Cheap Flight Deals to Chicago IL from CA $165
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How to find cheap flights to Chicago?
The cheapest prices found with in the last 7 days for return flights were CA $137 and CA $165 for one-way flights to Chicago for the period specified. Prices and availability are subject to change. Additional terms apply
| Origin | Destination | Travel dates | Flights from* |
|---|---|---|---|
| EWR | Chicago | June 25 to June 27 | CA $137 |
| DFW | Chicago | August 22 to August 25 | CA $144 |
| ATL | Chicago | August 16 to August 23 | CA $151 |
| LAX | Chicago | June 18 to June 24 | CA $187 |
| LAX | Chicago | September 10 to September 10 | CA $345 |
| EWR | Chicago | August 16 to August 22 | CA $429 |
| HKG | Chicago | July 17 to July 20 | CA $1,568 |
| PVG | Chicago | July 15 to July 24 | CA $1,623 |
| PEK | Chicago | June 19 to June 23 | CA $1,840 |
Your guide to flights to Chicago, IL
American 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 CA $137 and CA $1,840. Prices vary, but for the best fares, travel in October when prices are at their lowest.
Top tips for finding cheap flights to Chicago
The cheapest flight for a round trip to Chicago is currently CA $137. 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 September 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.
How to cancel flights to Chicago
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.
Why you should book your flight to Chicago with Travelocity
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.
Find The Perfect Hotel For After Your Flight
Amazing Place to Stay After Flight to Chicago
Freehand Chicago
Reviewed on Jun. 4, 2025
Travelodge by Wyndham Downtown Chicago
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Motel 6 Elk Grove Village, IL - O'Hare
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Ohio House Motel
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Our Top Chicago hotel with Airport Shuttles
Super 8 by Wyndham Chicago O'Hare Airport
Reviewed on Jun. 5, 2025
Country Inn & Suites by Radisson, Chicago O'Hare South, IL
Reviewed on Jun. 6, 2025
Hampton Inn Chicago-O'Hare International Airport
Reviewed on Jun. 3, 2025
Holiday Inn Chicago O'Hare Area by IHG
Reviewed on Jun. 7, 2025
Luxury Hotels in Chicago
Trump International Hotel & Tower Chicago
Reviewed on Jun. 7, 2025
The Langham, Chicago
Reviewed on May 28, 2025
The Peninsula Chicago
Reviewed on Jun. 2, 2025
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
Reviewed on May 30, 2025
Family Friendly Hotels in Chicago
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Reviewed on Jun. 2, 2025
Palmer House a Hilton Hotel
Reviewed on Jun. 7, 2025
Embassy Suites by Hilton Chicago Downtown River North
Reviewed on Jun. 6, 2025
Hyatt Regency Chicago
Reviewed on Jun. 7, 2025
Best Chicago Flight and Hotel Packages
Chicago flight + hotel packages - economy flights
Need a car after flight to Chicago?
Economy
CA $249
Special
CA $249
Standard
CA $250
Compact
CA $257
Flights To Chicago
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.
Transportation from Chicago Airports
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.
Hotels Near ORD and MDW
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 hotelOpens in a new window befitting of your fine taste:
- The Palmer House Hilton: This hotel bills itself as hip and historic, and one step inside the lobby lets you know the description is spot on. Opulent ceilings and marble accents remind you of an era when dinner was always a formal affair, while the rooms are adorned in bright furniture and clean modern lines.
- Wyndham Grand Chicago Riverfront: From the cocktails served fireside at Hoyt’s Patio to in-room massages, this downtown hotel is designed to pamper. Get a room with a view and overlook the Windy City from the moment you wake up, and let the concierge help you book excursions to Chicago attractions.
- Hyatt Regency Chicago: This four-diamond hotel is connected to the Illinois Center downtown, right in the heart of the city. You’ll be just a short and leisurely walk from the Magnificent Mile and Grant Park.
- Congress Plaza Hotel: Legendary hotels are just your style, so this Grant Park hotel has your name on it. Enjoy a view of Lake Michigan from your room, and revel in the property’s storied history, which dates back to 1893.
Things to Do in Chicago
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.