$54 Cheap flight deals from Chicago (CHI) to Toronto Islands (YTO)

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This Weekend's Flight Deals from Chicago to Toronto Islands

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Aug 8 - Mon, Aug 18
MDW
Midway Intl.
YTZ
Billy Bishop Toronto City
$356 Roundtrip, found 6 days ago
$356
Roundtrip
found 6 days ago
Select Porter Airlines flight, departing Fri, Aug 8 from Midway Intl. to Billy Bishop Toronto City, returning Mon, Aug 18, priced at $356 found 6 days ago
Fri, Aug 8 - Mon, Aug 11
ORD
O'Hare Intl.
YKF
Region of Waterloo Intl.
$434 Roundtrip, found 6 days ago
$434
Roundtrip
found 6 days ago
Select Bargain Flight flight, departing Fri, Aug 8 from O'Hare Intl. to Region of Waterloo Intl., returning Mon, Aug 11, priced at $434 found 6 days ago
Fri, Aug 8 - Mon, Aug 11
ORD
O'Hare Intl.
YHM
John C. Munro Hamilton Intl.
$435 Roundtrip, found 6 days ago
$435
Roundtrip
found 6 days ago
Select Air Canada flight, departing Fri, Aug 8 from O'Hare Intl. to John C. Munro Hamilton Intl., returning Mon, Aug 11, priced at $435 found 6 days ago
Sun, Aug 10 - Wed, Aug 13
MDW
Midway Intl.
YYZ
Pearson Intl.
$465 Roundtrip, found 5 days ago
$465
Roundtrip
found 5 days ago
Select Delta flight, departing Sun, Aug 10 from Midway Intl. to Pearson Intl., returning Wed, Aug 13, priced at $465 found 5 days ago

Airfares from $54 One Way, $158 Round Trip from Chicago to Toronto Islands

Prices starting at $158 for return flights and $54 for one-way flights to Toronto Islands were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Nov 7 - Tue, Nov 11
ORD
Chicago
YYZ
Toronto
$158 Roundtrip, found 4 hours ago
$158
Roundtrip
found 4 hours ago
Select Air Canada flight, departing Fri, Nov 7 from Chicago to Toronto, returning Tue, Nov 11, priced at $158 found 4 hours ago
Fri, Nov 7 - Tue, Nov 11
ORD
Chicago
YYZ
Toronto
$167 Roundtrip, found 4 hours ago
$167
Roundtrip
found 4 hours ago
Select United flight, departing Fri, Nov 7 from Chicago to Toronto, returning Tue, Nov 11, priced at $167 found 4 hours ago
Mon, Nov 24 - Thu, Nov 27
ORD
Chicago
YYZ
Toronto
$167 Roundtrip, found 1 hour ago
$167
Roundtrip
found 1 hour ago
Select Air Canada flight, departing Mon, Nov 24 from Chicago to Toronto, returning Thu, Nov 27, priced at $167 found 1 hour ago
Fri, Nov 7 - Tue, Nov 11
ORD
Chicago
YYZ
Toronto
$184 Roundtrip, found 4 hours ago
$184
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Fri, Nov 7 from Chicago to Toronto, returning Tue, Nov 11, priced at $184 found 4 hours ago
Sun, Aug 24 - Wed, Aug 27
MDW
Chicago
YTZ
Toronto
$187 Roundtrip, found 6 days ago
$187
Roundtrip
found 6 days ago
Select Porter Airlines flight, departing Sun, Aug 24 from Chicago to Toronto, returning Wed, Aug 27, priced at $187 found 6 days ago

Toronto Islands economy flight packages

Price found within the past 48 hours. Click for updated prices.
Sheraton Toronto Airport Hotel & Conference Centre
4.0-star property

Sheraton Toronto Airport Hotel & Conference Centre

8.6/10 Excellent! (1,050 reviews)

Sep 26 - Sep 30

4 night stay

Chicago (CHI) to Toronto (YYZ)

Air Canada • Coach

Toronto (YYZ) to Chicago (CHI)

American Airlines • Coach
per person
found 1 day ago
No affordable restaurants near the hotel.

Reviewed on Jun 28, 2025

Sterling Inn & Spa - an Ontario's Finest Inn
4.0-star property

Sterling Inn & Spa - an Ontario's Finest Inn

9.6/10 Exceptional! (1,927 reviews)

Sep 11 - Sep 14

3 night stay

Chicago (CHI) to Toronto (YYZ)

American Airlines • Non-stop • Coach

Toronto (YYZ) to Chicago (CHI)

United • Non-stop • Coach
Save 100% on your flight
per person
found 1 day ago
I liked this property and felt like it was a hidden gem. The staff and spa services were really good. The restaurant was also great. What I did not like was that we chose the hotel for the spa services and relaxation. For 3 of our 4 nights there, we had guests overhead with children that were really loud and noisy and we couldn’t sleep well. We ended up buying ear plugs, but then we couldn’t hear room service at our door in the morning. I think there needs to be a mindfulness of where guests with children are placed. That would be the only reason why I would not use this particular place again.

Reviewed on Jul 5, 2025

1 Hotel Toronto
5.0-star property

1 Hotel Toronto

9.4/10 Exceptional! (565 reviews)

Sep 12 - Sep 14

2 night stay

Chicago (CHI) to Toronto (YYZ)

American Airlines • Non-stop • Coach

Toronto (YYZ) to Chicago (CHI)

Porter Airlines • Non-stop • Coach
Save 100% on your flight
per person
found 4 hours ago
Very unique, warm and cozy décor. Very pleasant and accommodating staff. Enjoyed ourselves immensely even though it was for business.

Reviewed on Oct 31, 2021

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More About Flying To Toronto Islands from Chicago

Route Information for Flights from Chicago to Toronto Islands

Origin Airport IATA Code
CHI
Destination Airport IATA Code
YTO
Distance
436 mi
Direct Flight Airlines
American Airlines, Qatar Airways, Air Canada, JAL, EgyptAir, Copa Airlines, Air New Zealand, United Airlines, Alaska Airlines, Qantas, Finnair, Royal Jordanian, Iberia, ANA, British Airways
Earliest Flight Arrival
1:58PM UTC
Latest Flight Arrival
3:58AM UTC

Chicago to Toronto Islands

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.