Flights to Chicago from US $ 272*

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United's most popular flights to Chicago (ORD)

US $
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Mexico City (MEX)to

Chicago (ORD)
23/04/2026 - 28/04/2026
from
US $ 308
Viewed: 6 hours ago
Roundtrip
Economy

Cancun (CUN)to

Chicago (ORD)
10/02/2026 - 24/02/2026
from
US $ 272
Viewed: 8 hours ago
Roundtrip
Economy

Cabo San Lucas (SJD)to

Chicago (ORD)
16/01/2026 - 18/01/2026
from
US $ 443
Viewed: 9 hours ago
Roundtrip
Economy

Puerto Vallarta (PVR)to

Chicago (ORD)
11/12/2025 - 15/12/2025
from
US $ 485
Viewed: 6 hours ago
Roundtrip
Economy

Monterrey (MTY)to

Chicago (ORD)
05/02/2026 - 12/02/2026
from
US $ 395
Viewed: 6 hours ago
Roundtrip
Economy

Guadalajara (GDL)to

Chicago (ORD)
31/01/2026 - 04/02/2026
from
US $ 322
Viewed: 8 hours ago
Roundtrip
Economy

Leon (BJX)to

Chicago (ORD)
05/03/2026 - 09/03/2026
from
US $ 382
Viewed: 9 hours ago
Roundtrip
Economy

Queretaro (QRO)to

Chicago (ORD)
27/01/2026 - 10/02/2026
from
US $ 470
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. Schedules are subject to change without notice.

Business class deals on flights to Chicago (ORD)

US $

Mexico City (MEX)to

Chicago (ORD)
23/04/2026 - 28/04/2026

Roundtrip

Business

from
US $ 875
Viewed: 6 hours ago

Cancun (CUN)to

Chicago (ORD)
06/02/2026 - 08/02/2026

Roundtrip

Business

from
US $ 703
Viewed: 5 hours ago

Cabo San Lucas (SJD)to

Chicago (ORD)
16/01/2026 - 18/01/2026

Roundtrip

Business

from
US $ 1,156
Viewed: 9 hours ago

Puerto Vallarta (PVR)to

Chicago (ORD)
01/01/2026 - 07/01/2026

Roundtrip

Business

from
US $ 1,438
Viewed: 7 hours ago

Monterrey (MTY)to

Chicago (ORD)
22/01/2026 - 08/02/2026

Roundtrip

Business

from
US $ 866
Viewed: 1 day ago

Guadalajara (GDL)to

Chicago (ORD)
23/12/2025 - 01/01/2026

Roundtrip

Business

from
US $ 663
Viewed: 9 hours ago

San Luis Potosi (SLP)to

Chicago (ORD)
30/12/2025 - 01/01/2026

Roundtrip

Business

from
US $ 1,036
Viewed: 3 hours ago

Ixtapa-Zihuatanejo (ZIH)to

Chicago (ORD)
15/02/2026 - 25/03/2026

Roundtrip

Business

from
US $ 1,087
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.

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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.