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Destination airport | Chicago |
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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
The Chicago Hotel Collection Ambassador Gold Coast
"We like our room, very clean and spacious"
Reviewed on 4 July 2026
Congress Plaza Hotel
"Our room was nothing like it was advertised on Expedia. The room was small, old, and not well-maintained. Baseboards were clearly dirty and old. The window was also very small, like a 4x4 box so you can't really enjoy any views or any natural light. There was one nightstand only on one side, which ..."
Reviewed on 5 July 2026
Hilton Chicago O'Hare Airport
"Very convenient location for a short stay"
Reviewed on 4 July 2026
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^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.