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South Loop Vacation Packages

South Loop Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites Prospect Heights by IHG
DoubleTree Suites by Hilton Htl & Conf Cntr Downers Grove
The Langham, Chicago
The Emily Hotel
Level Chicago – Old Town
Hilton Chicago O'Hare Airport
Hotel Riu Plaza Chicago
Staybridge Suites Chicago O'Hare - Rosemont by IHG

3-4 Night Vacations in South Loop

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop
Hotel Riu Plaza Chicago
Ameristar Casino Hotel East Chicago
The Royal Sonesta Chicago Downtown

5-7 Night Vacations in South Loop

Price found within the past 48 hours. Click for updated prices.
DoubleTree Suites by Hilton Htl & Conf Cntr Downers Grove
Hotel Riu Plaza Chicago
Sable at Navy Pier Chicago, Curio Collection by Hilton
Pendry Chicago

Cheap Hotel Deals in South 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 ...
Opens in a new windowCongress Plaza Hotel
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 ...
Opens in a new windowHilton Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St, Chicago, IL
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
Opens in a new windowTravelodge by Wyndham Downtown Chicago
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Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
55 E 11th Street, Chicago, IL
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the ...
Opens in a new windowHilton Garden Inn Chicago Downtown South Loop
Sentral Michigan Avenue

Sentral Michigan Avenue

4 out of 5
808 SOUTH MICHIGAN AVENUE, Chicago, IL
Stay at this 4-star business-friendly aparthotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the ...
Opens in a new windowSentral Michigan Avenue
Best Western Grant Park Hotel

Best Western Grant Park Hotel

2.5 out of 5
1100 S Michigan Ave, Chicago, IL
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
Opens in a new windowBest Western Grant Park Hotel
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. ...
Opens in a new windowFreehand Chicago
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
Opens in a new windowHilton Chicago/Magnificent Mile Suites
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.

Frontier Airlines
Spirit Airlines
Frontier Airlines
All Nippon Airways