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Cheap Flights from Canada to O'Hare Intl

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Canada to O'Hare Intl

Wed, Oct 21 - Wed, Oct 28
Air Canada Logo
10:20 am - 8:12 pmYTZ  Toronto Island-ORD Chicago O'Hare Intl
10h 52m2 stops Ottawa Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
7:05 am - 6:19 pmORD  Chicago O'Hare Intl-YTZ Toronto Island
10h 14m2 stops Montreal Pierre Elliott Trudeau Intl Ottawa
$206Air Canada
Sat, Oct 24 - Sat, Oct 31
Air Canada Logo
12:15 pm - 1:25 pmYTZ  Toronto Island-ORD Chicago O'Hare Intl
2h 10mnonstop
Air Canada Logo
1:55 pm - 4:42 pmORD  Chicago O'Hare Intl-YTZ Toronto Island
1h 47mnonstop
$206Air Canada
Thu, Oct 1 - Sun, Oct 4
Lufthansa Logo
11:00 am - 12:00 pmYYZ  Toronto Pearson Intl-ORD Chicago O'Hare Intl
2h 00mnonstop
Lufthansa Logo
9:20 pm - 11:59 pmORD  Chicago O'Hare Intl-YYZ Toronto Pearson Intl
1h 39mnonstop
$206Lufthansa
Wed, Oct 28 - Mon, Nov 2
Porter Airlines Logo
4:35 pm - 5:40 pmYTZ  Toronto Island-ORD Chicago O'Hare Intl
2h 05mnonstop
Porter Airlines Logo
12:20 pm - 3:06 pmORD  Chicago O'Hare Intl-YTZ Toronto Island
1h 46mnonstop
$207Porter Airlines
Thu, Sep 24 - Sun, Sep 27
Lufthansa Logo
11:00 am - 12:00 pmYYZ  Toronto Pearson Intl-ORD Chicago O'Hare Intl
2h 00mnonstop
Lufthansa Logo
7:09 am - 9:54 amORD  Chicago O'Hare Intl-YYZ Toronto Pearson Intl
1h 45mnonstop
$207Lufthansa
Thu, Oct 29 - Mon, Nov 2
Porter Airlines Logo
10:35 am - 11:40 amYTZ  Toronto Island-ORD Chicago O'Hare Intl
2h 05mnonstop
Porter Airlines Logo
12:20 pm - 3:06 pmORD  Chicago O'Hare Intl-YTZ Toronto Island
1h 46mnonstop
$208Porter Airlines
Fri, Nov 13 - Sun, Nov 15
American Airlines Logo
6:07 pm - 12:01 amYYZ  Toronto Pearson Intl-ORD Chicago O'Hare Intl
6h 54m1 stop Charlotte Douglas
American Airlines Logo
2:50 pm - 5:41 pmORD  Chicago O'Hare Intl-YYZ Toronto Pearson Intl
1h 51mnonstop
$211American Airlines
Thu, Oct 15 - Sun, Oct 18
American Airlines Logo
6:00 am - 12:22 pmYYZ  Toronto Pearson Intl-ORD Chicago O'Hare Intl
7h 22m1 stop Charlotte Douglas
American Airlines Logo
9:46 am - 12:34 pmORD  Chicago O'Hare Intl-YYZ Toronto Pearson Intl
1h 48mnonstop
$211American Airlines
Fri, Oct 2 - Mon, Oct 5
United Airlines Logo
7:00 am - 8:00 amYYZ  Toronto Pearson Intl-ORD Chicago O'Hare Intl
2h 00mnonstop
United Airlines Logo
6:00 am - 11:43 amORD  Chicago O'Hare Intl-YYZ Toronto Pearson Intl
4h 43m1 stop Newark
$213United Airlines
Fri, Oct 2 - Mon, Oct 5
United Airlines Logo
8:50 am - 9:48 amYYZ  Toronto Pearson Intl-ORD Chicago O'Hare Intl
1h 58mnonstop
United Airlines Logo
6:06 pm - 11:54 pmORD  Chicago O'Hare Intl-YYZ Toronto Pearson Intl
4h 48m1 stop Washington, D.C. Dulles Intl
$214United Airlines
Booking Insights

KAYAK's insights & trends for flights to O'Hare Intl

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

What is the cheapest flight to Chicago O'Hare Airport?

In the last 5 days, the cheapest flight deal to Chicago O'Hare Airport was found on the route from Toronto, at $206 return. The most popular connection is from Montreal to Chicago O'Hare Airport and KAYAK users have found round-trip deals for as low as $281 in the last 5 days.

