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 Dallas

Depart from:
Sort By: Travelocity Picks| Price| Ratings| Hotel Name
Flight + Hotel* Hotel Only**
Hyatt Regency Chicago
Area: Loop/ Magnificent Mile/ River North
Hotel Rating User Rating
$775
$527
per person
Save $248
Save 32%
Oct  6 -9
includes flight + 3 nights hotel, taxes & fees
$119
per night
includes hotel only, excludes taxes and fees
Eaglewood Resort and Spa
Area: West Chicago
Hotel Rating User Rating
$577
$395
per person
Save $182
Save 32%
Oct  9 -13
includes flight + 4 nights hotel, taxes & fees
$71
per night
includes hotel only, excludes taxes and fees
The Tremont Chicago Hotel at Magnificent Mile
Area: Loop/ Magnificent Mile/ River North
Hotel Rating User Rating
$824
$576
per person
Save $248
Save 30%
Sep 30-Oct 4
includes flight + 4 nights hotel, taxes & fees
$76
per night
includes hotel only, excludes taxes and fees
Radisson Hotel Chicago O'Hare
Area: Chicago O'Hare Airport
Hotel Rating User Rating
$635
$454
per person
Save $181
Save 29%
Sep 30-Oct 4
includes flight + 4 nights hotel, taxes & fees
$70
per night
includes hotel only, excludes taxes and fees
The Ritz-Carlton Chicago, A Four Seasons Hotel
Area: Loop/ Magnificent Mile/ River North
Hotel Rating User Rating
$3,128
$2,255
per person
Save $873
Save 28%
Nov  4 -14
includes flight + 10 nights hotel, taxes & fees
$395
per night
includes hotel only, excludes taxes and fees
Renaissance Chicago O Hare Suites Hotel
Area: Chicago O'Hare Airport
Hotel Rating User Rating
$891
$642
per person
Save $249
Save 28%
Oct  7 -12
includes flight + 5 nights hotel, taxes & fees
$99
per night
includes hotel only, excludes taxes and fees
Ramada Suites Banquet and Conv Center
Area: Oakbrook/Downers Grove/Glendale Heights
Hotel Rating User Rating
$676
$495
per person
Save $181
Save 27%
Nov  4 -14
includes flight + 10 nights hotel, taxes & fees
$58
per night
includes hotel only, excludes taxes and fees
Holiday Inn Chicago-Mart Plaza
Area: Loop/ Magnificent Mile/ River North
Hotel Rating User Rating
$937
$692
per person
Save $245
Save 26%
Sep 30-Oct 4
includes flight + 4 nights hotel, taxes & fees
$110
per night
includes hotel only, excludes taxes and fees
The Palmer House Hilton
Area: Loop/ Magnificent Mile/ River North
Hotel Rating User Rating
$1,735
$1,304
per person
Save $431
Save 25%
Nov  4 -14
includes flight + 10 nights hotel, taxes & fees
$117
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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