The Loop Vacations from $471
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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
$775
per person
Nov 24 - Nov 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Breakfast had some cold cuts, but for a vegan there wasn't much more options than your standard US continental. The TV (which turns on automatically every time you enter the room - very annoying) was the worst setup I've seen in a hotel, the connection to cast wasn't working because the TV wasn't connected to wifi, the remote was weird (no volume/channel controls). Lobby was nauseatingly over-fragranced, makes me wonder what horrible scent they're trying to cover up. Tried to use the stairs instead of the slow elevators and couldn't get out on the 2nd floor for breakfast since the stair exits are locked.
Overall fair to ok but missing the attention to detail that would've been nice at the price point. I definitely wouldn't stay for business travel.
Reviewed on Sep 9, 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.
Theatre District
While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more the city at Washington Station or Monroe Station (Blue Line).
The Loop Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$151 nightly
$180 total
Sep 10 - Sep 11
Total with taxes and fees
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$181 nightly
$216 total
Sep 27 - Sep 28
Total with taxes and fees
8.8/10 Excellent! (5,409 reviews)
"I didn’t drive in so this was a great location. Staff was friendly. Small room as expected. Met all needs. Main highlight is the location"
Reviewed on Sep 9, 2026
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$224 nightly
$266 total
Sep 10 - Sep 11
Total with taxes and fees
8.6/10 Excellent! (3,168 reviews)
"The floor we stayed on was outdated and a bit run down and dingy. Staff were too concerned with VIPs to be helpful and accommodating to my disabled husband. The room wouldn't get cooler than 70 degrees and the ice machine was down our entire 5 day stay. Everything was overpriced and confusing."
Reviewed on Sep 9, 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
Photo by TM
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.
Photo by TM
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.
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.
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.
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 fascinating museums 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 City Hall
9.0/10 (10 reviews)
Chicago City Hall is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Stroll along the riverfront or experience the entertainment choices in this vibrant area.
Things to do
Chicago: Willis Tower Skydeck and The Ledge Ticket
$47
per adult
88% 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.