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Find cheap flights to Chicago from C$ 169

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 27/5. 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
0 bags
Sun 19/5
Sun 26/5

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 44,212,662 times on KAYAK, and here is why:

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Cheap flight deals to Chicago

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights 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 and deals for you by selecting your travel dates.
Choose your dates
8:50 p.m. - 9:37 p.m.YTZ-MDW
1h 47mdirect
11:05 a.m. - 1:47 p.m.MDW-YTZ
1h 42mdirect
C$ 278Porter Airlines
Find Deal
Wed, 8 May - Wed, 15 May
3:30 p.m. - 4:17 p.m.YTZ-MDW
1h 47mdirect
5:15 p.m. - 7:57 p.m.MDW-YTZ
1h 42mdirect
C$ 279Porter Airlines
Find Deal
Wed, 15 May - Wed, 22 May
12:30 p.m. - 5:05 p.m.YYC-ORD
3h 35mdirect
5:55 p.m. - 8:22 p.m.ORD-YYC
3h 27mdirect
C$ 303WestJet
Find Deal
Thu, 23 May - Thu, 30 May
1:00 p.m. - 2:04 p.m.YYZ-ORD
2h 04mdirect
6:00 a.m. - 8:45 a.m.ORD-YYZ
1h 45mdirect
C$ 307Air Canada
Find Deal
Wed, 8 May - Wed, 15 May
6:30 a.m. - 10:06 a.m.YYZ-ORD
4h 36m1 stop
6:00 a.m. - 8:45 a.m.ORD-YYZ
1h 45mdirect
C$ 314Air Canada
Find Deal
Wed, 8 May - Wed, 15 May
12:30 p.m. - 5:05 p.m.YYC-ORD
3h 35mdirect
5:55 p.m. - 8:22 p.m.ORD-YYC
3h 27mdirect
C$ 315WestJet
Find Deal
Thu, 23 May - Thu, 30 May
1:05 p.m. - 4:13 p.m.YUL-MDW
4h 08m1 stop
6:00 a.m. - 5:36 p.m.MDW-YUL
10h 36m1 stop
C$ 343Delta
Find Deal
Sat, 11 May - Wed, 15 May
7:50 p.m. - 8:44 p.m.YYZ-ORD
1h 54mdirect
6:00 a.m. - 8:45 a.m.ORD-YYZ
1h 45mdirect
C$ 370United Airlines
Find Deal
Wed, 8 May - Sun, 12 May
7:00 a.m. - 2:20 p.m.YUL-ORD
8h 20m1 stop
7:00 a.m. - 5:36 p.m.ORD-YUL
9h 36m1 stop
C$ 372Delta
Find Deal
Thu, 9 May - Wed, 15 May
7:43 p.m. - 7:54 a.m.YYZ-ORD
13h 11m1 stop
8:48 a.m. - 5:30 p.m.ORD-YYZ
7h 42m1 stop
C$ 378United Airlines
Find Deal
Fri, 10 May - Wed, 15 May

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 Toronto, 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$ 233 one-way and C$ 381 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$ 304.

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$ 884. The cheapest price found on KAYAK in the last 2 weeks cost C$ 171 and departed from Toronto Island Airport. The most popular routes on KAYAK are Vancouver to Chicago which costs C$ 752 on average, and Toronto to Chicago, which costs C$ 1,361 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 Thursday where tickets can be as cheap as C$ 541. On the other hand, the most expensive day to fly is Monday, where prices are C$ 619 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$ 490 on average for one-way flights. On the other hand, the most expensive months are September and January, where the average cost of tickets from Canada is C$ 700 and C$ 683 respectively. For return trips, the best month to travel is January with an average price of C$ 318.

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 at night, when flights cost C$ 405 on average. The most expensive time of day to fly to Chicago is generally in the evening, which is peak travel time and where the average cost of a ticket is C$ 429.

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$ 176 one-way - C$ 310 round-trip, from Calgary C$ 222 one-way - C$ 683 round-trip, from Vancouver Intl Airport C$ 249 one-way - C$ 556 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 78 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$ 233.

Which airlines fly to Chicago?

If you’re traveling from Canada, you might fly to Chicago with United Airlines, Air Canada, or American Airlines as they are the most frequent flyers. See the amount of flights per week for popular airlines flying to Chicago.

Which airline offers the most flights to Chicago?

