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Cheap Chicago Flights

The lowest prices to Chicago within the past 7 days were AU$1,172 for one-way flights and AU$683 for return flights for the period specified. Prices and availability are subject to change. Additional terms apply.

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Chicago Flight Info

Destination AirportORD
Airlines ServingAmerican Airlines, JAL, Air Canada, Fiji Airways, Austrian, Aer Lingus, Asiana Airlines, Air New Zealand, United Airlines, EVA Air, Alaska Airlines, Qantas, Royal Jordanian, SAS, Air Tahiti Nui, ANA, Brussels Airlines, Malaysia Airlines, Lufthansa, Spirit Airlines, Singapore Airlines, Air China LTD, British Airways
Flights Prices Starting AtAU$683

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 AU$683. 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: Iberia, British Airways, Delta, KLM, LOT-Polish Airlines, United, Lufthansa, Austrian Airlines, Swiss International Air Lines, Turkish Airlines, TAP Portugal, Air Canada, American Airlines, Finnair, Air France, Aer Lingus, Brussels Airlines, Jetstar, Qantas Airways, Etihad Airways.

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.