Introducing Weekly Deals from Chicago. Featured are some of our domestic and international destinations, such as Mexico, the Caribbean, Central, and South America, with great value. Book your next trip with United.
United Weekly Deals from Chicago
Top deals for domestic travel from Chicago for under $200 roundtrip
flight_land
$
Chicago (ORD)to
Orlando (MCO)01/14/26 - 01/17/26
from
$Â 157
Viewed: 5 hours ago
Roundtrip
Economy
Chicago (ORD)to
Los Angeles (LAX)01/17/26 - 01/20/26
from
$Â 159
Viewed: 5 hours ago
Roundtrip
Economy
Chicago (ORD)to
Las Vegas (LAS)01/17/26 - 01/20/26
from
$Â 131
Viewed: 1 minutes ago
Roundtrip
Economy
Chicago (ORD)to
Fort Myers (RSW)01/13/26 - 01/17/26
from
$Â 157
Viewed: 5 hours ago
Roundtrip
Economy
Chicago (ORD)to
Phoenix (PHX)01/17/26 - 01/24/26
from
$Â 177
Viewed: 5 hours ago
Roundtrip
Economy
Chicago (ORD)to
Newark/New York (LGA)01/21/26 - 01/24/26
from
$Â 139
Viewed: 13 hours ago
Roundtrip
Economy
Chicago (ORD)to
Fort Lauderdale (FLL)02/18/26 - 02/25/26
from
$Â 144
Viewed: 5 hours ago
Roundtrip
Economy
Chicago (ORD)to
Miami (MIA)01/13/26 - 01/16/26
from
$Â 157
Viewed: 5 hours ago
Roundtrip
Economy
Chicago (ORD)to
Denver (DEN)01/17/26 - 01/20/26
from
$Â 157
Viewed: 5 hours ago
Roundtrip
Economy
Chicago (ORD)to
Tampa (TPA)02/17/26 - 02/21/26
from
$Â 157
Viewed: 5 hours ago
Roundtrip
Economy
Chicago (ORD)to
Newark/New York (EWR)12/24/25 - 12/31/25
from
$Â 139
Viewed: 5 hours ago
Roundtrip
Economy
Chicago (ORD)to
Houston (IAH)01/13/26 - 01/20/26
from
$Â 157
Viewed: 5 hours ago
Roundtrip
Economy
Chicago (ORD)to
Boston (BOS)02/14/26 - 02/18/26
from
$Â 127
Viewed: 5 hours ago
Roundtrip
Economy
Chicago (ORD)to
San Diego (SAN)02/21/26 - 02/25/26
from
$Â 157
Viewed: 5 hours ago
Roundtrip
Economy
Chicago (ORD)to
Dallas (DFW)01/13/26 - 01/17/26
from
$Â 157
Viewed: 5 hours ago
Roundtrip
Economy
Chicago (ORD)to
Atlanta (ATL)01/17/26 - 01/21/26
from
$Â 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.
Not what you are looking for? Find more deals to the United States
Best deals to Mexico from Chicago for $300 or less roundtrip
flight_land
$
Chicago (ORD)to
Cancun (CUN)01/21/26 - 01/28/26
from
$Â 269
Viewed: 22 hours ago
Roundtrip
Economy
Chicago (ORD)to
Tulum (TQO)01/18/26 - 01/22/26
from
$Â 271
Viewed: 12 hours ago
Roundtrip
Economy
Chicago (ORD)to
Cancun (CUN)01/21/26 - 01/28/26
from
$Â 269
Viewed: 22 hours ago
Roundtrip
Economy
Chicago (ORD)to
Tulum (TQO)01/18/26 - 01/22/26
from
$Â 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.
Not what you are looking for? Find more deals to Mexico
Best deals to the Caribbean from Chicago for $400 or less roundtrip
flight_land
$
Chicago (ORD)to
Punta Cana (PUJ)01/11/26 - 01/15/26
from
$Â 351
Viewed: 22 hours ago
Roundtrip
Economy
Chicago (ORD)to
San Juan (SJU)01/19/26 - 01/30/26
from
$Â 216
Viewed: 1 day ago
Roundtrip
Economy
Chicago (ORD)to
Montego Bay (MBJ)03/08/26 - 03/12/26
from
$Â 377
Viewed: 22 hours ago
Roundtrip
Economy
Chicago (ORD)to
Punta Cana (PUJ)01/11/26 - 01/15/26
from
$Â 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.
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
flight_land
$
Chicago (ORD)to
San Jose, CR (SJO)01/26/26 - 01/30/26
from
$Â 343
Viewed: 21 hours ago
Roundtrip
Economy
Chicago (ORD)to
Guatemala City (GUA)01/21/26 - 01/28/26
from
$Â 212
Viewed: 21 hours ago
Roundtrip
Economy
Chicago (ORD)to
Panama City (PTY)03/14/26 - 03/18/26
from
$Â 578
Viewed: 22 hours ago
Roundtrip
Economy
Chicago (ORD)to
Bogota (BOG)01/26/26 - 02/02/26
from
$Â 353
Viewed: 21 hours ago
Roundtrip
Economy
Chicago (ORD)to
San Salvador (SAL)02/21/26 - 02/25/26
from
$Â 220
Viewed: 22 hours ago
Roundtrip
Economy
Chicago (ORD)to
San Jose, CR (SJO)01/26/26 - 01/30/26
from
$Â 343
Viewed: 21 hours ago
Roundtrip
Economy
Chicago (ORD)to
Lima (LIM)01/22/26 - 02/05/26
from
$Â 575
Viewed: 22 hours ago
Roundtrip
Economy
Chicago (ORD)to
Quito (UIO)01/25/26 - 01/29/26
from
$Â 417
Viewed: 21 hours ago
Roundtrip
Economy
Chicago (ORD)to
Liberia (Costa Rica) (LIR)01/11/26 - 01/15/26
from
$Â 458
Viewed: 22 hours ago
Roundtrip
Economy
Chicago (ORD)to
Panama City (PTY)03/14/26 - 03/18/26
from
$Â 578
Viewed: 22 hours ago
Roundtrip
Economy
Chicago (ORD)to
Guatemala City (GUA)01/21/26 - 01/28/26
from
$Â 212
Viewed: 21 hours ago
Roundtrip
Economy
Chicago (ORD)to
San Salvador (SAL)02/21/26 - 02/25/26
from
$Â 220
Viewed: 22 hours ago
Roundtrip
Economy
Chicago (ORD)to
Bogota (BOG)01/26/26 - 02/02/26
from
$Â 353
Viewed: 21 hours ago
Roundtrip
Economy
Chicago (ORD)to
Quito (UIO)01/25/26 - 01/29/26
from
$Â 417
Viewed: 21 hours ago
Roundtrip
Economy
Chicago (ORD)to
Lima (LIM)01/22/26 - 02/05/26
from
$Â 575
Viewed: 22 hours ago
Roundtrip
Economy
Chicago (ORD)to
Liberia (Costa Rica) (LIR)01/11/26 - 01/15/26
from
$Â 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.
Not what you are looking for? Find more deals to Guatemala, Nicaragua, El Salvador, Honduras, Panama, Costa Rica, Argentina, Colombia, Ecuador, Peru
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