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The Loop Vacation Packages

The Loop Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham South Holland
DoubleTree by Hilton Chicago Schaumburg
Arlo Chicago
Hilton Chicago/Oak Brook Suites
Pendry Chicago
SpringHill Suites by Marriott Chicago Naperville/Warrenville
Hotel Indigo Chicago-Vernon Hills by IHG
The Emily Hotel

3-4 Night Vacations in The Loop

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham South Holland
Hilton Chicago/Oak Brook Suites
Pendry Chicago
SpringHill Suites by Marriott Chicago Naperville/Warrenville

5-7 Night Vacations in The Loop

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham South Holland
DoubleTree by Hilton Chicago Schaumburg
SpringHill Suites by Marriott Chicago Naperville/Warrenville
Arlo Chicago

Cheap Hotel Deals in The Loop

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
323 E Wacker Dr, Chicago, IL
Book a stay at this eco-certified hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and ...
Swissotel - Chicago
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
Congress Plaza Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
River Hotel
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The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
171 W Randolph St, Chicago, IL
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the bar ...
The Allegro Royal Sonesta Hotel Chicago Loop
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the ...
citizenM Chicago Downtown
L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
225 N Wabash Ave, Chicago, IL
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and ...
L7 Chicago by LOTTE
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
200 North Columbus Drive, Chicago, IL
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Fairmont Chicago at Millennium Park
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

4 out of 5
71 E Wacker Dr, Chicago, IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the restaurant ...
The Royal Sonesta Chicago Downtown
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Spirit Airlines
Frontier Airlines
ITA Airways
EVA Airways