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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 $101. 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

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, 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, 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

Jan 16, 2019

Shouldn't have to pay for seats. Next time I plan a trip with AAI will check that first.

Jan 16, 2019

On time.

Jan 16, 2019

WiFi wasn’t working. That would have been nice but not that big of a deal.

Jan 15, 2019

Flights were on time and I got an empty seat next to me.

Jan 15, 2019

Actually left ahead of schedule. Roomy seats.

Jan 15, 2019

I inadvertently went to the wrong gate and missed my original flight, the Rep has me rebooked for a flight in seconds. Thank you American!

Jan 15, 2019

The flight was fine. Did not like the seating as this reservation was made several weeks in advance and my spouse and I were separated. That in itself would have been ok but suspiciously several passengers were also separated just around us. Wondered if because we chose Basic Economy instead of upgrade so therefore was purposeful by there being so many separated. (We actually attempted to upgrade at time of booking). Just wondering what trip back across country will hold. But we were some of the lucky ones. At least only across the aisle in the middle seats from one another. Like I said, separation wasn't that bad but why we're so many people separated?

Jan 15, 2019

I haven't flown on American in a long time. The plane was very clean and looked updated compared to other airlines that I have flown on.

Jan 15, 2019

Very professional staff they treated me very well

Jan 14, 2019

Tall people like myself could use a little more leg room without paying a premium for it.