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Find cheap flights from Canada to Chicago from $114

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 6/4. 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
Mon 6/3
Mon 6/10

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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
In the last 7 days travelers have searched 43,369,418 times on KAYAK, and here is why:

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Flights to Chicago - Travel Insights & Trends

Get data-powered insights and trends for flights to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest 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 $368. On the other hand, the most expensive day to fly is Monday, where prices are $478 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 $303 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 $507 and $494 respectively. For return trips, the best month to travel is April with an average price of $239.

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 $289 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 $334.

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 $133 one-way - $219 round-trip, from Toronto Pearson Intl Airport $189 one-way - $314 round-trip, from Montreal Pierre Elliott Trudeau Intl Airport $194 one-way - $378 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 37 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 $114.

Which airlines fly to Chicago?

Airlines flying the most to Chicago from Canada are United Airlines, Air Canada and American Airlines. See the amount of flights per week for popular airlines flying to Chicago.

Which airline offers the most flights to Chicago?

Of the 14 airlines that fly to Chicago, United Airlines offers the most flights, with around 5,222 per week, followed by American Airlines with 2,596 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 82% 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 31m, Toronto, which takes 3h 04m, Calgary, which takes 3h 21m, and Vancouver, which takes 4h 01m.

How many direct flights to Chicago are there each day?

There are around 1,572 direct flights from within Canada to Chicago every day. Most flights depart in the morning, with 6:00 am the most common departure time and 51% of flights departing in the morning.

How many direct flights to Chicago are there each week?

Each week there are around 11,003 direct flights from within Canada to Chicago. The most common day for departures is Tuesday, with 16% of flights taking off on this day.

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

Each week, there are 21 medium-haul flights (3-6 hour flight duration) and 271 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 151 direct flights each week.

Good to know

Low season

January

High season

December

Cheapest flight

$114
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 7% increase in price.
Flight from Toronto Pearson Airport to Chicago O'Hare Airport

FAQs - booking Chicago flights

  • What hotels are near Rockford International Airport?

    The Red Roof Inn is a budget-friendly choice that is a 15-minute drive from Rockford International Airport and a 6-minute drive to the Magic Waters Waterpark. The Radisson Hotel & Conference Center is a modern choice that is a 20-minute drive from the airport and an 8-minute drive from the Midway Village Museum.

  • What is the best way to travel from O'Hare International Airport to downtown Chicago?

    The easiest and quickest way to travel from O'Hare International Airport to downtown Chicago is by either renting a car or grabbing a taxi, as the drive only takes 25 to 30 minutes in good traffic. If you prefer a more affordable option, it is also possible to use public transportation, such as the local train, which takes approximately 45 minutes.

  • Does O'Hare International Airport have a prayer room?

    O'Hare International Airport has a multi-faith chapel that is located inside of Terminal 1 on the Mezzanine level. Religious books, rosaries and prayer rugs are available for use, and the chapel is open to all travelers, no matter what their religious affiliation is. It is open 7 days a week during standard business hours.

  • What shopping options are there at O'Hare International Airport?

    O'Hare International Airport has several duty-free stores located in Terminals 1, 2 and 3. In these stores, you can find a variety of electronics, clothing, liquor, cosmetics, food products and even local souvenirs. There are also several smaller shops that sell travel essentials, such as books, snacks, headphones and basic medicine.

  • Which Chicago airport is closest to central Chicago?

    There are 3 airports in Chicago. The closest airport to Chicago’s city center is Chicago Midway Airport (9 miles). Chicago O'Hare Airport and Chicago Greater Rockford are respectively 16 miles and 79 miles from the center of Chicago.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $390. The cheapest price found on KAYAK in the last 2 weeks cost $124 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 travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

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.
  • 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, +79 more

ANA, Aer Lingus, +80 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, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

See more direct flights

Nonstop returns

Chicago to Canada

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 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, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

See more direct flights
See more direct flights

Top 5 airlines serving from Canada to Chicago

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from Canada to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.5
WestJetOverall score based on 2962 reviews
7.3Comfort
6.5Food
6.5Entertainment
7.7Boarding
8.2Crew
Airline reviews

Airport monitors did not give the gate for our flight returning Detroit to Vancouver Juice served from glass storage containers are a far more healthy alternative for people. And would also minimize the need for recycling plastic or aluminum containers

2.0 MediocreAnonymous, Apr 2024YVR - MSP
Read more about WestJet reviews

Airport monitors did not give the gate for our flight returning Detroit to Vancouver Juice served from glass storage containers are a far more healthy alternative for people. And would also minimize the need for recycling plastic or aluminum containers

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.

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.

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.

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!

The plane was old and in new of a cleaning up and renovating on the interior. Seats and carpets were very worn and dirty looking. Cushioning on the seats was broken down and not as comfortable as newer jet seats. Food was a little below average but okay. Staff were friendly and hard working but did not pick up debris or food they spilled when collecting from the customers. But they were very helpful and professional.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

lounge was the highlight - seats weren't that comfortable - it was a full flight but no complaints

Limited snack options cause the snack vendor was on strike

The experience was generally above average. The only downside was the absence of WiFi during my flight from Vancouver to San Francisco.

on demand entertainment in seat back awesome Check in Kiosk too demanding with endless demand for more information information then says go to counter. Counter agent unfriendly. Do it yourself check in luggage procedure not intuitive, upset employees frustrated the whole procedure.

