$129 Cheap flight deals from Toronto (YTO) to Orland Park (CHI)

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This Weekend's Flight Deals from Toronto to Orland Park

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.

Sat, Jul 11 - Sat, Jul 18
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
$301 Roundtrip, found 8 hours ago
$301
Roundtrip
found 8 hours ago
Select Porter Airlines flight, departing Sat, Jul 11 from Billy Bishop Toronto City to Midway Intl., returning Sat, Jul 18, priced at $301 found 8 hours ago
Fri, Jul 10 - Sun, Jul 12
YYZ
Pearson Intl.
ORD
O'Hare Intl.
$432 Roundtrip, found 2 hours ago
$432
Roundtrip
found 2 hours ago
Select Porter Airlines flight, departing Fri, Jul 10 from Pearson Intl. to O'Hare Intl., returning Sun, Jul 12, priced at $432 found 2 hours ago
Sun, Jul 12 - Mon, Jul 27
YYZ
Pearson Intl.
MDW
Midway Intl.
$599 Roundtrip, found 2 days ago
$599
Roundtrip
found 2 days ago
Select WestJet flight, departing Sun, Jul 12 from Pearson Intl. to Midway Intl., returning Mon, Jul 27, priced at $599 found 2 days ago
Sat, Jul 11 - Mon, Jul 13
YTZ
Billy Bishop Toronto City
ORD
O'Hare Intl.
$779 Roundtrip, found 3 days ago
$779
Roundtrip
found 3 days ago
Select Porter Airlines flight, departing Sat, Jul 11 from Billy Bishop Toronto City to O'Hare Intl., returning Mon, Jul 13, priced at $779 found 3 days ago

Airfares from $129 One Way, $214 Round Trip from Toronto to Orland Park

Prices starting at $214 for return flights and $129 for one-way flights to Orland Park were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Sep 10 - Wed, Sep 16
YTZ
Toronto
ORD
Chicago
$214 Roundtrip, just found
$214
Roundtrip
just found
Select Porter Airlines flight, departing Thu, Sep 10 from Toronto to Chicago, returning Wed, Sep 16, priced at $214 just found
Fri, Oct 16 - Mon, Oct 19
YTZ
Toronto
ORD
Chicago
$214 Roundtrip, found 4 days ago
$214
Roundtrip
found 4 days ago
Select Air Canada flight, departing Fri, Oct 16 from Toronto to Chicago, returning Mon, Oct 19, priced at $214 found 4 days ago
Fri, Sep 11 - Fri, Sep 18
YKF
Kitchener
ORD
Chicago
$222 Roundtrip, found 1 day ago
$222
Roundtrip
found 1 day ago
Select Air Canada flight, departing Fri, Sep 11 from Kitchener to Chicago, returning Fri, Sep 18, priced at $222 found 1 day ago
Sun, Oct 18 - Sun, Oct 25
YYZ
Toronto
ORD
Chicago
$223 Roundtrip, found 2 days ago
$223
Roundtrip
found 2 days ago
Select Air Canada flight, departing Sun, Oct 18 from Toronto to Chicago, returning Sun, Oct 25, priced at $223 found 2 days ago
Sat, Sep 19 - Sat, Oct 3
YYZ
Toronto
ORD
Chicago
$223 Roundtrip, found 2 days ago
$223
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Sep 19 from Toronto to Chicago, returning Sat, Oct 3, priced at $223 found 2 days ago

Orland Park economy flight packages

Price found within the past 48 hours. Click for updated prices.
Omni Chicago Hotel
4.5-star property

Omni Chicago Hotel

9.2/10 Wonderful! (1,821 reviews)

Aug 28 - Aug 30

2 night stay

Toronto (YTO) to Chicago (ORD)

Air Canada • Roundtrip • Coach
Price was $789, price is now $572 per person
$572
per person
found 2 hours ago
The room was very clean and spacious. Very helpful staff. We were able to get into our room early and get a later checkout due to our flights. The Doorman were also very courteous and helpful. Great location!

Reviewed on Jul 3, 2026

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (4,518 reviews)

Aug 28 - Aug 30

2 night stay

Toronto (YTO) to Chicago (ORD)

Air Canada • Roundtrip • Coach
Save 100% on your flight
Price was $904, price is now $641 per person
$641
per person
found 2 hours ago
Great location and the rooftop bar was a bonus.

Reviewed on Jul 3, 2026

Level Chicago - River North
4.0-star property

Level Chicago - River North

9.2/10 Wonderful! (1,013 reviews)

Aug 28 - Aug 30

2 night stay

Toronto (YTO) to Chicago (ORD)

Air Canada • Roundtrip • Coach
Price was $778, price is now $594 per person
$594
per person
found 2 hours ago
This location is ideal for families. The amenities provided are exceptional, scoring a perfect ten out of ten. It offers ample space for a family, including two bathrooms, which was greatly appreciated by my children. The property is well-equipped to ensure a comfortable stay. My only reservation pertains to its distance from Michigan Avenue and the Riverwalk, necessitating a vehicle to access these popular destinations. Otherwise, the experience was flawless.

Reviewed on Jul 2, 2026

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More About Flying To Orland Park from Toronto

Route Information for Flights from Toronto to Orland Park

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

Toronto to Orland Park

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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.