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C$ 164 Find cheap flights 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 20/4. 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.
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Search hundreds of travel sites at once for deals on flights to Chicago

 
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
In the last 7 days, travellers have searched 46,214,184 times on KAYAK, and here is why:

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Cheap flight deals to Chicago

 
These are the cheapest deals for flights to Chicago currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals to Chicago

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Canada to Chicago.

Recent one-way flight deals to Chicago

Only flying one-way? Below are some of the best one-way flight deals from Canada to Chicago found on KAYAK recently.

Recent last-minute flight deals to Chicago

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Canada to Chicago.

Recent direct flight deals to Chicago

The latest deals for direct flights from Canada to Chicago so you can sit back and relax without the need for a layover.

Cheap bus & train deals to Chicago

Find recent round-trip train or bus tickets from Canada to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
11:30 a.m. - 3:56 p.m.YYC-ORD
3h 26mdirect
4:45 p.m. - 7:36 p.m.ORD-YYC
3h 51mdirect
C$ 282WestJet
Find Deal
Thu, 13 Feb - Mon, 17 Feb
6:20 a.m. - 1:49 p.m.YYC-ORD
6h 29m1 stop
12:17 p.m. - 11:18 p.m.ORD-YYC
12h 01m2 stops
C$ 307Delta
Find Deal
Thu, 9 Jan - Mon, 13 Jan
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 311Porter Airlines
Find Deal
Thu, 14 Nov - Sun, 24 Nov
8:30 a.m. - 12:49 p.m.YYC-ORD
3h 19mdirect
7:15 a.m. - 9:38 p.m.ORD-YYC
15h 23m1 stop
C$ 312United Airlines
Find Deal
Tue, 8 Apr - Sat, 12 Apr
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 315Porter Airlines
Find Deal
Mon, 18 Nov - Mon, 25 Nov
8:30 a.m. - 6:38 p.m.YYC-ORD
9h 08m1 stop
4:00 p.m. - 11:17 p.m.ORD-YYC
8h 17m1 stop
C$ 321Air Canada
Find Deal
Thu, 9 Jan - Mon, 13 Jan
9:00 p.m. - 10:07 p.m.YYZ-ORD
2h 07mdirect
10:51 a.m. - 1:42 p.m.ORD-YYZ
1h 51mdirect
C$ 321United Airlines
Find Deal
Tue, 12 Nov - Wed, 18 Dec
12:50 a.m. - 10:10 a.m.YYC-ORD
8h 20m1 stop
4:00 p.m. - 11:17 p.m.ORD-YYC
8h 17m1 stop
C$ 328Air Canada
Find Deal
Wed, 8 Jan - Mon, 13 Jan
6:15 a.m. - 7:30 a.m.YYZ-ORD
2h 15mdirect
1:25 p.m. - 4:00 p.m.ORD-YYZ
1h 35mdirect
C$ 328American Airlines
Find Deal
