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
Aug 23 - Sep 2
You Save $ 527
$ 1835  $ 1308
per person
 
Chicago Marriott Suites OHare
#2 Vacation Deal
Flight + 3 Nights*
Area: Chicago and Vicinity (All Areas)
Oct 3 - 6
You Save $ 144
$ 664  $ 520
per person
 
SpringHill Suites Chicago OHare
#3 Vacation Deal
Flight + 4 Nights*
Area: Chicago and Vicinity (All Areas)
Sep 19 - 23
You Save $ 156
$ 699  $ 543
per person
 
Millennium Knickerbocker Hotel Chicago
#4 Vacation Deal
Flight + 6 Nights*
Area: Loop/ Magnificent Mile/ River North
Sep 15 - 21
You Save $ 223
$ 1143  $ 920
per person
 
Intercontinental Chi Mag Mile
#5 Vacation Deal
Flight + 6 Nights*
Area: Loop/ Magnificent Mile/ River North
Sep 15 - 21
You Save $ 243
$ 1520  $ 1277
per person
 
Chicago South Loop Hotel
#6 Vacation Deal
Flight + 10 Nights*
Area: McCormick Place
Aug 23 - Sep 2
You Save $ 191
$ 1188  $ 997
per person
 
ACME Hotel Company Chicago
#7 Vacation Deal
Flight + 4 Nights*
Area: Loop/ Magnificent Mile/ River North
Sep 4 - 8
You Save $ 87
$ 722  $ 635
per person
 
The Peninsula Chicago
#8 Vacation Deal
Flight + 10 Nights*
Area: Loop/ Magnificent Mile/ River North
Aug 23 - Sep 2
You Save $ 302
$ 2616  $ 2314
per person
 
The Allerton Magnificent Mile
#9 Vacation Deal
Flight + 6 Nights*
Area: Loop/ Magnificent Mile/ River North
Sep 15 - 21
You Save $ 99
$ 1005  $ 906
per person
 
The Ritz-Carlton Chicago, A Four Seasons Hotel
#10 Vacation Deal
Flight + 4 Nights*
Area: Loop/ Magnificent Mile/ River North
Aug 21 - 25
You Save $ 195
$ 1988  $ 1793
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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