Beginning of main content
Round Trip Icon
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Search over 1,000,000 properties worldwide and 550 airlines worldwide.

Search over a million flights, hotels, packages, and more

No Expedia cancellation fee to change or cancel almost any hotel reservation.


How much is the cheapest round-trip flight to Chicago?

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Trending flights to Chicago

These prices were available within the past 7 days. 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 you're 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 you're hungry, you're 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 you've decided it's 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 you're 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 hasn't 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.

Flights to Chicago information

Destination Airport O'Hare Intl.
Destination Airport IATA Code ORD
Destination City Name Chicago

Reviews from verified customers

Dec 15, 2019

It was hot on the flight

Dec 15, 2019

Purchased two full one way tickets only had one required sized carry on and my purse. Had to place carry on because it weighted 10.8, I asked to take an article out, but was told no because my adding the weight of my purse make it 14.85. My question I had a right up to two carry on at 10.0 each. Because I did by two full size tickets, I could have removed one item to add to the other carry on. We both are senior citizens and was our first trip with viva Aerobus.

Dec 15, 2019

Great staff

Dec 14, 2019

Great value, even with the baggage fee.

Dec 14, 2019

It was very chilly on the flight; I sat in row 10.

Dec 14, 2019

Great prices an service

Dec 14, 2019

Poor Wi-Fi. Couldn’t get the movies to stay playing

Dec 14, 2019

Great captain

Dec 14, 2019

It’s cheap and usually on time

Dec 14, 2019

It’s nice to be cared for.