$52 Find Cheap Flights from Chicago to Hamilton

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Hamilton departing on 10/15. 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
1 adult, Economy

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Cheap Flights from Chicago to Hamilton (CHI-YYZ)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Hamilton 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Hamilton

Wed, Sep 3 - Tue, Sep 9
Air Canada Logo
10:40 am - 5:58 pmORD-YYZ
6h 18m1 stop
Air Canada Logo
6:15 am - 9:51 amYYZ-ORD
4h 36m1 stop
$153Air Canada
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Wed, Sep 3 - Tue, Sep 9
Air Canada Logo
8:25 pm - 11:08 pmORD-YYZ
1h 43mnonstop
Air Canada Logo
6:15 am - 9:51 amYYZ-ORD
4h 36m1 stop
$154Air Canada
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Wed, Aug 13 - Wed, Aug 13
United Airlines Logo
8:52 am - 5:19 pmORD-YYZ
7h 27m1 stop
United Airlines Logo
9:00 pm - 10:05 pmYYZ-ORD
2h 05mnonstop
$175United Airlines
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Wed, Sep 3 - Tue, Sep 9
United Airlines Logo
1:05 pm - 3:46 pmORD-YYZ
1h 41mnonstop
United Airlines Logo
11:00 am - 12:03 pmYYZ-ORD
2h 03mnonstop
$176United Airlines
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Wed, Aug 13 - Wed, Aug 13
American Airlines Logo
8:20 am - 2:44 pmORD-YYZ
5h 24m1 stop
American Airlines Logo
5:59 pm - 10:49 pmYYZ-ORD
5h 50m1 stop
$196American Airlines
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Wed, Aug 13 - Wed, Aug 13
American Airlines Logo
6:03 am - 2:54 pmORD-YYZ
7h 51m1 stop
American Airlines Logo
5:59 pm - 10:49 pmYYZ-ORD
5h 50m1 stop
$197American Airlines
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Sat, Sep 6 - Sat, Sep 13
Delta Logo
6:17 pm - 10:58 pmMDW-YYZ
3h 41m1 stop
Delta Logo
12:14 pm - 6:35 pmYYZ-MDW
7h 21m1 stop
$234Delta
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Wed, Aug 13 - Wed, Aug 20
Delta Logo
1:08 pm - 5:23 pmMDW-YYZ
3h 15m1 stop
Delta Logo
12:14 pm - 6:37 pmYYZ-MDW
7h 23m1 stop
$247Delta
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Sat, Jul 26 - Mon, Jul 28
WestJet Logo
7:21 pm - 11:59 amMDW-YYZ
15h 38m1 stop
WestJet Logo
6:15 am - 9:42 pmYYZ-MDW
16h 27m1 stop
$289WestJet
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Tue, Aug 5 - Wed, Aug 6
WestJet Logo
9:24 am - 6:34 pmMDW-YYZ
8h 10m1 stop
WestJet Logo
1:20 pm - 9:42 pmYYZ-MDW
9h 22m1 stop
$304WestJet
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Good to know

Low seasonJanuary
High seasonJuly
Cheapest flight$52
Best time to beat the crowds but there is an average 5% increase in price.
Most popular time to fly and prices are also 5% lower on average.
Flight from Chicago O'Hare Airport to Toronto Pearson Airport

When to book flights from Chicago to Hamilton

Are your dates flexible? Find out the best times to travel from Chicago to Hamilton based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

FAQs for booking flights from Chicago to Hamilton

  • Which airports will I be using when flying from Chicago to Hamilton?

    When flying out of Chicago you’ll be using one of these airports: Chicago Midway or Chicago O'Hare Intl. Hamilton does not have its own airport so you’ll be flying into nearby Toronto Pearson Intl airport, which is 32.0 mi away.

  • How long does a flight from Chicago to Hamilton take?

    Direct flights cover the 424 miles separating Chicago and Hamilton in about 1h 39m.

  • How many flights are there between Chicago and Hamilton?

    67 direct flights run between Chicago and Hamilton on a daily basis. On average, there are about 474 departures each week.

  • What’s the cheapest day of the week to fly between Chicago and Hamilton?

    Consider leaving on a Wednesday and avoid Saturdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Wednesdays and the most expensive ones on Fridays.

  • How does KAYAK find such low prices on flights from Chicago to Hamilton?

    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 from Chicago to Hamilton.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Hamilton from 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 from Chicago to Hamilton?

    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 Hamilton with an airline and back to Chicago with another airline.

