
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.



Level Chicago - River North
Downtown Chicago
per person
Sep 3 - Sep 9
found 14 hours ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (639 reviews)
Quick and easy check in. Parking in their private garage was breeze. Plenty of space, mostly empty, and our vehicle could stay in the garage until 2:00 PM the next day. Beautiful 1 BR condo. Full kitchen, beautiful views of the city on the balcony and from the living room, and very clean space overall. Need your key card for just about everything (pool, lounge, some of the outdoor bathrooms, elevators, etc.).
Reviewed on Jul. 27, 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 $186 per night from Sep 1 to Sep 2
CA $186
CA $218 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (9,038 reviews)
"This was a nice option for my wife and I . Nice location plenty of dining with in walking distance. Highly recommend this hotel"
Reviewed on Jul. 29, 2025

Travelodge by Wyndham Downtown Chicago
65 E Harrison St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $148 per night from Aug 25 to Aug 26
CA $148
CA $174 total
Aug 25 - Aug 26
includes taxes & fees
7.2/10 Good! (2,258 reviews)
"The building is old but clean. The bed was comfortable."
Reviewed on Jul. 29, 2025

Hilton Chicago
720 S Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $243 per night from Aug 17 to Aug 18
CA $243
CA $326 total
Aug 17 - Aug 18
includes taxes & fees
8.4/10 Very Good! (2,027 reviews)
"Enjoyed our stay. Great location."
Reviewed on Jul. 31, 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 Sightseeing River and Lake Cruise
CA $62
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.