Find flights
Deals
Insights
When to book
FAQs & Tips
Direct Flights
Airlines

Find cheap flights to Chicago from C$ 164

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 17/4. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Thu 18/4
Thu 25/4

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 47,600,107 times on KAYAK, and here is why:

Save 17% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

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.
8:50 p.m. - 9:37 p.m.YTZ-MDW
1h 47mdirect
8:40 a.m. - 11:22 a.m.MDW-YTZ
1h 42mdirect
C$ 280Porter Airlines
Find Deal
Fri, 12 Apr - Sun, 14 Apr
9:20 a.m. - 10:07 a.m.YTZ-MDW
1h 47mdirect
8:40 a.m. - 11:22 a.m.MDW-YTZ
1h 42mdirect
C$ 284Porter Airlines
Find Deal
Fri, 12 Apr - Sun, 14 Apr
8:00 a.m. - 8:54 a.m.YYZ-ORD
1h 54mdirect
9:15 p.m. - 11:58 p.m.ORD-YYZ
1h 43mdirect
C$ 318Air Canada
Find Deal
Thu, 11 Apr - Mon, 15 Apr
8:00 a.m. - 8:54 a.m.YYZ-ORD
1h 54mdirect
9:15 p.m. - 11:58 p.m.ORD-YYZ
1h 43mdirect
C$ 322Air Canada
Find Deal
Wed, 24 Apr - Mon, 27 May
2:10 p.m. - 12:59 a.m.YYC-ORD
9h 49m1 stop
1:45 p.m. - 11:16 p.m.ORD-YYC
10h 31m1 stop
C$ 338Delta
Find Deal
Tue, 9 Apr - Tue, 16 Apr
7:00 a.m. - 8:01 a.m.YYZ-ORD
2h 01mdirect
4:04 p.m. - 10:30 p.m.ORD-YYZ
5h 26m1 stop
C$ 348United Airlines
Find Deal
Tue, 16 Apr - Tue, 23 Apr
7:00 a.m. - 8:01 a.m.YYZ-ORD
2h 01mdirect
4:05 p.m. - 10:13 p.m.ORD-YYZ
5h 08m1 stop
C$ 349United Airlines
Find Deal
Sun, 14 Apr - Tue, 16 Apr
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$ 349WestJet
Find Deal
Fri, 12 Jul - Tue, 16 Jul
12:30 p.m. - 4:35 p.m.YYZ-ORD
5h 05m1 stop
6:20 a.m. - 11:31 a.m.ORD-YYZ
4h 11m1 stop
C$ 356Delta
Find Deal
Thu, 11 Apr - Sun, 14 Apr
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$ 370WestJet
Find Deal
Wed, 14 Aug - Wed, 21 Aug

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$ 221 one-way and C$ 379 for a round-trip flight. Also in the last 72 hours, the most popular connection to Chicago was from Montreal and the lowest price for a round-trip flight was C$ 348.

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$ 837. The cheapest price found on KAYAK in the last 2 weeks cost C$ 138 and departed from Vancouver Intl Airport. The most popular routes on KAYAK are Vancouver to Chicago which costs C$ 675 on average, and Toronto to Chicago, which costs C$ 1,258 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$ 537. On the other hand, the most expensive day to fly is Sunday, where prices are C$ 600 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$ 482 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$ 689 and C$ 671 respectively. For return trips, the best month to travel is January with an average price of C$ 313.

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$ 431.

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$ 166 one-way - C$ 281 round-trip, from Vancouver Intl Airport C$ 233 one-way - C$ 496 round-trip, from Montreal Pierre Elliott Trudeau Intl Airport C$ 248 one-way - C$ 529 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$ 237.

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 13 airlines that fly to Chicago, United Airlines offers the most flights, with around 4,490 per week, followed by American Airlines with 4,350 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 78% 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 39m, 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 42 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 288 direct flights from within Canada to Chicago. The most common day for departures is Sunday, with 16% of flights taking off on this day.

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

Each week there are around 521 long-haul flights (6-12 hour flight duration), 1,252 medium-haul (3-6 hour flight duration) and 12,883 short-haul (up to 3 hour flight duration) flights to Chicago. The most long-haul flights depart from London.

How many cities have direct flights to Chicago?

