$59 Cheap flight deals from Chicago (CHI) to Central Ontario (YTO)

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This Weekend's Flight Deals from Chicago to Central Ontario

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.

Sun, Aug 10 - Wed, Aug 13
MDW
Midway Intl.
YTZ
Billy Bishop Toronto City
$525 Roundtrip, found 2 days ago
$525
Roundtrip
found 2 days ago
Select Air Transat flight, departing Sun, Aug 10 from Midway Intl. to Billy Bishop Toronto City, returning Wed, Aug 13, priced at $525 found 2 days ago
Sat, Aug 9 - Sun, Aug 31
MDW
Midway Intl.
YYZ
Pearson Intl.
$622 Roundtrip, found 1 day ago
$622
Roundtrip
found 1 day ago
Select WestJet flight, departing Sat, Aug 9 from Midway Intl. to Pearson Intl., returning Sun, Aug 31, priced at $622 found 1 day ago
Fri, Aug 8 - Mon, Aug 11
ORD
O'Hare Intl.
YTZ
Billy Bishop Toronto City
$627 Roundtrip, found 6 days ago
$627
Roundtrip
found 6 days ago
Select Air Canada flight, departing Fri, Aug 8 from O'Hare Intl. to Billy Bishop Toronto City, returning Mon, Aug 11, priced at $627 found 6 days ago
Sat, Aug 9 - Sat, Aug 16
ORD
O'Hare Intl.
YYZ
Pearson Intl.
$761 Roundtrip, found 21 hours ago
$761
Roundtrip
found 21 hours ago
Select WestJet flight, departing Sat, Aug 9 from O'Hare Intl. to Pearson Intl., returning Sat, Aug 16, priced at $761 found 21 hours ago

Airfares from $59 One Way, $158 Round Trip from Chicago to Central Ontario

Prices starting at $158 for return flights and $59 for one-way flights to Central Ontario 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 19 hours ago
$158
Roundtrip
found 19 hours ago
Select Air Canada flight, departing Fri, Nov 7 from Chicago to Toronto, returning Tue, Nov 11, priced at $158 found 19 hours ago
Fri, Nov 7 - Tue, Nov 11
ORD
Chicago
YKF
Kitchener
$167 Roundtrip, found 19 hours ago
$167
Roundtrip
found 19 hours ago
Select Air Canada flight, departing Fri, Nov 7 from Chicago to Kitchener, returning Tue, Nov 11, priced at $167 found 19 hours ago
Fri, Nov 7 - Tue, Nov 11
ORD
Chicago
YHM
Hamilton
$167 Roundtrip, found 19 hours ago
$167
Roundtrip
found 19 hours ago
Select Air Canada flight, departing Fri, Nov 7 from Chicago to Hamilton, returning Tue, Nov 11, priced at $167 found 19 hours ago
Fri, Nov 7 - Tue, Nov 11
ORD
Chicago
YYZ
Toronto
$167 Roundtrip, found 19 hours ago
$167
Roundtrip
found 19 hours ago
Select United flight, departing Fri, Nov 7 from Chicago to Toronto, returning Tue, Nov 11, priced at $167 found 19 hours ago
Fri, Nov 7 - Tue, Nov 11
ORD
Chicago
YYZ
Toronto
$185 Roundtrip, found 19 hours ago
$185
Roundtrip
found 19 hours ago
Select American Airlines flight, departing Fri, Nov 7 from Chicago to Toronto, returning Tue, Nov 11, priced at $185 found 19 hours ago

Central Ontario economy flight packages

Price found within the past 48 hours. Click for updated prices.
Toronto Marriott City Centre Hotel
4.0-star property

Toronto Marriott City Centre Hotel

9.2/10 Wonderful! (1,390 reviews)

Sep 20 - Sep 23

3 night stay

Chicago (CHI) to Toronto (YYZ)

Air Canada • Non-stop • Coach

Toronto (YYZ) to Chicago (CHI)

Porter Airlines • Non-stop • Coach
Save 100% on your flight
per person
found 1 day ago
The hotel itself is getting pretty run down, the carpet and wallpaper is looking rather rough. The continental breakfast was suppose to be included in my stay but I required a room change and the free breakfast was no longer included.

Reviewed on Mar 15, 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 12 - Sep 15

3 night stay

Chicago (CHI) to Toronto (YYZ)

American Airlines • Coach

Toronto (YYZ) to Chicago (CHI)

Porter Airlines • 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 1 day 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 Central Ontario from Chicago

Route Information for Flights from Chicago to Central Ontario

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

Chicago to Central Ontario

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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.