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How Much Does It Cost To Fly To Chicago?

The cheapest tickets to Chicago available within the past 7 days were $108.80. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

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.

Chicago Flight + Hotel Deals

Reviews from verified customers

Oct 22, 2018

Very good air line

Oct 21, 2018

i received an email from expedia AFTER my flight had already taken place stating that my flight was CANCELLED. this concerns me, as if that email came earlier i may have assumed it was correct and missed my flight. this was on thurs oct 18, when hurricane/tropical storm michael was in my area.

Oct 19, 2018

Need to inforce one carry-on per person so those with only one don’t have to check their bag.

Oct 19, 2018

I didn’t get my assist.

Oct 18, 2018

I would fly on AA again

Oct 18, 2018

Seat said it had power but could never find it. More information should be provided

Oct 17, 2018

My wife and I didn't get to sit together. Disappointed in that.

Oct 17, 2018

Seats not so comfortable and did not seem to recline.

Oct 17, 2018

My flight was delayed but the attendant went above and beyond to make sure I was taken care of in the event I couldn’t get on the next flight. She had a great attitude was very apologetic and I felt very taken care of in a chaotic situation.

Oct 17, 2018

The kiosk wouldn't check or bag, but thre hotel was great and helped us out.