Cheap Flights From Billy Bishop Toronto City (YTZ) To O'Hare Intl. (ORD)

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Find The Best Dates To Fly

Cheapest Flights from Toronto (YTZ) to Chicago (ORD)

The cheapest flights to O'Hare Intl. found within the past 7 days were CA $341 round trip and CA $202 one way. Prices and availability subject to change. Additional terms may apply.

Fri, Sep 11 - Tue, Sep 15
YTZ
Toronto
ORD
Chicago
CA $341 Roundtrip, found 1 day ago
CA $341
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Fri, Sep 11 from Toronto to Chicago, returning Tue, Sep 15, priced at CA $341 found 1 day ago
Mon, Sep 7 - Wed, Sep 9
YTZ
Toronto
ORD
Chicago
CA $342 Roundtrip, found 1 day ago
CA $342
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Mon, Sep 7 from Toronto to Chicago, returning Wed, Sep 9, priced at CA $342 found 1 day ago
Fri, Sep 4 - Mon, Sep 7
YTZ
Toronto
ORD
Chicago
CA $344 Roundtrip, found 1 hour ago
CA $344
Roundtrip
found 1 hour ago
Select Porter Airlines flight, departing Fri, Sep 4 from Toronto to Chicago, returning Mon, Sep 7, priced at CA $344 found 1 hour ago
Thu, Sep 10 - Sun, Sep 13
YTZ
Toronto
ORD
Chicago
CA $360 Roundtrip, found 1 hour ago
CA $360
Roundtrip
found 1 hour ago
Select Porter Airlines flight, departing Thu, Sep 10 from Toronto to Chicago, returning Sun, Sep 13, priced at CA $360 found 1 hour ago
Sun, Sep 6 - Thu, Sep 10
YTZ
Toronto
ORD
Chicago
CA $360 Roundtrip, found 2 days ago
CA $360
Roundtrip
found 2 days ago
Select Porter Airlines flight, departing Sun, Sep 6 from Toronto to Chicago, returning Thu, Sep 10, priced at CA $360 found 2 days ago
Fri, Oct 16 - Thu, Oct 22
YTZ
Toronto
ORD
Chicago
CA $362 Roundtrip, found 5 days ago
CA $362
Roundtrip
found 5 days ago
Select Porter Airlines flight, departing Fri, Oct 16 from Toronto to Chicago, returning Thu, Oct 22, priced at CA $362 found 5 days ago
Sat, Oct 24 - Wed, Oct 28
YTZ
Toronto
ORD
Chicago
CA $367 Roundtrip, found 4 days ago
CA $367
Roundtrip
found 4 days ago
Select Porter Airlines flight, departing Sat, Oct 24 from Toronto to Chicago, returning Wed, Oct 28, priced at CA $367 found 4 days ago
Tue, Sep 1 - Wed, Sep 2
YTZ
Toronto
ORD
Chicago
CA $375 Roundtrip, found 6 days ago
CA $375
Roundtrip
found 6 days ago
Select Air Transat flight, departing Tue, Sep 1 from Toronto to Chicago, returning Wed, Sep 2, priced at CA $375 found 6 days ago
Fri, Sep 4 - Fri, Sep 4
YTZ
Toronto
ORD
Chicago
CA $377 Roundtrip, found 3 days ago
CA $377
Roundtrip
found 3 days ago
Select Porter Airlines flight, departing Fri, Sep 4 from Toronto to Chicago, returning Fri, Sep 4, priced at CA $377 found 3 days ago
Mon, Sep 21 - Sun, Sep 27
YTZ
Toronto
ORD
Chicago
CA $381 Roundtrip, found 20 hours ago
CA $381
Roundtrip
found 20 hours ago
Select Porter Airlines flight, departing Mon, Sep 21 from Toronto to Chicago, returning Sun, Sep 27, priced at CA $381 found 20 hours ago

O'Hare Intl. flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Price was CA $1,544, price is now CA $1,096 per person
CA $1,096
per person
Aug 3 - Aug 8
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Price was CA $2,991, price is now CA $2,125 per person
CA $2,125
per person
Aug 3 - Aug 8
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Price was CA $1,678, price is now CA $1,241 per person
CA $1,241
per person
Aug 15 - Aug 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Price was CA $1,933, price is now CA $1,453 per person
CA $1,453
per person
Aug 3 - Aug 8
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Price was CA $2,203, price is now CA $1,689 per person
CA $1,689
per person
Aug 3 - Aug 8
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
Don't see what you're looking for?
See all available trips from Billy Bishop Toronto City to O'Hare Intl.
View all trips

Explore More Ways to Travel with Travelocity

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.