Thu, 21 Nov - Thu, 28 Nov
6:15 a.m. - 7:30 a.m.YYZ-ORD
2h 15mdirect
8:10 a.m. - 10:59 a.m.ORD-YYZ
1h 49mdirect
C$ 350American Airlines
Find Deal
Wed, 13 Nov - Thu, 19 Dec
11:30 a.m. - 3:56 p.m.YYC-ORD
3h 26mdirect
C$ 164WestJet
Find Deal
Sun, 20 Apr
8:30 a.m. - 6:36 p.m.YYC-ORD
9h 06m1 stop
C$ 177Air Canada
Find Deal
Tue, 19 Nov
6:50 a.m. - 11:10 a.m.YUL-MDW
5h 20m1 stop
C$ 188Porter Airlines
Find Deal
Wed, 4 Dec
11:50 a.m. - 4:40 p.m.YUL-MDW
5h 50m1 stop
C$ 189Porter Airlines
Find Deal
Fri, 29 Nov
2:09 p.m. - 11:57 p.m.YYC-ORD
8h 48m1 stop
C$ 191United Airlines
Find Deal
Sat, 23 Nov
3:30 p.m. - 4:41 p.m.YYZ-ORD
2h 11mdirect
C$ 196United Airlines
Find Deal
Sun, 19 Jan
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
C$ 213Air Transat
Find Deal
Wed, 13 Nov
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
C$ 214Air Transat
Find Deal
Wed, 13 Nov
5:18 p.m. - 7:44 a.m.YUL-ORD
15h 26m1 stop
C$ 236American Airlines
Find Deal
Mon, 4 Nov
7:14 a.m. - 2:15 p.m.YUL-ORD
8h 01m1 stop
C$ 245American Airlines
Find Deal
Thu, 5 Dec
6:45 a.m. - 9:05 p.m.YYC-ORD
13h 20m2 stops
6:00 a.m. - 1:35 p.m.ORD-YYC
8h 35m1 stop
C$ 350Delta
Find Deal
Sat, 26 Oct - Tue, 29 Oct
8:15 a.m. - 2:26 p.m.YVR-ORD
4h 11mdirect
7:41 p.m. - 10:18 p.m.ORD-YVR
4h 37mdirect
C$ 401Air Canada
Find Deal
Thu, 24 Oct - Fri, 25 Oct
1:45 p.m. - 8:00 p.m.YVR-ORD
4h 15mdirect
9:20 p.m. - 10:01 a.m.ORD-YVR
14h 41m1 stop
C$ 427United Airlines
Find Deal
Fri, 25 Oct - Mon, 28 Oct
1:45 p.m. - 8:00 p.m.YVR-ORD
4h 15mdirect
9:20 p.m. - 10:01 a.m.ORD-YVR
14h 41m1 stop
C$ 429United Airlines
Find Deal
Fri, 25 Oct - Mon, 28 Oct
12:39 p.m. - 7:25 a.m.YYC-ORD
17h 46m1 stop
9:45 a.m. - 12:41 p.m.ORD-YYC
3h 56mdirect
C$ 446American Airlines
Find Deal
Fri, 25 Oct - Tue, 29 Oct
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
12:55 p.m. - 3:37 p.m.MDW-YTZ
1h 42mdirect
C$ 471Porter Airlines
Find Deal
Sun, 27 Oct - Sat, 30 Nov
10:45 a.m. - 11:32 a.m.YTZ-MDW
1h 47mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 475Porter Airlines
Find Deal
Sat, 26 Oct - Fri, 29 Nov
3:09 p.m. - 4:04 p.m.YYZ-ORD
1h 55mdirect
6:34 p.m. - 9:29 p.m.ORD-YYZ
1h 55mdirect
C$ 499American Airlines
Find Deal
Sat, 26 Oct - Fri, 29 Nov
1:25 p.m. - 9:38 p.m.YYZ-MDW
9h 13m1 stop
10:49 a.m. - 10:24 a.m.MDW-YYZ
22h 35m1 stop
C$ 568WestJet
Find Deal
Sat, 26 Oct - Tue, 29 Oct
12:30 p.m. - 10:06 p.m.YYZ-ORD
10h 36m1 stop
12:25 p.m. - 6:18 a.m.ORD-YYZ
16h 53m2 stops
C$ 578WestJet
Find Deal
Sat, 26 Oct - Fri, 29 Nov
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 311Porter Airlines
