$99 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 10/17. 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
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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

Fri, Oct 17 - Sun, Oct 19
WestJet Logo
12:15 pm - 4:43 pmYYC-ORD
3h 28mnonstop
WestJet Logo
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
$151WestJet
Find Deal
Fri, Oct 17 - Sun, Oct 19
WestJet Logo
12:15 pm - 4:43 pmYYC-ORD
3h 28mnonstop
WestJet Logo
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
$154WestJet
Find Deal
Sat, Nov 1 - Sat, Nov 8
Air Canada Logo
8:30 am - 2:41 pmYVR-ORD
4h 11mnonstop
Air Canada Logo
3:40 pm - 6:15 pmORD-YVR
4h 35mnonstop
$167Air Canada
Find Deal
Wed, Oct 1 - Tue, Oct 7
United Airlines Logo
1:45 pm - 8:04 pmYVR-ORD
4h 19mnonstop
United Airlines Logo
8:51 am - 11:33 amORD-YVR
4h 42mnonstop
$173United Airlines
Find Deal
Sat, Nov 1 - Sat, Nov 8
Air Canada Logo
5:35 am - 3:10 pmYYC-ORD
8h 35m1 stop
Air Canada Logo
2:00 pm - 8:39 pmORD-YYC
7h 39m1 stop
$175Air Canada
Find Deal
Wed, Oct 1 - Sat, Oct 4
United Airlines Logo
10:30 am - 4:42 pmYVR-ORD
4h 12mnonstop
United Airlines Logo
7:41 pm - 10:18 pmORD-YVR
4h 37mnonstop
$176United Airlines
Find Deal
Fri, Oct 3 - Sat, Oct 4
American Airlines Logo
6:30 am - 12:45 pmYVR-ORD
4h 15mnonstop
American Airlines Logo
3:08 pm - 9:19 pmORD-YVR
8h 11m1 stop
$178American Airlines
Find Deal
Fri, Oct 3 - Sat, Oct 4
American Airlines Logo
11:40 am - 11:59 pmYVR-ORD
10h 19m1 stop
American Airlines Logo
1:20 pm - 9:19 pmORD-YVR
9h 59m1 stop
$193American Airlines
Find Deal
Thu, Oct 23 - Sun, Oct 26
Porter Airlines Logo
1:10 pm - 4:24 pmYUL-MDW
4h 14m1 stop
Porter Airlines Logo
4:15 pm - 10:45 pmMDW-YUL
5h 30m1 stop
$237Porter Airlines
Find Deal
Fri, Oct 24 - Sun, Oct 26
Porter Airlines Logo
1:10 pm - 4:24 pmYUL-MDW
4h 14m1 stop
Porter Airlines Logo
4:15 pm - 10:45 pmMDW-YUL
5h 30m1 stop
$238Porter Airlines
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by KAYAK users
United's carry-on size is smaller for US-bound flights.
WestJet charges 100% more for checked bags at airports.
User tips
User tips
User tips
User tips
Top airlines
United Airlines
Most flights • 136 per week
Porter Airlines
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
YVR-CHI
Cheapest
YYZ-CHI
Most popular
Insights
Insights
Insights
Insights
When to book
4 weeks
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 46% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
July
Cheapest • 15% price drop
October
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$151
Overall average: $348
WestJet
Fri 10/17Sun 10/19
YYC - ORD • Non-stop
Cheapest one-way
$99
Typical prices: $135-231
WestJet
Fri 10/17
YVR - ORD • 1 stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Booking Insights

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 flight to Chicago?

These are the best round-trip prices found by users searching on KAYAK in the last 72 hours.

In the last 3 days, the cheapest flight deal to Chicago was found on the route from Vancouver, at $151 return. The most popular connection is from Toronto to Chicago and KAYAK users have found round-trip deals for as low as $215 in the last 3 days.

