Affordable Chicago Vacation Packages

Departing From: See the Top

See the Top
  • Popular picks
  • 4 & 5 Star Vacations
  • Vacations under $500
  • Vacations Under $1000
  • 3 & 4 Night Vacations
  • 7 to 10 Night Vacations


See the Top
  • Popular picks
  • 3 & 4 Night Vacations
  • 7 to 10 Night Vacations
  • Vacations under $500
  • Vacations Under $1000
  • 4 & 5 Star Vacations
Wyndham Blake Chicago
#11 Vacation Deal
Flight + 9 Nights*
Area: Loop/ Magnificent Mile/ River North
Sep 6 - 15
You Save $ 140
$ 1414  $ 1274
per person
 
Sofitel Chicago Water Tower
#12 Vacation Deal
Flight + 9 Nights*
Area: Loop/ Magnificent Mile/ River North
Sep 6 - 15
You Save $ 169
$ 1901  $ 1732
per person
 
Allegro Chicago, a Kimpton Hotel
#13 Vacation Deal
Flight + 5 Nights*
Area: Loop/ Magnificent Mile/ River North
Sep 11 - 16
You Save $ 85
$ 990  $ 905
per person
 
W Chicago City Center
#14 Vacation Deal
Flight + 9 Nights*
Area: Loop/ Magnificent Mile/ River North
Sep 6 - 15
You Save $ 180
$ 2009  $ 1829
per person
 
Congress Plaza Hotel
#15 Vacation Deal
Flight + 9 Nights*
Area: Loop/ Magnificent Mile/ River North
Sep 6 - 15
You Save $ 86
$ 1246  $ 1160
per person
 
Aloft Chicago City Center
#16 Vacation Deal
Flight + 9 Nights*
Area: Loop/ Magnificent Mile/ River North
  •  
Sep 6 - 15
You Save $ 120
$ 1651  $ 1531
per person
 
Chicago Marriott Downtown Magnificent Mile
#17 Vacation Deal
Flight + 4 Nights*
Area: Loop/ Magnificent Mile/ River North
Sep 11 - 15
You Save $ 59
$ 1013  $ 954
per person
 
Central Loop Hotel
#18 Vacation Deal
Flight + 9 Nights*
Area: Loop/ Magnificent Mile/ River North
Sep 6 - 15
You Save $ 71
$ 1281  $ 1210
per person
 
Hilton Chicago Michigan Avenue Cultural Mile
#19 Vacation Deal
Flight + 4 Nights*
Area: Loop/ Magnificent Mile/ River North
Sep 11 - 15
You Save $ 52
$ 887  $ 835
per person
 
Burnham, a Kimpton Hotel
#20 Vacation Deal
Flight + 9 Nights*
Area: Loop/ Magnificent Mile/ River North
Sep 6 - 15
You Save $ 92
$ 1669  $ 1577
per person
 
 
* Prices are in USD for one adult based on double occupancy and include tax recovery charges. Sample prices were found recently by Travelocity or its customers. Our real-time dynamic packaging engine is constantly updating prices and availability. Please click prices for current information.
 
 

Enjoy Your Chicago Vacation

Room Adults
(18-64)
Minors
(2-17)
Seniors
(65+)
Room 1
 

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