Find Deal
Thu, 14 Nov - Sun, 24 Nov
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 315Porter Airlines
Find Deal
Mon, 18 Nov - Mon, 25 Nov
3:30 p.m. - 4:30 p.m.YYZ-ORD
2h 00mdirect
2:05 p.m. - 4:46 p.m.ORD-YYZ
1h 41mdirect
C$ 329Air Canada
Find Deal
Sun, 15 Dec - Sat, 11 Jan
6:52 a.m. - 8:05 a.m.YYZ-ORD
2h 13mdirect
7:19 a.m. - 9:58 a.m.ORD-YYZ
1h 39mdirect
C$ 335Air Canada
Find Deal
Thu, 28 Nov - Mon, 2 Dec
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 354Air Transat
Find Deal
Thu, 14 Nov - Sun, 17 Nov
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 355Air Transat
Find Deal
Thu, 14 Nov - Sun, 17 Nov
9:00 a.m. - 10:05 a.m.YYZ-ORD
2h 05mdirect
12:52 p.m. - 3:45 p.m.ORD-YYZ
1h 53mdirect
C$ 359United Airlines
Find Deal
Tue, 12 Nov - Tue, 12 Nov
8:00 a.m. - 8:57 a.m.YYZ-ORD
1h 57mdirect
7:19 a.m. - 9:58 a.m.ORD-YYZ
1h 39mdirect
C$ 365United Airlines
Find Deal
Thu, 14 Nov - Sun, 17 Nov
6:20 p.m. - 7:20 p.m.YYZ-ORD
2h 00mdirect
1:25 p.m. - 4:00 p.m.ORD-YYZ
1h 35mdirect
C$ 366American Airlines
Find Deal
Mon, 18 Nov - Mon, 25 Nov
4:44 p.m. - 5:44 p.m.YYZ-ORD
2h 00mdirect
8:11 a.m. - 10:51 a.m.ORD-YYZ
1h 40mdirect
C$ 380American Airlines
Find Deal
Fri, 29 Nov - Wed, 4 Dec
11:30 a.m. - 3:56 p.m.YYC-ORD
3h 26mdirect
4:45 p.m. - 7:36 p.m.ORD-YYC
3h 51mdirect
C$ 282WestJet
Find Deal
Thu, 13 Feb - Mon, 17 Feb
6:20 a.m. - 1:49 p.m.YYC-ORD
6h 29m1 stop
12:17 p.m. - 11:18 p.m.ORD-YYC
12h 01m2 stops
C$ 307Delta
Find Deal
Thu, 9 Jan - Mon, 13 Jan
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 311Porter Airlines
Find Deal
Thu, 14 Nov - Sun, 24 Nov
8:30 a.m. - 12:49 p.m.YYC-ORD
3h 19mdirect
7:15 a.m. - 9:38 p.m.ORD-YYC
15h 23m1 stop
C$ 312United Airlines
Find Deal
Tue, 8 Apr - Sat, 12 Apr
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 315Porter Airlines
Find Deal
Mon, 18 Nov - Mon, 25 Nov
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 317Porter Airlines
Find Deal
Thu, 14 Nov - Sun, 17 Nov
11:10 a.m. - 12:00 p.m.YTZ-MDW
1h 50mdirect
12:55 p.m. - 3:37 p.m.MDW-YTZ
1h 42mdirect
C$ 318Porter Airlines
Find Deal
Tue, 14 Jan - Thu, 16 Jan
7:45 a.m. - 2:17 p.m.YYC-ORD
5h 32m1 stop
7:00 a.m. - 9:02 p.m.ORD-YYC
15h 02m2 stops
C$ 319Delta
Find Deal
Thu, 9 Jan - Sun, 12 Jan
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 319Porter Airlines
Find Deal
Wed, 25 Dec - Sun, 29 Dec
9:00 p.m. - 10:07 p.m.YYZ-ORD
2h 07mdirect
10:51 a.m. - 1:42 p.m.ORD-YYZ
1h 51mdirect
C$ 321United Airlines
Find Deal
Tue, 12 Nov - Wed, 18 Dec