From Canada, there are direct flights to Chicago from 5 cities. The city with the most direct flights is Toronto, with 209 direct flights each week.

Good to know

Low season

January

High season

August

Cheapest flight

C$ 164
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 Pearson Airport 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 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$ 221 one-way and C$ 379 for a round-trip flight. Also in the last 72 hours, the most popular connection to Chicago was from Montreal and the lowest price for a round-trip flight was C$ 348.

  • 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$ 837. The cheapest price found on KAYAK in the last 2 weeks cost C$ 138 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.

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, +77 more

ANA,Aer Lingus, +78 more

Tuesday

ANA,Aer Lingus,Aerolineas Argentinas, +77 more

ANA,Aer Lingus, +78 more

Wednesday

ANA,Aer Lingus,Aeromexico, +75 more

ANA,Aer Lingus, +76 more

Thursday

ANA,Aer Lingus,Aeromexico, +76 more

ANA,Aer Lingus, +77 more

Friday

ANA,Aer Lingus,Aerolineas Argentinas, +79 more

ANA,Aer Lingus, +80 more

Saturday

ANA,Aer Lingus,Aeromexico, +76 more

ANA,Aer Lingus, +77 more

Sunday

ANA,Aer Lingus,Aerolineas Argentinas, +77 more

ANA,Aer Lingus, +78 more

See more nonstop flights

Nonstop returns

Chicago to Canada

Monday

ANA,Aer Lingus,Aeromexico, +77 more

ANA,Aer Lingus, +78 more

Tuesday

ANA,Aer Lingus,Aerolineas Argentinas, +77 more

ANA,Aer Lingus, +78 more

Wednesday

ANA,Aer Lingus,Aeromexico, +75 more

ANA,Aer Lingus, +76 more

Thursday

ANA,Aer Lingus,Aeromexico, +76 more

ANA,Aer Lingus, +77 more

Friday

ANA,Aer Lingus,Aerolineas Argentinas, +79 more

ANA,Aer Lingus, +80 more

Saturday

ANA,Aer Lingus,Aeromexico, +76 more

ANA,Aer Lingus, +77 more

Sunday

ANA,Aer Lingus,Aerolineas Argentinas, +77 more

ANA,Aer Lingus, +78 more

See more nonstop flights
See more nonstop flights

Top 5 airlines flying to Chicago

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 KAYAK reviews.
8.0
DeltaOverall score based on 11551 reviews
86crew
81entertainment
79comfort
81overall
75food
82boarding
Airline reviews

Boarding was a sh!t show. JFK BOARDING was awful. The agent called three sections at a time Clogging the area then yelling at people to not block the walk way. How are you going to call delta one , premium select and comfort plus at once and the yell at highest paying passengers. Need to do a lot better and the flight attendants in the galley need to understand that their voices travel. They were talking about others and everyone in the cabin heard them

Read more about Delta

Boarding was a sh!t show. JFK BOARDING was awful. The agent called three sections at a time Clogging the area then yelling at people to not block the walk way. How are you going to call delta one , premium select and comfort plus at once and the yell at highest paying passengers. Need to do a lot better and the flight attendants in the galley need to understand that their voices travel. They were talking about others and everyone in the cabin heard them

Uncomfortable seats on 14 hour flight. Mediocre food. On time and great crew.

MSP to Atlanta was much better than Atlanta to St. Kitts. Paid $180 each for myself and wife for Delta comfort from Atlanta to St. Kitts. Seats were more narrow and obviously old and worn out. Tailbone is killing me. Seat would not recline. Seats behind reclined and we were not an exit row or in front of an exit row. Entertainment did not work in that the movie jumped forward and back and there was no audio. The plug in the arm rest was loose. Flight attendant tried “resetting” the video for my seat but no good. She never checked back. Someone else near me had the same issue. Touch screen was unresponsive. No where near as comfortable as MSP to Atlanta flight. 3 plus hrs. flight time without the basic amenities and not even remotely close to comfortable but paid for Comfort plus. I will be very disappointed if I have the same on my return “Comfort Plus” flight St. Kitts to Atlanta. At the very least my wife and I should be refunded for round trip “Comfort Plus” charges. Please feel free to contact me directly for more details.

