The Loop Vacations from $715
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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 Riu Plaza Chicago
Downtown Chicago
$1,077
per person
Oct 27 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
I liked the friendliness of the staff. Although I liked the “safety”aspect of having to use your hotel key to ride in the elevator, that was negated when I saw hotel staff using their key cards to let in people off the streets to go to the rooftop bar.
Reviewed on Aug 26, 2026
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
4 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.
Magnificent Mile
Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.
River North
Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.
Lincoln Park
Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.
Streeterville
This lakefront neighborhood features some of the city’s best shopping alongside art galleries, beach parks, fairground rides and a 94th-floor observation deck.
The Loop Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$109 nightly
$130 total
Sep 8 - Sep 9
Total with taxes and fees
8/10 Very Good! (10,318 reviews)
"Very good location. Walking distance to many attractions. Clean no frills room. Smaller TV that wasn’t HD. Shower was older and water didn’t get very hot. Overall good experience. Liked old school classic feel of the hotel."
Reviewed on Aug 26, 2026
The Allegro Royal Sonesta Hotel Chicago Loop
171 W Randolph St Chicago IL
Fully refundableReserve now, pay when you stay
$230 nightly
$273 total
Sep 7 - Sep 8
Total with taxes and fees
River Hotel
75 East Wacker Drive Chicago IL
$145 nightly
$172 total
Sep 7 - Sep 8
Total with taxes and fees
8.8/10 Excellent! (5,453 reviews)
"Overall a great stay location is perfect and the view was amazing. Room was basic and simple but it was clean. Everything worked so I’d recommend it for future travelers."
Reviewed on Aug 26, 2026
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.
Stay near popular The Loop attractions
Chicago Riverwalk
9.6/10 (13,574 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.
Millennium Park
9.4/10 (30,446 reviews)
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
Art Institute of Chicago
9.4/10 (7,898 reviews)
Explore a massive collection of works celebrating different cultures and historical times, from ancient Egypt to modern installations.
Willis Tower
9.0/10 (9,893 reviews)
Visit the Skydeck and gaze down over the Chicago cityscape from a dazzling 1,353 feet above the sidewalk.
Photo by © Choose Chicago
Chicago Theatre
9.0/10 (1,866 reviews)
See a stage show at this iconic cultural beacon, which still captures all the splendor of a trip to the movie theater in the early 20th century.
Cloud Gate
9.4/10 (104 reviews)
You can learn about the history of Chicago with a stop at Cloud Gate. Discover the entertainment choices and notable monuments in this vibrant area.
Buckingham Fountain
9.2/10 (1,301 reviews)
This enormous art deco installation gives free regular water and light shows symbolizing the power and might of Lake Michigan.
Chicago Cultural Center
9.2/10 (220 reviews)
Enjoy a stop at Chicago Cultural Center, an entertaining place to visit in Chicago. Discover the fascinating museums and notable monuments in this vibrant area.
Things to do
Chicago: Willis Tower Skydeck and The Ledge Ticket
$47
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
90% of travellers recommend
Explore a world of travel with Expedia
- Columbia College Chicago
- Monadnock Building
- Jane Addams' Hull-House Museum
- Wrigley Field
- Fisher Building
- Aon Center
- Chicago Cultural Center
- Richard J. Daley Center
- Roosevelt University
- Cibc Theatre
- Cna Center
- United Center
- Crown Fountain
- Merchandise Mart
- Skydeck Ledge
- Marina City
- Richard Norton Gallery
- St. James Cathedral
- Art Institute of Chicago
- Old Colony Building
- Gen. John Logan Memorial
- Chicago Loop Synagogue
- Fourth Presbyterian Church
- Shops at North Bridge
- Santa Fe Building
- Millennium Park
- Chicago Board of Trade Building
- Tribune Tower
- Amazing Chicago's Funhouse Maze
- Chicago Museum Campus Vacations
- Sullivan Center
- Chicago Place Mall
- Picasso Statue
- International Museum of Surgical Science
- Ronald McDonald House near Lurie Children’s
- Chase Tower
- University of Illinois Chicago
- Harold Washington Library Center
- North Avenue Beach
- Buckingham Fountain
- Unity Temple
- The East Bank Club
- Water Tower Place
- 333 West Wacker Drive
- Ohio Street Beach
- Grant Park
- 311 S Wacker Dr
- Ann and Robert H. Lurie Children's Hospital
- Chicago Children's Museum
- Bridgehouse and Chicago River Museum
- Chicago City Hall
- Rookery
- Cloud Gate
- Magnificent Mile Vacations
- House of Blues Chicago
- Chicago Water Tower
- Marshall Field Building
- Lincoln Park Zoo
- Michigan Avenue Bridge
- Civic Opera House
- Cadillac Palace Theatre
- Lincoln Park Conservatory
- Bally's Casino Chicago
- State Street
- Chicago Vacations
- Goodman Theater
- Michigan Avenue
- Robie House
- Driehaus Museum
- The Salt Shed
- Navy Pier
- Ping Tom Memorial Park
- Oak Street Beach
- Film Row Cinema
- Chicago Architecture Foundation
- Marquette Building
- Daley Plaza
- Willis Tower
- Chicago History Museum
- Pontiac Building
- 900 North Michigan Shops
- Northwestern Memorial Hospital
- Holy Name Cathedral
- Carbide and Carbon Building
- Chicago Riverwalk
- Chicago Symphony Orchestra
- Auditorium Building and Theatre
- Montrose Beach
- Cooking & Hospitality Institute of Chicago
- Maggie Daley Park
- Haskell Building
- Depaul University-Loop Campus
- Downtown Chicago Vacations
- Dave & Buster's
- Chicago Temple
- River North Vacations
- Theatre District Vacations
- Symphony Center
- Wrigley Building
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.