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C$ 158 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 20/9. 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
Wed 21/8
Wed 28/8

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These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago
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Cheap 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
9:25 a.m. - 11:50 p.m.YVR-ORD
12h 25m1 stop
6:39 p.m. - 1:35 p.m.ORD-YVR
20h 56m2 stops
C$ 275
Find Deal
Wed, 4 Sep - Mon, 9 Sep
9:25 a.m. - 11:50 p.m.YVR-ORD
12h 25m1 stop
6:39 p.m. - 1:37 p.m.ORD-YVR
20h 58m2 stops
C$ 276
Find Deal
Fri, 13 Sep - Tue, 17 Sep
8:50 p.m. - 9:37 p.m.YTZ-MDW
1h 47mdirect
8:00 a.m. - 10:42 a.m.MDW-YTZ
1h 42mdirect
C$ 284Porter Airlines
Find Deal
Mon, 19 Aug - Mon, 26 Aug
6:35 p.m. - 9:37 p.m.YUL-MDW
4h 02m1 stop
11:05 a.m. - 3:58 p.m.MDW-YUL
3h 53m1 stop
C$ 294Porter Airlines
Find Deal
Tue, 20 Aug - Tue, 27 Aug
12:00 p.m. - 12:54 p.m.YYZ-ORD
1h 54mdirect
6:00 a.m. - 8:48 a.m.ORD-YYZ
1h 48mdirect
C$ 312United Airlines
Find Deal
Thu, 22 Aug - Sun, 25 Aug
1:30 a.m. - 11:56 a.m.YYC-ORD
9h 26m1 stop
10:55 a.m. - 6:32 p.m.ORD-YYC
8h 37m1 stop
C$ 318Air Canada
Find Deal
Wed, 18 Sep - Mon, 23 Sep
7:00 a.m. - 7:56 a.m.YYZ-ORD
1h 56mdirect
6:00 a.m. - 8:48 a.m.ORD-YYZ
1h 48mdirect
C$ 325Air Canada
Find Deal
Thu, 22 Aug - Sun, 25 Aug
11:35 p.m. - 5:40 a.m.YVR-ORD
4h 05mdirect
7:10 a.m. - 6:19 p.m.ORD-YVR
13h 09m1 stop
C$ 334United Airlines
Find Deal
Thu, 29 Aug - Wed, 4 Sep
6:30 a.m. - 5:09 p.m.YVR-ORD
8h 39m1 stop
5:55 p.m. - 12:13 a.m.ORD-YVR
8h 18m1 stop
C$ 354WestJet
Find Deal
Thu, 3 Oct - Sun, 6 Oct
12:30 p.m. - 4:57 p.m.YYC-ORD
3h 27mdirect
5:55 p.m. - 8:40 p.m.ORD-YYC
3h 45mdirect
C$ 390WestJet
Find Deal
Sun, 8 Sep - Fri, 13 Sep

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 Vancouver, 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$ 215 one-way and C$ 376 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$ 312.

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$ 762. The cheapest price found on KAYAK in the last 2 weeks cost C$ 147 and departed from Calgary. The most popular routes on KAYAK are Toronto to Chicago which costs C$ 1,389 on average, and Montreal to Chicago, which costs C$ 760 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 Wednesday where tickets can be as cheap as C$ 494. On the other hand, the most expensive day to fly is Monday, where prices are C$ 542 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$ 416 on average for one-way flights. On the other hand, the most expensive months are November and October, where the average cost of tickets from Canada is C$ 715 and C$ 674 respectively. For return trips, the best month to travel is April with an average price of C$ 328.

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$ 364 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$ 404.

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$ 181 one-way - C$ 296 round-trip, from Winnipeg C$ 240 one-way - C$ 592 round-trip, from Vancouver Intl Airport C$ 244 one-way - C$ 485 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 150 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$ 217.

Which airlines fly to Chicago?

If you’re traveling from Canada, you might fly to Chicago with United Airlines, American Airlines, or Air Canada 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 15 airlines that fly to Chicago, United Airlines offers the most flights, with around 4,808 per week, followed by American Airlines with 3,834 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 77% 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 06m, Calgary, which takes 3h 25m, and Vancouver, which takes 4h 01m.

