
Uptown Vacation Packages
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Top Holiday Package Deals in Uptown

Level Chicago – Old Town
Reviewed on Aug. 27, 2025

Trump International Hotel & Tower Chicago
Reviewed on Aug. 29, 2025

Pendry Chicago
Reviewed on Aug. 26, 2025


Level Chicago - River North
Reviewed on Aug. 25, 2025
Where to stay in Uptown

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.
Uptown Hotel Deals

The Wade
Reviewed on Aug. 27, 2025

Congress Plaza Hotel
Reviewed on Aug. 26, 2025

Embassy Suites by Hilton Chicago Downtown River North
Reviewed on Aug. 27, 2025
Frequently asked questions
Discover the most popular places to visit in Uptown

Montrose Beach
Soak up the sun with views of Lincoln Park and Lake Michigan at this city beach known for its fun sports and extensive amenities.
Aragon Ballroom
Catch an event at Aragon Ballroom during your trip to Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.
Riviera Theatre
You can enjoy a show at Riviera Theatre during your stay in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.
Things to do

Wendella's 90-min Chicago River Architecture Tour
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