A street with outdoor seating, brick buildings, and signs for a barbershop and a restaurant.
Photo by TM
Open Photo by TM

Old Town Chicago Vacations

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Where to stay in Old Town Chicago

Find the best Old Town Chicago 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 Old Town Chicago

Second City

9.6/10 (15 reviews)
You can enjoy a show at Second City during your stay in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.
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Old Town Chicago Hotel Deals

A rooftop terrace with a fire feature, seating, and a cityscape view.

Hotel Lincoln

Hotel Lincoln
4.0 star property
Old Town Chicago
8.0 out of 10, Very good, (1,158 reviews)
The price is AED 372
AED 532 total
includes taxes & fees
22 Nov - 23 Nov
Hotel Lincoln
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.