YTZ - CHI

$135 Find Cheap Flights from Toronto Island to Chicago - Compare and Save

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 7/31. 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
$202
Porter Airlines
Tue 9/1Sat 9/5
YTZ - ORD • Non-stop
Cheapest one-way
$135
Porter Airlines
Fri 7/31
YTZ - MDW • Non-stop
Top airlines
Cheapest • from $201 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Air Canada and Porter Airlines. Average duration is 1h 57m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 16% average savings
Most popular
Insights
Insights
Insights
Insights
Avoid delays
Most punctual • 85% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to travel
Cheapest • 43% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
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

Tue, Sep 1 - Sat, Sep 5
Porter Airlines Logo
10:05 am - 11:00 am
YTZ
-
ORD
1h 55mnonstop
Porter Airlines Logo
7:00 am - 9:40 am
ORD
-
YTZ
1h 40mnonstop
$202Porter Airlines
Thu, Jul 9 - Sun, Jul 12
Porter Airlines Logo
8:50 am - 9:40 am
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
3:20 pm - 6:00 pm
MDW
-
YTZ
1h 40mnonstop
$203Porter Airlines
Mon, Sep 14 - Wed, Sep 16
Porter Airlines Logo
8:40 pm - 9:35 pm
YTZ
-
ORD
1h 55mnonstop
Porter Airlines Logo
7:00 am - 9:40 am
ORD
-
YTZ
1h 40mnonstop
$203Porter Airlines
Sun, Jul 12 - Wed, Jul 15
Porter Airlines Logo
8:50 am - 9:40 am
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
3:20 pm - 6:00 pm
MDW
-
YTZ
1h 40mnonstop
$204Porter Airlines
Sun, Sep 6 - Fri, Sep 11
Porter Airlines Logo
1:40 pm - 2:35 pm
YTZ
-
ORD
1h 55mnonstop
Porter Airlines Logo
7:00 am - 9:40 am
ORD
-
YTZ
1h 40mnonstop
$204Porter Airlines
Sat, Jul 25 - Wed, Jul 29
Porter Airlines Logo
8:50 am - 9:40 am
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
3:20 pm - 6:00 pm
MDW
-
YTZ
1h 40mnonstop
$205Porter Airlines
Fri, Sep 4 - Tue, Sep 8
Porter Airlines Logo
1:40 pm - 2:35 pm
YTZ
-
ORD
1h 55mnonstop
Porter Airlines Logo
7:00 am - 9:40 am
ORD
-
YTZ
1h 40mnonstop
$205Porter Airlines
Fri, Jul 10 - Sun, Jul 12
Porter Airlines Logo
8:50 am - 9:40 am
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
3:20 pm - 6:00 pm
MDW
-
YTZ
1h 40mnonstop
$206Porter Airlines
Wed, Sep 16 - Wed, Sep 23
Air Canada Logo
9:30 am - 2:52 pm
YTZ
-
ORD
6h 22m
1 stop
Air Canada Logo
2:00 pm - 4:42 pm
ORD
-
YTZ
1h 42mnonstop
$209Air Canada
Fri, Oct 2 - Mon, Oct 5
Air Canada Logo
7:25 pm - 8:29 pm
YTZ
-
ORD
2h 04mnonstop
Air Canada Logo
8:45 am - 3:50 pm
ORD
-
YTZ
6h 05m
1 stop
$210Air 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.

How much is a round-trip flight from Toronto Island Airport to Chicago?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Toronto Island Airport to Chicago departing in September.

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 $141 on the route between Toronto Island Airport (YTZ) and Chicago Midway Airport (MDW). Over the past month, this route was, on average, 16% cheaper than other Toronto Island Airport-Chicago routes. The most popular route is between Toronto Island Airport (YTZ) and Chicago O'Hare Intl Airport (ORD).

What’s the cheapest day of the week to fly from Toronto Island to Chicago?

The average price of all round-trip flights from Toronto Island Airport to Chicago clicked on KAYAK for each day over the last 12 months.

For Toronto Island to Chicago, Thursday is the cheapest day to fly on average and Monday is the most expensive. Flying from Chicago back to Toronto Island, the best deals are generally found on Friday, with Tuesday being the most expensive.

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 $80 (return) on average. On the other hand, the most expensive months are March and November, where the average cost of round-trip tickets is $189 and $180 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 $263, prices are generally cheapest when you fly direct.

Good to know

Low seasonFebruary
Cheapest flight$135
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly and prices are also 46% 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 5 days, the lowest price for a flight from Toronto Island Airport to Chicago was $135 for a one-way ticket and $201 for a round-trip.

  • Do I need a passport to fly between Toronto Island and Chicago?

    A passport is required to fly from Toronto Island to Chicago.

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

    When flying out of Toronto Island you will be using Toronto Island. You will be landing 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.

  • Which airline alliances offer flights from Toronto Island to Chicago?

    Star Alliance is the only airline alliance operating flights between Toronto Island and Chicago.

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

    There are nonstop 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 travelers 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 $141 or less one-way and $235 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

Air Canada,Porter Airlines

Air Canada,Porter Airlines

Tuesday

Air Canada,Porter Airlines

Air Canada,Porter Airlines

Wednesday

Air Canada,Porter Airlines

Air Canada,Porter Airlines

Thursday

Air Canada,Porter Airlines

Air Canada,Porter Airlines

Friday

Air Canada,Porter Airlines

Air Canada,Porter Airlines

Saturday

Air Canada,Porter Airlines

Air Canada,Porter Airlines

Sunday

Air Canada,Porter Airlines

Air Canada,Porter Airlines

See more direct flights

Direct returns

Chicago to Toronto Island

Monday

Air Canada,Porter Airlines

Air Canada,Porter Airlines

Tuesday

Air Canada,Porter Airlines

Air Canada,Porter Airlines

Wednesday

Air Canada,Porter Airlines

Air Canada,Porter Airlines

Thursday

Air Canada,Porter Airlines

Air Canada,Porter Airlines

Friday

Air Canada,Porter Airlines

Air Canada,Porter Airlines

Saturday

Air Canada,Porter Airlines

Air Canada,Porter Airlines

Sunday

Air Canada,Porter Airlines

Air Canada,Porter Airlines

See more direct 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 441 reviews
7.5Food
8.2Boarding
8.6Crew
6.9Entertainment
8.0Comfort
Airline reviews

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.

6.0 GoodJen, Jan 2026
YTZ - BOS
Read more Porter Airlines reviews

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.

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

Our flight was cancelled at the last minute for maintenance reasons and we were rebooked on a late flight when we purposefully booked our flight to be home early due to work.

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.

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.

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.

Nothing to like about porter. Flight cancelled. No flight back to Boston for 2 days. No hotel accommodation. Terrible. Never again by porter.

Porter is the airline that does care. All trips with Porter have been smooth and relaxing. The extras are the customer appreciation. The others just don’t do that.

The flight was delayed for more than 2 hrs. The plane was changed and staff couldn’t count people so we had to wait even longer while waiting for take off.

Communication at the gate was adequate. Boarding was orderly. Seats are decent, with a reasonable amount of leg room. Flight was only 1.5 hours, so only a modest snack service (short bread cookie or small bag of chips) and a drink (coffee, tea, soda, cup of beer or wine). Exiting the plane was also orderly. Overall the flight was fine and the price reasonable.

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

Information on your arrival and departure airports