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
theWit Chicago - a DoubleTree by Hilton Hotel
#21 Vacation Deal
Flight + 4 Nights*
Area: Loop/ Magnificent Mile/ River North
Aug 29 - Sep 2
You Save $ 48
$ 930  $ 882
per person
 
Crowne Plaza Avenue Magnificent Mile
#22 Vacation Deal
Flight + 9 Nights*
Area: Loop/ Magnificent Mile/ River North
Sep 6 - 15
You Save $ 98
$ 2072  $ 1974
per person
 
JW Marriott Chicago
#23 Vacation Deal
Flight + 3 Nights*
Area: Loop/ Magnificent Mile/ River North
Oct 11 - 14
You Save $ 57
$ 1083  $ 1026
per person
 
The James Chicago
#24 Vacation Deal
Flight + 9 Nights*
Area: Loop/ Magnificent Mile/ River North
Sep 6 - 15
You Save $ 101
$ 1991  $ 1890
per person
 
Omni Chicago Hotel
#25 Vacation Deal
Flight + 9 Nights*
Area: Loop/ Magnificent Mile/ River North
Sep 6 - 15
You Save $ 99
$ 1906  $ 1807
per person
 
Courtyard Chicago DowntownMagnificent Mile
#26 Vacation Deal
Flight + 9 Nights*
Area: Loop/ Magnificent Mile/ River North
Sep 6 - 15
You Save $ 82
$ 1772  $ 1690
per person
 
The Ritz-Carlton Chicago, A Four Seasons Hotel
#27 Vacation Deal
Flight + 3 Nights*
Area: Loop/ Magnificent Mile/ River North
Nov 7 - 10
You Save $ 34
$ 855  $ 821
per person
 
Wyndham Grand Chicago Riverfront
#28 Vacation Deal
Flight + 4 Nights*
Area: Loop/ Magnificent Mile/ River North
Sep 11 - 15
You Save $ 36
$ 952  $ 916
per person
 
Wyndham Lisle
#29 Vacation Deal
Flight + 2 Nights*
Area: Naperville and Aurora
Sep 13 - 15
You Save $ 18
$ 441  $ 423
per person
 
Fairmont Chicago, Millennium Park
#30 Vacation Deal
Flight + 4 Nights*
Area: Loop/ Magnificent Mile/ River North
Sep 11 - 15
You Save $ 26
$ 821  $ 795
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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