Of the 13 airlines that fly to Chicago, United Airlines offers the most flights, with around 4,287 per week, followed by American Airlines with 3,894 flights per week.

How many airports are there in Chicago?

There are 3 airports in Chicago: Chicago O'Hare Airport (ORD), Chicago Midway Airport (MDW) and Chicago Greater Rockford Airport (RFD). The busiest airport is Chicago O'Hare Airport (ORD), with 85% of all flights arriving there.

How long is the flight to Chicago?

The duration of your flight to Chicago depends on your departure and arrival airports. Obviously any flights that include a layover will also be longer. The most popular routes to Chicago on KAYAK are from Montreal, which takes 2h 30m, Toronto, which takes 3h 07m, Calgary, which takes 3h 25m, and Vancouver, which takes 4h 01m.

How many direct flights to Chicago are there each day?

There are around 44 direct flights from within Canada to Chicago every day. Most flights depart in the morning, with 6:00 a.m. the most common departure time and 48% of flights departing in the morning.

How many direct flights to Chicago are there each week?

Each week there are around 307 direct flights from within Canada to Chicago. The most common day for departures is Sunday, with 15% of flights taking off on this day.

How many long-haul flights are there to Chicago each week?

Each week, there are 23 medium-haul flights (3-6 hour flight duration) and 284 short-haul flights (up to 3 hour flight duration) to Chicago. There aren't any long-haul flights (6-12 hour flight duration).

How many cities have direct flights to Chicago?

From Canada, there are direct flights to Chicago from 6 cities. The city with the most direct flights is Toronto, with 190 direct flights each week.

Good to know

Low season

January

High season

August

Cheapest flight

C$ 169
Best time to beat the crowds (16% less expensive on average)
Most popular time to fly and prices are also 5% lower on average.
Flight from Toronto Island to Chicago Midway 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 Toronto, 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$ 233 one-way and C$ 381 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$ 304.

  • 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$ 884. The cheapest price found on KAYAK in the last 2 weeks cost C$ 171 and departed from Toronto Island 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.

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

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, +80 more

ANA,Aer Lingus, +81 more

Tuesday

ANA,Aer Lingus,Aerolineas Argentinas, +78 more

ANA,Aer Lingus, +79 more

Wednesday

ANA,Aer Lingus,Aeromexico, +79 more

ANA,Aer Lingus, +80 more

Thursday

ANA,Aer Lingus,Aeromexico, +78 more

ANA,Aer Lingus, +79 more

Friday

ANA,Aer Lingus,Aerolineas Argentinas, +81 more

ANA,Aer Lingus, +82 more

Saturday

ANA,Aer Lingus,Aeromexico, +78 more

ANA,Aer Lingus, +79 more

Sunday

ANA,Aer Lingus,Aerolineas Argentinas, +78 more

ANA,Aer Lingus, +79 more

See more nonstop flights

Nonstop returns

Chicago to Canada

Monday

ANA,Aer Lingus,Aeromexico, +80 more

ANA,Aer Lingus, +81 more

Tuesday

ANA,Aer Lingus,Aerolineas Argentinas, +78 more

ANA,Aer Lingus, +79 more

Wednesday

ANA,Aer Lingus,Aeromexico, +79 more

ANA,Aer Lingus, +80 more

Thursday

ANA,Aer Lingus,Aeromexico, +78 more

ANA,Aer Lingus, +79 more

Friday

ANA,Aer Lingus,Aerolineas Argentinas, +81 more

ANA,Aer Lingus, +82 more

Saturday

ANA,Aer Lingus,Aeromexico, +78 more

ANA,Aer Lingus, +79 more

Sunday

ANA,Aer Lingus,Aerolineas Argentinas, +78 more

ANA,Aer Lingus, +79 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.
8.0
DeltaOverall score based on 11094 reviews
8.6crew
7.9comfort
8.2boarding
8.0entertainment
7.5food
Airline reviews

Seat back monitors and outlets were dead and not working.

8.0 ExcellentCarl, Apr. 2024JFK - FLL
Read more about Delta reviews

Seat back monitors and outlets were dead and not working.

Everything was great except for the seat. The backrest would not stay in the upright position.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

Flight delayed about 2 hrs so it made it a VERY late night

It was a crowded flight. They did the best they could.

Super good crew... food was pretty awful- overall Delta is my favorite carrier- takes off on time, good boarding process etc.

