United Weekly Deals from Chicago

Top deals for domestic travel from Chicago for under $200 roundtrip

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Chicago (ORD)to

Orlando (MCO)
01/14/26 - 01/17/26
from
$ 157
Viewed: 5 hours ago
Roundtrip
Economy

Chicago (ORD)to

Los Angeles (LAX)
01/17/26 - 01/20/26
from
$ 159
Viewed: 5 hours ago
Roundtrip
Economy

Chicago (ORD)to

Las Vegas (LAS)
01/17/26 - 01/20/26
from
$ 131
Viewed: 1 minutes ago
Roundtrip
Economy

Chicago (ORD)to

Fort Myers (RSW)
01/13/26 - 01/17/26
from
$ 157
Viewed: 5 hours ago
Roundtrip
Economy

Chicago (ORD)to

Phoenix (PHX)
01/17/26 - 01/24/26
from
$ 177
Viewed: 5 hours ago
Roundtrip
Economy

Chicago (ORD)to

Newark/New York (LGA)
01/21/26 - 01/24/26
from
$ 139
Viewed: 13 hours ago
Roundtrip
Economy

Chicago (ORD)to

Fort Lauderdale (FLL)
02/18/26 - 02/25/26
from
$ 144
Viewed: 5 hours ago
Roundtrip
Economy

Chicago (ORD)to

Miami (MIA)
01/13/26 - 01/16/26
from
$ 157
Viewed: 5 hours ago
Roundtrip
Economy

Chicago (ORD)to

Denver (DEN)
01/17/26 - 01/20/26
from
$ 157
Viewed: 5 hours ago
Roundtrip
Economy

Chicago (ORD)to

Tampa (TPA)
02/17/26 - 02/21/26
from
$ 157
Viewed: 5 hours ago
Roundtrip
Economy

Chicago (ORD)to

Newark/New York (EWR)
12/24/25 - 12/31/25
from
$ 139
Viewed: 5 hours ago
Roundtrip
Economy

Chicago (ORD)to

Houston (IAH)
01/13/26 - 01/20/26
from
$ 157
Viewed: 5 hours ago
Roundtrip
Economy

Chicago (ORD)to

Boston (BOS)
02/14/26 - 02/18/26
from
$ 127
Viewed: 5 hours ago
Roundtrip
Economy

Chicago (ORD)to

San Diego (SAN)
02/21/26 - 02/25/26
from
$ 157
Viewed: 5 hours ago
Roundtrip
Economy

Chicago (ORD)to

Dallas (DFW)
01/13/26 - 01/17/26
from
$ 157
Viewed: 5 hours ago
Roundtrip
Economy

Chicago (ORD)to

Atlanta (ATL)
01/17/26 - 01/21/26
from
$ 137
Viewed: 5 hours ago
Roundtrip
Economy

*Prices have been available for round trips within the last 48 hours and may not be currently available. 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. No claim to original U.S. Government works.

 

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Not what you are looking for? Find more deals to the United States

Best deals to Mexico from Chicago for $300 or less roundtrip

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Chicago (ORD)to

Cancun (CUN)
01/21/26 - 01/28/26
from
$ 269
Viewed: 22 hours ago
Roundtrip
Economy

Chicago (ORD)to

Tulum (TQO)
01/18/26 - 01/22/26
from
$ 271
Viewed: 12 hours ago
Roundtrip
Economy

Chicago (ORD)to

Cancun (CUN)
01/21/26 - 01/28/26
from
$ 269
Viewed: 22 hours ago
Roundtrip
Economy

Chicago (ORD)to

Tulum (TQO)
01/18/26 - 01/22/26
from
$ 271
Viewed: 12 hours ago
Roundtrip
Economy

*Prices have been available for round trips within the last 48 hours and may not be currently available. 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. No claim to original U.S. Government works.

 

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Not what you are looking for? Find more deals to Mexico

Best deals to the Caribbean from Chicago for $400 or less roundtrip

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Chicago (ORD)to

Punta Cana (PUJ)
01/11/26 - 01/15/26
from
$ 351
Viewed: 22 hours ago
Roundtrip
Economy

Chicago (ORD)to

San Juan (SJU)
01/19/26 - 01/30/26
from
$ 216
Viewed: 1 day ago
Roundtrip
Economy

Chicago (ORD)to

Montego Bay (MBJ)
03/08/26 - 03/12/26
from
$ 377
Viewed: 22 hours ago
Roundtrip
Economy

Chicago (ORD)to

Punta Cana (PUJ)
01/11/26 - 01/15/26
from
$ 351
Viewed: 22 hours ago
Roundtrip
Economy

*Prices have been available for round trips within the last 48 hours and may not be currently available. 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. No claim to original U.S. Government works.

 

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Not what you are looking for? Find more deals to the Caribbean

Best deals to Central & South America from Chicago for $600 or less roundtrip

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Chicago (ORD)to

San Jose, CR (SJO)
01/26/26 - 01/30/26
from
$ 343
Viewed: 21 hours ago
Roundtrip
Economy

Chicago (ORD)to

Guatemala City (GUA)
01/21/26 - 01/28/26
from
$ 212
Viewed: 21 hours ago
Roundtrip
Economy

Chicago (ORD)to

Panama City (PTY)
03/14/26 - 03/18/26
from
$ 578
Viewed: 22 hours ago
Roundtrip
Economy

Chicago (ORD)to

Bogota (BOG)
01/26/26 - 02/02/26
from
$ 353
Viewed: 21 hours ago
Roundtrip
Economy

Chicago (ORD)to

San Salvador (SAL)
02/21/26 - 02/25/26
from
$ 220
Viewed: 22 hours ago
Roundtrip
Economy

Chicago (ORD)to

San Jose, CR (SJO)
01/26/26 - 01/30/26
from
$ 343
Viewed: 21 hours ago
Roundtrip
Economy

Chicago (ORD)to

Lima (LIM)
01/22/26 - 02/05/26
from
$ 575
Viewed: 22 hours ago
Roundtrip
Economy

Chicago (ORD)to

Quito (UIO)
01/25/26 - 01/29/26
from
$ 417
Viewed: 21 hours ago
Roundtrip
Economy

Chicago (ORD)to

Liberia (Costa Rica) (LIR)
01/11/26 - 01/15/26
from
$ 458
Viewed: 22 hours ago
Roundtrip
Economy

Chicago (ORD)to

Panama City (PTY)
03/14/26 - 03/18/26
from
$ 578
Viewed: 22 hours ago
Roundtrip
Economy

Chicago (ORD)to

Guatemala City (GUA)
01/21/26 - 01/28/26
from
$ 212
Viewed: 21 hours ago
Roundtrip
Economy

Chicago (ORD)to

San Salvador (SAL)
02/21/26 - 02/25/26
from
$ 220
Viewed: 22 hours ago
Roundtrip
Economy

Chicago (ORD)to

Bogota (BOG)
01/26/26 - 02/02/26
from
$ 353
Viewed: 21 hours ago
Roundtrip
Economy

Chicago (ORD)to

Quito (UIO)
01/25/26 - 01/29/26
from
$ 417
Viewed: 21 hours ago
Roundtrip
Economy

Chicago (ORD)to

Lima (LIM)
01/22/26 - 02/05/26
from
$ 575
Viewed: 22 hours ago
Roundtrip
Economy

Chicago (ORD)to

Liberia (Costa Rica) (LIR)
01/11/26 - 01/15/26
from
$ 458
Viewed: 22 hours ago
Roundtrip
Economy

*Prices have been available for round trips within the last 48 hours and may not be currently available. 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. No claim to original U.S. Government works.

 

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