How much is a flight to Chicago O'Hare Intl Airport?

A flight to Chicago O'Hare Intl Airport costs $479 on average. The cheapest price found on KAYAK in the last 2 weeks cost $118 and departed from Toronto Island Airport. The most popular routes on KAYAK are Toronto to Chicago O'Hare Intl Airport which costs $602 on average, and Montreal to Chicago O'Hare Intl Airport, which costs $541 on average.

What is the cheapest day to fly to Chicago?

Based on KAYAK data, the cheapest day to fly to Chicago is Friday where round-trip tickets can be as cheap as $482. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $661 on average.

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The cheapest month for flights to Chicago O'Hare Intl Airport is February, where tickets cost $311 on average for return flights. On the other hand, the most expensive months are June and July, where the average cost of tickets from Canada is $398 and $383 respectively. For one-way flights, the best month to travel is February with an average price of $208.

What is the cheapest time of day to fly to Chicago O'Hare Intl Airport?

The cheapest time of day to fly to Chicago O'Hare Intl Airport is generally at night, when round-trip flights cost $403 on average. The most expensive time of day to fly to Chicago O'Hare Intl Airport is generally in the evening, which is peak travel time and where the average cost of a ticket is $798.

What is a good deal for flights to Chicago O'Hare Intl Airport?

If you’re looking for cheap airfare to Chicago O'Hare Intl Airport, 25% of our users found tickets to Chicago O'Hare Intl Airport for the following prices or less: From Toronto Island Airport $257 round-trip, from Calgary $306 round-trip, from Montreal Pierre Elliott Trudeau Intl Airport $382 round-trip.

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

To get a below average price, you should book around 4 weeks before departure, which saves you about 41% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Good to know

Low season

January

Cheapest flight

$131
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 3% increase in price.
Flight from Toronto to Chicago O'Hare Airport

Flights from Canada to O'Hare Intl: the best tips from KAYAK users

Insights shared by verified travelers who flew the route from Canada to O'Hare Intl 
NicholFlew with United Airlines-Aug 2026
If you are a US citizen, make sure you allow enough time for customs in Toronto Pearson airport. My trip was really quick and smooth, but I've seen it at other times where it has been busier and needed more time.
MMFlew with United Airlines-Jan 2026
Pay extra for Boarding Zone 2 to make sure your carry on, gets on the plane.
LisaFlew with United Airlines-Dec 2024
Turn on your data or the wifi in case gates change.
Verified travelerFlew with WestJet-Jun 2024
checkin luggage online as they jack up the price 100% at airport
Verified travelerFlew with United Airlines-Apr 2024
Come prepared with your own entertainment as the flight did not offer in flight entertainment
Verified travelerFlew with United Airlines-Mar 2024
Carry-on baggage sizing for United US bound flights appears to be much smaller than for Canadian flights, which forced me to check my bag at the last minute. So check online ahead of time

FAQs - booking Chicago O'Hare Airport flights

  • What is the cheapest flight to Chicago O'Hare Airport?

    In the last 5 days, the cheapest flight deal to Chicago O'Hare Airport was found on the route from Toronto, at $206 return. The most popular connection is from Montreal to Chicago O'Hare Airport and KAYAK users have found round-trip deals for as low as $281 in the last 5 days.

  • How far is Chicago O'Hare Intl Airport from central Chicago?

    The city center of Chicago is 16 miles from Chicago O'Hare Intl Airport.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $479. The cheapest price found on KAYAK in the last 2 weeks cost $118 and departed from Toronto Island Airport.

  • How does KAYAK find such low prices on flights to Chicago O'Hare Airport?

    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 O'Hare Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chicago O'Hare Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago O'Hare Airport 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 O'Hare Airport?

    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 O'Hare Airport 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 O'Hare Airport?

    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 O'Hare Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Chicago O'Hare Airport

  • Looking for cheap airfare to Chicago O'Hare Airport? 25% of our users found round-trip tickets to Chicago O'Hare Airport for the following prices or less: From Vancouver Intl $489, from Calgary $603, from Ottawa $697
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago O'Hare Airport flight deals.

Reviews of the top 5 airlines serving from Canada to O'Hare Intl

 
Need help choosing which airline to fly with to O'Hare Intl? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
Porter AirlinesOverall score based on 460 reviews
8.2Boarding
6.9Entertainment
8.0Comfort
8.6Crew
7.6Food
Airline reviews

A very comfortable flight, an additional wash room could have made it almost perfect.

10.0 ExcellentAnonymous, Aug 2026
Read more Porter Airlines reviews

A very comfortable flight, an additional wash room could have made it almost perfect.