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

    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 Hamilton from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines provide the cheapest flights from Chicago to Hamilton?

    In the last 72 hours, the cheapest one-way ticket between Chicago and Hamilton found on KAYAK was with Air Canada for $52. Air Canada offered a round-trip connection from $153 and United Airlines from $175.

Top tips for finding cheap flights from Chicago to Hamilton

  • There is no airport in Hamilton. Instead, you’ll be flying into Toronto Pearson Airport when flying between Chicago and Hamilton.
  • The cheapest flight from Chicago to Hamilton was found 68 days before departure, on average.
  • Book at least 2 weeks before departure in order to get a below-average price.
  • High season is considered to be October, November and December. The cheapest month to fly is April.

Reviews of the top 4 airlines serving Chicago to Hamilton

 
Need help choosing which airline to fly with from Chicago to Hamilton? 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 296 reviews
8.7Crew
8.2Boarding
7.6Food
7.0Entertainment
8.1Comfort
Airline reviews

Great! Personable crew. I love that they pour complimentary beer and wine.

10.0 ExcellentSteve, Jun 2025LAS - YOW
Read more Porter Airlines reviews

Great! Personable crew. I love that they pour complimentary beer and wine.

I love the 2 seats per row. More room. The crew were excellent.

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. :)

Overall very good... staff were friendly and helpful. boarding was good for the most part, but a little hard to get our carry-on bags on there.... I think people should be directed to keep their coats and small bags with them until all the carry-ons are loaded, and then, if there is space, they can put their small bags and coats up top.. makes it much easier to put baggage up. i loved the internet feature, but the entertainment was not there unless you have your own Netflix or similar platform. My chair did not recline, which was very annoying, and the arms won't go up near the isle, which makes it tough to get in and out of the seat.

Staff were excellant. Only snacks served. Some turbulence so we were offered Free beer or wine.

The staff is always great. Just the fact that our flight was the only one delayed from Halifax when all other carries were still flying. It happen a year ago out of Toronto as well. All others were flying but our flight got cancelled 1 hr before the time of departure.

The only issue had when i mentioned about comfort was the man beside me was on the larger side and took about 1/3 of my seat where i was pressed against the wall/window of the plane for the trip.

The check-in staff, boarding staff, and flight crew were all very friendly. Really miss the Porter lounge in Ottawa.

Thanks for giving a beer to everyone in the seat infront of me and then telling me that I can’t have one because they are going to land. I guess I need to pay for a seat and then pick one in the very front of the plane

The flight was delayed by more than one hour. The terminal was consequently overcrowded and hot. We lost our car reservation and hit rush hour traffic in Boston, which added two hours stuck in traffic to our trip.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

I do prefer to fly United and have always had excellent service, except for bad weather. Flights are on time and staff is alway curtious and helpful

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

Abandoned me in hallway in a wheelchair… which I asked for because I sprained my back. After waiting in the hallway, I decided to walk the rest of the way since someone respecting me up.. My experience with the united was totally the opposite. Wheelchair access, propped swift and save me a lot of grief. Air Canada totally disorganized.

Bad experience boarding and flight got delayed didn’t make it to my next flight

The food on the trip Toronto to Athens could be better: the chicken didn’t taste good.

Terrible confusion btw air Canada and United. Wasn’t able to change ticket because I had purchased on kayak. Rethinking booking tickets on this site, and will try to avoid United and aircanada going forward.

Conflicting information provided about baggage allowance. One screen said I had a carry on and another said I didnt.

Flight was delayed but the real issue is how long we sat after boarding. Space very limited for an overnight flight and seatbacks didn’t recline so it was almost impossible to sleep.

The staff made sure I was comfortable, moved me to a better seat with more leg room

Somehow, my booking was under my preferred name instead of my legal name so they almost didn’t let me board the plane at LAX. This problem should have been notified to me when I was still in Toronto.

When arriving over 2 hours early to check k in at Charlotte airport I was told I would have to check my carry on ? Apparently the flight was full and may not be room. I was not given a choice and the agent was quite unpleasant about it. I am a senior amd was not comfortable me having to worry about my bag being lost vut it didn’t seem to bother him. There were lots and lots of people of all ages in line when we boarded with carryons and most larger than mine .the rest of my journey was pleasant vut this was totally unacceptable.

The layover was 6 PLUS hours and we were only given a $15.00 voucher. We missed our first activity in Quebec due to the delay.

Everything you need to know for your flight from Chicago to Hamilton

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