A frozen river with a city skyline in the background.

Uptown Vacations

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Where to stay in Uptown

Find the best Uptown areas and neighborhoods for the activities you enjoy most.
A cityscape with tall skyscrapers and a historic tower.

Downtown Chicago

Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Navy Pier and Michigan Avenue are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

A busy urban street at dusk with tall buildings, a historic tower, and pedestrians.
Photo by © City of Chicago
Open Photo by © City of Chicago

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.

A river with yellow boats, a bridge, and tall buildings.

The Loop

Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.

A large, historic building with a central tower and multiple windows, located near a body of water.

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.

A river with a city skyline in the background, surrounded by green trees and grass.

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.

Discover the most popular places to visit in Uptown

A historic theater with ornate architecture and a prominent marquee.

Aragon Ballroom

9.2/10 (10 reviews)
Catch an event at Aragon Ballroom during your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.
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Uptown Hotel Deals

A rooftop patio with outdoor seating, a pergola, and a city skyline view.

The Guesthouse Hotel

The Guesthouse Hotel
4.0 star property
Uptown
9.8 out of 10, Exceptional, (429 reviews)
"The location is perfect for wandering around Andersonville's many small businesses (great restaurants and really cool shops) and is very close to a couple of playgrounds for the kids. There was the perfect amount of space for our two families in the "room" we chose and the staff were very accommodating and helpful with parking and extra stuff we forgot to bring - the only thing we wanted more of were coffee beans (we only had one serving on hand for our two night stay) and tea (we ran out of...
The price is AED 1,107
AED 1,300 total
includes taxes & fees
29 Nov - 30 Nov
The Guesthouse Hotel
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.
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