
South Loop Vacation Packages
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Top Holiday Package Deals in South Loop
Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago
Downtown Chicago
per person
Oct 17 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,270 reviews)
This was my first time staying. The staff was very friendly and helpful. Our room was very nice and perfectly located downtown. Also, the breakfast buffet was amazing and a nice surprise.
Reviewed on Aug. 9, 2025



The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
per person
Sep 28 - Oct 2
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Chicago (ORD)
8.8/10 Excellent! (1,925 reviews)
Transport access walking distance to take train to midway airport was easy and convenient
Reviewed on Aug. 7, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (2,063 reviews)
It is located on Navy Pier which was very convenient for us. The view was wonderful of the skyline and harbor. The room was very nice and had a refrigerator,,but lacked a microwave. The room and restaurant were quite expensive for what they were, but I guess we were paying for the location.
Reviewed on Aug. 9, 2025
Where to stay in South Loop
Find the best South Loop areas and neighborhoods for the activities you enjoy most. Learn more about South Loop

Downtown Chicago
5 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
South Loop Hotel Deals

Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $185 per night from Sep 1 to Sep 2
CA $185
CA $217 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (8,926 reviews)
"Took water awhile to get hot for shower, and parking is ridiculously expensive. Other than that enjoyed staying at hotel"
Reviewed on Aug. 8, 2025

Hilton Chicago
720 S Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $193 per night from Sep 2 to Sep 3
CA $193
CA $266 total
Sep 2 - Sep 3
includes taxes & fees
8.4/10 Very Good! (2,050 reviews)
"Amazing. Family friendly. The staff were so good"
Reviewed on Aug. 7, 2025

Travelodge by Wyndham Downtown Chicago
65 E Harrison St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $130 per night from Aug 25 to Aug 26
CA $130
CA $153 total
Aug 25 - Aug 26
includes taxes & fees
7.2/10 Good! (2,278 reviews)
"Hotel staff greeted us every time we entered or exited the building and even said good night :) A security guard was available every night and the red line subway entrance was right down the corner. Bonus points because there is a dunkin donuts/baskinrobbins across the street that's open 24/7!!!"
Reviewed on Aug. 7, 2025
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.
Frequently asked questions
Things to do

Chicago's Dark Side Self-Guided Smartphone Walking Tour
CA $13
per adult
98% of travellers recommend

Field Museum of Natural History Ticket with Self-Guided Audio Tour
CA $87
per adult
100% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.