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 July, where tickets cost $217 on average for return flights. On the other hand, the most expensive months are December and February, where the average cost of tickets from Canada is $291 and $289 respectively. For one-way flights, the best month to travel is May with an average price of $338.

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 Edmonton $155 round-trip, from Toronto Island Airport $181 round-trip, from Vancouver Intl Airport $191 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 4 weeks before departure, which saves you about 46% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 25 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 $204.

Good to know

Low seasonJanuary
Cheapest flight$99
Best time to beat the crowds but there is an average 11% increase in price.
Most popular time to fly and prices are also 3% lower on average.
Flight from Vancouver 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.

  • What is the cheapest flight to Chicago?

    In the last 3 days, the cheapest flight deal to Chicago was found on the route from Vancouver, at $151 return. The most popular connection is from Toronto to Chicago and KAYAK users have found round-trip deals for as low as $215 in the last 3 days.

  • 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 $474. The cheapest price found on KAYAK in the last 2 weeks cost $103 and departed from Calgary 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 $451. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $613 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 $391 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 $575.

Top tips for finding cheap flights to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $278 or less one-way and $333 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.
7.9
Porter AirlinesOverall score based on 365 reviews
7.0Entertainment
8.6Crew
7.6Food
8.2Boarding
7.9Comfort
Airline reviews

Poor landing as we overshot the runway and had to re land the plane. Lost both of my luggage not found as of yet. Had to pay extra money for my luggage in USD, now great my luggage is gone. Will not fly with Porter again.

2.0 MediocreAnonymous, Sep 2025YDF - YHZ
Read more Porter Airlines reviews

Poor landing as we overshot the runway and had to re land the plane. Lost both of my luggage not found as of yet. Had to pay extra money for my luggage in USD, now great my luggage is gone. Will not fly with Porter again.

This flight to St. Johns was really good. Boarding was a breeze. We left spot on time. Seats were actually pretty good. Recliner further than I expected. Three more flights to go we will see if this is the status quo for Porter.👍

I was not happy with AirfareAssist, the agency that kayak advised me would be handling my booking. I was advised by porter airlines that I had been overcharged for the Basic express , a option that I had asked airfare assist to help arrange after I realized that the basic fare I had chosen with porter did not include a carryon. At each checkin porter advised I had been overcharged for this . They advised that money would be refunded to my credit card, however, this is not likely to happen as it is not my name and credit card that appeared on the porter invoice, but that of another individual/agent. When airfare assist was arranging the basic express with porter on my behalf, they asked me to confirm that I agreed to pay $263 USD for this. I did agree, as I was advised this was needed to proceed. When I checked the invoice on the porter website and saw that it was not my name and credit card on the invoice, I was advised that this was how airfareassist processed the payment. The Porter invoice indicated a billed amount of $126USD I will not use Kayak or their designated AirfareAssist again

Our flight was delayed by a bit. I appreciated that we were kept informed on why periodically. Boarding was fine. I overheard one flight attendant sounding very rude to a passenger who was not paying attention to the safety demonstration. The snacks were minimal as it was a short flight. There was no entertainment. Overall the flight was good back to LGA.

There was a 5 hour delay. Missed connection and now an almost 21 hour lay over!

The flight was fine see earlier note for the problem

Three hours on the tarmac with almost zero communication from the cockpit. Not when offered a water in the interim. In my 67 years of flying all over the world the worst experience ever. The plane was half empty, however had to pay for seats to sit next to my girlfriend. Extra to take a carry on. I would never fly Porter again even for free.

All good the seats a little tight and no I pad screen

Everything was good except the fact you charge more for a carry on bag vs a check in bag and to top it off in US$ that was not impressive

Our flight was cancelled at the last minute for maintenance reasons and we were rebooked on a late flight when we purposefully booked our flight to be home early due to work.

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Inoperable monitor left no entert for 9 hours. Crew was not helpful Food was awful.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

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.

