United flights to Chicago from CA *

United's most popular flights to Chicago (ORD)

CA $
Select travel class

Toronto (YYZ)to

Chicago (ORD)
2025/01/14 - 2025/01/21
from
CA $ 432*
Viewed: 13 hours ago
Roundtrip
|
Economy

Vancouver (YVR)to

Chicago (ORD)
2025/01/15 - 2025/01/29
from
CA $ 399*
Viewed: 7 hours ago
Roundtrip
|
Economy

Calgary (YYC)to

Chicago (ORD)
2025/01/17 - 2025/01/21
from
CA $ 473*
Viewed: 6 hours ago
Roundtrip
|
Economy

Montreal (YUL)to

Chicago (ORD)
2025/01/13 - 2025/01/27
from
CA $ 545*
Viewed: 6 hours ago
Roundtrip
|
Economy

Edmonton (YEG)to

Chicago (ORD)
2025/01/11 - 2025/01/15
from
CA $ 443*
Viewed: 6 hours ago
Roundtrip
|
Economy

Ottawa (YOW)to

Chicago (ORD)
2025/01/20 - 2025/01/27
from
CA $ 602*
Viewed: 7 hours ago
Roundtrip
|
Economy

Winnipeg (YWG)to

Chicago (ORD)
2025/01/04 - 2025/01/09
from
CA $ 963*
Viewed: 14 hours ago
Roundtrip
|
Economy

Québec (YQB)to

Chicago (ORD)
2025/01/11 - 2025/01/18
from
CA $ 717*
Viewed: 6 hours ago
Roundtrip
|
Economy

*Prices have been available for round trips within the last 48 hours and may not be currently available. For Economy class, fares listed may be Basic Economy, which is our most restrictive fare option and subject to additional restrictions. Additional baggage charges and fees for other optional service may apply. Other terms and conditions may apply.

Business class deals on flights to Chicago (ORD)

CA $

Toronto (YYZ)to

Chicago (ORD)
2025/01/14 - 2025/01/21

Roundtrip

|

Business

from
CA $ 839*
Viewed: 13 hours ago

Vancouver (YVR)to

Chicago (ORD)
2025/01/13 - 2025/01/16

Roundtrip

|

Business

from
CA $ 1,550*
Viewed: 8 hours ago

Calgary (YYC)to

Chicago (ORD)
2025/01/14 - 2025/01/17

Roundtrip

|

Business

from
CA $ 1,623*
Viewed: 14 hours ago

Montreal (YUL)to

Chicago (ORD)
2025/01/03 - 2025/02/26

Roundtrip

|

Business

from
CA $ 1,064*
Viewed: 10 hours ago

Edmonton (YEG)to

Chicago (ORD)
2024/12/28 - 2025/01/04

Roundtrip

|

Business

from
CA $ 1,874*
Viewed: 3 hours ago

Winnipeg (YWG)to

Chicago (ORD)
2025/01/04 - 2025/01/09

Roundtrip

|

Business

from
CA $ 1,226*
Viewed: 14 hours ago

*Prices have been available for round trips within the last 48 hours and may not be currently available. For Economy class, fares listed may be Basic Economy, which is our most restrictive fare option and subject to additional restrictions. Additional baggage charges and fees for other optional service may apply. Other terms and conditions may apply.

Things to do after your flight to Chicago (ORD)

In Chicago, you can have it all

Chicago is the perfect urban getaway. “The Second City” is home to stunning architecture, endless shopping on the Magnificent Mile, one of the world’s most dynamic dining scenes, and a collection of critically acclaimed museums, all nestled on a lakefront lined with running trails and natural sand beaches.

Chicago’s top attractions

  • Stroll through Millennium Park and take in the art and architecture, including Cloud Gate, which is also known as “The Bean,” Crown Fountain and Lurie Garden.
  • Go shopping along the Magnificent Mile on Michigan Avenue.
  • Discover the fun attractions at Navy Pier, including a large Ferris wheel, theater and carousel.
  • Enjoy a day with the kids at the Shedd Aquarium and Lincoln Park Zoo.
  • Tour Wrigley Field, home of the Chicago Cubs and one of the oldest baseball parks in the U.S.
  • Take in city views from the Willis Tower’s Skydeck.
  • Enjoy Chicago's family atractions.

Chicago is a popular place to visit all year round, though visitors will find that spring and fall have the most pleasant weather. Summertime activities include Lollapalooza music festival, Taste of Chicago, Chicago Jazz Festival and the Chicago Gay Pride Parade. Other major events throughout the year include the Chicago Underground Film Festival in the spring, the Chicago International Film Festival in the fall and the Magnificent Mile Lights Festival in the winter.

Find your vacation package to Chicago with United Packages.

Find more flights to Chicago (ORD) with United

CA $
Select travel class
Find more flights to Chicago (ORD) with United
From
To
Fare Type
Dates
Price
FromToronto (YYZ)ToChicago (ORD)Roundtrip
|
Economy
2025/02/01 - 2025/02/02

from

CA $ 381*

Viewed: 2 hours ago

FromVancouver (YVR)ToChicago (ORD)Roundtrip
|
Economy
2025/02/04 - 2025/02/07

from

CA $ 399*

Viewed: 1 day ago

FromCalgary (YYC)ToChicago (ORD)Roundtrip
|
Economy
2025/01/30 - 2025/02/03

from

CA $ 467*

Viewed: 6 hours ago

FromMontreal (YUL)ToChicago (ORD)Roundtrip
|
Economy
2025/03/03 - 2025/03/17

from

CA $ 545*

Viewed: 6 hours ago

FromEdmonton (YEG)ToChicago (ORD)Roundtrip
|
Economy
2025/02/25 - 2025/03/11

from

CA $ 443*

Viewed: 6 hours ago

FromOttawa (YOW)ToChicago (ORD)Roundtrip
|
Economy
2025/01/29 - 2025/02/05

from

CA $ 602*

Viewed: 7 hours ago

FromWinnipeg (YWG)ToChicago (ORD)Roundtrip
|
Economy
2025/02/19 - 2025/02/25

from

CA $ 612*

Viewed: 7 hours ago

FromQuébec (YQB)ToChicago (ORD)Roundtrip
|
Economy
2025/03/10 - 2025/03/17

from

CA $ 717*

Viewed: 6 hours ago

*Prices have been available for round trips within the last 48 hours and may not be currently available. For Economy class, fares listed may be Basic Economy, which is our most restrictive fare option and subject to additional restrictions. Additional baggage charges and fees for other optional service may apply. Other terms and conditions may apply.

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