Important: This destination may have COVID-19 travel restrictions in place, including specific restrictions for lodging. Check any national, local and health advisories for this destination before you book.

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Chicago Flight Info

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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

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.

What are the cheapest days to book a flight?

Looking at travel demand in 2020, Friday is often the best day to book flights, when prices are generally at their cheapest. You may be tempted to wait to finalise your booking early into the week, but our data tells us ticket prices can creep up earlier in the week, especially on Tuesdays. Something to consider when planning your next holiday!

What is the cheapest month to fly?

Here’s the lowdown on the lowest airfares: March is the cheapest month to fly. When looking at 2020 flight demand on, flights departing in March generally have the lowest ticket prices. As for the most expensive month to fly, our demand data found that on average, airfares are highest in June.

How can I book cheap flights?

Get a little creative when booking your next trip to save big time! You don’t have to stick to the one airline or fare type for your return trip, so consider mixing and matching to get the most savings. Is it worth it? Well in 2020, savvy shoppers on saved over 45% when they booked return flights with two different airlines or fare types. The good news is we can help you mix and match to find the best deal… just start shopping!

How far in advance can you book a flight?

Itching to book your dream trip? We totally get it. You can start looking at flights on as early as 12 months in advance, but just keep in mind some airlines may not release all their available fares that early. But good news for last minute travellers, with 2020 data proving spontaneous travellers can still bag a bargain with some of the cheapest airfares appearing 2-4 weeks prior to travel.

*According to flight demand on from January to December 2020. Savings are subject to change and may vary depending on selections made.

Can I fly to Chicago (CHI) on holiday right now?

Make sure your trip to Chicago (CHI) goes smoothly by checking out our Covid-19 Travel Advisor for the lowdown on the current situation.