Flights to Chicago from US $ 272*
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1 Passenger, Economy
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today
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United's most popular flights to Chicago (ORD)
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US $
Cancun (CUN)to
Chicago (ORD)05/02/2026 - 09/02/2026
from
US $ 272
Viewed: 17 hours ago
Roundtrip
Economy
Mexico City (MEX)to
Chicago (ORD)15/12/2025 - 16/02/2026
from
US $ 297
Viewed: 13 hours ago
Roundtrip
Economy
Monterrey (MTY)to
Chicago (ORD)05/03/2026 - 19/03/2026
from
US $ 395
Viewed: 15 hours ago
Roundtrip
Economy
Puerto Vallarta (PVR)to
Chicago (ORD)26/12/2025 - 30/12/2025
from
US $ 555
Viewed: 15 hours ago
Roundtrip
Economy
Cabo San Lucas (SJD)to
Chicago (ORD)30/12/2025 - 04/01/2026
from
US $ 491
Viewed: 12 hours ago
Roundtrip
Economy
Guadalajara (GDL)to
Chicago (ORD)31/01/2026 - 04/02/2026
from
US $ 322
Viewed: 17 hours ago
Roundtrip
Economy
San Luis Potosi (SLP)to
Chicago (ORD)03/03/2026 - 17/03/2026
from
US $ 488
Viewed: 14 hours ago
Roundtrip
Economy
Leon (BJX)to
Chicago (ORD)04/03/2026 - 18/03/2026
from
US $ 382
Viewed: 18 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
US $
Cancun (CUN)to
Chicago (ORD)
25/03/2026 - 31/03/2026
Roundtrip
Business
from
US $ 807
Viewed: 8 hours ago
Mexico City (MEX)to
Chicago (ORD)
12/12/2025 - 21/01/2026
Roundtrip
Business
from
US $ 911
Viewed: 13 hours ago
Monterrey (MTY)to
Chicago (ORD)
12/02/2026 - 15/02/2026
Roundtrip
Business
from
US $ 930
Viewed: 1 day ago
Puerto Vallarta (PVR)to
Chicago (ORD)
28/12/2025 - 29/12/2025
Roundtrip
Business
from
US $ 1,778
Viewed: 18 hours ago
Cabo San Lucas (SJD)to
Chicago (ORD)
30/12/2025 - 04/01/2026
Roundtrip
Business
from
US $ 1,209
Viewed: 12 hours ago
Guadalajara (GDL)to
Chicago (ORD)
15/12/2025 - 31/12/2025
Roundtrip
Business
from
US $ 815
Viewed: 23 hours ago
San Luis Potosi (SLP)to
Chicago (ORD)
23/12/2025 - 28/12/2025
Roundtrip
Business
from
US $ 941
Viewed: 8 hours ago
Leon (BJX)to
Chicago (ORD)
06/02/2026 - 08/02/2026
Roundtrip
Business
from
US $ 684
Viewed: 13 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. 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.