$88 Find Cheap Flights from Canada to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 10/4. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

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These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago
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Cheap Flights from Canada to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Canada to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Canada to Chicago

Tue, Sep 9 - Sun, Sep 14
Porter Airlines Logo
10:45 am - 4:24 pmYUL-MDW
6h 39m1 stop
Porter Airlines Logo
5:20 pm - 10:15 pmMDW-YUL
3h 55m1 stop
$115Porter Airlines
Find Deal
Fri, Sep 5 - Mon, Sep 8
Porter Airlines Logo
7:30 am - 8:19 amYTZ-MDW
1h 49mnonstop
Porter Airlines Logo
9:15 am - 11:57 amMDW-YTZ
1h 42mnonstop
$130Porter Airlines
Find Deal
Mon, Nov 17 - Sun, Nov 23
Air Canada Logo
9:25 am - 11:18 amYUL-ORD
2h 53mnonstop
Air Canada Logo
12:50 pm - 3:57 pmORD-YUL
2h 07mnonstop
$136Air Canada
Find Deal
Mon, Nov 17 - Sun, Nov 23
Air Canada Logo
9:25 am - 11:18 amYUL-ORD
2h 53mnonstop
Air Canada Logo
12:50 pm - 3:57 pmORD-YUL
2h 07mnonstop
$137Air Canada
Find Deal
Mon, Sep 8 - Thu, Sep 11
WestJet Logo
12:15 pm - 4:43 pmYYC-ORD
3h 28mnonstop
WestJet Logo
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
$143WestJet
Find Deal
Wed, Sep 17 - Fri, Sep 19
WestJet Logo
12:15 pm - 4:43 pmYYC-ORD
3h 28mnonstop
WestJet Logo
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
$146WestJet
Find Deal
Mon, Sep 1 - Fri, Sep 5
American Airlines Logo
6:30 am - 7:26 amYYZ-ORD
1h 56mnonstop
American Airlines Logo
3:05 pm - 5:47 pmORD-YYZ
1h 42mnonstop
$161American Airlines
Find Deal
Sat, Aug 30 - Fri, Sep 5
American Airlines Logo
7:35 am - 8:11 pmYYZ-ORD
13h 36m1 stop
American Airlines Logo
3:05 pm - 5:47 pmORD-YYZ
1h 42mnonstop
$178American Airlines
Find Deal
Thu, Oct 30 - Sun, Nov 2
United Airlines Logo
11:00 am - 11:59 amYYZ-ORD
1h 59mnonstop
United Airlines Logo
9:20 pm - 11:59 pmORD-YYZ
1h 39mnonstop
$182United Airlines
Find Deal
Fri, Sep 5 - Mon, Sep 8
United Airlines Logo
7:00 am - 7:59 amYYZ-ORD
1h 59mnonstop
United Airlines Logo
10:43 am - 5:19 pmORD-YYZ
5h 36m1 stop
$185United Airlines
Find Deal
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KAYAK's insights & trends for flights to Chicago

Get data-powered insights and trends for flights to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights to Chicago is April, where tickets cost $235 on average for return flights. On the other hand, the most expensive months are December and November, where the average cost of tickets from Canada is $301 and $293 respectively. For one-way flights, the best month to travel is May with an average price of $339.

What is a good deal for flights to Chicago?

If you’re looking for cheap airfare to Chicago, 25% of our users found tickets to Chicago for the following prices or less: From Toronto Island Airport $175 round-trip, from Edmonton $183 round-trip, from Toronto Pearson Intl Airport $259 round-trip.

How far in advance should I book a flight to Chicago?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price, you should book around 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 12 weeks before departure.

Which is the cheapest airport to fly into in Chicago?

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Chicago is Chicago Greater Rockford Airport (RFD), with an average flight price of $114.


Good to know

Low seasonJanuary
High seasonAugust
Cheapest flight$88
Best time to beat the crowds but there is an average 8% increase in price.
Most popular time to fly and prices are also 7% lower on average.
Flight from Toronto Pearson Airport to Chicago O'Hare Airport

Flights from Canada to Chicago: the best tips from KAYAK users

Insights shared by verified travelers who flew the route from Canada to Chicago 
LisaFlew with United AirlinesYWG-ORDDec 2024
Turn on your data or the wifi in case gates change.
Verified travelerFlew with WestJetYYC-ORDJun 2024
checkin luggage online as they jack up the price 100% at airport
Verified travelerFlew with United AirlinesYUL-ORDApr 2024
Come prepared with your own entertainment as the flight did not offer in flight entertainment
Verified travelerFlew with United AirlinesYYZ-ORDMar 2024
Carry-on baggage sizing for United US bound flights appears to be much smaller than for Canadian flights, which forced me to check my bag at the last minute. So check online ahead of time

FAQs - booking Chicago flights

  • What hotels are near Rockford International Airport?