Flights to Chicago - Travel Insights & Trends

Get data-powered insights and trends into 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 prices found by users searching on KAYAK in the last 72 hours.
Based on KAYAK searches from the last 72 hours, if you fly from Calgary, you should have a good chance of getting the best deal to Chicago as it was the cheapest place to fly from. Prices were found for as low as C$ 227 one-way and C$ 388 for a round-trip flight. Also in the last 72 hours, the most popular connection to Chicago was from Toronto and the lowest price for a round-trip flight was C$ 321.

How much is a flight to Chicago?

The average and cheapest price for all flights to Chicago from each origin found by users searching on KAYAK in the last month.
On average, a flight to Chicago costs C$ 862. The cheapest price found on KAYAK in the last 2 weeks cost C$ 166 and departed from Vancouver Intl Airport. The most popular routes on KAYAK are Toronto to Chicago which costs C$ 1,310 on average, and Montreal to Chicago, which costs C$ 970 on average.
See prices from:

What is the cheapest day to fly to Chicago?

The average price of all flights to Chicago clicked on KAYAK for each day over the last 12 months.
Based on KAYAK data, the cheapest day to fly to Chicago is Tuesday where tickets can be as cheap as C$ 479. On the other hand, the most expensive day to fly is Sunday, where prices are C$ 540 on average.

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 C$ 420 on average for one-way flights. On the other hand, the most expensive months are October and January, where the average cost of tickets from Canada is C$ 633 and C$ 625 respectively. For return trips, the best month to travel is April with an average price of C$ 330.

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

The average price for all flights to Chicago depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.
The cheapest time of day to fly to Chicago is generally in the evening, when flights cost C$ 362 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 C$ 407.

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 C$ 183 one-way - C$ 315 round-trip, from Vancouver Intl Airport C$ 215 one-way - C$ 479 round-trip, from Québec City C$ 255 one-way - C$ 642 round-trip.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 124 days 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 Midway Airport, with an average flight price of C$ 266.

Good to know

Low season

January

High season

August

Cheapest flight

C$ 164
Best time to beat the crowds (6% less expensive on average)
Most popular time to fly (1% more expensive on average)
Flight from Calgary to Chicago O'Hare Airport

When to book flights to Chicago

Are your dates flexible? Find out the best times to travel to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. The information is for flights to Chicago based on your location. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs - booking Chicago flights

  • Which other cities does Chicago O'Hare International Airport (ORD) serve?

    Apart from serving Chicago, Chicago O'Hare International Airport also serves as the arrival airport for those travelling to Oak Park and Cicero. Therefore, booking a flight to Chicago is an opportunity to access these nearby cities conveniently. Car rentals at ORD provide the most convenient means of transport from the airport to Cicero and Oak Park.

  • How convenient is it to travel to Chicago with kids?

    You will enjoy a variety of kid-friendly perks with a number of airlines that fly to Chicago, with JetBlue ranking the highest. If you book JetBlue, you and your kids are guaranteed to travel in a much more comfortable way, with the airline popular for its spacious seats and extra legroom in all the cabins. Additionally, parents enjoy extra baggage allowance and are allowed to board the plane first before other travellers.

  • 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?

    Based on KAYAK searches from the last 72 hours, if you fly from Calgary, you should have a good chance of getting the best deal to Chicago as it was the cheapest place to fly from. Prices were found for as low as C$ 227 one-way and C$ 388 for a round-trip flight. Also in the last 72 hours, the most popular connection to Chicago was from Toronto and the lowest price for a round-trip flight was C$ 321.

  • Which Chicago airport is closest to central Chicago?

    Chicago is served by 3 major airports. Chicago Midway Airport (14 km) is the closest to the centre of Chicago. Chicago O'Hare Airport is 26 km from the centre and Chicago Greater Rockford is 126 km away from the centre.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs C$ 862. The cheapest price found on KAYAK in the last 2 weeks cost C$ 166 and departed from Vancouver Intl Airport.

  • 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 travellers 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.

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

    Each week there are around 225 direct flights from within Canada to Chicago. The most common day for departures is Friday, with 15% of flights taking off on this day.

See more FAQs

Top tips for finding cheap flights to Chicago

  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.
  • The highest number of flights to Chicago have Chicago O'Hare International Airport (ORD) as the arrival airport. The airport is located about 16 miles (27 km) northwest of Chicago. Most travellers prefer landing here because of the availability of a variety of transport options, which makes it easier for them to connect to various parts within and outside Chicago.
  • You have better chances of getting cheaper flight deals when booking your flight to Chicago if you choose to book one that has Chicago Midway International Airport (MDW) as the arrival airport. This is because the flights that arrive at MDW have a lower demand among travellers flying to Chicago. Additionally, you will enjoy shorter queues at the security checkpoints and baggage claim area when you land at MDW as opposed to if you land at ORD.
  • You will make one stop or travel nonstop to Chicago, depending on the airline you book. Spirit Airlines is one of the carriers that makes one stop when flying to Chicago, with the layover airport being Hartsfield–Jackson Atlanta International Airport (ATL). However, if you book Air Canada, JetBlue, or Porter Airlines, you will enjoy direct flights to Chicago.
  • 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.
See more tips