The pilot was excellent - he flew us around a storm and even though predicted it would be a bumpy ride - was able to avoid all turbulence and land us safely with only a 15 min delay. Kudos!

public website still broken for years randomly blocking browsers with privacy options active after loading a page maybe once. check-in on laptop was almost impossible but eventually randomly worked. had to print pass at airport since couldn't get back in to load digital pass on mobile firefox or chrome. red eye flight so smooth onboarding, plenty of room to spread out, easy offboarding. onboard wifi instructions mention vpn can cause problems connecting but fails to also mention private dns. no printed or built in menu list, seems weird to require personal device to point at qr code link for menu which does not even allow direct ordering. people with health condition risk related dietary restrictions trying to avoid for example cholesterol and sugar are left guessing what they can order either way without nutritional info highlights (cranberry juice was minute maid cocktail with as much suger as typical can of soda). tap to pay wasn't working and always seems sketchy to manually enter card info. good movie variety, so limited tv was okay.

Great experience overall. Check in at Austin was congested as they only have about 6 check in kiosks, one was broken, and there was a lot of Spring Break travelers.

The main person that was coordinating everything was a short white/light skin Spanish man and he was very rude. It honestly made me feel like it was everyone’s First day at work. His announcements were very not reasonable and they did not make sense. The stewardess on the flight that made the announcements she didn’t even know what she was talking about she sounded inebriated. There were no snacks or drinks on our flight there wasn’t even much turbulence. This flight was not enjoyable nor was it what a Delta flight should be and just this past week I flew with Delta 3 times.

Worst food I've ever seen on a plane. One flight attendant must have been going through a bad breakup, although the one who kept covering for her was excellent.

Great flight crew, easy boarding, delicious snacks and spacious seats. Love flying delta - worth the price.

The landing was bad and the hostess came two times and i was sleeping but when she served the person that nexts to me I woke up and she didn’t even asked me if I need any drink or snacks two times!!!!

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!

They could Isaac's announced our gate at Atlanta. Whet we arrived at the gate he thought we were joking and we didn't board. The plane left without us

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.

New jet. Lots of leg room. On time departure. Early arrival. Reasonable airfare. Excellent online experience.

I had checked in online the day before but was instructed to collect our boarding passes when we arrived. I am not completely comfortable using the automated Kiosks and always enjoy the nostalgia of speaking with someone when checking in for a flight. Upon doing so however, we were immediately asked,"did you check in online already?" To which I replied, "yes, but we were asked to retrieve our boarding passes upon arrival." She then said, "that's what those machines over there are for. We really encourage people to use those." That unfortunately sparked a series of shortness and overall poor behavior in my opinion from the woman who checked us in. I understand it was early in the morning but I am always excited to experience flying and that interaction has unfortunately left a bitter taste in my mouth to the point I will forever now hesitate to book with Porter again. Thank you for taking the time to read this. Cheers, JD

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.

Great crew, friendly. Found the trip long just sitting with no onboard entertainment

The Palm Springs to Chicago O’Hare was on Time and Palm Springs airport is easier navigate. As our connection was only an approximately 50 minutes, we asked staff for insights for the Chicago airport in terms of transferring into the other terminal from which our flight left, and they were unhelpful. However, the United App was very helpful in terms of notifications and even providing directions. The Chicago to Detroit flight was significantly delayed which we all know does happen. However, there were very few updates or notifications as to why this was happening when we would actually arrive. It took nearly 30 minutes for bags to make it to baggage claim. We arrived nearly 1 hour late on a 40 minute flight.

Liked the excellent United crew, the food selection, the comfortable cabin and the excellent movie and tv shows selection. The interface on the screen is also excellent and gives the option to let the crew know to wake you up for meals, or not. I disliked the onboarding experience at the Brussels airport. The process is convoluted and was not explained to any passengers. I also don't understand why thee is an additional security screening when getting off the plane from Africa, when there was none when getting off the plane from the US.

Friendly flight crew, clean plane, on time, great tandoori chicken

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

The flight was delayed by 4 hours !!!!! It was very uncomfortable , and they told us only one our before departure

As is pretty much the norm with Air Canada now, we left late from the gate (45 minutes late). This is my 12th flight with AC in the last 12 months and 10 of those flights were either late or cancelled. AC essentially has a monopoly in Canada so they have carte blanche to charge exorbitant rates now and give poor service, with no repercussions.

