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



Level Chicago - River North
Downtown Chicago
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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 The Loop
Find the best The Loop areas and neighborhoods for the activities you enjoy most. Learn more about The 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.
The 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

citizenM Chicago Downtown
80 East Wacker Place, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $216 per night from Aug 26 to Aug 27
CA $216
CA $254 total
Aug 26 - Aug 27
includes taxes & fees
9.2/10 Wonderful! (3,472 reviews)
"The staff was so nice and very accommodating!"
Reviewed on Jul. 28, 2025

Swissotel - Chicago
323 E Wacker Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $273 per night from Sep 1 to Sep 2
CA $273
CA $362 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (2,524 reviews)
Was not what I anticipated.
"When I booked my stay I was willing to pay the price of the room after seeing the gorgeous pictures of the bathroom featuring a city/river view. When I got into my room there was no bathroom window, thus taking away the primary appeal of the room leaving me feeling upset. It is in my honest thoughts ..."
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
Discover the most popular places to visit in The Loop

Millennium Park
4.5/5(722 reviews)
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Chicago Riverwalk
4.5/5(149 reviews)
Stroll along the waterfront of the Chicago River to pass some of the city’s most appealing attractions and appreciate how a once grim area has been successfully revamped.

Art Institute of Chicago
4.5/5(304 reviews)
Explore a massive collection of works celebrating different cultures and historical times, from ancient Egypt to modern installations.
Things to do

Chicago Sightseeing River and Lake Cruise
CA $62
per adult
100% of travellers recommend
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Packages
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.