I love flying DELTA it's my favorite airline to fly I love the staff the flight attendants and most importantly the safe flights that the pilots bring every time!!!! period!! My experience has been beautiful every time....I hope the good standards will always be kept

Service was good for such a short flight. Small plane but smooth flight.

Boarding was a little confusing as many folks were trying to get on through priority boarding instead of general. Everything else was excellent.

Worst flight in my life. Only was scheduled for a 45 min flight to get our connection flight. It was late by 40 minutes and we missed our connection. Delta was totally useless trying to help and unable to get my family on the next flight because they overbooked it Thus had to get a hotel at my expense and lost a day at Disney as a result. Cost me about a $1000 if you add 2 hotels meals shuttles etc to get thru the day Awful customer service by Delta in Detroit totally useless people

I wish that seats closer to the front of the plan were available, but when I booked the flight the seats were VERY expensive so I did not book seats at that time. The day before flying only seats at the back of the plane were available. It takes so long to board the plane and empty the plane on arrival due to SO many roller bags.

Good flight. No I’m seat entertainment. But my phone worked just fine on the west jet app.

I had planned to watch the Westjet entertainment for the entire flight however, because the seat mounted outlets in our row did not work.

Not a bad flight but our priority tagged luggage was the very last to come down the carousel.

Plane had a flat tire, delayed boarding and takeoff but one in the air, smooth. Make sure you have downloaded the WJ app before you leave. When on board, you can watch movies or TV shows offered on the app, it passed the time very quickly.

Our recent flight from edmontown to kahalui was excellent. The service staff was very friendly, knowledgeable, funny and attentive. Thanks to all involved that made or travel such a pleasant experience and we hope to fly with west jet again soon

The flight was delayed and I missed boarding my 7 day cruise. I had to book a separate flight home

No real issues just wasnt able to hear / understand any announcements flight attendant was making but everything else was really good- ended up checking my carry on case for free which made deboarding quicker. I would fly West Jet for all my flights.

Seats were comfortable and leg room was good. Slight delay for boarding but nothing too bad. Would fly with them again.

Long lines to board with only two staff checking boarding passes!

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

Wifi wasn't working on one of the UA flights after boarding.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Crew was not very helpful. They forgot to serve me coffee and had to wait for a long time.It looked as if they were not very happy with what they were doing.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Unfortunately this is not a happy ending comment. Positive: flown United before no issue Negative: it only takes one bad experience to not plan future travel with United Cancún departure was delayed by 1h20 minutes, connection in Chicago was 1h30 minutes. Flight departure time 6:08 Miraculously 7 of us ran 4 kilometres through Chicago to arrive at 6:00 to be told very rudely by the 2 unprofessional United attendants you missed your flight and that we should of arrived early. Did I mention that reason I was flying? I received a call that my brother was dying and to get home. They provided no assistance would not answer any of our questions, ignorantly walked away. Deplorable

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

If United expects people to use their own devices for entertainment they should put charging outlets in each seating area. I arrived with 14%battery power. That is not good when you arrive anywhere and need to communicate for transportation.

Boarding was friendly and quick. While the plane model was older with no live tv, the entertainment was full of movies and tv shows. All food was available. Pilots were very communicative with status of the flight. Flight landed on time.

First time with Porter and I can say this is best airline company in Canada. Great service, free WiFi, free snack and drinks (including beer and wine). Seats were super comfy on the Embraer jet and I appreciated the folding try table too. Staff were excellent both legs of the trip.

Tight transfer in Montreal. (15 min) However, we made it, as did my luggage.

Check in was slow because of passenger ahead in Reserve line. Seats were somewhat uncomfortable.

First time with Porter. Amazing experience overall, will be my airline of choice in North America whenever possible. Liked the quality of food and how it was served but one suggestion- a hot meal on the longer flights, perhaps?

Delayed by 2.5 hours. This happened previously on my flight from YOW to YVR on Dec. 26.2023. This is a terrible airline. The reason was there was lack of ground crew. This is a known event. AVOID PORTER AIRLINES IF YOU CAN. There is a reason half the plane was empty.

The airline arrival at the downtown airport is a big plus.. Food and beverage was excellent. Their non weather related cancellation is horrible. Overall I gave the airline 7 over 10 Tips for people flying porter from Boston. The airline doesn’t have inflight entertainment No TV No WIFI. Bring your entertainment with you.

