful parks, making it an ideal vacation spot for travelers of all ages.

Dublin, Ireland, is one of the cheapest places to fly from Chicago
River Liffey in downtown Dublin.

One of the most popular attractions in Dublin is the Guinness Storehouse, which offers a fascinating look into the history and production of Ireland’s most famous beer. You can tour the brewery, learn how to pour the perfect pint, and enjoy a drink in the rooftop Gravity Bar. Other must-see museums include the National Museum of Ireland, the Chester Beatty Library, and the Dublin Writers Museum, which celebrates the city’s rich literary tradition.

Dublin is also famous for its many historical landmarks, including Dublin Castle, St. Patrick’s Cathedral, and Trinity College, where you can see the ancient Book of Kells. I also recommend taking a stroll through the charming Temple Bar district, filled with lively pubs, live music, and street performers.

If you want to check out some traditional Irish fare while you’re in town, check out The Brazen Head, which claims to be Ireland’s oldest pub, or The Old Storehouse, which offers live music and hearty meals. For a more upscale experience, Chapter One offers modern Irish cuisine in a sophisticated atmosphere.

Bell tower at Trinity College in Dublin
Trinity College in Dublin.

Dublin is a fantastic destination for those looking for a mix of history, culture, and lively entertainment. It’s also a cheap destination from Chicago, thanks to one of Ireland’s cheapest airports, Dublin Airport (DUB)

7. Chicago to Stockholm, Sweden ($441)

For a cheap international flight from Chicago, consider Stockholm, Sweden. This city is a must-visit for anyone seeking a unique European experience. From its picturesque streets to its rich cultural history, Stockholm offers visitors a mix of both modern and traditional attractions that are sure to leave a lasting impression.

Stockholm, Sweden, is one of the cheapest places to fly from Chicago
Old Town Stockholm, Sweden.

Stockholm is situated on fourteen islands, which are connected by over fifty bridges. This gives you an opportunity to explore the city by boat and witness its stunning architecture, including the Royal Palace, Stockholm City Hall, and the Vasa Museum. Vasa Museum is one of the most popular tourist destinations and is home to the Vasa ship, which sank on its maiden voyage in 1628 and was salvaged in 1961.

Another popular attraction in Stockholm is Gamla Stan, the old town. It is one of the best-preserved medieval city centers in Europe and offers visitors a glimpse into Stockholm’s rich history. You can walk the narrow cobblestone streets, explore the Royal Palace, and visit Storkyrkan, the city’s oldest church. 

When walking the city, it’s also worth sampling Stockholm’s delicious food. Try some delicious Swedish meatballs, smoked salmon, and traditional fika, a Swedish coffee break that includes pastries and coffee. You can indulge in these delicacies at one of the many cafes and restaurants throughout the city.

a forest on Ingaro Island in Sweden
A forest on the island of Ingaro in the Stockholm archipelago.

When it comes to getting to Stockholm, the cheapest airport to fly to is Arlanda Airport (ARN). It is located approximately 23 miles north of Stockholm and offers a variety of transportation options to the city center. You can expect an 8.5-hour flight from Chicago to Stockholm, so pack your favorite book and a comfortable blanket. 

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. 

a view of the Chicago river
The Chicago River in downtown Chicago.

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.

NOLA is one of the cheapest places to fly from Chicago
St Louis Cathedral in New Orleans.

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 
Cheapest places to fly from Chicago text overlay on a photo of Chicago skyline at sunset
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