The Loop Vacations from $430
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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.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was $634, price is now $430 per person
$430
per person
Dec 10 - Dec 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,181 reviews)
Room and common areas need a little TLC, but otherwise very clean and well located.
Reviewed on Sep 21, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $962, price is now $578 per person
$578
per person
Oct 24 - Oct 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Stayed 2 nights in sept, everything was nice and clean. very good breakfast buffet and breakfast staff were very friendly. Front desk gentleman ok but not very welcoming for a good hotel where you're the first impression. room and bed comfortable but no ice bucket or machines, card needs to be placed in slot for room electrics to work, no air exhaust in our bathroom, and after I asked for a/c to be looked at and no-one showed I pulled out cover and reset system myself. front door people were very friendly.
Reviewed on Sep 22, 2025
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $955, price is now $615 per person
$615
per person
Nov 28 - Dec 3
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (294 reviews)
I had such a lovely time here. I love the extra things that come with staying here! The pool was very nice and clean. I really loved the space of the rooms and how clean it was. Will be coming here again!
Reviewed on Sep 21, 2025
Viceroy Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,196, price is now $798 per person
$798
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,107 reviews)
Loved my visit.
Smells amazing! A highlight of my trip!
Reviewed on Sep 23, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,318, price is now $881 per person
$881
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Worth every penny! Not much more than the "average" hotel when comparing all of the amenities. Will definitely stay here again!
Reviewed on Sep 23, 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
$168 nightly
The price is $197 total per night from Sep 24 to Sep 25
$197 total
Sep 24 - Sep 25
Total with taxes and fees
7.8/10 Good! (9,265 reviews)
"Big hotel with lots of floors."
Reviewed on Sep 22, 2025
citizenM Chicago Downtown
80 East Wacker Place, Chicago, IL
Fully refundableReserve now, pay when you stay
$182 nightly
The price is $214 total per night from Sep 28 to Sep 29
$214 total
Sep 28 - Sep 29
Total with taxes and fees
9.2/10 Wonderful! (3,813 reviews)
"Please try to restock luggage tag bands"
Reviewed on Sep 17, 2025
The Allegro Royal Sonesta Hotel Chicago Loop
171 W Randolph St, Chicago, IL
Fully refundableReserve now, pay when you stay
$221 nightly
The price is $260 total per night from Oct 5 to Oct 6
$260 total
Oct 5 - Oct 6
Total with taxes and fees
8.8/10 Excellent! (2,028 reviews)
"Staff very friendly."
Reviewed on Sep 16, 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: Navy Pier Centennial Wheel Ticket
$25
per adult
84% of travellers recommend
Chicago: Architecture Boat Tour with Drinks
$42
per adult
90% 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.