$112 Cheap flight deals from Chicago (CHI) to Oakville (YTO)

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This Weekend's Flight Deals from Chicago to Oakville

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, Jun 5 - Sun, Jun 7
ORD
O'Hare Intl.
YTZ
Billy Bishop Toronto City
$400 Roundtrip, found 6 days ago
$400
Roundtrip
found 6 days ago
Select Bargain Flight flight, departing Fri, Jun 5 from O'Hare Intl. to Billy Bishop Toronto City, returning Sun, Jun 7, priced at $400 found 6 days ago
Sun, Jun 7 - Thu, Jun 11
MDW
Midway Intl.
YTZ
Billy Bishop Toronto City
$452 Roundtrip, found 8 hours ago
$452
Roundtrip
found 8 hours ago
Select Porter Airlines flight, departing Sun, Jun 7 from Midway Intl. to Billy Bishop Toronto City, returning Thu, Jun 11, priced at $452 found 8 hours ago
Sun, Jun 7 - Thu, Jun 11
ORD
O'Hare Intl.
YYZ
Pearson Intl.
$685 Roundtrip, found 8 hours ago
$685
Roundtrip
found 8 hours ago
Select WestJet flight, departing Sun, Jun 7 from O'Hare Intl. to Pearson Intl., returning Thu, Jun 11, priced at $685 found 8 hours ago
Sun, Jun 7 - Sat, Jun 20
MDW
Midway Intl.
YYZ
Pearson Intl.
$719 Roundtrip, found 3 days ago
$719
Roundtrip
found 3 days ago
Select WestJet flight, departing Sun, Jun 7 from Midway Intl. to Pearson Intl., returning Sat, Jun 20, priced at $719 found 3 days ago

Airfares from $112 One Way, $243 Round Trip from Chicago to Oakville

Prices starting at $243 for return flights and $112 for one-way flights to Oakville 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, Sep 25 - Sun, Sep 27
ORD
Chicago
YTZ
Toronto
$243 Roundtrip, found 18 hours ago
$243
Roundtrip
found 18 hours ago
Select Porter Airlines flight, departing Fri, Sep 25 from Chicago to Toronto, returning Sun, Sep 27, priced at $243 found 18 hours ago
Tue, Jun 16 - Thu, Jun 18
ORD
Chicago
YYZ
Toronto
$258 Roundtrip, found 7 hours ago
$258
Roundtrip
found 7 hours ago
Select United flight, departing Tue, Jun 16 from Chicago to Toronto, returning Thu, Jun 18, priced at $258 found 7 hours ago
Fri, Sep 25 - Sun, Sep 27
ORD
Chicago
YTZ
Toronto
$267 Roundtrip, found 18 hours ago
$267
Roundtrip
found 18 hours ago
Select Air Canada flight, departing Fri, Sep 25 from Chicago to Toronto, returning Sun, Sep 27, priced at $267 found 18 hours ago
Thu, Sep 3 - Wed, Sep 9
ORD
Chicago
YTZ
Toronto
$267 Roundtrip, just found
$267
Roundtrip
just found
Select Porter Airlines flight, departing Thu, Sep 3 from Chicago to Toronto, returning Wed, Sep 9, priced at $267 just found
Sat, Jun 20 - Mon, Jun 22
MDW
Chicago
YTZ
Toronto
$269 Roundtrip, just found
$269
Roundtrip
just found
Select Porter Airlines flight, departing Sat, Jun 20 from Chicago to Toronto, returning Mon, Jun 22, priced at $269 just found

Oakville economy flight packages

Price found within the past 48 hours. Click for updated prices.
Finlay House Bed and Breakfast Niagara - on - the - Lake
3.5-star property

Finlay House Bed and Breakfast Niagara - on - the - Lake

9.4/10 Exceptional! (237 reviews)

Jul 17 - Jul 20

3 night stay

Chicago (CHI) to Toronto (YYZ)

Air Canada • Coach

Toronto (YYZ) to Chicago (CHI)

Delta • Coach
Price was $1,112, price is now $814 per person
$814
per person
found 1 day ago
Hotel Riu Plaza Toronto
4.0-star property

Hotel Riu Plaza Toronto

9.2/10 Wonderful! (3,296 reviews)

Jul 21 - Jul 25

4 night stay

Chicago (CHI) to Toronto (YYZ)

American Airlines • Coach

Toronto (YYZ) to Chicago (CHI)

Air Canada • Coach
Price was $1,771, price is now $1,084 per person
$1,084
per person
found 1 day ago
Excellent location with lots of dining options within a couple blocks and a 10-minute walk to the CN Tower. The room was decent. Could use a night light in the bathroom. If you need to use the bathroom in the middle of the night, your only options are either pitch blackness or every light in the bathroom. Despite a lot of people staying there, the elevators were quick and usually empty. They have a breakfast buffet (included, free), but we found the food quality to be inconsistent over our three meals. One morning the scrambled eggs were delicious, the next they had the texture of styrofoam. One morning the pork sausage was so undercooked as to be unsafe to eat. But there are lots of food options, so you can always find something good to eat. Ordered a pizza at the bar, and that was very good. Room had a mini-fridge but no microwave.

Reviewed on May 26, 2026

1 Hotel Toronto
5.0-star property

1 Hotel Toronto

9.6/10 Exceptional! (724 reviews)

Jul 24 - Jul 28

4 night stay

Chicago (CHI) to Toronto (YYZ)

Porter Airlines • Coach

Toronto (YYZ) to Chicago (CHI)

Air Canada • Coach
Price was $1,810, price is now $1,306 per person
$1,306
per person
found 3 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 Oakville from Chicago

Route Information for Flights from Chicago to Oakville

Origin Airport IATA Code
CHI
Destination Airport IATA Code
YTO
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Oakville

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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.