A 2 hour delay because they couldn’t fit some oversized cargo in the small hold doors of an Embraer! Surely they know the sizes before attempting to load it?

It took 5 hour to get a crew to D Ice the plan. We had to sit on the runway for 5 hrs. in Calgary. It snows most of the winter. No proactive plan. In addition, after 3 calls to customer service they couldn't figure out how to have my wife and myself sit together on her birthday weekend. Everybody kept passing the buck. No decision from customer service, luggage drop off or check in team. The experience was a complete mess! I don't think we'll ever fly on this airline again.

When we got to the airport for our flight from Chicago to Montreal which was scheduled for 2.00 p.m. they had no record of it and booked us on a flight at 3.30 very disappointing . We also had to pay 50.00 each for a seat. All things considered ,I will never book thru Kayak again. Next time I will only book directly thru Air Canada no second party booking Sue

-kayak did not give me advanced notice to my e-mail for my flight and I had major trouble finding the code to access Air Canada’s site because you did not provide it to me and incompetent Air Canada did not have any access based on my name alone. WTF -The flight was delayed twice. -They moved the boarding area -They said I would give free checked baggage because the plane was full and they charged me over $30 -They didn’t get my luggage on to the plane and left without it and I’m heading to a cruise ship. -I have lost one FULL day of my limited holiday and had to cancel scheduled events because my luggage did not get on the plane (even though the plane was delayed). -The “wheresmyluggage.com site is a total incompetent disaster that caused additional stress. -I will be sharing this experience

Plane was a Rouge vacation flyer for some reason. No legroom and entertainment. People were desperately looking for USB ports and such. And then there is this notorious and unsolved space problem where not all carry-on fits in the cabin….

The wifi I paid for did not work. The seats are tight.

There were no free snacks…little pretzel bag or cookies like we had on our flight out.

They did not have any meal options left on the menu. Only snacks.

Of our SIX flights in my travel group, five were delayed, and all (except possibly one) were just company screwups. One traveler had her CARRY ON baggage put on another flight because Air Canada could not properly do "weight and Balance". Bags missing for a day. Another traveler never made it. Then, (humor here) the flagship airline of the socialist country has NOTHING FOR FREE on board. Expect to pay for pretzels, folks. How's that socialism working out for ya, aye? I might book air Canada in the future if I have a meeting that I REALLY want to MISS!

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.
12/4Fri
directPorter Airlines
1h 47mYTZ-MDW
14/4Sun
directPorter Airlines
1h 42mMDW-YTZ
C$ 280
12/4Fri
directPorter Airlines
1h 47mYTZ-MDW
14/4Sun
directPorter Airlines
1h 42mMDW-YTZ
C$ 284
11/4Thu
directAir Canada
1h 54mYYZ-ORD
15/4Mon
directAir Canada
1h 43mORD-YYZ
C$ 318
24/4Wed
directAir Canada
1h 54mYYZ-ORD
27/5Mon
directAir Canada
1h 43mORD-YYZ
C$ 322
9/4Tue
1 stopDelta
9h 49mYYC-ORD
16/4Tue
1 stopDelta
10h 31mORD-YYC
C$ 338
16/4Tue
directUnited Airlines
2h 01mYYZ-ORD
23/4Tue
1 stopUnited Airlines
5h 26mORD-YYZ
C$ 348
14/4Sun
directUnited Airlines
2h 01mYYZ-ORD
16/4Tue
1 stopUnited Airlines
5h 08mORD-YYZ
C$ 349
12/7Fri
directWestJet
3h 27mYYC-ORD
16/7Tue
directWestJet
3h 45mORD-YYC
C$ 349
11/4Thu
1 stopDelta
5h 05mYYZ-ORD
14/4Sun
1 stopDelta
4h 11mORD-YYZ
C$ 356
14/8Wed
directWestJet
3h 27mYYC-ORD
21/8Wed
directWestJet
3h 45mORD-YYC
C$ 370