How many direct flights to Chicago are there each day?

There are around 53 direct flights from within Canada to Chicago every day. Most flights depart in the morning, with 11:00 a.m. the most common departure time and 48% of flights departing in the morning.

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

Each week, there are 28 medium-haul flights (3-6 hour flight duration) and 342 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 7 cities. The city with the most direct flights is Toronto, with 178 direct flights each week.

Good to know

Low season

January

High season

August

Cheapest flight

C$ 158
Best time to beat the crowds (15% less expensive on average)
Most popular time to fly (11% more expensive on average)
Flight from Vancouver 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 Vancouver, 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$ 215 one-way and C$ 376 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$ 312.

  • 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$ 762. The cheapest price found on KAYAK in the last 2 weeks cost C$ 147 and departed from Calgary 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 370 direct flights from within Canada to Chicago. The most common day for departures is Monday, 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

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, +81 more

ANA,Aer Lingus, +82 more

Tuesday

ANA,Aer Lingus,Aerolineas Argentinas, +80 more

ANA,Aer Lingus, +81 more

Wednesday

ANA,Aer Lingus,Aeromexico, +80 more

ANA,Aer Lingus, +81 more

Thursday

ANA,Aer Lingus,Aeromexico, +81 more

ANA,Aer Lingus, +82 more

Friday

ANA,Aer Lingus,Aerolineas Argentinas, +82 more

ANA,Aer Lingus, +83 more

Saturday

ANA,Aer Lingus,Aeromexico, +80 more

ANA,Aer Lingus, +81 more

Sunday

ANA,Aer Lingus,Aerolineas Argentinas, +82 more

ANA,Aer Lingus, +83 more

See more nonstop flights

Nonstop returns

Chicago to Canada

Monday

ANA,Aer Lingus,Aeromexico, +81 more

ANA,Aer Lingus, +82 more

Tuesday

ANA,Aer Lingus,Aerolineas Argentinas, +80 more

ANA,Aer Lingus, +81 more

Wednesday

ANA,Aer Lingus,Aeromexico, +80 more

ANA,Aer Lingus, +81 more

Thursday

ANA,Aer Lingus,Aeromexico, +81 more

ANA,Aer Lingus, +82 more

Friday

ANA,Aer Lingus,Aerolineas Argentinas, +82 more

ANA,Aer Lingus, +83 more

Saturday

ANA,Aer Lingus,Aeromexico, +80 more

ANA,Aer Lingus, +81 more

Sunday

ANA,Aer Lingus,Aerolineas Argentinas, +82 more

ANA,Aer Lingus, +83 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.
7.6
Porter AirlinesOverall score based on 343 reviews
8.4Crew
7.6Food
7.7Comfort
6.8Entertainment
7.9Boarding
Airline reviews

Chaotic boarding, but mostly my issues are with Toronto airport

6.0 GoodArti, Jul. 2024YYZ - YUL
Read more about Porter Airlines reviews

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.

Due to mechanical problems it was delayed causing problems the actual flight. Was fune

Wish we had music during take off and landing like the last flight

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.

Flight was smooth and comfortable. The crew were exceptional. Amanda, Nichole and Hershel were attentive to our every need. So friendly. My daughter and I were surprised at quality of service. Loved the double row seating. Snacks were delicious. We would definitely fly with Porter again. Flight PD 670 SFO to YYZ Thank you so much for the best flight experience we have had

The E195-E2 is a great aircraft! Leather seats, lots of legroom and SO quiet! The flight crew is terrific!

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

The new Airbus A231neo has neat tech but the economy seats are so tight together that I always had my shoulders against one passenger or the other. I was very miffed that Basic Economy REQUIRES check-in of bags other than your personal carry-on; if you want to offer low-cost airline prices and then add services for a fee, just let me carry on my duffel. Hell, I could have put my carry on IN the duffel and called it a day but the gate agent would not let me; I ended up paying $40 for the risk of losing my bag. Not the worst flight, but far from the best.

My flight was delayed by a whole day, so I lost a day of my vacation.