    The Red Roof Inn is a budget-friendly choice that is a 15-minute drive from Rockford International Airport and a 6-minute drive to the Magic Waters Waterpark. The Radisson Hotel & Conference Center is a modern choice that is a 20-minute drive from the airport and an 8-minute drive from the Midway Village Museum.

  • What is the best way to travel from O'Hare International Airport to downtown Chicago?

    The easiest and quickest way to travel from O'Hare International Airport to downtown Chicago is by either renting a car or grabbing a taxi, as the drive only takes 25 to 30 minutes in good traffic. If you prefer a more affordable option, it is also possible to use public transportation, such as the local train, which takes approximately 45 minutes.

  • Does O'Hare International Airport have a prayer room?

    O'Hare International Airport has a multi-faith chapel that is located inside of Terminal 1 on the Mezzanine level. Religious books, rosaries and prayer rugs are available for use, and the chapel is open to all travelers, no matter what their religious affiliation is. It is open 7 days a week during standard business hours.

  • What shopping options are there at O'Hare International Airport?

    O'Hare International Airport has several duty-free stores located in Terminals 1, 2 and 3. In these stores, you can find a variety of electronics, clothing, liquor, cosmetics, food products and even local souvenirs. There are also several smaller shops that sell travel essentials, such as books, snacks, headphones and basic medicine.

  • Which Chicago airport is closest to central Chicago?

    There are 3 airports in Chicago. The closest airport to Chicago’s city center is Chicago Midway Airport (9 miles). Chicago O'Hare Airport and Chicago Greater Rockford are respectively 16 miles and 79 miles from the center of Chicago.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $365. The cheapest price found on KAYAK in the last 2 weeks cost $99 and departed from Toronto Island Airport.

  • What is the cheapest day to fly to Chicago?

    Based on KAYAK data, the cheapest day to fly to Chicago is Friday where round-trip tickets can be as cheap as $434. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $616 on average.

  • How does KAYAK find such low prices on flights to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Chicago?

    The cheapest time of day to fly to Chicago is generally at night, when round-trip flights cost $343 on average. The most expensive time of day to fly to Chicago is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $579.

  • How many direct flights to Chicago are there each week?

    Each week there are around 10,038 direct flights from within Canada to Chicago. The most common day for departures is Friday, with 15% of flights taking off on this day.

Top tips for finding cheap flights to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $197 or less one-way and $305 or less round-trip.
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.
  • If you’re interested in flights to Chicago, there are three primary airports that you can fly into. While Chicago Midway International Airport is most convenient for travelers that will be staying in the city center, O'Hare International Airport services the highest number of flights. Chicago Rockford International Airport is a practical choice for individuals staying in the suburbs.
  • For those that would like a direct flight to Chicago, there are several airlines that you can choose from. While American and Porter Airlines are known for having affordable flights and comfortable chairs, United Airlines provides travelers with above-average legroom.
  • To unwind after a long day of traveling, stop by the yoga room in Chicago Midway International Airport. Located in Concourse C, this room provides travelers with complimentary mats and DVD footage of popular yoga positions. It is open 7 days a week from 6 AM to 10 PM.
  • Traveling with your family? Chicago Midway International Airport has a large baby care room that contains a sink, a private nursing area and change tables, making it a convenient place to tend to your child after your flight has landed.
  • If you would like to freshen up after a long day of traveling, purchase an access pass to either the Hilton Athletic Club, Airlines Admirals Club or United Club in O'Hare International Airport in order to access their private showers. Each of these locations provides complimentary towels and toiletries, so you will have everything you need.

Reviews of the top 5 airlines serving from Canada to Chicago

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from Canada to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
Porter AirlinesOverall score based on 298 reviews
8.7Crew
7.0Entertainment
8.2Boarding
8.1Comfort
7.7Food
Airline reviews

was okay except.. 1)the porter check in webpage doesn't let you print your boarding pass from home 2)that there was a 90 min cut off for checking in on the kiosk in general, and to print a boarding pass, even tho i checked in online already....

8.0 ExcellentChaim, Jul 2025YYZ - LGA
Read more Porter Airlines reviews

was okay except.. 1)the porter check in webpage doesn't let you print your boarding pass from home 2)that there was a 90 min cut off for checking in on the kiosk in general, and to print a boarding pass, even tho i checked in online already....

Great! Personable crew. I love that they pour complimentary beer and wine.

I love the 2 seats per row. More room. The crew were excellent.