Flights to Chicago: the best tips from KAYAK users' own experiences

Insights shared by verified travellers who flew to Chicago 
Verified travelerFlew with Air CanadaYYZ-ORDJun 2024
It seemed that anyone who checked a bag was able to retrieve it quickly.
Verified travelerFlew with WestJetYYC-ORDJun 2024
checkin luggage online as they jack up the price 100% at airport
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
Verified travelerFlew with United AirlinesYUL-ORDApr 2024
Come prepared with your own entertainment as the flight did not offer in flight entertainment

Prefer to fly non-stop to Chicago?

Find which airlines fly direct to Chicago, which days they fly and book direct flights.

Nonstop departures

Canada to Chicago

Monday

ANA,Aer Lingus,Aeromexico, +78 more

ANA,Aer Lingus, +79 more

Tuesday

ANA,Aer Lingus,Aeromexico, +77 more

ANA,Aer Lingus, +78 more

Wednesday

ANA,Aer Lingus,Aeromexico, +80 more

ANA,Aer Lingus, +81 more

Thursday

ANA,Aer Lingus,Aeromexico, +78 more

ANA,Aer Lingus, +79 more

Friday

ANA,Aer Lingus,Aeromexico, +77 more

ANA,Aer Lingus, +78 more

Saturday

ANA,Aer Lingus,Aeromexico, +77 more

ANA,Aer Lingus, +78 more

Sunday

ANA,Aer Lingus,Aeromexico, +79 more

ANA,Aer Lingus, +80 more

See more nonstop flights

Nonstop returns

Chicago to Canada

Monday

ANA,Aer Lingus,Aeromexico, +78 more

ANA,Aer Lingus, +79 more

Tuesday

ANA,Aer Lingus,Aeromexico, +77 more

ANA,Aer Lingus, +78 more

Wednesday

ANA,Aer Lingus,Aeromexico, +80 more

ANA,Aer Lingus, +81 more

Thursday

ANA,Aer Lingus,Aeromexico, +78 more

ANA,Aer Lingus, +79 more

Friday

ANA,Aer Lingus,Aeromexico, +77 more

ANA,Aer Lingus, +78 more

Saturday

ANA,Aer Lingus,Aeromexico, +77 more

ANA,Aer Lingus, +78 more

Sunday

ANA,Aer Lingus,Aeromexico, +79 more

ANA,Aer Lingus, +80 more

See more nonstop flights
See more nonstop flights

Top 5 airlines flying 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.
7.8
Porter AirlinesOverall score based on 295 reviews
6.9Entertainment
7.9Comfort
8.1Boarding
8.6Crew
7.6Food
Airline reviews

The flight was delayed by more than one hour. The terminal was consequently overcrowded and hot. We lost our car reservation and hit rush hour traffic in Boston, which added two hours stuck in traffic to our trip.

4.0 OkayJanna, Oct 2024YTZ - BOS
Read more Porter Airlines reviews

The flight was delayed by more than one hour. The terminal was consequently overcrowded and hot. We lost our car reservation and hit rush hour traffic in Boston, which added two hours stuck in traffic to our trip.

Awesome, the whole way through. Thank you, this is the new Canadian Airline benchmark.

We were given a complimentary seat upgrade which was so unexpected but so lovely!

Porter was excellent. Boarding was a breeze. The seats were a little uncomfortably but the overall trip was excellent.

Only packaged snacks were served. It was a flight at lunchtime and a hot meal would have been a great.

Reserve check-in was very slow compared to regular check-in. Internet was slow

Lavatories broke with an hour to go. At least we were on time.

Chaotic boarding, but mostly my issues are with Toronto airport

Flight delayed by half hour, causing rush to get to connecting flight in Toronto Pearson which doesn’t have good flow for managing immigration check and connections.

Service was amazing, and the plane was comfortable even for this long haul. But they could have more movies selections. But they were still a lot to choose from.

Did not have enough time from Venice seaport at Ravenna to get to Venice airport in order to make the scheduled flights. Need to have at least 3+ hours from ship docking to airport.

