Cheap Flight Deals to Chicago IL from CA $184
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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 $108 and CA $184 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 | April 9 to April 14 | CA $108 |
| ATL | Chicago | May 3 to May 12 | CA $108 |
| DFW | Chicago | April 15 to April 19 | CA $158 |
| LAX | Chicago | April 15 to April 22 | CA $198 |
| DFW | Chicago | April 13 to April 20 | CA $544 |
| EWR | Chicago | March 31 to April 12 | CA $994 |
| HKG | Chicago | April 24 to November 17 | CA $1,273 |
| PVG | Chicago | April 4 to April 6 | CA $1,809 |
| PEK | Chicago | March 28 to April 10 | CA $2,071 |
Your guide to flights to Chicago, IL
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 CA $108 and CA $2,071. Prices vary, but for the best fares, travel in April 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 $108. 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 May 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
The rooms only have 2 lights. One in bathroom and one in bedroom that is super super dim and can’t hardly see anything. Couldn’t make it on our first night due to flight delays and Freehand wouldn’t reimburse it and they take so long to pick up for customer service. The rooms are much smaller than ...
Reviewed on Mar 15, 2026
Travelodge by Wyndham Downtown Chicago
Boiler went out and so did the hot water. Booker repaired but lost steam heat in the morning so we could have hot water. Had steam heat over night. Windows didn’t seal so cold and sound came in the room and the tv didn’t work correctly.
Reviewed on Mar 16, 2026
Motel 6 Elk Grove Village, IL - O'Hare
Ty
Reviewed on Mar 14, 2026
Ohio House Motel
Our Top Chicago hotel with Airport Shuttles
Super 8 by Wyndham Chicago O'Hare Airport
Had a great stay. Will be staying there again.
Reviewed on Mar 15, 2026
Country Inn & Suites by Radisson, Chicago O'Hare South, IL
Hot tub was warm but not hot. It was actually kicking out colder water. Pool hours are great. They have really nice finishes.... But they didn't get completed well. Calk looks bad, paint isn't great, patch jobs on the walls aren't great. Overall it's a good stay. Breakfast was good. I would stay ...
Reviewed on Mar 16, 2026
Hampton Inn Chicago-O'Hare International Airport
My family loves this Hampton Inn: we like the location, the staff is very friendly, it is clean and the internet is fast.
Reviewed on Mar 16, 2026
Holiday Inn Chicago O'Hare Area by IHG
Rooms were standard and clean. Reviews and booking werr misleading as we were charged for parking upon check in. There was a loud thumping noise all night. It sounded like maybe a pipe in the wall was loose and moving around.
Reviewed on Mar 13, 2026
Luxury Hotels in Chicago
Trump International Hotel & Tower Chicago
Room was perfect/staff was great
Reviewed on Mar 12, 2026
The Langham, Chicago
Great location and property
Reviewed on Mar 14, 2026
The Peninsula Chicago
We had everything we needed and more! Great location for shopping and viewing a the beautiful city of Chicago.
Reviewed on Mar 13, 2026
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
Family Friendly Hotels in Chicago
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
We asked for an extra blanket 2 nights in a row and they had no extra blankets. One set of elevators was not working so we took the stairs to the 12th floor a lot. They came and cleaned our room and made the beds but didn’t give us clean towels the 1st night but then after the 2nd night we did get ...
Reviewed on Mar 16, 2026
Palmer House a Hilton Hotel
Ceiling of bathroom was peeling and the hair rinse was out of battle dispenser. I was expecting coffee or hot water dispenser in room but no and there’s no complimentary water either.
Reviewed on Mar 15, 2026
Embassy Suites by Hilton Chicago Downtown River North
Nice location
Reviewed on Mar 16, 2026
Hyatt Regency Chicago
Very good
Reviewed on Mar 13, 2026
Best Chicago Flight and Hotel Packages
Chicago flight + hotel packages - economy flights
Chicago flight + hotel packages - first class flights
Need a car after flight to Chicago?
Economy
Compact
Midsize
SUV
Frequently asked questions
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.
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