YTZ - CHI

C$ 170 Find Cheap Flights from Toronto Island to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Toronto Island to Chicago departing on 29/4. 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
1 adult, Economy, 0 bags

KAYAK searches 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 in flight searches from Toronto to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Toronto to Chicago, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
C$ 264
Porter Airlines
Sat 2/5Sat 9/5
YTZ - MDW • Direct
Cheapest one-way flights
C$ 170
Typical prices: C$ 160-C$ 227
Porter Airlines
Wed 29/4
YTZ - MDW • Direct
Top airlines
Cheapest • from C$ 266 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Direct flights
You can fly direct with Porter Airlines. Average duration is 1h 50m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 24% average savings
Most popular
Insights
Insights
Insights
Insights
Avoid delays
Most punctual • 86% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to travel
Cheapest • 31% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches hundreds of sites at once to find you the best travel deals.
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Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Toronto Island to Chicago (YTZ-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Toronto Island to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Toronto Island to Chicago

Sat, 2 May - Sat, 9 May
Porter Airlines Logo
8:50 a.m. - 9:40 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
10:25 a.m. - 1:05 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 264Porter Airlines
Wed, 2 Sep - Mon, 7 Sep
Porter Airlines Logo
10:05 a.m. - 11:00 a.m.
YTZ
-
ORD
1h 55mdirect
Porter Airlines Logo
7:00 a.m. - 9:40 a.m.
ORD
-
YTZ
1h 40mdirect
C$ 266Porter Airlines
Thu, 30 Apr - Fri, 1 May
Porter Airlines Logo
9:25 a.m. - 10:15 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
3:20 p.m. - 6:00 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 270Porter Airlines
Mon, 20 Apr - Mon, 27 Apr
Porter Airlines Logo
9:25 a.m. - 10:15 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
11:00 a.m. - 1:42 p.m.
MDW
-
YTZ
1h 42mdirect
C$ 271Porter Airlines
Thu, 23 Apr - Mon, 27 Apr
Porter Airlines Logo
9:25 a.m. - 10:15 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
11:00 a.m. - 1:42 p.m.
MDW
-
YTZ
1h 42mdirect
C$ 272Porter Airlines
Sat, 4 Apr - Tue, 7 Apr
Porter Airlines Logo
11:20 a.m. - 12:10 p.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
11:00 a.m. - 1:42 p.m.
MDW
-
YTZ
1h 42mdirect
C$ 274Porter Airlines
Tue, 7 Apr - Wed, 8 Apr
Porter Airlines Logo
9:25 a.m. - 10:15 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
11:00 a.m. - 1:42 p.m.
MDW
-
YTZ
1h 42mdirect
C$ 275Porter Airlines
Fri, 10 Apr - Sun, 12 Apr
Porter Airlines Logo
2:30 p.m. - 3:20 p.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
4:05 p.m. - 6:47 p.m.
MDW
-
YTZ
1h 42mdirect
C$ 277Porter Airlines
Mon, 13 Apr - Tue, 14 Apr
Multiple Airlines Logo
11:40 a.m. - 12:22 a.m.
YTZ
-
ORD
13h 42m
2 stops
Multiple Airlines Logo
6:01 p.m. - 10:25 a.m.
ORD
-
YTZ
15h 24m
1 stop
C$ 329Multiple Airlines
Wed, 9 Sep - Sun, 13 Sep
Air Canada Logo
7:20 p.m. - 8:16 p.m.
YTZ
-
ORD
1h 56mdirect
Air Canada Logo
7:25 a.m. - 10:06 a.m.
ORD
-
YTZ
1h 41mdirect
C$ 330Air Canada
Booking Insights

KAYAK's insights & trends for Toronto Island to Chicago flights

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

What is the cheapest Toronto Island Airport to Chicago flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Toronto Island Airport to Chicago costs C$ 223 on the route between Toronto Island Airport (YTZ) and Chicago Midway Airport (MDW). Over the past month, this route was, on average, 24% cheaper than other Toronto Island Airport-Chicago routes. It is also the most popular route.

What is the cheapest month to fly from Toronto Island Airport to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Toronto Island Airport 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 from Toronto Island Airport to Chicago is August, where tickets cost C$ 230 (return) on average. On the other hand, the most expensive months are October and December, where the average cost of round-trip tickets is C$ 442 and C$ 386 respectively.

Can I save money by flying with a layover from Toronto Island Airport to Chicago?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of C$ 376, prices are generally cheapest when you fly direct.

Good to know

Low seasonMarch
Cheapest flightC$ 170
Best time to beat the crowds but there is an average 12% increase in price.
Most popular time to fly and prices are also 31% lower on average.
Flight from Toronto Island to Chicago Midway Airport

When to book flights from Toronto Island to Chicago

Are your dates flexible? Find out the best times to travel from Toronto Island 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. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Toronto Island to Chicago flights

  • What is the cheapest flight from Toronto Island Airport to Chicago?

