Cheap Flights to Chicago , IL from CA $228

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How much is the cheapest flight to Chicago?

Prices were available within the past 7 days and start at CA $228 for one-way flights and CA $329 for roundtrip, for the period specified. Prices and availability are subject to change. Additional terms apply.
United
Toronto — Chicago
YYZ - ORD with United
Sat, Jan 11
United
Chicago — Toronto
ORD - YYZ with United
Sat, Jan 11
Found 18 hours ago
From CA $329
Select flight from Toronto to Chicago, departing on January 11 with United, and returning from Chicago to Toronto on January 11 with United. Price from CA $329, Found 18 hours ago.
Delta
Toronto — Chicago
YYZ - MDW with Delta
Tue, Feb 4
Delta
Chicago — Toronto
MDW - YYZ with Delta
Tue, Feb 4
Found 3 days ago
From CA $349
Select flight from Toronto to Chicago, departing on February 4 with Delta, and returning from Chicago to Toronto on February 4 with Delta. Price from CA $349, Found 3 days ago.
Delta
Toronto — Chicago
YYZ - ORD with Delta
Thu, Jan 30
Delta
Chicago — Toronto
ORD - YYZ with Delta
Thu, Jan 30
Found 2 days ago
From CA $349
Select flight from Toronto to Chicago, departing on January 30 with Delta, and returning from Chicago to Toronto on January 30 with Delta. Price from CA $349, Found 2 days ago.
United
Montreal — Chicago
YUL - ORD with United
Thu, Jan 9
United
Chicago — Montreal
ORD - YUL with United
Fri, Jan 10
Just found
From CA $350
Select flight from Montreal to Chicago, departing on January 9 with United, and returning from Chicago to Montreal on January 10 with United. Price from CA $350, Just found.
American Airlines
Toronto — Chicago
YYZ - ORD with American Airlines
Mon, Jan 13
American Airlines
Chicago — Toronto
ORD - YYZ with American Airlines
Sun, Feb 16
Found 4 days ago
From CA $363
Select flight from Toronto to Chicago, departing on January 13 with American Airlines, and returning from Chicago to Toronto on February 16 with American Airlines. Price from CA $363, Found 4 days ago.

Expedia.ca gives you the best tools to secure great deals on flights to Chicago. Use our easy and convenient booking engine to browse nonstop flights and convenient departure points every day of the year. Search airfares from the top airlines to book your perfect flight to Chicago. Whatever your travel needs, you can always rely on Expedia.ca to help you find cheap flights to Chicago.

Using our booking engine is simple - just type in your points of travel and preferred dates and Expedia.ca does the rest! If your travel times are flexible, you can find even better bargains by adjusting your flight dates. Browse connecting flights to increase your chances of finding even lower fares. Thanks to Expedia's Best Price Guarantee, you can book your Chicago flights with full confidence knowing that you've found the best deal online.

Expedia.ca makes the booking process easy and stress-free by offering support along the entire way. Our friendly staff is available 24 hours a day to provide assistance and help you book your ticket. Call us toll-free at 1-888-397-3342 to answer any questions that you may have about your trip to Chicago.

Looking to save even more? Get additional savings by bundling your Chicago flight with a hotel and/or car rental to create a bargain travel package. Early birds can discover terrific savings by booking in advance while last minute travelers can enjoy great last minute deals. With Expedia.ca, there's no shortage of options to save even more on your Chicago trip!

