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How Much Does it Cost To Fly To Chicago?

The cheapest flights to Chicago found within the past 7 days were NZ$1,408. Prices quoted are per person, round trip, for the period specified. Prices and availability subject to change. Additional terms may apply.

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!

Which Airlines Fly To Chicago?

United, American Airlines, Qantas Airways, Japan Airlines, Jetstar, Etihad Airways, Air New Zealand

Frequently Asked Questions

  • Question : Looking for a bargain to Chicago?
    Answer : We love visiting Chicago. But sometimes finding a good deal can be hard. At Wotif we've made booking a trip to Chicago easy. Right now we have flights going to Chicago starting at just NZ$1,408. With all that cash you just saved on your flight you now have plenty of cash to spend on your next adventure.
  • Question : What are the most popular airlines that fly to Chicago?
    Answer : Did you know airlines that fly to a city or region frequently tend to offer lower ticket prices on those flights? Here are the airlines that fly most frequently to Chicago, with flights starting from NZ$1,408:
    • Delta Air Lines: 1134 flights per week between Chicago and Atlanta.
    • American Airlines: 1032 flights per week between Chicago and Charlotte.
    • United Airlines: 778 flights per week between Chicago and Houston.
    • Lufthansa: 319 flights per week between Chicago and Frankfurt.
    • Air Canada: 310 flights per week between Chicago and Montreal.
  • Question : When should I check in for my flight to Chicago?
    Answer : The general rule for international flights is to check-in at least three (3) hours prior to your flight. We all know what flying is like these days, and anything can hold you up. Maybe the kiddos have decided they're going to take an extra hour to pack. Or maybe you'll be checking in behind someone who thought they couldn't pack 100 kilos of clothing into a carry-on bag. No matter the reason, always plan ahead. Just remember to pack your own bags, ditch the swords and nail clippers, and throw out that massive bottle of water before going through security, and you'll be right on time. Of course, some airlines may have different rules, so be sure to check with them before the day of your flight to Chicago.
  • Question : Which hotels are located near airports or major attractions in Chicago?
    Answer : If you're on the hunt for a great hotel in Chicago, check out the hotels below. They are all located near airports and points of interest in Chicago.
    • PUBLIC Chicago: PUBLIC Chicago, designed by famed hotelier Ian Schrager, is 2 blocks from Lake Michigan beaches, 3 blocks from Rush Street restaurants and nightlife, and a half-mile from Magnificent Mile shops. This hotel has a 4.00 star rating.
    • Warwick Allerton Hotel Chicago: Located on Michigan Avenue in the middle of Chicago's Magnificent Mile, this 1920s Italian Renaissance hotel is surrounded by fashionable shops, 1 mile from Lake Michigan and the Art Institute. This hotel has a 4.00 star rating.
    • Wyndham Grand Chicago Riverfront: This 39-story Chicago hotel is across the river from Magnificent Mile shopping, six blocks from Lake Michigan, and a half-mile from the Loop's theater district and the Art Institute of Chicago. This hotel has a 4.00 star rating.
  • Question : What are the top attractions in Chicago?
    Answer : Chicago has over 357 amazing sights, points of interest, and attractions. We recommend visiting Lincoln Park and Wrigley Field first, because these are some of Chicago’s most popular sights. But don’t stop there. Travellers also recommend McCormick Place, Gurnee Mills, and Navy Pier. With so much to see, check out our great deals on car hires so that you can travel through Chicago hassle-free! What’s better than an awesome getaway? An awesome getaway for an even more awesome price.
  • Question : What are the top car rental deals in Chicago?
    Answer : Renting a car is the best way to get around Chicago on your own schedule. We've found the top deals on hire cars in Chicago for you:
    • Chevrolet Spark—a Economy car from Hertz—starting at only $56.43 per day.*
    • Nissan Versa—a Compact car from Advantage—starting at only $34.14 per day.*
    • Ford Fiesta Sedan—a Economy car from Budget—starting at only $58.57 per day.*

    *Prices vary and will be updated when you view current rental car availability results. Deals displayed here are based on rental car pricing and availability as of May 15, 2019 and may change as you get closer to the actual rental date. Deals displayed whose dates are in the past are no longer valid.