Uptown Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $1,045 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
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
Hilton Chicago/Magnificent Mile Suites
Room was warm Recommend softer toilet paper please
Reviewed on Dec 23, 2025
Palmer House a Hilton Hotel
Room is comfortable and clean. It is nice to stay at a historical site
Reviewed on Dec 23, 2025
Silversmith Hotel Chicago Downtown
Very friendly and helpful staff
Reviewed on Dec 23, 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.
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.
Hutchinson Street Historic District
You can learn about the history of Chicago when you stop by Hutchinson Street Historic District. Experience the entertainment choices and acclaimed theater scene in this vibrant area.
Things to do
Chicago Bulls Basketball Game at United Center
