The Loop Vacations from $380
Book a Hotel + Flight or Car together to unlock savings
Your The Loop Vacation
Experience the best that The Loop has to offer with a tailor-made The Loop vacation package. From its bars and pubs and history to its festivals, get ready to fall for the charms of this food-lovers neighborhood. Your trip to The Loop wouldn't be complete without seeing popular attractions nearby such as Millennium Park, Willis Tower and Art Institute of Chicago. Expedia can help you turn your ideal The Loop vacation into reality, no matter your budget or travel plans.
The Latest The Loop Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago O'Hare – Rosemont by IHG
O'Hare
Save 100% on your flight
per person
Oct 10 - Oct 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (2,250 reviews)
Just stayed for a couple hours of sleep with the family between two flights. Shuttle to and from airport was convenient. Excellent service on the phone and at reception between midnight and 1am. Some snacks can be bought in the lobby 24/24, and there is a microwave there; this is convenient also.
Reviewed on Aug 16, 2025
The Emily Hotel
Downtown Chicago
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,159 reviews)
The hotel is situated in Fulton market and has many options for dining.
The bed was comfortable, but the linens were very wrinkled and the comforter had stains on it.
Reviewed on Aug 15, 2025
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (1,991 reviews)
Great location, a little outdated with elevators and hallways. Check in and out were easy.
Love the fridge and microwave in the room and loved that housekeeping only comes if you request it.
Reviewed on Aug 14, 2025
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
per person
Oct 10 - Oct 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,063 reviews)
I really love this place it was my first time at sable hotel and i will definitely come again here. Moreover, it was my wedding anniversary and they gave little surprise with rose petals and champagne also the view is awesome from our room
Reviewed on Aug 15, 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
$157 nightly
The price is $184 total per night from Sep 1 to Sep 2
$184 total
Sep 1 - Sep 2
Total includes taxes and fees
7.8/10 Good! (8,982 reviews)
"Great location! Quiet and comfortable room. Love the history and architectural charm of this classic Chicago Hotel! Exercise room was the best equipped I've used!"
Reviewed on Aug 14, 2025
Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
$198 nightly
The price is $229 total per night from Sep 2 to Sep 3
$229 total
Sep 2 - Sep 3
Total includes taxes and fees
8.4/10 Very Good! (1,856 reviews)
"Pleasant experience. Accommodations were good. Surrounding area was convenient to shopping, eateries and p parks."
Reviewed on Aug 13, 2025
citizenM Chicago Downtown
80 East Wacker Place, Chicago, IL
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $164 total per night from Sep 2 to Sep 3
$164 total
Sep 2 - Sep 3
Total includes taxes and fees
9.2/10 Wonderful! (3,571 reviews)
"The hotel is on the 4th floor with limited signage in front. Parking is two blocks away at $50 a day. I arrived in the middle of a heavy rain storm. They handed me an umbrella for the walk back. Facility is immaculate and perfect if you are not driving."
Reviewed on Aug 15, 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.
Discover the most popular places to visit in The Loop
Millennium Park
4.5/5(7,198 reviews)
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
Chicago Riverwalk
4.5/5(1,535 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(3,410 reviews)
Explore a massive collection of works celebrating different cultures and historical times, from ancient Egypt to modern installations.
Things to do
Chicago By Night River & Lake Cruise
$45
per adult
96% of travellers recommend
Chicago: Architecture Boat Tour with Drinks
$42
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
86% of travellers recommend
Explore a world of travel with Expedia
Explore a world of travel with Expedia
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- Chicago Vacations
- Visit Downtown Chicago
- Visit Chicago
- Where to stay in Chicago
- Daley Plaza
- Chicago Theatre
- Picasso Statue
- Chase Tower
- Willis Tower
- Marshall Field Building
- Richard J. Daley Center
- Noble Fool Theater
- Goodman Theater
- Miró's Chicago
- Chicago Riverwalk
- Chicago Temple
- State Street
- Chicago Cultural Center
- Sullivan Center
- Chicago City Hall
- Navy Pier
- Millennium Park
- Chicago Loop Synagogue
- Chagall's Four Seasons
- CIBC Theatre
- Cadillac Palace Theatre
- Art Institute of Chicago
- Haskell Building
- Cloud Gate
- Marina City
- Carbide and Carbon Building
- Marquette Building
- House of Blues Chicago
- Aon Center
- Crown Fountain
- Rookery
- Chicago Board of Trade Building
- Harris Theater
- Harold Washington Library Center
- Museum of Broadcast Communications
- Monadnock Building
- DePaul University-Loop Campus
- 333 West Wacker Drive
- Symphony Center
- Chicago Symphony Orchestra
- Skydeck Ledge
- Michigan Avenue Bridge
- Civic Opera House
- Fisher Building
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.