Everything was very good. Was able to change a make run flight leaving on direct earlier in the app -seamless!!! Well done

Being stick waiting for gate at ORD cause me to almost miss my connecting flight…being deaf United made no no effort to keep me updated as I couldn’t hear the PA

As usual, United scheduling is completely misleading. A 54-minute layover at O’Hare is too short to make a lot of connections, especially since the flight landed “on time” but had to wait on the taxiway 15 minutes for a gate to open up. Then it takes another 10 minutes to exit the plane before one can run to another concourse to catch a connecting flight.

The seats on the aircraft are like sitting in a rock. During the boarding process they recognize Active Duty Military, why don’t they recognize Retired Military. I’ve always preferred Delta, this flight confirmed why I still prefer Delta.

The plane used to go to Chicago was a bit outdated and needed a refresh

My connecting gate in .Chicago was across the aisle from my arriving gate. Otherwise I would not have made my connection. So that was very fortunate.

when you can say you don't remember being at any point upset during a flight, the airline is winning .

The staff was very friendly. The seats seemed quite small. Overall the flight was pleasant.

It was literally one of the worst travel experiences ever. My flight got delayed by over an hour and there was no communication of this from the gate staff. I realized it by checking the screen periodically. Once on board the flight attendants continued to serve alcohol to a man who was clearly already drunk and that was making a bunch of commotion. Never again will I fly United!

I had a problem checking in as I didn’t have the correct code. I had to phone BudgetAir.com. They charged me an additional 174US for some tax or something in order to provide me with my booking number. I will never use a third party seller again. Absolutely criminal activity. But I did get to where I wanted to go

Still sitting in a hotel when I'm due for work

My trip was two parts flying from Canada to ATL then to PNS I had confirmed seats with tickets at boarding in Canada and bags tagged for said flight. Got to ATL got help to plane before boarding ended and was told at the gate that I had no seats on this flight even though I had tickets that said so I was told by a supervisor with Delta that I was booked on flight 5 hours later not the one on my ticket had to sit in ATL not knowing if my bags were on flight I was booked on or the one I was told at the gate for 5 hours later or even if I would have seat on that flight as seats were to be assigned at gate. Will never recommend West Jet product and am not sure about Delta any longer and had never booked thru Kayak for flight before and will probably never again and will be sharing my experience with who ever will listen to me about it to warn them to avoid the problems I went thru.

Terrible experience at the gate. Charged for carry on luggage despite them meeting the requirements for sizing.

It was not clear that a shopping bag with gifts would need to be checked. Lucky that my friend checked her carry on so that she could take mine on. It contained fragile items ( and expensive). Plus they charged me $100 for that last minute change.

Never been on a long haul flight that didn't have on flight entertainment. I hope the way back is better !

It was fine for a low cost trip. No entertainment and poor food offer. The sits were ok. It was on time.

Seat barely reclined. Boarding took forever. Flight attendants were not very friendly

Worst airlines. I will never fly this again. Please warn customers. They cancelled our first flight and then gave us flight vouchers that were declined.

Needs to be clearer about baggage allowances upon purchasing tickets

3hour delay In the last 3 months i had 3 flights and 2 of these had a more than 2:40 hrs delayed

My initial flight to ORD was extended without reason. We circled the airport a few time and then drove on the ground for at least 20 minutes. These kinds of delays are annoying but somewhat expected… it would be nice if the crew would make an announcement to give updates on how long we could expect to be delayed.

Fantastic. I am low vision and was impressed with how helpful and accommodating the service tam was. It was super appreciated! I was pleasantly surprised about how delicious the food was. Like, “I wish I had more even though I’m no longer hungry” delicious. 100% enjoyable trip.

The flight was uneventful. What was a problem was I was delayed getting home one entire day because the flight from Sacramento was delayed. That made getting to my connecting flight impossible. I had to stay another night at the hotel and incur that expense as a result.

Flights were on time both ways, such a big plus! Staff was very accommodating and friendly. Question the choice of snacks that, which on both flights was dairy based. Appreciated using bottled water.

This flight was fine but had no time to breathe as the connection was late from Sea to ORD.. Super stressful. If we checked bags, the trip would have been very distressed.

