Chicago Vacation Packages and Deals

Whether you call it the Windy City, Pie Town, or the Hub of the Midwest, you'll find great deals to Chicago!

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Room Adults (18-64) Minors (0-17)
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Room Adults (18-64) Minors (2-17) Seniors (65+)
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Room Adults (18-64) Minors (2-17) Seniors (65+)
Room 1
Room 2
Room 3
Room 4
Room Adults (18-64) Minors (0-17)
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Today's Best Chicago Vacation Deals from Minneapolis St. Paul

Depart from:
Sort By: Travelocity Picks| Price| Ratings| Hotel Name
Flight + Hotel* Hotel Only**
Hotel Indigo Gold Coast
Area: Chicago
Hotel Rating User Rating
$227
per person
Save 33%
Feb  13 -14
includes flight + 1 night hotel, taxes & fees
$112
per night
includes hotel only, excludes taxes and fees
Club Quarters Central Loop
Area: Chicago
Hotel Rating User Rating
$218
per person
Save 32%
Dec  4 -6
includes flight + 2 nights hotel, taxes & fees
$84
per night
includes hotel only, excludes taxes and fees
Millennium Knickerbocker Hotel Chicago
Area: Chicago
Hotel Rating User Rating
$376
per person
Save 32%
Dec  3 -6
includes flight + 3 nights hotel, taxes & fees
$139
per night
includes hotel only, excludes taxes and fees
Days Inn Elk Grove Village
Area: Chicago
Hotel Rating User Rating
$185
per person
Save 32%
Dec  3 -6
includes flight + 3 nights hotel, taxes & fees
$42
per night
includes hotel only, excludes taxes and fees
River Hotel
Area: Chicago
Hotel Rating User Rating
$197
per person
Save 32%
Feb  13 -14
includes flight + 1 night hotel, taxes & fees
$94
per night
includes hotel only, excludes taxes and fees
Chicago's Essex Inn
Area: Chicago
Hotel Rating User Rating
$223
per person
Save 31%
Dec  4 -6
includes flight + 2 nights hotel, taxes & fees
$71
per night
includes hotel only, excludes taxes and fees
Crowne Plaza Metro
Area: Chicago
Hotel Rating User Rating
$294
per person
Save 30%
Dec  26 -29
includes flight + 3 nights hotel, taxes & fees
$96
per night
includes hotel only, excludes taxes and fees
Central Loop Hotel
Area: Chicago
Hotel Rating User Rating
$301
per person
Save 30%
Dec  26 -29
includes flight + 3 nights hotel, taxes & fees
$84
per night
includes hotel only, excludes taxes and fees
Courtyard by Marriott Chicago Downtown River North
Area: Chicago
Hotel Rating User Rating
$254
per person
Save 29%
Dec  26 -29
includes flight + 3 nights hotel, taxes & fees
$99
per night
includes hotel only, excludes taxes and fees
* 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.

**Hotel-only prices are in USD, per room, based on double occupancy. Hotel-only prices do not include taxes. Offers vary by hotel, are subject to availability, and may be discontinued without notice. Additional restrictions and blackout dates may apply. Prices may vary, depending on travel dates and seasonality.
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