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One-way flights were as low as AU$1,049 and round trip flights were AU$1,546 within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
All roads lead to Chicago. The Windy City was the birthplace of the skyscraper and today it’s full of historical sites of Industrial America, rich foods and an artsy, bluesy culture. All of that is wrapped in a working-class mentality, like a Chicago dog is wrapped in in a bun. Pack your guitar (and your antacids) and get ready for Chicago!
Chicago’s O’Hare International Airport (ORD) is one of the largest in the world. You can catch the Blue Line train into “The Loop”, or the main part of the city. There are also buses and taxis that will pick you up at the airport. Downtown is very walkable, and there is even an underground system of tunnels that helps you get around no matter what the weather is outside. Want to feel the wind in your hair? Check out Wotif’s car hire options and put the pedal to the metal.
Are you on one of the flights to Chicago that arrives in the morning? Sweet! There are plenty of museums for you to explore all day long in the Museum Campus. Check out the Field Museum of Natural History, the Museum of Science and Industry, and the Art Institute of Chicago.
If afternoon Chicago flights leave you with a grumbling tummy, find the nearest hot dog cart and order yourself a Chicago dog. But for the love of all that’s Chicagoan, don’t you dare apply any ketchup!
If you land after dark, head downtown and check out all the brightly-lit skyscrapers before checking into Chicago hotels.
You’ll find tons to do after you book one of Wotif’s Chicago holiday packages. Dip your toes in the water of Lake Michigan or just stroll along the famous waterfront. You won’t regret it! But if you really want to live like a Chicagoan, head to Soldier Field, grab a beer and tell the stadium how you really feel about that ref’s last call against Da’ Bears. You’ll fit right in.
Whether this is your first trip or not, you can visit the Second City like a pro with Wotif’s cheap flights to Chicago. Save yourself some time and money. Book today and enjoy your flight!
Need insider tips on must-see attractions in Chicago? Check out our Chicago travel guide!
Flights to Chicago start as low as AU$1,546. Once you’ve snagged your flight, it’s time to build that itinerary. If your flight touches down in a bustling city, you’ll want a head start, so you can get from jet-way to getaway as quickly as possible. Flying for business? Squeeze in some sightseeing and a snack at a locally loved restaurant between meetings—you’ll have plenty of cash thanks to our cheap business class flights to Chicago. You know what they say about all work and no play, after all.
Fiji Airways, Korean Air, Qantas Airways, Air New Zealand, Finnair, Etihad Airways, Malaysia Airlines, Qatar Airways, Japan Airlines, Singapore Airlines, American Airlines, United. Pack your favourite magazines or stack your video queue for a mini-marathon of that television show your co-workers have been raving about. And if you get hooked a few episodes in, don’t worry; there’s always the return flight to finish the binge. Ready to book cheap flights to Chicago? Check out our selection of airfares and start putting together a holiday that fits your schedule and price range. We offer sweet deals, so you don’t have to move mountains to see the world. In fact, we’ll help you get to those mountains (or ocean, or forest) today!
Here’s an insider tip: Sunday is typically the cheapest day to fly! Looking at flight demand on Wotif in 2020, we found that flights departing on a Sunday generally had the lowest average price, closely followed by flights on a Tuesday. You might want to think twice about flying on a Saturday though; generally, our data showed that it had the highest average ticket price.
Guess what? Boring old Thursday really is the best day to score the cheapest plane tickets. Looking at flight demand on Wotif in 2020, we found that flights purchased on a Thursday had the lowest airfares on average. Booking your plane ticket on a Sunday also seems to score pretty good deals. However, airfares purchased on a Tuesday generally have a higher than average ticket value, so you might want to prepare your budget if you’re booking early in the week.
When comparing airfares booked through Wotif in 2020, our data shows March is one of the cheapest months to fly. On the other hand, the month of June can be one of the most expensive times to travel, with the highest average ticket price, so it’s best to get in early if June is your preferred travel month.
Trying to figure out how early you should book your flight? It’s possible to start comparing international airfares on Wotif up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to Wotif’s 2020 flight demand trends, you can bag a bargain with some of the cheapest airfares appearing 4 weeks to 3 months prior to travel.
Looking for clever ways to save on your next trip? Try mixing and matching airlines and fare types. Our data tells us, travellers who booked flights on Wotif in 2020 saved close to 50% off their airfare, when their return flights consisted of two different airlines or fare types.
*According to flight demand on Wotif.com from January to December 2020. Savings are subject to change and may vary depending on selections made.
For all the latest info on the travel situation in Chicago, see our Covid-19 Travel Advisor.
Reviewed on 27 Dec. 2019
Reviewed on 24 Jul. 2019
^Savings based on all package bookings made with Flight + Hotel on Wotif.com from , as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.