United flights to Chicago from $ 97*

United's most popular flights to Chicago (ORD)

$
Select travel class

Boston (BOS)to

Chicago (ORD)
01/15/25 - 01/19/25
from
$ 157*
Viewed: 1 day ago
Roundtrip
|
Economy

New York/Newark (EWR)to

Chicago (ORD)
01/22/25 - 01/25/25
from
$ 139*
Viewed: 4 hours ago
Roundtrip
|
Economy

San Francisco (SFO)to

Chicago (ORD)
01/18/25 - 01/22/25
from
$ 197*
Viewed: 2 hours ago
Roundtrip
|
Economy

San Diego (SAN)to

Chicago (ORD)
01/18/25 - 01/21/25
from
$ 260*
Viewed: 14 hours ago
Roundtrip
|
Economy

New York/Newark (LGA)to

Chicago (ORD)
01/22/25 - 01/25/25
from
$ 147*
Viewed: 21 hours ago
Roundtrip
|
Economy

Orlando (MCO)to

Chicago (ORD)
01/22/25 - 01/29/25
from
$ 157*
Viewed: 20 hours ago
Roundtrip
|
Economy

Seattle (SEA)to

Chicago (ORD)
01/20/25 - 01/22/25
from
$ 178*
Viewed: 2 hours ago
Roundtrip
|
Economy

Denver (DEN)to

Chicago (ORD)
01/22/25 - 01/25/25
from
$ 139*
Viewed: 3 hours ago
Roundtrip
|
Economy

Phoenix (PHX)to

Chicago (ORD)
01/15/25 - 01/22/25
from
$ 189*
Viewed: 4 hours ago
Roundtrip
|
Economy

Los Angeles (LAX)to

Chicago (ORD)
01/22/25 - 02/04/25
from
$ 179*
Viewed: 8 hours ago
Roundtrip
|
Economy

Fort Lauderdale (FLL)to

Chicago (ORD)
01/21/25 - 01/22/25
from
$ 187*
Viewed: 2 hours ago
Roundtrip
|
Economy

Washington, D.C. (DCA)to

Chicago (ORD)
01/22/25 - 01/25/25
from
$ 191*
Viewed: 22 hours ago
Roundtrip
|
Economy

Honolulu (HNL)to

Chicago (ORD)
01/20/25 - 01/27/25
from
$ 913*
Viewed: 17 hours ago
Roundtrip
|
Economy

West Palm Beach (PBI)to

Chicago (ORD)
01/21/25 - 01/28/25
from
$ 179*
Viewed: 15 hours ago
Roundtrip
|
Economy

Lincoln (LNK)to

Chicago (ORD)
01/12/25 - 01/15/25
from
$ 277*
Viewed: 16 hours ago
Roundtrip
|
Economy

Las Vegas (LAS)to

Chicago (ORD)
01/22/25 - 01/25/25
from
$ 139*
Viewed: 1 hour ago
Roundtrip
|
Economy

Fort Myers (RSW)to

Chicago (ORD)
01/22/25 - 01/26/25
from
$ 163*
Viewed: 4 hours ago
Roundtrip
|
Economy

Washington, D.C. (IAD)to

Chicago (ORD)
01/13/25 - 01/15/25
from
$ 194*
Viewed: 2 hours ago
Roundtrip
|
Economy

Raleigh (RDU)to

Chicago (ORD)
01/22/25 - 01/25/25
from
$ 212*
Viewed: 17 hours ago
Roundtrip
|
Economy

Sacramento (SMF)to

Chicago (ORD)
01/18/25 - 01/20/25
from
$ 404*
Viewed: 23 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.

Members who purchase a travel package from United Packages and provide a valid MileagePlus account number at the time of booking are eligible to earn miles. For full terms and conditions, visit packages.united.com.

Business class deals on flights to Chicago (ORD)

