Uptown Vacations from $385
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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
Pendry Chicago
Reviewed on Nov 8, 2026
Where to stay in Uptown
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.
Uptown Hotel Deals
Congress Plaza Hotel
"Love that this is a classic Chicago downtown hotel experience! The lobby area is such a throwback to a different era in Chicago, which is cool. The rooms (we were in 933) are in desperate need of an upgrade by whatever parent company owns this hotel. The bathroom was severely outdated with a bathroom ..."
Reviewed on Nov 10, 2026
The Chicago Hotel Collection Ambassador Gold Coast
River Hotel
"Hotel is a perfect location in downtown Chicago. Pedro and Jock at the front desks were very accommodating. Historic property. Great view from a Riverview room. I will stay again when I revisit Chicago!"
Reviewed on Nov 10, 2026
Stay near popular Uptown attractions
Things to do