Seats were very uncomfortable. I paid extra for a seat with more leg room, the seat was no different than a seat at the back of the plane. Flight attendant was rude.

Seating accommodations in Premium Economy are excellent. Some of the food was very good but leaving room for improvement. All the AA Associates were courteous and professional.

the food choice of packaged chips and popcorn was utterly ridiculous for first class

Check in agent was helpful and nice. Flight was OK. Our flight in Chicago was delayed 8 hours without an explination. This was our journey home. After a horrible flight experience on on the way to our vacation where our plane was diverted for an emergency medical issue, was grounded for hours, we missed our connecting flight by 25 minutes, and it took a day yo get re-booked, this was yet another bad experience that American seemed unwilling to help out with, much less compensate us for the

Awful. Late. Basic. Phone charger jacks didn't work. No entertainment No coffee even.

Multiple change of the gates at Pearson, delayed flight was extremely uncomfortable.

The flight went very smoothly, the staff was friendly and very helpful and the pilot flew the plane really, really well. Take off, landing were great and a smooth flight in between!

No issues with the flight and flight crew. cleaner seats in economy section would have been better

Very good. But seat selection was not good. We were put on different rows. Would have been nicer to sit besides each other as a couple.

Air Canada is great! Got to my destination earlier than expected and was a smooth ride the whole way there.

I have flown on many airlines all over the world, and this plane flight was the most uncomfortable I have ever experienced.

Boarding was OK. The overhead bins on the Havilland 400 are smaller than the allowable carry on bag sizes, making the bags to be jammed in and as a result slowing the boarding process.

After i biked my flights, i was informed my flight was rescheduled for later time

I was mostly pleased. My greatest disappointment was with respect to the timely update to the estimated departure and arrival times. It was especially sad that the arrival time was not updated online once we were in flight so as to allow my wife to arrive on time to the airport. She was not happy.

Book Cheap Chicago Plane Tickets

Recent round-trip flight deals

 
These are the cheapest round-trip flights to Chicago found on KAYAK in the last 72 hours.
13/2Thu
directWestJet
3h 26mYYC-ORD
17/2Mon
directWestJet
3h 51mORD-YYC
C$ 282
9/1Thu
1 stopDelta
6h 29mYYC-ORD
13/1Mon
2 stopsDelta
12h 01mORD-YYC
C$ 307
14/11Thu
directPorter Airlines
1h 50mYTZ-MDW
24/11Sun
directPorter Airlines
1h 42mMDW-YTZ
C$ 311
8/4Tue
directUnited Airlines
3h 19mYYC-ORD
12/4Sat
1 stopUnited Airlines
15h 23mORD-YYC
C$ 312
18/11Mon
directPorter Airlines
1h 50mYTZ-MDW
25/11Mon
directPorter Airlines
1h 42mMDW-YTZ
C$ 315
9/1Thu
1 stopAir Canada
9h 08mYYC-ORD
13/1Mon
1 stopAir Canada
8h 17mORD-YYC
C$ 321
12/11Tue
directUnited Airlines
2h 07mYYZ-ORD
18/12Wed
directUnited Airlines
1h 51mORD-YYZ
C$ 321
8/1Wed
1 stopAir Canada
8h 20mYYC-ORD
13/1Mon
1 stopAir Canada
8h 17mORD-YYC
C$ 328
21/11Thu
directAmerican Airlines
2h 15mYYZ-ORD
28/11Thu
directAmerican Airlines
1h 35mORD-YYZ
C$ 328
13/11Wed
directAmerican Airlines
2h 15mYYZ-ORD
19/12Thu
directAmerican Airlines
1h 49mORD-YYZ
C$ 350

