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How Much Does it Cost To Fly To Chicago?

Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

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Flight Info
Destination airport
Chicago

Flights To Chicago

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!

Getting Around 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.

When You Land…

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.

Live Like a Local

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.

Book with Wotif

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!

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Hotels in Chicago

Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is AU$316 per night from 4 Aug to 5 Aug
AU$316
4 Aug - 5 Aug
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (8,926 reviews)
"Good location.good staff."

Reviewed on 9 Jul. 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
The price is AU$432 per night from 10 Aug to 11 Aug
AU$432
10 Aug - 11 Aug
includes taxes & fees
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in ...
9/10 Wonderful! (2,009 reviews)
"We had a wonderful stay at the Intercontinental Magnificent Mile over the July 4th weekend! We enjoyed all 3 restaurants/bars- especially Casa Chi! The staff were all excellent. The spot is super convenient/walkable to everywhere you would want to go in downtown Chicago, a block from the riverwalk ..."

Reviewed on 9 Jul. 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
The price is AU$301 per night from 6 Aug to 7 Aug
AU$301
6 Aug - 7 Aug
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
8.8/10 Excellent! (2,420 reviews)
Great stay
"Convenient to attractions, clean and comfortable. Wish they had an airport shuttle. Pool was closed for maintenance but I doubt we would have used anyway"

Reviewed on 10 Jul. 2025

Hilton Chicago/Magnificent Mile Suites
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

^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.