Look, I understand that Kayak doesn't know I cancelled my flight on Porter. So I didn't actually fly yesterday. My main disappointment is with Porter ticket fare policies, and maybe you can pass this on to them: At my employer's request, I had booked a full fare ticket with no change fees since my trip to Toronto would likely be extended. Indeed, when I went to change my flight home to a later date, I was told the Fare Difference would cost an additional $550. So much for no change fees lol! While I had the agent on the line, I hopped over to Kayak, searched for new flights on the date in question, and saw a one-way ticket that got me home for only $355. So I got reimbursed about $450for the unused half of my roundtrip and bought a new ticket for $355. What good is a full fare / no change fee ticket if they screw you with "fare difference" BS. I'm still flying home on Porter Airlines but they just lost a hundred bucks with their stupid shenanigans.

I flew with Porter yesterday and overall had a positive experience. The flight was delayed, but the airline did a good job keeping passengers informed with frequent updates throughout the process. My biggest challenge was actually in Terminal 3, where the speaker system wasn’t very clear. It was often difficult to hear the announcements, which made it harder to follow updates at the gate. On board, the experience improved significantly. The aircraft felt very new and well maintained, and the seats were surprisingly comfortable for a short-haul flight. One of the flight attendants seemed a little disengaged, but the other was excellent—friendly, professional, and a pleasure to interact with. Despite the delay, the comfortable aircraft, clear communication from Porter, and positive onboard service made for a good overall experience.

It was okay. Had a thing with the front desk, she had me repack my suitcases to have them be under the weight restrictions, but then the other one was overweight, she argued with me about it when there were tons of people in line. Wasn’t great.

Organization and the adjusted times but the snacks could be of a bigger portion

Our flight was delayed by a bit. I appreciated that we were kept informed on why periodically. Boarding was fine. I overheard one flight attendant sounding very rude to a passenger who was not paying attention to the safety demonstration. The snacks were minimal as it was a short flight. There was no entertainment. Overall the flight was good back to LGA.

All good the seats a little tight and no I pad screen

Just an evening before they canceled my ticket and offered me ticket costing 3 x times more than. I will not fall prey to these scams,Will never book through kayak now. Such a bad experience.

was okay except.. 1)the porter check in webpage doesn't let you print your boarding pass from home 2)that there was a 90 min cut off for checking in on the kiosk in general, and to print a boarding pass, even tho i checked in online already....

It was amazing although they did bump us up to the front which gave us more leg room and a meal. The service was great! The staff were friendly. :)

Prefer not to have an almost 3 hour delay with useless communication that wasn't accurate.

Starlink is great Crew was polite Business class didn’t get a welcome drink just water and snacks were ok

very average service no complimentary alcoholics drinks unlike other airlines such as Porter airlines No decent seats available during check-in time the day before

Reliable, nice crew, I fly often on that flight and I like it all.

Efficient all round, very good crew. Short flight so the food, of course, was just snacks

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

So far so good but food and entertainment are not available for this flight

It was my first time with United Airlines and I would say it was very good experience and best of all the flights were on time. Will definitely fly with United Airlines next time.

lots of delays the crew were unclear about where to pick up my carry-on, which they took from me to check in on the plane.

They needed people to check a bag, they did check my bag and I had to wait 10 minutes after the flight to get it it wasn’t too bad

Horrible, delayed 3 hours due to a mechanical issue where the plane is deemed unsafe so we had to deplane after an hour on the tarmac. No credit was given even though plenty of passengers missed their connecting flights and then the baggage claim info showed that no flight was being loaded on the carousel whilst the bags were being dropped, so no one knew if it was the right flight or not since the arrivals screen didn’t show anything.

I'm so frustrated my flight was canceled they give flight on August 5 which is not sure. Its was big mistake I booked my ticket from kayak.

Maybe glass of wine would be nice at no charge

We traveled with a 7 year old that has autism and he is significantly cognitively delayed. Your site makes it known there are no wagons allowed even if they fold down flat and many autistic children cannot travel without one because they are unable to follow directions or cooperate with walking through the airport and are too big for a stroller. Please consider making exceptions for our special needs children. Also it would be very thoughtful if you’d allow seat selection for no fee for special needs families. The autistic child we traveled with must sit behind another adult in our family because he continuously kicks the seat in front of him and is unable to understand why that is disruptive. We had to pay quite a bit extra to have our 4 seats situated with 2 in row 19 and 2 in row 20 directly behind.