Search by stops

Search by airline

Search by price

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.
17/4Wed
1 stop
12h 16mYYZ-ORD
C$ 164
17/4Wed
1 stop
11h 15mYYZ-ORD
C$ 165
22/4Mon
directPorter Airlines
1h 47mYTZ-MDW
C$ 165
21/4Sun
directPorter Airlines
1h 47mYTZ-MDW
C$ 167
16/4Tue
1 stopAir Canada
6h 54mYYC-ORD
C$ 194
23/5Thu
directAir Canada
1h 54mYYZ-ORD
C$ 195
16/4Tue
directUnited Airlines
1h 59mYYZ-ORD
C$ 206
25/8Sun
directWestJet
3h 27mYYC-ORD
C$ 211
5/5Sun
directUnited Airlines
2h 46mYUL-ORD
C$ 225
5/9Thu
directWestJet
3h 27mYYC-ORD
C$ 227

Search by stops

Search by airline

Search by price

Recent domestic flight deals

14/5Tue
directSpirit Airlines
2h 39mLGA-ORD
14/5Tue
directSpirit Airlines
2h 11mORD-LGA
C$ 83
7/5Tue
directSpirit Airlines
2h 40mLGA-ORD
8/5Wed
directSpirit Airlines
2h 09mORD-LGA
C$ 96
27/4Sat
directAlaska Airlines
4h 10mSEA-ORD
30/4Tue
directAlaska Airlines
4h 34mORD-SEA
C$ 157
16/4Tue
directDelta
3h 58mSEA-ORD
25/4Thu
directDelta
4h 45mORD-SEA
C$ 158
6/5Mon
directAlaska Airlines
3h 59mSEA-ORD
7/5Tue
directAlaska Airlines
4h 34mORD-SEA
C$ 165
18/6Tue
directDelta
2h 45mLGA-ORD
23/7Tue
directDelta
2h 18mORD-LGA
C$ 172
17/4Wed
directUnited Airlines
2h 15mDCA-ORD
24/4Wed
directUnited Airlines
1h 55mORD-DCA
C$ 252
17/4Wed
directUnited Airlines
2h 11mDCA-ORD
24/4Wed
multi-stopUnited Airlines
7h 38mORD-DCA
C$ 291
3/6Mon
directAmerican Airlines
2h 18mBWI-ORD
10/6Mon
directAmerican Airlines
1h 59mORD-BWI
C$ 421
3/6Mon
multi-stopAmerican Airlines
4h 43mBWI-ORD
10/6Mon
directAmerican Airlines
1h 59mORD-BWI
C$ 432

Search by stops

Search by airline

Search by price

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.
23/3Sat
directPorter Airlines
1h 50mYTZ-MDW
31/3Sun
directPorter Airlines
1h 42mMDW-YTZ
C$ 402
21/3Thu
directPorter Airlines
1h 50mYTZ-MDW
7/4Sun
directPorter Airlines
1h 42mMDW-YTZ
C$ 449
23/3Sat
multi-stopAir Canada
7h 22mYTZ-ORD
31/3Sun
multi-stopAir Canada
5h 43mORD-YTZ
C$ 451
23/3Sat
multi-stopAir Canada
5h 52mYYZ-ORD
31/3Sun
multi-stopAir Canada
5h 09mORD-YYZ
C$ 458
23/3Sat
multi-stopWestJet
5h 15mYYZ-ORD
6/4Sat
multi-stopWestJet
14h 46mORD-YYZ
C$ 566
23/3Sat
multi-stopDelta
5h 15mYYZ-ORD
28/3Thu
multi-stopDelta
6h 17mORD-YYZ
C$ 578
23/3Sat
multi-stopDelta
3h 46mYYZ-MDW
30/3Sat
multi-stopDelta
4h 03mMDW-YYZ
C$ 578
23/3Sat
multi-stopWestJet
6h 06mYYZ-ORD
24/3Sun
multi-stopWestJet
4h 04mORD-YYZ
C$ 586
20/3Wed
multi-stopUnited Airlines
4h 40mYYZ-ORD
25/3Mon
directUnited Airlines
1h 33mORD-YYZ
C$ 762
23/3Sat
multi-stopUnited Airlines
9h 51mYYC-ORD
30/3Sat
directUnited Airlines
3h 48mORD-YYC
C$ 769

Search by stops

Search by airline

Search by price