$98 Cheap flight deals from Toronto (YTO) to Des Plaines (CHI)

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This Weekend's Flight Deals from Toronto to Des Plaines

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 24 - Wed, Sep 3
YKF
Region of Waterloo Intl.
ORD
O'Hare Intl.
$367 Roundtrip, found 6 days ago
$367
Roundtrip
found 6 days ago
Select Air Canada flight, departing Sun, Aug 24 from Region of Waterloo Intl. to O'Hare Intl., returning Wed, Sep 3, priced at $367 found 6 days ago
Sat, Aug 23 - Tue, Sep 9
YYZ
Pearson Intl.
ORD
O'Hare Intl.
$395 Roundtrip, found 1 day ago
$395
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Sat, Aug 23 from Pearson Intl. to O'Hare Intl., returning Tue, Sep 9, priced at $395 found 1 day ago
Sat, Aug 23 - Wed, Sep 3
YTZ
Billy Bishop Toronto City
ORD
O'Hare Intl.
$498 Roundtrip, found 8 hours ago
$498
Roundtrip
found 8 hours ago
Select Bargain Flight flight, departing Sat, Aug 23 from Billy Bishop Toronto City to O'Hare Intl., returning Wed, Sep 3, priced at $498 found 8 hours ago
Sun, Aug 24 - Wed, Sep 3
YHM
John C. Munro Hamilton Intl.
ORD
O'Hare Intl.
$575 Roundtrip, found 8 hours ago
$575
Roundtrip
found 8 hours ago
Select Air Canada flight, departing Sun, Aug 24 from John C. Munro Hamilton Intl. to O'Hare Intl., returning Wed, Sep 3, priced at $575 found 8 hours ago

Airfares from $98 One Way, $147 Round Trip from Toronto to Des Plaines

Prices starting at $147 for return flights and $98 for one-way flights to Des Plaines 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 - Mon, Nov 10
YYZ
Toronto
ORD
Chicago
$147 Roundtrip, found 5 hours ago
$147
Roundtrip
found 5 hours ago
Select Air Canada flight, departing Fri, Nov 7 from Toronto to Chicago, returning Mon, Nov 10, priced at $147 found 5 hours ago
Fri, Nov 7 - Mon, Nov 10
YYZ
Toronto
ORD
Chicago
$147 Roundtrip, found 5 hours ago
$147
Roundtrip
found 5 hours ago
Select United flight, departing Fri, Nov 7 from Toronto to Chicago, returning Mon, Nov 10, priced at $147 found 5 hours ago
Fri, Nov 7 - Mon, Nov 10
YYZ
Toronto
ORD
Chicago
$160 Roundtrip, found 5 hours ago
$160
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Fri, Nov 7 from Toronto to Chicago, returning Mon, Nov 10, priced at $160 found 5 hours ago
Fri, Sep 12 - Sun, Sep 14
YTZ
Toronto
MDW
Chicago
$197 Roundtrip, found 1 hour ago
$197
Roundtrip
found 1 hour ago
Select Porter Airlines flight, departing Fri, Sep 12 from Toronto to Chicago, returning Sun, Sep 14, priced at $197 found 1 hour ago
Sat, Oct 11 - Sun, Oct 12
YYZ
Toronto
ORD
Chicago
$202 Roundtrip, found 8 hours ago
$202
Roundtrip
found 8 hours ago
Select Delta flight, departing Sat, Oct 11 from Toronto to Chicago, returning Sun, Oct 12, priced at $202 found 8 hours ago

Des Plaines economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Wade
4.5-star property

The Wade

8.2/10 Very Good! (1,156 reviews)

Sep 29 - Oct 6

7 night stay

Toronto (YTZ) to Chicago (ORD)

Air Canada • Roundtrip • Coach
Save 100% on your flight
Price was $1,591, price is now $911 per person
$911
per person
found 1 day ago
I was pleasantly surprised on how nice the hotel was. Room decor was modern and very functional. Beds were amazing. Furniture edges were cheaped here and there; that would be my only complain. Heads up - be ready to pay for $85 parking per day. Do not park overnight in the area, you will get towed. The breakfast was amazing. Two vouchers were for 4 people.

Reviewed on Aug 10, 2025

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (2,270 reviews)

Sep 29 - Oct 6

7 night stay

Toronto (YTZ) to Chicago (ORD)

Air Canada • Roundtrip • Coach
Save 100% on your flight
Price was $2,321, price is now $1,259 per person
$1,259
per person
found 1 day ago
Good until next time

Reviewed on Aug 16, 2025

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,679 reviews)

Sep 29 - Oct 6

7 night stay

Toronto (YTZ) to Chicago (ORD)

Air Canada • Roundtrip • Coach
Save 100% on your flight
Price was $2,964, price is now $1,666 per person
$1,666
per person
found 1 day ago
I recently stayed at the Trump International Hotel & Tower Chicago, and it exceeded every expectation. From the moment I arrived, I was impressed by the warmth and professionalism of the staff. Check-in was smooth and welcoming, and I was personally escorted to my room—which turned out to be nothing short of spectacular. The room itself was spacious, immaculately clean, and beautifully designed with modern touches and classic elegance. Floor-to-ceiling windows offered breathtaking views of the Chicago River and city skyline. The kitchenette was a nice bonus and made the room feel more like a luxury apartment than a typical hotel room. The service throughout my stay was consistently excellent—attentive without being overbearing. Every request was handled promptly and with a smile, and it was clear that the staff genuinely cared about making my stay enjoyable. I also had the chance to dine at Rebar, and the food and views were equally impressive. The atmosphere was relaxed yet refined, and it made for a perfect evening. The location is ideal—walking distance to the Magnificent Mile, Millennium Park, and plenty of restaurants and shops. Despite being in the heart of downtown, the hotel felt like a peaceful retreat above the city. Whether you're visiting Chicago for business or pleasure, I highly recommend the Trump International Hotel. It’s a standout experience in every way—luxury, location, service, and comfort all rolled into one.

Reviewed on Aug 14, 2025

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More About Flying To Des Plaines from Toronto

Route Information for Flights from Toronto to Des Plaines

Origin Airport IATA Code
YTO
Destination Airport IATA Code
CHI
Distance
436 mi
Direct Flight Airlines
American Airlines, Qatar Airways, JAL, Air Canada, EgyptAir, Copa Airlines, Air New Zealand, United Airlines, Alaska Airlines, Qantas, Finnair, Royal Jordanian, Iberia, ANA, British Airways
Earliest Flight Arrival
11:26AM UTC
Latest Flight Arrival
2:07AM UTC

Toronto to Des Plaines

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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.