The airline arrival at the downtown airport is a big plus.. Food and beverage was excellent. Their non weather related cancellation is horrible. Overall I gave the airline 7 over 10

Wasn’t on the flight- again. Bad weather in Halifax and I was in an accident. What a poor experience to have to pay for all this flight and not be on it

I didn’t make my flight due to poor weather and I had an accident driving there. I tried to get my money back or even credit and nothing. I have an entire flight both to Florida and back that I paid for and no one will give me any money back. I know this isn’t just Porter and it’s 3rd party- however airlines should allow these companies to take money for things they don’t get. I’m so upset. Who can afford a full flight they never take?

Flight Ottawa to Toronto canceled and no crew was available to direct me on what to do. I opened a file and I wait to be compensated.

Headphones for the movies have too much bass and can't be adjusted. Almost impossible to hear. Great movie selections but can't really watch them because you can't hear them. Also the system is very slow.

This was the first AC flight in a long time that we experienced no delays or frustrations. The gate attendant was extremely polite and accommodating to my husband who has Parkinson’s disease which made boarding extremely stress free. Flight departed ON TIME and was a smooth ride. If only all my AC experiences could be like this.

I didn’t like the fact that all the customs officers went to lunch so I was in line for 90 minutes due to where the staff directed me. We were told three very different reasons for why the plane was delayed. It was a crowded plane with difficult storage situations for the Carry On bags. The Air Canada airline staff were all very good and professional. I was so disappointed in my cheese and fruit box as the cheese had molded and the fruit wasn’t fresh so I couldn’t eat the majority of the food. This was the last meal I could find as the restaurants had closed when I got in to my destination. I think you could work on improving the food quality.

There was no entertainment at our seats. The flight was comfortable and we had leg room. The snack we had was really good.

Economy seats were surprisingly comfortable, and snacks not too bad. Checked luggage arrived at destination without problems. It was annoying to wait until last to board as lowest-tier seats but understand it’s difficult to gauge when loading a full plane At least checked carryon luggage seemed to come off first. Annoying to have to use app to order food/drink when wifi availability didn’t allow time for it. Advance communication would have helped Food on menu seemed highly processed and unpalatable, overpriced and over packaged. So maybe a good thing to have missed chance to order

Once again my complaint is how close the seats are together. Also, the bathrooms were not very clean by the second half of the flight.

Excellent in flight service, perhaps the best we've ever had. Business class feels tired and needs improvement to compete with other airlines. The food looked good but tasted terrible. Check in was quick, the flight arrived early and our luggage was on our flight with us.

The staff were so kind and helpful. We flew back from NY with another airline and it was horrible. We will always stick with Air Canada as everything was far better!

The boarding process in Toronto bad as they share space with domestic flights and when those domestic flights come in you are locked out behind closed doors until they are done and then its a mad rush to get your boarding gates and board. This is not so much due to Air Canada but with the GTAA, but Air Canada could use different gates especially early morning in order to prevent such travel angst.

Terrible quality wifi and they charge a lot for it. They nickel and dime you for everything.

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.
8/5Wed
directPorter Airlines
1h 47mYTZ-MDW
15/5Wed
directPorter Airlines
1h 42mMDW-YTZ
C$ 278
15/5Wed
directPorter Airlines
1h 47mYTZ-MDW
22/5Wed
directPorter Airlines
1h 42mMDW-YTZ
C$ 279
23/5Thu
directWestJet
3h 35mYYC-ORD
30/5Thu
directWestJet
3h 27mORD-YYC
C$ 303
8/5Wed
directAir Canada
2h 04mYYZ-ORD
15/5Wed
directAir Canada
1h 45mORD-YYZ
C$ 307
8/5Wed
1 stopAir Canada
4h 36mYYZ-ORD
15/5Wed
directAir Canada
1h 45mORD-YYZ
C$ 314
23/5Thu
directWestJet
3h 35mYYC-ORD
30/5Thu
directWestJet
3h 27mORD-YYC
C$ 315
11/5Sat
1 stopDelta
4h 08mYUL-MDW
15/5Wed
1 stopDelta
10h 36mMDW-YUL
C$ 343
8/5Wed
directUnited Airlines
1h 54mYYZ-ORD
12/5Sun
directUnited Airlines
1h 45mORD-YYZ
C$ 370
9/5Thu
1 stopDelta
8h 20mYUL-ORD
15/5Wed
1 stopDelta
9h 36mORD-YUL
C$ 372
10/5Fri
1 stopUnited Airlines
13h 11mYYZ-ORD
15/5Wed
1 stopUnited Airlines
7h 42mORD-YYZ
C$ 378