It is a modern tragedy that any airline expects you to travel for 14 hours in such discomfort and that the only way to add comfort is exorbitant prices. I was in pain by the time we landed. Shameful.

After the morning frenzy of 35 min wait through CLT security at 4;30 AM, it was nice to have a smooth pleasant boarding experience. This 6:30 AM flight was not full. We were able to get seated swiftly and took off promptly. Nice touch they distributed the old fashioned headsets with 8 mm jacks. Snacks were decent and arrival was uneventful.

I had a great flight. Everything went smoothly and the flight arrived early.

The flight and boarding were easy peasy. I was traveling with my 4-year-old, so a smooth boarding experience was especially appreciated. My only piece of feedback is really about where our gate was in O'Hare. They've shoved four gates into a tiny corner of the B terminal and there isn't early enough room or seating for everyone. Not United's problem, but did dent the overall experience.

It was good! Appreciated that it was very on schedule so it made the connecting flight less stressful

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

We were delayed an hour leaving Munich (No fault of the crew). They kept us posted on the status so we knew what was going on, but as a result we missed our connection in Chicago and the communication on connecting flights was pretty poor as we disembarked. It was already stressful and some of that could have been reduced by better communications about where to find transfers, etc.

One problem, but a serious one - the plane is built with electric windows that tint dark to reduce light. Sitting next to the window is VERY UNCOMFORTABLE as it emits so much HEAT in the face when tinted.

I always worry about flying budget airlines but I was impressed by Westjet. The checkin agent was terrific. Seated my husband & me together w/o us asking. TSA checkin was smooth & easy. Plane was clean & comfortable. Drink & snack was unexpected. I will fly with them again.

WiFi was not working. Zero entertainment. Did not receive a discount etc to make up for this.

Calgary WJET supervisor was the most professional, and diligent official who I have experienced personally to resolve our flight issues.

Flight was canceled last minute and no re-booking was offered. Had to buy a same day flight from another carrier at double the price. I’ll never fly WestJet again.

Don’t actually know how this flight would have been since we missed it.

It was fine. I had a lot of trouble trying to buy a seat. The Westjet website charged me and then didn’t give me my seat. I ended up keeping the seat I was assigned and hope that the charges didn’t go through.. they didn’t. But this problem with the website (trying to purchase a seat at check in) has happened a few times before. But overall the flight was good.

Terrible! Delayed three times, landed at some corner of airport, walked in bitter cold night, took a bus, bad experience

My wife and I had an uncomfortable experience with your WestJet ticket counter rep at the WestJet Priority Member ticket counter at YYC (Calgary) on May 15, 2024. I not knowing this individual’s exact name, however, in order to easily identify her, she was one (of only two at the time) ticket counter reps at your Priority members ticket counter check-in, upon our arrival around 12:15 p.m. She was a Caucasian woman with blonde hair, and wore spectacles, approximate age being probably somewhere in her 30’s or 40’s. Background: After arriving in to the West Jet terminal in Calgary (YYC), I asked a terminal employee where the West Jet check-in ticket counter was. He told me, “Column 16”. My wife and I continuing to walk through the terminal, we finally arrived at the Column 16 area, i.e. this woman’s ticket counter area, which we discovered later was the Priority Member ticket counter. However, I was simply going by the directions given to me by the previous employee, i.e. “Walk to column 16.” Standing in her line (my wife and I being the only people in her line at the time), I tried to get her attention, and I then gestured to her, motioning to her as if to ask her if I should then possibly leave the waiting line in order to then proceed to walk up to her ticket counter. She never really motioned me to come forward. I sort of had to figure this out on my own, as my wife and I then finally decided to walk forward to her station. From this point on, after I arrived at her ticket counter, never once did she ever look me in the eye. She was always looking at her computer screen, or down at the ground, as she and I occasionally exchanged conversation with one another in order for me to be able to acquire my boarding passes from her. Shortly after she began servicing us, she commented that her work section is for Priority members only. Fair enough. I did not realize this at the time. Wishing to be polite, I then mentioned to her that, if I should, I could then walk over to the regular West Jet check-in ticket counter in order to complete the check-in process. She remained quiet, never responding to this goodwill gesture of mine. She continued to work in order to print out my boarding passes, and then finally handed them to me, never at all the entire time looking at me. I told her, “Thank you.” Never once did she respond. My wife and I then walked away. Even my wife commented to me afterward that this woman absolutely never looked at us. I cannot say that this attendant was outright rude. However, she certainly was not at all warm, congenial, nor friendly. Additionally, … After getting on the plane, we then discovered that she had needlessly assigned us seats in the very last row of the plane, these being the seats adjacent to the restroom back wall, thus, unfortunately not at all reclinable. I think that the row number of this last row of seats was 30. [However, I am not sure.] How strangely awkward that we were assigned these uncomfortable row of seats when in fact the row immediately ahead of us, i.e. I think that was row 29, had two vacancies, which could have otherwise easily seated my wife and me. That is, my wife and I could have easily been assigned these more comfortable seats, which would be reclinable, and then row 30 could have otherwise had instead our two vacancies. After our flight departed, and the fasten seatbelt sign was turned off, my wife and I had hoped to “jump seats”, that is, to leave row 30 and instead sit in row 29 to utilize the reclinable seats. However, another couple apparently had the same idea as us. That is, these other two people, for whatever reason, decided to leave their previously assigned seats, and instead, seat themselves in row 29. Thus, my wife and I were stuck with these miserably cramped row 30 seats for the entire 3.5 hour flight. To reiterate, the WestJet rep we originally encountered, knowledgeable of the plane lay-out as it appeared on her computer screen, could have easily assigned us the more comfortable row 29 seats, instead of the non-reclinable row 30 seats.

