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How Much Does it Cost To Fly To Chicago?

One-way flights were as low as AU$1,097 and round trip flights were AU$1,537 within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
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Qantas Airways
Air Canada
Qantas Airways

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!

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Hotels in Chicago

Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
The price is AU$204 per night from 29 May to 30 May
AU$204
per night
29 May - 30 May
Book a stay at this family-friendly hotel in Chicago. Enjoy a 24-hour fitness center, valet parking (surcharge), and in-room massages. Our guests praise the ...
7.6/10 Good! (2,572 reviews)
"na"

Reviewed on 10 May 2024

Warwick Allerton - Chicago
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is AU$267 per night from 12 May to 13 May
AU$267
per night
12 May - 13 May
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 ...
7.6/10 Good! (6,691 reviews)
"Nice hotel. Have stayed here before and always pleasant."

Reviewed on 10 May 2024

Congress Plaza Hotel
The Westin Michigan Avenue Chicago
The Westin Michigan Avenue Chicago
4.5 out of 5
909 North Michigan Ave, Chicago, IL
The price is AU$322 per night from 13 May to 14 May
AU$322
per night
13 May - 14 May
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,004 reviews)
"It was close to everything"

Reviewed on 9 May 2024

The Westin Michigan Avenue Chicago
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.