It was an excellent experience, traveling from Toronto to Denver with United.

Ontime boarding. Almost 1 hour take off delay. We could have boarded slightly later since the pilots were in traffic

Flight was delayed, I had to put my luggage all the way in the back! They served only a beverage no snack on the way in Air Canada, definitely not a good first impression.

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.

Book cheap flights from Canada to Chicago

Recent round-trip flight deals

 
These are the cheapest round-trip flights to Chicago found on KAYAK in the last 72 hours.
5/29Wed
1 stop
11h 05mYYZ-ORD
6/5Wed
1 stop
18h 20mORD-YYZ
$196
6/18Tue
nonstopWestJet
3h 27mYYC-ORD
6/25Tue
nonstopWestJet
3h 45mORD-YYC
$197
5/31Fri
nonstopPorter Airlines
1h 47mYTZ-MDW
6/3Mon
nonstopPorter Airlines
1h 42mMDW-YTZ
$232
5/29Wed
nonstopPorter Airlines
1h 47mYTZ-MDW
6/4Tue
nonstopPorter Airlines
1h 42mMDW-YTZ
$233
6/2Sun
nonstopAir Canada
1h 56mYYZ-ORD
6/15Sat
nonstopAir Canada
1h 43mORD-YYZ
$257
6/29Sat
nonstopUnited Airlines
1h 56mYYZ-ORD
7/2Tue
nonstopUnited Airlines
1h 48mORD-YYZ
$258
5/29Wed
nonstopAir Canada
2h 02mYYZ-ORD
6/5Wed
nonstopAir Canada
1h 45mORD-YYZ
$260
6/1Sat
1 stopUnited Airlines
4h 37mYYZ-ORD
6/8Sat
nonstopUnited Airlines
1h 43mORD-YYZ
$272
6/8Sat
nonstopAmerican Airlines
1h 55mYYZ-ORD
6/12Wed
1 stopAmerican Airlines
7h 32mORD-YYZ
$286
5/23Thu
nonstopAmerican Airlines
1h 55mYYZ-ORD
5/27Mon
nonstopAmerican Airlines
1h 40mORD-YYZ
$291

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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.
6/4Tue
1 stop
11h 05mYYZ-ORD
$114
6/4Tue
1 stop
17h 59mYYZ-ORD
$115
6/4Tue
1 stopAir Canada
7h 36mYYC-ORD
$130
6/26Wed
nonstopPorter Airlines
1h 47mYTZ-MDW
$135
6/3Mon
1 stopAir Canada
7h 54mYYC-ORD
$136
6/1Sat
nonstopPorter Airlines
1h 47mYTZ-MDW
$138
6/4Tue
nonstopAmerican Airlines
1h 55mYYZ-ORD
$153
6/5Wed
nonstopAmerican Airlines
3h 25mYYC-ORD
$165
7/5Fri
1 stopUnited Airlines
6h 17mYYZ-ORD
$169
6/8Sat
1 stopUnited Airlines
18h 37mYVR-ORD
$179

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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.
5/9Thu
nonstopPorter Airlines
1h 47mYTZ-MDW
5/19Sun
nonstopPorter Airlines
1h 42mMDW-YTZ
$331
5/6Mon
nonstopPorter Airlines
1h 47mYTZ-MDW
5/31Fri
nonstopPorter Airlines
1h 42mMDW-YTZ
$345
5/9Thu
nonstopAir Canada
1h 54mYYZ-ORD
5/19Sun
nonstopAir Canada
1h 45mORD-YYZ
$377
5/9Thu
multi-stopWestJet
4h 16mYYZ-ORD
5/19Sun
multi-stopWestJet
4h 32mORD-YYZ
$388
5/7Tue
nonstopAir Canada
2h 01mYYZ-ORD
6/8Sat
nonstopAir Canada
1h 43mORD-YYZ
$399
5/6Mon
multi-stopWestJet
7h 31mYYZ-ORD
5/31Fri
multi-stopWestJet
5h 00mORD-YYZ
$402
5/6Mon
multi-stopUnited Airlines
13h 11mYYZ-ORD
5/31Fri
nonstopUnited Airlines
1h 45mORD-YYZ
$423
5/7Tue
nonstopAmerican Airlines
1h 55mYYZ-ORD
5/15Wed
multi-stopAmerican Airlines
6h 29mORD-YYZ
$431
5/6Mon
multi-stopAmerican Airlines
5h 29mYYZ-ORD
5/14Tue
nonstopAmerican Airlines
1h 35mORD-YYZ
$438
5/8Wed
multi-stopUnited Airlines
5h 04mYYZ-ORD
5/17Fri
nonstopUnited Airlines
1h 48mORD-YYZ
$449

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