$140 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.

Sun, Nov 1 - Tue, Dec 15
YYZ
Pearson Intl.
ORD
O'Hare Intl.
$508 Roundtrip, found 1 day ago
$508
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Sun, Nov 1 from Pearson Intl. to O'Hare Intl., returning Tue, Dec 15, priced at $508 found 1 day ago
Fri, Oct 30 - Tue, Nov 3
YTZ
Billy Bishop Toronto City
ORD
O'Hare Intl.
$553 Roundtrip, found 13 hours ago
$553
Roundtrip
found 13 hours ago
Select Porter Airlines flight, departing Fri, Oct 30 from Billy Bishop Toronto City to O'Hare Intl., returning Tue, Nov 3, priced at $553 found 13 hours ago
Fri, Oct 30 - Tue, Nov 3
YYZ
Pearson Intl.
MDW
Midway Intl.
$585 Roundtrip, found 2 days ago
$585
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Oct 30 from Pearson Intl. to Midway Intl., returning Tue, Nov 3, priced at $585 found 2 days ago

Airfares from $140 One Way, $237 Round Trip from Toronto to Orland Park

Prices starting at $237 for return flights and $140 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, Jan 7 - Mon, Jan 11
YTZ
Toronto
ORD
Chicago
$237 Roundtrip, found 1 hour ago
$237
Roundtrip
found 1 hour ago
Select Porter Airlines flight, departing Thu, Jan 7 from Toronto to Chicago, returning Mon, Jan 11, priced at $237 found 1 hour ago
Wed, Nov 25 - Fri, Nov 27
YYZ
Toronto
ORD
Chicago
$244 Roundtrip, found 2 days ago
$244
Roundtrip
found 2 days ago
Select United flight, departing Wed, Nov 25 from Toronto to Chicago, returning Fri, Nov 27, priced at $244 found 2 days ago
Mon, Nov 23 - Sun, Nov 29
YHM
Hamilton
ORD
Chicago
$249 Roundtrip, found 6 days ago
$249
Roundtrip
found 6 days ago
Select Air Canada flight, departing Mon, Nov 23 from Hamilton to Chicago, returning Sun, Nov 29, priced at $249 found 6 days ago
Thu, Dec 17 - Mon, Jan 4
YTZ
Toronto
ORD
Chicago
$252 Roundtrip, found 2 days ago
$252
Roundtrip
found 2 days ago
Select Air Canada flight, departing Thu, Dec 17 from Toronto to Chicago, returning Mon, Jan 4, priced at $252 found 2 days ago
Fri, Nov 20 - Sun, Nov 22
YTZ
Toronto
ORD
Chicago
$255 Roundtrip, found 2 days ago
$255
Roundtrip
found 2 days ago
Select Porter Airlines flight, departing Fri, Nov 20 from Toronto to Chicago, returning Sun, Nov 22, priced at $255 found 2 days ago

Orland Park economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection
4.5-star property

The Talbott, Autograph Collection

9.4/10 Exceptional! (185 reviews)

Nov 27 - Nov 29

2 night stay

Toronto (YYZ) to Chicago (ORD)

Air Canada • Roundtrip • Coach
Price was $651, price is now $503 per person
$503
per person
found 1 day ago
It’a a beautiful and charming building with just the right amount of modernity. My room was a tad bit smalller than I’d expected (queen bed) and the view was nonexistent but cozy and comfortable for for a single person. The room came with a fully stocked mini fridge, a Nespresso machine and two very plush bath robes. The staff was very accommodating and friendly. Each day I was there(three), housekeeping was excellent Shopping, dining and spectacular architecture are in ample supply right outside your door. Will definitely stay here when I’m there city!

Reviewed on Oct 26, 2026

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (5,555 reviews)

Nov 27 - Nov 29

2 night stay

Toronto (YYZ) to Chicago (ORD)

Air Canada • Roundtrip • Coach
Save 100% on your flight
Price was $1,020, price is now $693 per person
$693
per person
found 1 day ago

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.6/10 Exceptional! (2,057 reviews)

Nov 27 - Nov 29

2 night stay

Toronto (YYZ) to Chicago (ORD)

Air Canada • Roundtrip • Coach
Save 100% on your flight
Price was $1,143, price is now $832 per person
$832
per person
found 1 day ago

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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.