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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!

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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 NZ$170 per night from 27 Nov to 28 Nov
NZ$170
per night
27 Nov - 28 Nov
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! (8,135 reviews)
"Great staff made the stay worth it. Will go back when I return to Chicago."

Reviewed on 19 Nov. 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
The price is NZ$209 per night from 22 Dec to 23 Dec
NZ$209
per night
22 Dec - 23 Dec
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (3,558 reviews)
"Great location. Rooms were tight but it doesn’t really matter for a weekend trip. Would stay here again."

Reviewed on 19 Nov. 2024

River 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 NZ$328 per night from 21 Dec to 22 Dec
NZ$328
per night
21 Dec - 22 Dec
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! (1,001 reviews)
"The staff was very welcoming. The rooms were clean. Great location and view! Good cocktails!"

Reviewed on 19 Nov. 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.co.nz 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.