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

More Flash, Less Cash - Take advantage of our Best Price Pledge* (even on luxey stays)

We keep it easy - No cancellation fees, plus the option to pay now or later

Book up 'til the last second - millions of rooms to crash in tonight^

Book Your Flight & Hotel Together & Save

Our best flight & hotel packages

Chicago Flight Info

Destination AirportORD
Airlines ServingJAL, LOT - Polish Airlines, Fiji Airways, Air New Zealand, United Airlines, EVA Air, Qantas, SAS, Iberia, Brussels Airlines, Malaysia Airlines, Air China LTD, Singapore Airlines, Gulf Air, American Airlines, Air Canada, Azul, Aer Lingus, Austrian, Asiana Airlines, Alaska Airlines, Royal Jordanian, ANA, Air Tahiti Nui, Lufthansa, Spirit Airlines, British Airways
Flights Prices Starting At

Chicago Flights

Everyone from Kanye Westto Frank Sinatra has fallen for this town, and while one might serenade it in a slightly classier fashion, there’s no denying the love is there. If you don’t know by now, we’re talking ‘bout Chi-Town. Jump on our Chicago holiday packages like Yeezy jumps on the microphone at awards shows. You won’t be disappointed.

Getting Around Chicago

Chicago flights touch down about 30km northwest of the city centre at O'Hare International Airport (ORD). Just hop on the “L” Blue Line and you’ll be at your hotel before you can say “deepdish pizza”.

When You Land…

Those on early flights to Chicago can hook up with the Lakefront Trail for a morning walk watching the sun rise over the skyline. Better yet, grab a set of two wheels from the city’s bike-sharing system and roll like a local.

You know how Portland and Austin think they’re so “weird”? Well they don’t have the International Museum of Surgical Science, do they? This lakefront goldmine of the oddly captivating has an old-school iron lung, a few lobotomised skulls and a collection of “asthma cigarettes”. Yep, you read that right.

Landing late at night? You’re probably hungry! Book one of our Chicago hotels in the River North neighbourhood so you can drop your stuff before you stuff your face—with deep dish pizza, obviously.

Live Like a Local

If you’re itching to hear people say things like “Lemme get some tips and links”, go north to Wrigleyville. Yes, it’s home to finger-lickin’ BBQ and the famous Wrigley Field, but it’s also got comedy clubs, fantastic bars and a goat curse. Just ask a local about the Curse of the Billy Goat to learn about that last thing.

One thing that definitely isn’t cursed is’s awesome selection of cheap flights to Chicago. No need to have a billy goat nearby—just book with us and your holiday is sure to be a home run.

Chicago Flight Deals

If you thought flights to Chicago were out of the question, you haven’t seen these fares on You might say our fares are so low you have to drop it like it’s hot to pick them up. And while that’s not exactly true, we wouldn’t judge you if you did it anyway. In any case, when you grab a huge discount on your flight, we’re happy to report that you’ll still have a healthy budget for spontaneous late-night purchases. You know, for when you really need to buy a fedora and oversized pretzel from some downtown street vendors at 1 a.m. (we’ve all been there).

What is the cheapest flight to Chicago?
We offer plenty of flight options to Chicago starting at . Sounds like it’s time to book one of the best deals on cheap Chicago flights on

What airlines fly to Chicago?
Each week we have flight options to Chicago. These are some of the most popular airlines with flights to Chicago airports: .

At, we make it easy to compare cheap flights to Chicago from loads of different airlines. Once you find an itinerary that works for you, booking the flight is as easy as forgetting the bartender’s name after your last drink. There’s no reason to wait—start booking your tickets now, and you’ll be sitting on your suitcase to force it shut in no time.