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The cheapest prices found with in the last 7 days for return flights were C$75 and C$196 for one-way flights to Chicago for the period specified. Prices and availability are subject to change. Additional terms apply
Porter Airlines fly to Chicago, so use Travelocity to search, find, and compare some truly tempting deals from the 2 airlines—that way you can be sure you’ve found the best deal for you. A flight to Chicago IL currently costs between C$75 and C$337. Prices vary, but for the best fares, travel in October when prices are at their lowest.
The cheapest flight for a round trip to Chicago is currently C$75. When you search for flights to Chicago, enter your preferred travel dates then click on ‘flexible dates’ to compare cheap flight tickets to Chicago for nearby days. The cheapest month to travel to Chicago is October from our list of deals available.
But if you’re flexible about when you travel, you can find great deals on flights across the year. If you’re planning a vacation, you can save more on Travelocity when you bundle flights with car rental and hotel bookings, too. Many airlines currently offer flexible booking options, so look for flights offering no change fees.
We know plans change, that’s why at Travelocity, we make it as easy as possible for you to cancel or amend your plane tickets. Go to My Trips, enter your itinerary number, then follow the instructions. Many airlines let you cancel flights online free of charge if you booked it in the last 24 hours. Visit Customer Service for more advice.
We have top deals on plane tickets even for last minute flights to Chicago, so you can simply type in your travel dates and compare our best prices. Booking with Travelocity means you get flexible cancellation options, 24/7 support, and, thanks to our Price Match Promise, if the airfare drops after you book, you can get a refund! Whether you’re planning a business trip, weekend getaway, or a family vacation—let Travelocity get you to Chicago for less.
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For the latest complete info regarding passengers on flights bound for Chicago, check out our Covid-19 Travel Advisor. Everything you need to know about current travel restrictions and quarantine requirements is located here in one convenient place.
When it comes to airlines that offer flights to Chicago, you're flush with choice. There are 20 companies that operate in this major city. Book your favorite seat on one of these leading carriers:
For more info about changing your flight to Chicago, please visit our Customer Service Portal.
When looking up flights in and out of Chicago, explore all available options. With a few airports near the city, the price of your tickets may differ depending on which one you select. Here are the most popular of them:
Researching a trip to Chicago? Let Travelocity help you create some extraordinary new memories. You'll find 4,256 instantly bookable accommodations to choose from on our site.
Indulge in a bit of luxury at the Palmer House a Hilton Hotel or the Silversmith Hotel Chicago Downtown. After all, it's not every day you take a vacation! However, if you don't think you'll spend much time in your suite, how about a cheaper option like the HI Chicago or the Travelodge by Wyndham Downtown Chicago?
Fancy staying close to McCormick Place? Now's the time! Both the Hyatt Regency McCormick Place and the Marriott Marquis Chicago are comfortable places and are just a walk away.
With so many unmissable attractions in Chicago, you might just have to let the boss know that you need an extra week off. Begin with Art Institute of Chicago, and Millennium Park. You'd also be nuts to miss out on seeing Skydeck Ledge, and Willis Tower.
Experience the fabulous flavors of this lively metropolis by enjoying places like Chicago Cultural Center, and Buckingham Fountain. If you want more options, Merchandise Mart, and Wrigley Building are worth a look too.
If you are a fan of theater, be sure to take in a play at Chicago Theatre. Like some more options? Many of the best tourist attractions are situated in Chicago Riverwalk area. But that's not all. Venture to Water Tower Place and look up. You'll be thrilled by how grand this building is.
How to get through airport security fast when traveling to ChicagoMake your flight to Chicago a little bit easier by following these helpful tips and pointers:
Each time you visit Chi-Town, you’ll fall in love anew. Even if you’ve stood in front of the famous metallic bean and stood along the Navy Pier, you won’t be left wanting for original ways to spend your time. As Mark Twain posited, “She is novelty, for she is never the same Chicago you saw when you passed through the last time.” The modern city on the shores of Lake Michigan is always evolving and will never fail to enchant you. Between the exciting sports culture and buildings that hearken back to a time when Frank Sinatra and Al Capone ran the scene, Chicago always impresses.
Flights to Chicago depart from tons of destinations; just sit back, start dreaming of deep-dish pizza, and before you know it you’ll be touching down in the Windy City. Book your airfare on Travelocity today, and you’ll save enough cash to afford all the famous frankfurters you want.
Chicago flights land at one of the two major airports: O’Hare International Airport (ORD) and Midway International Airport (MDW). Getting to downtown Chicago from ORD is a breeze when you take the Blue line train, which is part of the Chicago Transit Authority train system. From MDW, jump on the Orange line train.
If you’re not staying downtown, buses are available to most parts of the city from both airports. When a private ride is more your style, hail a taxi outside the baggage claim area. Many hotels also have shuttle buses that will take you to and from the airport. But if independence is more your style, there are many rental car companies located within the airport if you need your own wheels; book your ride when you purchase your airfare to Chicago and your vacation is set.
A savvy traveler such as yourself is sure to purchase one of our top flight deals to Chicago. Not only will you travel on one of the most affordable and convenient flights, but you’re wise enough to book a Chicago hotel befitting of your fine taste:
The Windy City is known for its pizza and beloved sports teams, but the Midwest powerhouse packs a cultural punch and can impress even seasoned world travelers. Begin your exploration with an investigation of Millennium Park, and then get a taste of Chi-Town’s creative offerings at the Art Institute of Chicago. From the observation deck of the Willis Tower, you can spot your favorite attractions and plot your route of the city. Like the savvy tourist you are, you booked cheap plane tickets to Chicago. Go ahead, buy entrance to the Lincoln Park Conservatory and Brookfield Zoo.
Use Travelocity to search through the flight options to the Windy City. Once you find one of the cheapest flights to Chicago and buy your tickets, there is nothing left to do but start dreaming of mozzarella and pack your bags. Chi-Town is waiting to welcome you with open arms and delight you with its Midwest charms.