It was very, very cold extremely uncomfortable almost unbearable I was sitting at the front of the cabin

Was the longest flight I have ever taken to Orlando. Not Westjet’s fault necessarily. There was a traffic issue in Orlando. We sat in the airplane for about 2 hrs before leaving Calgary on a 5 hour flight was just a little long to be stuck in the plane. Once we arrived in Orlando we were stuck in traffic on the ground for another 30min. I guess maybe the flight could be delayed so boarding would have been later so we wouldn’t have to have the discomfort of being on the plane so long.

Great flight. The captain did a great job of minimizing some minor turbulence and in general it was a smooth flight. Early departure and early arrival at destination. Great service.

Our flight left on time and we arrived a few minutes early. Great service!

Our 9:10 am scheduled flight continued to get delayed all day with no information given from the agents as to why. It wasn’t until I went to the customer service desk and got us switched to another flight at 2:44 pm (that wasn’t nonstop like our booked flight) that the agent finally was able to find out it was due to a fuel leak. I don’t know if our original flight ever took off but I don’t find it acceptable to leave people sitting in an airport all day with no explanation.

I am very disappointed with american. We have flown American airlines numerous times, as well as other airlines and never had such an experience. My son's flight for Sunday afternoon was cancelled around 11 am. We were told not to do anything bec AA would. After an hour of not seeing a change in his flight status. I called AA. I was on hold for half hour then opted for a call back. That call back never came. So I called again, in meantime I started looking online at my options. No flights were leaving that day from AA. But other airlines were flying out. We needed our son in Chicago asap.i kept calling AA for a callback, but never received one. Finally i called back later in the afternoon and a representative answered the call. She told me there were no flights out till Tuesday morning. I asked how this is possible, I had seen flights from AA and other airlines leaving Monday. She said she checked all NYC airports and there were no AA flights till Tuesday AM. Then I asked about getting on another airline. She responded i would be responsible for that. When I asked how AA would reimburse. She became nasty and told me AA has not responsibility to reimburse anything they will put me in a flight for Tuesday morning. When i explained he must be there Monday by 8am, she told me there's nothing to do and practically hung up. At that point I just asked her to book the Tuesday morning flight. I had this experience with other airlines, cancelled due to weather and they and their reps were much more helpful. Either way Tuesday morning flight was delayed as well. Over an hour! I expect more from AA.

