Uptown Vacations from $609
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Your Uptown Vacation
Take the stress out of travel planning with an Uptown vacation package. With all the details organized before you set off, all you have to do is simply enjoy this residential neighborhood's cafes, history and culture. Not sure what to see and do during your trip to Uptown? Nearby attractions like Lincoln Park, Loyola University Chicago and Aragon Ballroom are great places to start. Expedia can help you turn your ideal Uptown vacation into reality, no matter your travel plans or budget.
The Latest Uptown Vacation Packages
Swissotel - Chicago
Reviewed on Aug 31, 2026
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.
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.
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.
Uptown Hotel Deals
Congress Plaza Hotel
"Check-in was super quick and staff was very efficient and helpful. Booked a standard room with a king size bed facing the lake and it was a very nice weekend stay. Room was very clean. The AC is off central heatingThe location is incredibly convenient if you’re going somewhere near the lake or ..."
Reviewed on Aug 31, 2026
The Chicago Hotel Collection Ambassador Gold Coast
Kasa Magnificent Mile Chicago
"More cutlery more awalible front desk"
Reviewed on Aug 31, 2026
Stay near popular Uptown attractions
Aragon Ballroom
Montrose Beach
Montrose Harbor
Hutchinson Street Historic District
Riviera Theatre
Pegasus Players
Aragon Entertainment Center
Carol's Pub
Things to do