Lost bag and 2 days no word leaving for cruise no clothes or stuff

The flight was on time and crew were nice, seats were tight and there was entertainment available

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

Worst flight ever. I was suppose to have a 3 1/2 hour layover in Chicago but got to the gate 4 minutes before boarding.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

They should have MSNBC available on board. A 4- hour flight should provide more than a cookie.

Was not able to watch most shows on the entertainment site. They would not load

On Wednesday, July 30 we were in mid flight from Manchester to Charlotte and we turned around because the right engine was malfunctioning. That was the last flight out of Manchester that night. I was rebooked for Thursday, which became a weather event Friday. There were no seats left on the flight from Manchester to Charlotte. Consequently I didn’t leave Manchester until Saturday morning and we flew to Chicago so to say the least my scheduled flight and return to Iowa was three days off and it messed with my business schedule. Consequently cash flow. I would like some sort of acknowledgment of this event.

Do not fly on WestJet if you have a connection. It failed to integrate with my connecting Delta flight and I almost missed it.

There was a man who was very rude at boarding. On the other hand personal bag measuring box is too small compared to USA airlines,

A little better seat cushions would be appreciated. Crews were all good.

The process and flight were both smooth and trouble free

Flight delayed 3 hours, missed my connection in Atlanta. Instead of getting to Savannah at 6PM arrived after 10:00PM Middle seat, couldn't get isle or window, couldn't book my seats in advance, had to book at the gate. That's a 1st for me and I used to travel a lot

my carry-on bag was delayed and I did not receive it until the day of my return at the airport. This delay caused me significant inconvenience, as I did not have access to my personal belongings for the duration of my trip. I had expected to rely on my carry-on items, and being without them negatively impacted my travel experience.

Technology issues at the bag-check counter caused a delay, and we were unable to check out our bags, ultimately missing our flight. They offered no assistance other than telling us to book another flight out of Calgary. We arrived with plenty of time; if there hadn't been an issue with the kiosk and the length of the lines due to the technical issues, we could have made it home.

Worst check in and bag drop off experience. Staff were incredibly rude given that it’s the WestJet system that is faulty.

The staff at the airport and on the plane were wonderful I especially wanna acknowledge the staff who boarded us at the Calgary airport. The women who helped us board at the airport were incredible… they were so kind and sweet…I very happy with WestJet and I am hoping I can fly more often to Canada.

We were happy with our experience. The price for tickets was much less than Delta and we actually took off and landed a little ahead of scheduled times.

A sandwich and a drink would have been better thank a snack bar...

I liked the behaviour of the crew members.The flight was good.

1 hour late No hot drinks No restroom in the back of the plane

I swear airplane seats keep getting smaller and smaller but everything else was great. Smooth sailing and we got in early.

No food to provide, they forgot that, in some cases, people stay at the airport for hours without food. Now, to provide them with food, they have to ask them to pay, because some don't have money. That way, they can't eat.

After a long flight from Tokyo, our connecting flight home was canceled due to “maintenance” while we were on our layover in Toronto. Very frustrating to close out our honeymoon, although I’m sure others had it even worse during last week’s strike. Air Canada staff at Pearson Airport are the one thing that kept me remotely at peace during this — they were very helpful and deserve a lot of props. But I would not fly Air Canada again.

I had wonderful wheelchair assistance through the Montreal airport onto the flight. Air Canada was excellent in this both at the Fredericton airport and the Montreal one where an attendant helped us through customs as well as transport and baggage security.

Horrible flight cancelled had to buy another very expensive ticket

Flight was cancelled last minute due to Air Canada strike leaving us stranded and having to stressfully find a way home that cost hundreds of dollars in excess cost added to the trip. Having just experienced our mother's funeral service, this was not a good way to end our trip.

Air Canada marooned me in Canada with no way back home during my summer vacation. I had to buy a last minute flight ticket for over $500 to make it back home. I have their credit card and have flown them for years. Never again.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
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Valparaiso
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Porter
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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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