The Loop Vacations from $361
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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
Where to stay in The Loop
Downtown Chicago
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.
West Loop
Consider a visit to The Old Post Office and take some time to enjoy the abundant dining options during your time in West Loop. If you want to see more of the city, jump on the metro at Racine Station or Ogilvie Transportation Center.
The Loop Hotel Deals
Congress Plaza Hotel
River Hotel
"Great hotel"
Reviewed on Oct 11, 2026
Hilton Chicago
"I enjoyed the property's elegance and location, with all the sightseeing sites within walking distance of the hotel. I also enjoyed the Irish pub and restaurant in the main lobby."
Reviewed on Oct 10, 2026
Stay near popular The Loop attractions
Millennium Park
Chicago Riverwalk
Willis Tower
Art Institute of Chicago
Chicago Theatre
Cloud Gate
Daley Plaza
Buckingham Fountain
Things to do
Wendella's 90-min Chicago River Architecture Tour
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
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