The flight from Venice to Chicago was flawless. The flight crew was outstanding

When you pay for Premium Economy on an 787 and you’re promised amenities for the extra money, you expect them to work. They didn’t. USB connector wouldn’t charge continuously. 120v outlet wouldn’t hold anything you plugged into it. The adapter would just fall out. The noise canceling headphones stopped noise cancelling in the first 15 minutes for EVERYONE. No one on the plane knew how to fix it so I couldn’t listen to any movies. I just put in my AirPods and went to sleep. Very unhappy with the crappy Panasonic entertainment system. I won’t buy premium again.

Our flight was delayed by 18 hours. Poor accommodations made and no apology.

This flight was awful all around. Delays on the tarmac at PHL before takeoff and at the tarmac in Chicago caused me to miss my final connection. This was completely avoidable, in my opinion.

Good with British Airways - terrible with American Airlines! Stood at gate for “mechanical problem” - plane delayed. Had to check my personal belonging with 5 empty bins available in plane, desk staff rude!!! Toilet not working- asked “to use working toilet sparingly - it may overflow in cabin!”

Internet service was erratic. Crew service was poor and slow. My luggage on this non-stop flight was lost and not recovered

Flight was excellent in all aspects, - comfort , food, drinks, service, entertainment. Inspite of the computer glitch, the flight was on schedule and flawlessly. Thank you, air Canada.

We paid $110 for more leg room. My traveling companion’s knees were right up against the seat in front. Where was more leg room. We feel ripped off. Food,,,there wasn’t any not even a bag of pretzels. As a result, there was very little service.

The crew and the flight was excellent. Captain kept us informed about weather and possibly of turbulence and I appreciated that! The only thing is they didn’t have tv monitors. Other than that, everything was great.

One of the flight attendants was very attentive to a couple traveling with a child under 1 one year old.

We were delayed. Only got 1 snack. Seats were comfortable in preferred seating.

Flight was cancelled. Still stuck at airport. Going on 2 days straight, no sleep. Never fly Air Canada

Terrible. Flight in the morning was circling in air for 45 min due to weather then rerouted to a location further than the final destination to refuel. Sat on tarmac for almost 2 hrs to refuel. Flight was originally to land at 9:30am, we arrived at 2pm and then waited another 30 “for an agent”. Then afternoon return flight was delayed again 3 times for weather then cancelled. Auto rebooked was for the next evening! Just miserable.

It was fine. Give us free headphones or allow Bluetooth or something, or an app to watch on your phone. Grow up

I have never been on an older or dirtier plane.

Unfortunately my flight experience was poor as my flight was delayed with multiple gate changes. I did not reach my destination until almost midnight. I'm hesitant to fly Air Canada in the future.

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.
4/9Wed
1 stop
12h 25mYVR-ORD
9/9Mon
2 stops
20h 56mORD-YVR
C$ 275
13/9Fri
1 stop
12h 25mYVR-ORD
17/9Tue
2 stops
20h 58mORD-YVR
C$ 276
19/8Mon
directPorter Airlines
1h 47mYTZ-MDW
26/8Mon
directPorter Airlines
1h 42mMDW-YTZ
C$ 284
20/8Tue
1 stopPorter Airlines
4h 02mYUL-MDW
27/8Tue
1 stopPorter Airlines
3h 53mMDW-YUL
C$ 294
22/8Thu
directUnited Airlines
1h 54mYYZ-ORD
25/8Sun
directUnited Airlines
1h 48mORD-YYZ
C$ 312
18/9Wed
1 stopAir Canada
9h 26mYYC-ORD
23/9Mon
1 stopAir Canada
8h 37mORD-YYC
C$ 318
22/8Thu
directAir Canada
1h 56mYYZ-ORD
25/8Sun
directAir Canada
1h 48mORD-YYZ
C$ 325
29/8Thu
directUnited Airlines
4h 05mYVR-ORD
4/9Wed
1 stopUnited Airlines
13h 09mORD-YVR
C$ 334
3/10Thu
1 stopWestJet
8h 39mYVR-ORD
6/10Sun
1 stopWestJet
8h 18mORD-YVR
C$ 354
8/9Sun
directWestJet
3h 27mYYC-ORD
13/9Fri
directWestJet
3h 45mORD-YYC
C$ 390