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Recent one-way flight deals

 
Only flying one-way? Below are some of the best deals for one-way flights to Chicago found on KAYAK in the last 72 hours.
20/4Sun
directWestJet
3h 26mYYC-ORD
C$ 164
19/11Tue
1 stopAir Canada
9h 06mYYC-ORD
C$ 177
4/12Wed
1 stopPorter Airlines
5h 20mYUL-MDW
C$ 188
29/11Fri
1 stopPorter Airlines
5h 50mYUL-MDW
C$ 189
23/11Sat
1 stopUnited Airlines
8h 48mYYC-ORD
C$ 191
19/1Sun
directUnited Airlines
2h 11mYYZ-ORD
C$ 196
13/11Wed
directAir Transat
1h 50mYTZ-MDW
C$ 213
13/11Wed
directAir Transat
1h 50mYTZ-MDW
C$ 214
4/11Mon
1 stopAmerican Airlines
15h 26mYUL-ORD
C$ 236
5/12Thu
1 stopAmerican Airlines
8h 01mYUL-ORD
C$ 245

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Recent domestic flight deals

15/11Fri
directSpirit Airlines
2h 36mEWR-ORD
18/11Mon
directSpirit Airlines
2h 13mORD-EWR
C$ 158
7/11Thu
directSpirit Airlines
2h 36mEWR-ORD
10/11Sun
directSpirit Airlines
2h 13mORD-EWR
C$ 159
21/11Thu
directUnited Airlines
2h 56mBOS-ORD
24/11Sun
directUnited Airlines
2h 19mORD-BOS
C$ 194
16/11Sat
directDelta
3h 01mBOS-ORD
17/11Sun
directDelta
2h 20mORD-BOS
C$ 198
15/11Fri
directUnited Airlines
2h 31mEWR-ORD
17/11Sun
directUnited Airlines
2h 08mORD-EWR
C$ 203
15/11Fri
directAmerican Airlines
2h 55mBOS-ORD
20/11Wed
directAmerican Airlines
2h 20mORD-BOS
C$ 209
9/11Sat
directDelta
2h 52mBOS-ORD
14/11Thu
directDelta
2h 20mORD-BOS
C$ 210
25/12Wed
directAlaska Airlines
4h 04mSEA-ORD
7/1Tue
directAlaska Airlines
4h 51mORD-SEA
C$ 234
19/11Tue
directAlaska Airlines
3h 53mSEA-ORD
25/11Mon
directAlaska Airlines
4h 44mORD-SEA
C$ 246
15/11Fri
multi-stopAmerican Airlines
5h 46mJFK-ORD
18/11Mon
directAmerican Airlines
2h 12mORD-JFK
C$ 278

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Last minute flights to Chicago

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights to Chicago that are departing in the next 10 days.
26/10Sat
multi-stopDelta
13h 20mYYC-ORD
29/10Tue
multi-stopDelta
8h 35mORD-YYC
C$ 350
24/10Thu
directAir Canada
4h 11mYVR-ORD
25/10Fri
directAir Canada
4h 37mORD-YVR
C$ 401
25/10Fri
directUnited Airlines
4h 15mYVR-ORD
28/10Mon
multi-stopUnited Airlines
14h 41mORD-YVR
C$ 427
25/10Fri
directUnited Airlines
4h 15mYVR-ORD
28/10Mon
multi-stopUnited Airlines
14h 41mORD-YVR
C$ 428
25/10Fri
multi-stopAmerican Airlines
17h 46mYYC-ORD
29/10Tue
directAmerican Airlines
3h 56mORD-YYC
C$ 446
27/10Sun
directPorter Airlines
1h 50mYTZ-MDW
30/11Sat
directPorter Airlines
1h 42mMDW-YTZ
C$ 471
26/10Sat
directPorter Airlines
1h 47mYTZ-MDW
29/11Fri
directPorter Airlines
1h 42mMDW-YTZ
C$ 475
26/10Sat
directAmerican Airlines
1h 55mYYZ-ORD
29/11Fri
directAmerican Airlines
1h 55mORD-YYZ
C$ 499
26/10Sat
multi-stopWestJet
9h 13mYYZ-MDW
29/10Tue
multi-stopWestJet
22h 35mMDW-YYZ
C$ 568
26/10Sat
multi-stopWestJet
10h 36mYYZ-ORD
29/11Fri
multi-stopWestJet
16h 53mORD-YYZ
C$ 578

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Everything you need to know for your flight to Chicago

Flights with popular airlines flying to Chicago
Flights from the other most popular airlines that fly to Chicago according to KAYAK users. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.