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Flights to Chicago from $ 127*
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1 Passenger, Economy
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today
today
United's most popular flights to Chicago (ORD)
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$
San Francisco (SFO)to
Chicago (ORD)02/28/26 - 03/03/26
from
$ 255
Viewed: 13 hours ago
Roundtrip
Economy
Newark/New York (EWR)to
Chicago (ORD)12/14/25 - 12/14/25
from
$ 138
Viewed: 1 day ago
Roundtrip
Economy
Los Angeles (LAX)to
Chicago (ORD)01/17/26 - 01/20/26
from
$ 159
Viewed: 16 hours ago
Roundtrip
Economy
Denver (DEN)to
Chicago (ORD)01/17/26 - 01/20/26
from
$ 157
Viewed: 17 hours ago
Roundtrip
Economy
Houston (IAH)to
Chicago (ORD)12/25/25 - 01/01/26
from
$ 157
Viewed: 16 hours ago
Roundtrip
Economy
Newark/New York (LGA)to
Chicago (ORD)01/10/26 - 01/10/26
from
$ 134
Viewed: 1 day ago
Roundtrip
Economy
Fort Myers (RSW)to
Chicago (ORD)12/31/25 - 01/07/26
from
$ 132
Viewed: 5 hours ago
Roundtrip
Economy
Phoenix (PHX)to
Chicago (ORD)01/10/26 - 01/17/26
from
$ 177
Viewed: 14 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. Schedules are subject to change without notice.
Business class deals on flights to Chicago (ORD)
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flight_land
$
San Francisco (SFO)to
Chicago (ORD)
02/14/26 - 02/17/26
Roundtrip
Business
from
$ 985
Viewed: 8 hours ago
Newark/New York (EWR)to
Chicago (ORD)
12/14/25 - 12/14/25
Roundtrip
Business
from
$ 451
Viewed: 1 day ago
Los Angeles (LAX)to
Chicago (ORD)
12/24/25 - 12/31/25
Roundtrip
Business
from
$ 889
Viewed: 1 day ago
Denver (DEN)to
Chicago (ORD)
12/31/25 - 01/03/26
Roundtrip
Business
from
$ 375
Viewed: 1 day ago
Houston (IAH)to
Chicago (ORD)
12/12/25 - 12/14/25
Roundtrip
Business
from
$ 460
Viewed: 6 hours ago
Newark/New York (LGA)to
Chicago (ORD)
01/10/26 - 01/10/26
Roundtrip
Business
from
$ 504
Viewed: 1 day ago
Fort Myers (RSW)to
Chicago (ORD)
12/31/25 - 01/07/26
Roundtrip
Business
from
$ 532
Viewed: 5 hours ago
Phoenix (PHX)to
Chicago (ORD)
12/24/25 - 01/18/26
Roundtrip
Business
from
$ 777
Viewed: 1 day 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. Schedules are subject to change without notice.
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.