    In the last 3 days, the lowest price for a flight from Toronto Island Airport to Chicago was C$ 170 for a one-way ticket and C$ 266 for a round-trip.

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

    Toronto Island is served by only 1 airport and there are 2 airports in Chicago. You will leave Toronto Island from Toronto Island and you will be arriving in Chicago at one of these airports: Chicago Midway or Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from Toronto Island to Chicago?

    Air Canada, United Airlines, and American Airlines offer inflight Wi-Fi service on the Toronto Island to Chicago flight route.

  • Which aircraft models fly most regularly from Toronto Island to Chicago?

    The De Havilland (Bombardier) DHC-8-400 Dash 8Q is the aircraft model that flies most regularly on the Toronto Island to Chicago flight route.

  • On which days can I fly direct from Toronto Island to Chicago?

    There are direct flights from Toronto Island to Chicago on a daily basis.

  • How does KAYAK find such low prices on flights from Toronto Island 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 from Toronto Island to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Toronto Island is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Toronto Island 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 to Toronto Island with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Toronto Island 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 from Toronto Island up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Toronto Island Airport to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for C$ 643 or less round-trip.

Prefer to fly direct from Toronto Island to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Toronto Island to Chicago.
Find which airlines fly direct from Toronto Island Airport to Chicago, which days they fly and book direct flights.

Direct departures

Toronto Island to Chicago

Monday

Porter Airlines

Porter Airlines

Tuesday

Porter Airlines

Porter Airlines

Wednesday

Porter Airlines

Porter Airlines

Thursday

Porter Airlines

Porter Airlines

Friday

Porter Airlines

Porter Airlines

Saturday

Porter Airlines

Porter Airlines

Sunday

Porter Airlines

Porter Airlines

See more nonstop flights

Direct returns

Chicago to Toronto Island

Monday

Porter Airlines

Porter Airlines

Tuesday

Porter Airlines

Porter Airlines

Wednesday

Porter Airlines

Porter Airlines

Thursday

Porter Airlines

Porter Airlines

Friday

Porter Airlines

Porter Airlines

Saturday

Porter Airlines

Porter Airlines

Sunday

Porter Airlines

Porter Airlines

See more nonstop flights

Reviews of the top airline flying from Toronto Island to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Toronto to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Toronto Island 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.
8.0
Porter AirlinesOverall score based on 424 reviews
8.0Comfort
8.6Crew
7.6Food
7.0Entertainment
8.2Boarding
Airline reviews

Even tho the flight was a bit delayed the team was apologetic. Everyone was friendly and efficient.

10.0 ExcellentDeanna, Mar 2026
YWG - YOW
Read more Porter Airlines reviews

Even tho the flight was a bit delayed the team was apologetic. Everyone was friendly and efficient.

The Flight took off 2hrs late because there was no pilot showing up when the flight was ready to board.. Though the cabin crew was present and had prepared the plane, the FO turned around after 15 min and went away. A crew to fly the plane finally arrived over an hour later and we were able to board 1h30 min later than planned time... until everything was loaded, we left 2h late from the gate. This was a small plane, so don't expect any Entertainment... Wi-Fi access on board would work, but took an awful amount of time to figure out and get it work (I'm an IT person). Flying as VIPorter customer, I was expecting at least some warm meal, but everything served was just cold.. except the coffee maybe. Even in so-called VIPorter seats, space is cramped and trays are so tiny, you can barely setup your food. Flight caught up during the coast-to-coast crossing and was able to recoup about 45 min from the delay.. still arrived very late in Vancouver and had to wait a long time to get our registered bags. Let's see how the return flight will be in a few days..

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.

Due to a known technical error that Porter has not fixed in over a year, I was unable to check in the children on my reservation online and had to do it at the airport. Upon check in, there were no seats together, which was an issue as we had young children. The gate agent did manage to seat us together by moving other passengers, which was appreciated, but the other passengers were never informed, leading to confusion and delay upon boarding. The flight was over an hour late; no explanation or apology was ever issued. The bags on Porter take a long time to arrive--over half an hour at Hamilton on my inbound flight, and not much better on my return to Edmonton.

On my e-boarding pass it shows free wifi, yet the plane I was on didn’t have wifi. Please remove false advertising from your website and boarding passes

3.5 hr delay for a 1 hr work flight. No information as to why the delay until 20 mins before boarding.

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

Smaller plane. Food and bar service for free is amazing. Drinks were in glass not plastic cups.

Poor landing as we overshot the runway and had to re land the plane. Lost both of my luggage not found as of yet. Had to pay extra money for my luggage in USD, now great my luggage is gone. Will not fly with Porter again.

This flight to St. Johns was really good. Boarding was a breeze. We left spot on time. Seats were actually pretty good. Recliner further than I expected. Three more flights to go we will see if this is the status quo for Porter.👍

Everything you need to know for your flight from Toronto Island to Chicago

Information on your arrival and departure airports