Frequently asked questions

What is the name of Chicago's airport?
Chicago has more than one airport, but most travelers fly into O’Hare Intl. Airport (ORD).
How far is O'Hare Intl. Airport (ORD) from central Chicago?
ORD is 26 kilometres from downtown Chicago, so be prepared for a bit of a journey into the city.
What airport is best to fly into Chicago?
If you’re jumping on a plane to Chicago, you’ll most likely land at O’Hare Intl. Airport (ORD) (26 kilometres from downtown). Midway Intl. Airport (MDW) (14 kilometres from downtown) is the other major airport here.
How many airlines fly to Chicago?
Chicago is serviced by 45 air carriers from at least 220 worldwide airports.
Which airlines fly to Chicago?
In general, travelers fly with American Airlines, United Airlines and Delta Air Lines when going to Chicago. The largest number of these flights come in from Queens Village, with American Airlines flying this route the most frequently.
How many nonstop flights are there to Chicago?
Arranging an unforgettable Chicago getaway is a cinch when there are 8,014 nonstop flights each week to pick from.
Where are the most popular flights to Chicago departing from?
Travelers frequently depart from Atlanta, Denver and Dallas airports when heading to Chicago.
How long is the flight to Chicago Airport?
If you’re flying to Chicago from Queens Village, you’re looking at a flight duration of 2 hours and 34 minutes. Those leaving from Washington can expect to be traveling for 2 hours and 5 minutes. From Denver it’s approximately 2 hours and 23 minutes away.
How to book the cheapest flight to Chicago?
Don’t leave locking in your flight to Chicago until the very last minute. That’s one move well-versed travelers use to get the best deals. Booking in advance means more options and cheaper flights. Don’t stop there, though. Do some research and see if there is more than one airport at your destination. Ticket prices often differ depending on which airport you pick. Make sure you compare fares across airlines too. And finally, remember that the early bird catches the worm. Know what a typical airfare costs and have your credit card ready to book your ticket as soon as you see a great bargain. The best deals never last long.
How to survive the flight to Chicago?
If you’re not prepared, airports and flying can be testing. But don’t hit the panic button just yet. Follow these useful tips and enjoy a trouble-free start to your getaway in Chicago.What to pack in your hand luggage:

  • It’s simple — first, pack in your passport, important documents, cash and daily medications. Next, you’ll want some entertainment to while away the time. A thrilling novel and a laptop crammed with your favorite movies are some fantastic options. If you intend to take a short snooze, a quality neck pillow and a pair of noise-canceling headphones will also come in handy. Finally, make room for a toothbrush and some facial wipes to ensure you arrive at your destination looking fresh and raring to go.

Do not pack the following items in your hand luggage:

  • While the list of prohibited items differs between airlines, the general guide to follow is nothing flammable, sharp or explosive. This includes knives, scissors, spray paint and flares. Sporting equipment like bows and arrows, and objects that could harm passengers, such as pepper spray and firearms, can’t come on board with you either.

What to wear on a flight:

  • Your number one priority is to be as comfortable as possible. Layer up with loose, breathable clothing and remember to bring a pullover in case it gets cool in the cabin. Pick a pair of well-fitting, flat shoes as it’s possible that your feet and ankles will swell a little during the journey. Leave the high heels and hiking boots in your checked baggage.
  • The serious condition by the name of DVT (deep vein thrombosis) is a potential risk on long-haul flights. It’s the result of blood clots forming due to poor circulation. Walking up and down the aisle and doing leg and foot exercises while seated is a great way to prevent this from happening. Wearing a quality pair of compression socks or tights is also recommended.

How to get through airport security fast when flying to Chicago?
A little pre-planning before your flight can make your getaway to Chicago easy and painless. Check out our handy tips and tricks for a stress-free journey past security:

  • First things first. Your passport and travel documents will need to be shown to security personnel. Keep them within easy reach to avoid fumbling around for them.
  • Time to strip down. Well kind of. Your jacket, belt, keys and other contents of your pockets, like your headphones, will need to go on a tray through the X-ray machine. Make the whole process faster by removing them as it gets closer to your turn.
  • All your electronic devices, including your tablet and phone, are also required to be separately scanned.
  • Remember to remove gels and liquids from your hand luggage. They often need to be sent through the X-ray separately. Each product should be no larger than 3.4 ounces (100 milliliters) and everything must fit inside a quart-size (one liter), clear zip-lock bag.
  • Lightweight sneakers are a clever footwear choice as you’re less likely to be asked to remove them when passing through security. Safety boots and other heavy shoes are often subjected to additional screening.
  • Sharp or pointed objects (like knives and scissors) can’t be taken on board. They’ll be confiscated at security, so pack them safely away in your checked bags.

Flights to Chicago information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Roundtrip price
CA $103

Trending flights to Chicago

Prices were available within the past 7 days and start at CA $228 for one-way flights and CA $329 for roundtrip, for the period specified. Prices and availability are subject to change. Additional terms apply.
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