$

Boston (BOS)to

Chicago (ORD)
01/19/25 - 01/29/25

Roundtrip

|

Business

from
$ 427*
Viewed: 19 hours ago

New York/Newark (EWR)to

Chicago (ORD)
01/07/25 - 01/07/25

Roundtrip

|

Business

from
$ 482*
Viewed: 17 hours ago

San Francisco (SFO)to

Chicago (ORD)
12/31/24 - 01/04/25

Roundtrip

|

Business

from
$ 769*
Viewed: 21 hours ago

New York/Newark (LGA)to

Chicago (ORD)
01/16/25 - 01/18/25

Roundtrip

|

Business

from
$ 517*
Viewed: 18 hours ago

Orlando (MCO)to

Chicago (ORD)
01/22/25 - 01/29/25

Roundtrip

|

Business

from
$ 647*
Viewed: 20 hours ago

Seattle (SEA)to

Chicago (ORD)
01/20/25 - 01/22/25

Roundtrip

|

Business

from
$ 677*
Viewed: 2 hours ago

San Diego (SAN)to

Chicago (ORD)
01/18/25 - 01/23/25

Roundtrip

|

Business

from
$ 917*
Viewed: 13 minutes ago

Denver (DEN)to

Chicago (ORD)
01/22/25 - 01/25/25

Roundtrip

|

Business

from
$ 399*
Viewed: 3 hours ago

Phoenix (PHX)to

Chicago (ORD)
01/15/25 - 01/22/25

Roundtrip

|

Business

from
$ 789*
Viewed: 4 hours ago

Los Angeles (LAX)to

Chicago (ORD)
01/16/25 - 01/21/25

Roundtrip

|

Business

from
$ 905*
Viewed: 4 hours ago

Fort Lauderdale (FLL)to

Chicago (ORD)
01/06/25 - 01/06/25

Roundtrip

|

Business

from
$ 657*
Viewed: 4 minutes ago

Honolulu (HNL)to

Chicago (ORD)
12/31/24 - 01/08/25

Roundtrip

|

Business

from
$ 2,452*
Viewed: 1 day ago

West Palm Beach (PBI)to

Chicago (ORD)
01/09/25 - 01/13/25

Roundtrip

|

Business

from
$ 704*
Viewed: 22 hours ago

Lincoln (LNK)to

Chicago (ORD)
01/06/25 - 01/09/25

Roundtrip

|

Business

from
$ 599*
Viewed: 1 day ago

Las Vegas (LAS)to

Chicago (ORD)
01/22/25 - 01/25/25

Roundtrip

|

Business

from
$ 869*
Viewed: 1 hour ago

Fort Myers (RSW)to

Chicago (ORD)
01/22/25 - 01/26/25

Roundtrip

|

Business

from
$ 663*
Viewed: 4 hours ago

Tampa (TPA)to

Chicago (ORD)
01/22/25 - 01/28/25

Roundtrip

|

Business

from
$ 532*
Viewed: 2 hours ago

Washington, D.C. (IAD)to

Chicago (ORD)
01/13/25 - 01/15/25

Roundtrip

|

Business

from
$ 464*
Viewed: 2 hours ago

Raleigh (RDU)to

Chicago (ORD)
01/22/25 - 01/25/25

Roundtrip

|

Business

from
$ 482*
Viewed: 17 hours ago

Sacramento (SMF)to

Chicago (ORD)
01/18/25 - 01/20/25

Roundtrip

|

Business

from
$ 974*
Viewed: 23 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

$
Select travel class
Find more flights to Chicago (ORD) with United
From
To
Fare Type
Dates
Price
FromBoston (BOS)ToChicago (ORD)Roundtrip
|
Economy
02/07/25 - 02/10/25

from

$ 157*

Viewed: 1 day ago

FromNew York/Newark (EWR)ToChicago (ORD)Roundtrip
|
Economy
01/29/25 - 02/01/25

from

$ 139*

Viewed: 22 hours ago

FromSan Francisco (SFO)ToChicago (ORD)Roundtrip
|
Economy
01/25/25 - 01/28/25

from

$ 197*

Viewed: 1 day ago

FromSan Diego (SAN)ToChicago (ORD)Roundtrip
|
Economy
02/18/25 - 02/22/25

from

$ 247*

Viewed: 14 hours ago

FromNew York/Newark (LGA)ToChicago (ORD)Roundtrip
|
Economy
01/25/25 - 01/28/25

from

$ 147*

Viewed: 21 hours ago

FromOrlando (MCO)ToChicago (ORD)Roundtrip
|
Economy
02/01/25 - 02/04/25

from

$ 157*

Viewed: 15 hours ago

FromSeattle (SEA)ToChicago (ORD)Roundtrip
|
Economy
02/04/25 - 02/10/25

from

$ 178*

Viewed: 4 hours ago

FromFort Lauderdale (FLL)ToChicago (ORD)Roundtrip
|
Economy
03/01/25 - 03/04/25

from

$ 176*

Viewed: 17 hours ago

FromPhoenix (PHX)ToChicago (ORD)Roundtrip
|
Economy
02/19/25 - 02/25/25

from

$ 177*

Viewed: 6 hours ago

FromDenver (DEN)ToChicago (ORD)Roundtrip
|
Economy
02/08/25 - 02/15/25

from

$ 139*

Viewed: 1 day ago

FromLos Angeles (LAX)ToChicago (ORD)Roundtrip
|
Economy
03/01/25 - 03/04/25

from

$ 179*

Viewed: 3 hours ago

FromWashington, D.C. (DCA)ToChicago (ORD)Roundtrip
|
Economy
02/10/25 - 02/13/25

from

$ 191*

Viewed: 22 hours ago

FromWest Palm Beach (PBI)ToChicago (ORD)Roundtrip
|
Economy
02/22/25 - 03/03/25

from

$ 159*

Viewed: 20 hours ago

FromLincoln (LNK)ToChicago (ORD)Roundtrip
|
Economy
02/14/25 - 02/18/25

from

$ 259*

Viewed: 16 hours ago

FromLas Vegas (LAS)ToChicago (ORD)Roundtrip
|
Economy
02/12/25 - 02/18/25

from

$ 139*

Viewed: 3 hours ago

FromHonolulu (HNL)ToChicago (ORD)Roundtrip
|
Economy
02/01/25 - 02/23/25

from

$ 883*

Viewed: 8 hours ago

FromWashington, D.C. (IAD)ToChicago (ORD)Roundtrip
|
Economy
02/14/25 - 02/16/25

from

$ 191*

Viewed: 4 hours ago

FromRaleigh (RDU)ToChicago (ORD)Roundtrip
|
Economy
02/13/25 - 02/20/25

from

$ 140*

Viewed: 15 hours ago

FromFort Myers (RSW)ToChicago (ORD)Roundtrip
|
Economy
02/26/25 - 03/05/25

from

$ 157*

Viewed: 13 hours ago

FromPalm Springs (PSP)ToChicago (ORD)Roundtrip
|
Economy
02/13/25 - 02/19/25

from

$ 349*

Viewed: 22 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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