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
Ramada Chicago Hyde Park
#31 Vacation Deal
Flight + 2 Nights*
Area: McCormick Place
Sep 13 - 15
You Save $ 16
$ 509  $ 493
per person
 
The Palmer House Hilton
#32 Vacation Deal
Flight + 4 Nights*
Area: Loop/ Magnificent Mile/ River North
Sep 11 - 15
You Save $ 16
$ 864  $ 848
per person
 
Hampton Inn Majestic-Chicago Theatre District
#33 Vacation Deal
Flight + 4 Nights*
Area: Loop/ Magnificent Mile/ River North
Sep 11 - 15
You Save $ 20
$ 887  $ 867
per person
 
Embassy Suites Chicago - Downtown/Lakefront
#34 Vacation Deal
Flight + 5 Nights*
Area: Loop/ Magnificent Mile/ River North
Sep 11 - 16
You Save $ 21
$ 901  $ 880
per person
 
The Tremont Chicago Hotel at Magnificent Mile
#35 Vacation Deal
Flight + 9 Nights*
Area: Loop/ Magnificent Mile/ River North
Sep 6 - 15
You Save $ 16
$ 995  $ 979
per person
 
BEST WESTERN Grant Park Hotel
#36 Vacation Deal
Flight + 2 Nights*
Area: Loop/ Magnificent Mile/ River North
Sep 13 - 15
You Save $ 13
$ 568  $ 555
per person
 
Radisson Blu Aqua Hotel Chicago
#37 Vacation Deal
Flight + 9 Nights*
Area: Loop/ Magnificent Mile/ River North
Sep 6 - 15
You Save $ 16
$ 1632  $ 1616
per person
 
Comfort Suites Chicago
#38 Vacation Deal
Flight + 9 Nights*
Area: Loop/ Magnificent Mile/ River North
Sep 6 - 15
You Save $ 15
$ 1675  $ 1660
per person
 
Sheraton Chicago Hotel and Towers
#39 Vacation Deal
Flight + 9 Nights*
Area: Loop/ Magnificent Mile/ River North
Sep 6 - 15
You Save $ 15
$ 1590  $ 1575
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
 

Why Book Packages with Travelocity?

Vacation Package Savings up to $525, Price and

Service Guarantee, and  much more.

Pack peace of mind.

With any American Express® Card emergency assistance is just a phone call away.
> LEARN MORE