$95 Cheap flight deals from Toronto (YTO) to Evanston (CHI)

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This Weekend's Flight Deals from Toronto to Evanston

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, Nov 14 - Tue, Dec 2
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
$320 Roundtrip, found 3 days ago
$320
Roundtrip
found 3 days ago
Select Porter Airlines flight, departing Fri, Nov 14 from Billy Bishop Toronto City to Midway Intl., returning Tue, Dec 2, priced at $320 found 3 days ago
Sat, Nov 15 - Sat, Nov 29
YKF
Region of Waterloo Intl.
ORD
O'Hare Intl.
$338 Roundtrip, found 3 days ago
$338
Roundtrip
found 3 days ago
Select Air Canada flight, departing Sat, Nov 15 from Region of Waterloo Intl. to O'Hare Intl., returning Sat, Nov 29, priced at $338 found 3 days ago
Sat, Nov 15 - Sat, Nov 29
YHM
John C. Munro Hamilton Intl.
ORD
O'Hare Intl.
$338 Roundtrip, found 3 days ago
$338
Roundtrip
found 3 days ago
Select Air Canada flight, departing Sat, Nov 15 from John C. Munro Hamilton Intl. to O'Hare Intl., returning Sat, Nov 29, priced at $338 found 3 days ago
Sat, Nov 15 - Sat, Nov 29
YTZ
Billy Bishop Toronto City
ORD
O'Hare Intl.
$344 Roundtrip, found 3 days ago
$344
Roundtrip
found 3 days ago
Select Air Canada flight, departing Sat, Nov 15 from Billy Bishop Toronto City to O'Hare Intl., returning Sat, Nov 29, priced at $344 found 3 days ago

Airfares from $95 One Way, $146 Round Trip from Toronto to Evanston

Prices starting at $146 for return flights and $95 for one-way flights to Evanston were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Feb 24 - Wed, Mar 4
YTZ
Toronto
MDW
Chicago
$146 Roundtrip, found 6 hours ago
$146
Roundtrip
found 6 hours ago
Select Porter Airlines flight, departing Tue, Feb 24 from Toronto to Chicago, returning Wed, Mar 4, priced at $146 found 6 hours ago
Tue, Jan 13 - Tue, Jan 27
YYZ
Toronto
ORD
Chicago
$153 Roundtrip, found 4 days ago
$153
Roundtrip
found 4 days ago
Select Air Canada flight, departing Tue, Jan 13 from Toronto to Chicago, returning Tue, Jan 27, priced at $153 found 4 days ago
Tue, Dec 9 - Tue, Dec 23
YYZ
Toronto
ORD
Chicago
$167 Roundtrip, found 8 hours ago
$167
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Tue, Dec 9 from Toronto to Chicago, returning Tue, Dec 23, priced at $167 found 8 hours ago
Mon, Jan 19 - Fri, Jan 23
YTZ
Toronto
MDW
Chicago
$177 Roundtrip, found 5 days ago
$177
Roundtrip
found 5 days ago
Select Air Transat flight, departing Mon, Jan 19 from Toronto to Chicago, returning Fri, Jan 23, priced at $177 found 5 days ago
Thu, Dec 4 - Thu, Dec 11
YYZ
Toronto
ORD
Chicago
$200 Roundtrip, found 16 hours ago
$200
Roundtrip
found 16 hours ago
Select United flight, departing Thu, Dec 4 from Toronto to Chicago, returning Thu, Dec 11, priced at $200 found 16 hours ago

Evanston economy flight packages

Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott Chicago Magnificent Mile
3.0-star property

Courtyard by Marriott Chicago Magnificent Mile

8.8/10 Excellent! (1,545 reviews)

Dec 11 - Dec 14

3 night stay

Toronto (YYZ) to Chicago (ORD)

United • Roundtrip • Coach
Price was $462, price is now $350 per person
$350
per person
found 1 day ago
Staff was not helpful and when called for housekeeping they did not show up. Had to call 2 days until they showed up.

Reviewed on Aug 26, 2025

Pendry Chicago
4.5-star property

Pendry Chicago

9.4/10 Exceptional! (1,110 reviews)

Dec 11 - Dec 14

3 night stay

Toronto (YYZ) to Chicago (ORD)

United • Roundtrip • Coach
Price was $679, price is now $501 per person
$501
per person
found 1 day ago
Pendry was historic and great

Reviewed on Jul 5, 2024

The Royal Sonesta Chicago Downtown
4.0-star property

The Royal Sonesta Chicago Downtown

9.4/10 Exceptional! (3,013 reviews)

Dec 20 - Dec 23

3 night stay

Toronto (YYZ) to Chicago (ORD)

United • Non-stop • Coach

Chicago (ORD) to Toronto (YYZ)

American Airlines • Non-stop • Coach
Price was $541, price is now $414 per person
$414
per person
found 16 hours ago
Beautiful, comfortable, large room. Hotel staff phenomenal. Always ready and waiting to help with whatever you needed. The restaurant staff and food were great too. Fantastic hotel. Will always stay there when in Chicago. I have stayed in many hotels and this was my best experience yet.

Reviewed on Oct 19, 2025

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More About Flying To Evanston from Toronto

Route Information for Flights from Toronto to Evanston

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

Toronto to Evanston

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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.