It was amazing although they did bump us up to the front which gave us more leg room and a meal. The service was great! The staff were friendly. :)

Overall very good... staff were friendly and helpful. boarding was good for the most part, but a little hard to get our carry-on bags on there.... I think people should be directed to keep their coats and small bags with them until all the carry-ons are loaded, and then, if there is space, they can put their small bags and coats up top.. makes it much easier to put baggage up. i loved the internet feature, but the entertainment was not there unless you have your own Netflix or similar platform. My chair did not recline, which was very annoying, and the arms won't go up near the isle, which makes it tough to get in and out of the seat.

Staff were excellant. Only snacks served. Some turbulence so we were offered Free beer or wine.

The staff is always great. Just the fact that our flight was the only one delayed from Halifax when all other carries were still flying. It happen a year ago out of Toronto as well. All others were flying but our flight got cancelled 1 hr before the time of departure.

The only issue had when i mentioned about comfort was the man beside me was on the larger side and took about 1/3 of my seat where i was pressed against the wall/window of the plane for the trip.

The check-in staff, boarding staff, and flight crew were all very friendly. Really miss the Porter lounge in Ottawa.

Thanks for giving a beer to everyone in the seat infront of me and then telling me that I can’t have one because they are going to land. I guess I need to pay for a seat and then pick one in the very front of the plane

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

All flight attendants could benefit by taking an international flight on Qantas Airline. Qantas attendants are much more hospitable in every way. Much superior than and attendants on any US airline.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

So far so good but food and entertainment are not available for this flight

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

It was my first time with United Airlines and I would say it was very good experience and best of all the flights were on time. Will definitely fly with United Airlines next time.

Very modern plane. Good seat spacing. Meals were good. Screens had tons of movies and worked

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

The flight was fine but the 8 hour delay in Chicago was awful - 5 gate changes and repeated delays without an explanation. No vouchers. Nothing.

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

Not sure the logic of the boarding in Groups. I was loaded first on the aisle. Then the guy in the middle. Then the guy by the window. Constantly holding up the other people boarding behind them with us blocking the aisle and this happened in most of the other rows

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

WestJet canceled my booking, replaced it with a booking that didn't work (departing from cruise ship), and didn't offer any flights that did work. Their only option was for me to cancel and go to another airline for more money. Which I did.

Nothing to like because my inbound flight was cancelled without notification by West Jet or third party, JustFly. I couldn’t take the inbound flight due to cancellation; therefore could not take the outbound flight back.

The seats are totally uncomfortable making the flight less than pleasant. The cookies & pretzels were terrible!!!

Late departure, so I missed connection in Detroit. But Delta gave me a great hotel & breakfast. Just sorry I could not get anything from my checked baggage.

Crew was friendly. Lost our luggage and told us it’d be in later in the evening of the day we returned. It was not. Still after 5 days have not received it.

Internet on both flights was sketchy. Thus in flight entertainment was non- existent on MN - Balrimote leg.

It took 30 minutes to check in with the Westjet rep. They didn’t have enough seats and she needed to make a call… I am always “randomly” selected to be checked at security. Their “randomly “ selection system may need some updating. They treat people like criminals. It is not appropriate behavior.

Will never book through you again. Very disappointed in the notices and action taken or provided when planes are rescheduled, enough to cause missed connections

Lost my luggage. Filed a report and there is no response. Received a phone call from another airline that said they had the bag and they did not know what to do with it

Very good over all , would have been nice to have entertainment on the flight

Took off on-time and staff was very nice. Got stuck on tarmac at ATL due to storms, but staff was still wonderful even though they were working and not getting paid.

In a nutshell, my bag, the one I have to pay for, because now you can’t even bring a carry on, did not make it. I am still waiting for an update. The fact that not only were have to pay for it, but on top of that we are stuck without getting it, it’s ridiculous..

The plane was filthy!!!! There were empty food wrappers in the pockets and worst of all a wad of hair where someone had obviously brushed their hair, cleaned out the brush and left the wad of hair in the pocket. It was the most disgusting thing I’ve ever seen!! The seats are so crammed together with NO leg room. The AC vent controllers do not adjust. I will likely not book another AC flight from Florida to Montreal.

This was an excellent experience for a very short flight.

Registered my luggage at 5pm. Arrived at JFK at 1:00 am. Worst trip ever. Never again

Really good, super comfy flight and the stewardess was great.

Air Canada never runs on time. You’re lucky if your flight is not cancelled or diverted. Worst airline in the world for gas lighting its customers.

No space in overhead bin, one cookie, 2 oz of juice - is not customer service.

Good flight, friendly crew and overall - good service on United Airlines.

Received email saying that there won’t be a seat back entertainment screen and inflight WiFi would be available. But no WiFi both ways. Say it in the email.

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Chicago

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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