
Uptown Vacations from $295
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Find the right fit
Rest easy
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

The French Country Inn Lake Geneva
Reviewed on Sep 27, 2025

The Westin Michigan Avenue Chicago
Reviewed on Oct 2, 2025

Hotel Riu Plaza Chicago
Reviewed on Oct 1, 2025

Park Hyatt Chicago
Reviewed on Oct 1, 2025

DoubleTree Suites by Hilton Htl & Conf Cntr Downers Grove
Reviewed on Sep 23, 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

Congress Plaza Hotel
Reviewed on Oct 1, 2025

Freehand Chicago
Reviewed on Oct 1, 2025

Embassy Suites by Hilton Chicago Downtown River North
Reviewed on Oct 1, 2025
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.

Lincoln Park
This expansive public park along Lake Michigan offers museums, beaches, nature reserves and sporting facilities.

Montrose Harbor
With trails, a beach and a bird sanctuary, this spacious city harbor is a good place to sail from and a great place to hang out.
Things to do

Chicago Sightseeing River and Lake Cruise