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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.
20/9Fri
2 stops
24h 35mYVR-ORD
C$ 158
19/9Thu
1 stop
12h 25mYVR-ORD
C$ 163
13/8Tue
directPorter Airlines
1h 47mYTZ-MDW
C$ 169
21/8Wed
directWestJet
3h 27mYYC-ORD
C$ 172
23/9Mon
1 stopAir Canada
7h 45mYYC-ORD
C$ 177
21/8Wed
1 stopPorter Airlines
4h 27mYUL-MDW
C$ 180
18/9Wed
1 stopAir Canada
9h 26mYYC-ORD
C$ 185
20/8Tue
1 stopUnited Airlines
13h 36mYYC-ORD
C$ 191
30/8Fri
1 stopWestJet
7h 57mYVR-ORD
C$ 209
23/8Fri
1 stopUnited Airlines
4h 31mYYZ-ORD
C$ 221

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Recent domestic flight deals

17/8Sat
directSpirit Airlines
2h 29mDFW-ORD
19/8Mon
directSpirit Airlines
2h 29mORD-DFW
C$ 93
14/8Wed
multi-stopSpirit Airlines
4h 26mBOS-ORD
17/8Sat
multi-stopSpirit Airlines
5h 17mORD-BOS
C$ 96
31/8Sat
directDelta
3h 07mBOS-ORD
1/9Sun
directDelta
2h 28mORD-BOS
C$ 155
1/9Sun
directDelta
2h 54mLGA-ORD
4/9Wed
directDelta
2h 09mORD-LGA
C$ 172
27/9Fri
directAlaska Airlines
3h 56mSEA-ORD
28/9Sat
directAlaska Airlines
4h 34mORD-SEA
C$ 217
5/9Thu
directAlaska Airlines
3h 56mSEA-ORD
10/9Tue
directAlaska Airlines
4h 34mORD-SEA
C$ 218
4/9Wed
directAmerican Airlines
4h 04mSEA-ORD
8/9Sun
directAmerican Airlines
4h 38mORD-SEA
C$ 272
18/9Wed
directAmerican Airlines
4h 04mSEA-ORD
23/9Mon
directAmerican Airlines
4h 38mORD-SEA
C$ 291
27/8Tue
directUnited Airlines
2h 34mDFW-ORD
27/8Tue
directUnited Airlines
2h 34mORD-DFW
C$ 299
13/8Tue
directUnited Airlines
2h 37mEWR-ORD
15/8Thu
directUnited Airlines
2h 33mORD-EWR
C$ 317

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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.
25/7Thu
multi-stopAlaska Airlines
13h 30mYVR-ORD
29/7Mon
multi-stopAlaska Airlines
6h 37mORD-YVR
C$ 390
26/7Fri
multi-stopDelta
9h 35mYYC-ORD
30/7Tue
multi-stopDelta
8h 52mORD-YYC
C$ 424
25/7Thu
multi-stopUnited Airlines
6h 39mYVR-ORD
26/7Fri
multi-stopUnited Airlines
8h 33mORD-YVR
C$ 434
26/7Fri
directPorter Airlines
1h 47mYTZ-MDW
3/8Sat
directPorter Airlines
1h 42mMDW-YTZ
C$ 494
26/7Fri
directPorter Airlines
1h 47mYTZ-MDW
1/9Sun
directPorter Airlines
1h 42mMDW-YTZ
C$ 495
26/7Fri
multi-stopAir Canada
11h 47mYYC-ORD
30/7Tue
multi-stopAir Canada
9h 14mORD-YYC
C$ 502
23/7Tue
directWestJet
3h 27mYYC-ORD
29/7Mon
directWestJet
3h 45mORD-YYC
C$ 511
25/7Thu
directAir Canada
3h 28mYYC-ORD
26/7Fri
multi-stopAir Canada
9h 14mORD-YYC
C$ 542
27/7Sat
directUnited Airlines
1h 57mYYZ-ORD
29/7Mon
directUnited Airlines
1h 43mORD-YYZ
C$ 546
27/7Sat
multi-stopWestJet
6h 13mYYZ-ORD
29/7Mon
multi-stopWestJet
4h 34mORD-YYZ
C$ 548

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