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The Loop Vacation Packages

The Loop Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Admiral Motel By Oyo Chicago I-94
Hotel Riu Plaza Chicago
Pendry Chicago
Hilton Chicago
Holiday Inn Chicago O'Hare – Rosemont, an IHG Hotel
Fairmont Chicago at Millennium Park
LondonHouse Chicago, Curio Collection by Hilton
Courtyard by Marriott Chicago Magnificent Mile

3-4 Night Vacations in The Loop

Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott Chicago Magnificent Mile
Fairmont Chicago at Millennium Park
La Banque Hotel
Hilton Chicago

5-7 Night Vacations in The Loop

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago
Pendry Chicago
Congress Plaza Hotel
LondonHouse Chicago, Curio Collection by Hilton

Cheap Hotel Deals in The Loop

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
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
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Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave, Chicago, IL
Stay at this 4-star historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
Hilton Chicago
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful ...
Club Quarters Hotel, Central Loop, Chicago
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and ...
Palmer House a Hilton Hotel
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr, Chicago, IL
Book a stay at this eco-certified hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the bar and the helpful staff in our ...
Hyatt Regency Chicago
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
323 E Wacker Dr, Chicago, IL
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant ...
Swissotel - Chicago
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
Spirit Airlines
Frontier Airlines
Icelandair