$20 Cheap Flights to Chicago , IL

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How much is the cheapest flight to Chicago?

Prices were available within the past 7 days and start at $20 for one-way flights and $40 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Spirit Airlines
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Jan 25, 2020

Great trip!

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Fort Myers to Chicago · United

Chicago Flights

Chicago Airports

When youíre looking to book flights to Chicago, Illinois, there are two airports that serve the Windy City. O'Hare International Airport is the main one, while Chicago Midway International Airport is considered the secondary tarmac.

O'Hare sits 17 miles northwest of the Loop. It provides plenty of amenities to keep you entertained while you wait for your flight or transportation into Chi-Town. If youíre hungry, youíre in luck. This airport boasts a variety of restaurants and cafes, providing sit-down cuisine and meals-on-the-go. The airport also features various shops, where you can find Chicago souvenirs, designer goods, electronics, and duty-free products. To top it all off, O'Hare provides spa services and even a yoga room to help keep you relaxed and rejuvenated during your travels. Find out additional information about O'Hare on Flights.com.

Located roughly 12 miles northwest of downtown Chicago, Midway Airport includes several shops, the majority of which are located in the Midway Boulevard. You can also find restaurants, snack shops, and fast-food options when youíre looking fuel up before or after your flight. While youíre traveling through the airport, look for the public art and installation collections throughout the terminal.

Airport Transportation

When you have Chicago flights, rest assured knowing that both airports provide ground transportation. Here at Expedia.com, you can reserve Chicago car rentals and pick up your vehicle at your preferred airport. Alternatively, you can take advantage of public transportation as the Chicago Transit Authority provides both train and bus service to Midway and OíHare. Other transportation options include taxis, shuttles, and limousines.

Chicago Activities

Once youíve decided itís time to book plane tickets to Chicago, IL, start planning your adventures. The Windy City is home to fascinating exhibits, from the galleries at the Museum of Contemporary Art to the artifacts at the Chicago History Museum. For some of the best views of the skyline, venture up to the 360 Chicago observatory deck in the John Hancock building or the Skydeck Chicago in the Willis Tower. While youíre in town, chow down on some famous deep-dish pizza or Chicago-style hot dogs for an authentic taste of the city. Then round out your day with reservations at one of the best hotels in Chicago.

Planning Your Trip

The best times to visit Chicago are between April and May and September and October. Temperatures are moderate during these months, and the high season hasnít hit yet. Summertime is considered the most popular time to visit, so you may face more crowds and more expensive rates during this season. Meanwhile, winter brings temperatures in the low 30s F and a high chance of snowstorms.

Regardless of when you plan to visit, Expedia.com is here to match you with cheap flights to Chicago. Sort through our selection to find discounts on round-trip tickets that suit your price range. You can even use our mobile booking app for convenient access to exclusive online deals on airfare to Chicago. Book your affordable flights right here and start getting a taste for that delicious deep-dish pizza.

Frequently asked questions

How far is O'Hare Intl. Airport (ORD) from central Chicago?
ORD is 16 mi from downtown Chicago, so be prepared for a bit of a journey into the city.
What airport is best to fly into Chicago?
If you’re jumping on a plane to Chicago, you’ll most likely land at O’Hare Intl. Airport (ORD) (16 mi from downtown). Midway Intl. Airport (MDW) (9 mi from downtown) is the other major airport here.
How many nonstop flights are there to Chicago?
Arranging an unforgettable Chicago getaway is a cinch when there are 8,014 nonstop flights each week to pick from.
Where are the most popular flights to Chicago departing from?
Travelers frequently depart from Atlanta, Denver and Dallas airports when heading to Chicago.
Flights to Chicago information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Roundtrip price
$40

Trending flights to Chicago

Prices were available within the past 7 days and start at $20 for one-way flights and $40 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines

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