Search by stops

Search by airline

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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.
27/5Mon
directPorter Airlines
1h 47mYTZ-MDW
C$ 169
22/5Wed
1 stop
17h 59mYYZ-ORD
C$ 172
19/5Sun
directWestJet
3h 35mYYC-ORD
C$ 189
18/6Tue
directAir Canada
1h 54mYYZ-ORD
C$ 190
18/5Sat
directAir Canada
3h 30mYYC-ORD
C$ 190
11/5Sat
directUnited Airlines
3h 30mYYC-ORD
C$ 206
12/5Sun
1 stopDelta
7h 48mYYZ-ORD
C$ 209
11/5Sat
1 stopDelta
5h 48mYUL-MDW
C$ 211
23/5Thu
directUnited Airlines
3h 29mYYC-ORD
C$ 212
18/5Sat
1 stopWestJet
5h 25mYYZ-MDW
C$ 245

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Recent domestic flight deals

7/5Tue
directJetBlue
2h 50mJFK-ORD
8/5Wed
directJetBlue
2h 23mORD-JFK
C$ 161
8/5Wed
directDelta
2h 35mLGA-ORD
14/5Tue
directDelta
2h 15mORD-LGA
C$ 161
15/5Wed
directAlaska Airlines
4h 10mSEA-ORD
22/5Wed
directAlaska Airlines
4h 27mORD-SEA
C$ 191
17/5Fri
directSpirit Airlines
2h 37mLGA-ORD
20/5Mon
multi-stopSpirit Airlines
13h 20mORD-LGA
C$ 230
14/8Wed
multi-stopAlaska Airlines
6h 30mSEA-ORD
31/8Sat
directAlaska Airlines
4h 34mORD-SEA
C$ 231
18/6Tue
directAmerican Airlines
2h 37mEWR-ORD
20/6Thu
directAmerican Airlines
2h 04mORD-EWR
C$ 263
17/5Fri
multi-stopSpirit Airlines
13h 11mLGA-ORD
20/5Mon
multi-stopSpirit Airlines
13h 20mORD-LGA
C$ 275
7/5Tue
directUnited Airlines
2h 40mEWR-ORD
9/5Thu
directUnited Airlines
2h 17mORD-EWR
C$ 288
26/6Wed
directUnited Airlines
2h 35mEWR-ORD
10/7Wed
directUnited Airlines
2h 20mORD-EWR
C$ 301
17/5Fri
multi-stopAmerican Airlines
5h 27mJFK-ORD
20/5Mon
multi-stopAmerican Airlines
4h 36mORD-JFK
C$ 387

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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.
24/4Wed
directPorter Airlines
1h 47mYTZ-MDW
28/4Sun
directPorter Airlines
1h 42mMDW-YTZ
C$ 465
23/4Tue
multi-stop
15h 15mYYZ-ORD
26/4Fri
multi-stop
15h 30mORD-YYZ
C$ 498
22/4Mon
directAir Canada
1h 54mYYZ-ORD
5/5Sun
directAir Canada
1h 45mORD-YYZ
C$ 552
24/4Wed
multi-stopWestJet
6h 09mYYZ-ORD
28/4Sun
multi-stopWestJet
4h 11mORD-YYZ
C$ 555
22/4Mon
multi-stopAir Canada
6h 39mYYZ-ORD
5/5Sun
directAir Canada
1h 45mORD-YYZ
C$ 559
22/4Mon
multi-stopWestJet
6h 58mYYZ-ORD
5/5Sun
multi-stopWestJet
4h 11mORD-YYZ
C$ 563
23/4Tue
directUnited Airlines
2h 36mYUL-ORD
29/4Mon
multi-stopUnited Airlines
10h 59mORD-YUL
C$ 649
22/4Mon
multi-stopUnited Airlines
4h 46mYYZ-ORD
25/4Thu
directUnited Airlines
1h 48mORD-YYZ
C$ 663
24/4Wed
multi-stopDelta
8h 37mYUL-ORD
1/5Wed
multi-stopDelta
6h 49mORD-YUL
C$ 680
22/4Mon
multi-stopDelta
5h 51mYYZ-ORD
25/4Thu
multi-stopDelta
7h 24mORD-YYZ
C$ 685

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