Our itinerary included a 1 hour and 30 minute layover, which should have been sufficient under normal circumstances. However, our original flight was delayed. Before we even deplaned, we were instructed to collect our checked bags from baggage claim, clear immigration and customs, and then recheck our bags for the connecting flight. The airline knew—or should have known—that this was impossible. Checked baggage acceptance closes one hour before departure, meaning there was no realistic way for passengers from the delayed flight to recheck their bags in time. Despite this, the airline gave us misleading instructions instead of informing us that we would likely miss our connection. We completed immigration and customs in approximately 10 minutes, but our checked bags did not arrive at the carousel for more than 30 minutes. After collecting them, we had another 10-minute walk to the baggage drop area, only to find that no airline attendant was present. We then went to another airline counter, where an employee told us this had happened before and that there was nothing they could do because the baggage acceptance window had already closed. At that point, there were still 40 minutes remaining before our flight's departure, yet no one was willing to assist or offer a practical solution. When we asked to be rebooked, we were simply told to call the airline's 800 number ourselves. There was no accountability or customer support at the airport, leaving us stranded in a foreign country with no immediate assistance. After finally reaching an agent on the 800 number, we were rebooked on a flight for the following day. However, we were initially told that the airline would not provide any hotel accommodation and that we would have to arrange and pay for it ourselves. Only after making multiple calls and speaking with several different agents did one representative finally issue a hotel voucher. The entire experience was an exhausting and frustrating ordeal. What should have been a 20-hour journey ultimately became more than 30 hours due to the airline's poor planning, misleading instructions, lack of accountability, and inadequate customer service. The unnecessary delays, confusion, and absence of meaningful assistance caused significant physical exhaustion and severe mental stress. This experience fell far below the level of service passengers should reasonably expect.

Despite travelling ultra basic for the first time due to such increased rates we both managed with one bag each. Even boarding last wasn’t SO bad.

I loved the fact it was on time and it was a smooth flight to my destination.

Service was okay except attendant over served alcohol to passenger and passenger got tipsy and made me uncomfortable

Could not make the flight. No one would help us at all

The agents at the Kelowna YLW airport were really grumpy. Same with oversized baggage person. Staff on the plane were great.

Our flight from Chicago to Des Moines was the problem flight due to a dismissive flight attendant. His conduct was unnecessary and unprofessional.. I will avoid using Americam Airlines again because of the situation. Very disappointing.

Mostly excellent. However, many too many gate changes. Connecting flight at ORD changed gate 6 times.

Mechanical issues and delays. I get it but bad experience. Turned my 3 hour airport experience into a 9 hours

The baggage process at the gate was terrible. Stay was not friendly at all

Flight was delayed because of mechanical. Could not get landing space which caused me to miss my connection. Messy and not organized.

This may have been the hottest cabin temperatures I have experienced on any flight prior to take off lasting for approximately 30 minutes. I am not typically one to complain but I was genuinely worried about the health of several passengers on the flight due to the extreme temperatures including a small toddler.

The flight was on time and crew were nice, seats were tight and there was entertainment available

Worst flight ever. I was suppose to have a 3 1/2 hour layover in Chicago but got to the gate 4 minutes before boarding.

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

Incompetent crew at the boarding counter. Never flying AA again.

Snacks and drinks should be served together and air hostess was not supportive with no smile which was kind of disappointing.

After 3 hours of delays, they ended up cancelling my flight. And although I could purchase one-way tickets to get to my destination, they would not offer me these flights as compensation for the cancelled flight, and I didn't end up making it home until 13 hours after I was originally supposed to arrive. It made for an extremely strenuous end to an otherwise good trip.

It's kindof ridiculous that your system is even asking me about this since my flight was canceled and I wasn't rescheduled.

Bad service as well. Another 3hr delayed flight from chicago to Charlotte.

Terrible. 3 missed flights and 24 hours delayed with lost bag and promised $100 compensation from United and absolutely nothing from them…

flight was delayed 6 hours for weather, then cancelled because of the crash in toronto, but none of the links to cancel or rebook my flights are working

Minimal food offered (crackers). Had to clean the seat with a wet wipe because of dried food.

They charge 5 dollars for plastic headphones for a flight of 1 hour! Seats are awful. Service is terrible.

Everything was seamless. I would have appreciated knowing there would not be any real food available for purchase in advance. Otherwise a great experience. Thank you!

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

Traveling to a place near O'Hare Intl?

Book flights to O'Hare Intl if you plan to visit one of these locations
Merrillville
Gurnee
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Oak Brook
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Hoffman Estates
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Portage
Oakbrook Terrace
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More options for your flight to O'Hare Intl