Where to stay around Uptown, Chicago?

Our 2018 property listings offer a large selection of 1,346 vacation rentals near Uptown. From 651 Condos/Apartments to 544 Hotels, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Uptown for a holiday or a weekend are on VRBO.

What is the best area to stay when traveling to Uptown?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Uptown:

  • Lakeview: 286 vacation rentals
  • Chicago Loop: 723 vacation rentals
  • Streeterville: 203 vacation rentals
  • Old Town: 235 vacation rentals
  • Wrigleyville: 314 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular point of interests near where I can stay when traveling to Uptown?

VRBO offers a large selection of vacation rentals near lovely places in Uptown. From VRBO travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Montrose Beach: 2,256 vacation rentals
  • Louis A. Weiss Memorial Hospital: 2,293 vacation rentals
  • Montrose Harbor: 2,241 vacation rentals
  • Aragon Entertainment Center: 2,306 vacation rentals
  • About Face Theater: 2,316 vacation rentals

But there are many other points of interest around Uptown listed on VRBO where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Condos/Apartments in Uptown?

Yes, of course. VRBO has 651 Condos/Apartments in Uptown. Our other popular types of vacation rentals in Uptown include:

  • Hotels: 544 rentals available
  • Studios: 488 rentals available
  • Houses: 104 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Townhouses and more.

Can I find a vacation rental with pool in Uptown?

Yes, you can select your prefered vacation rental with pool among our 304 vacation rentals with pool available in Uptown. Please use our search bar to access the selection of vacation rentals available.

    The exciting city of Uptown awaits you

    Enjoy the area's theater scene, live music and opera and make a vacation rental your home during your stay in Uptown. Well-liked for its bird watching, lake and skyscrapers, this city is both cosmopolitan and scenic. Wrigley Field and John Hancock Center are just a couple of the must-sees in the area. If you're looking for accommodations with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

    Activities and attractions in and around Uptown

    Do you want to find attractions to see in the city? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Uptown a fun place to get away. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city center:

    • Skydeck Ledge (6.1 mi / 9.8 km)
    • Lincoln Park Zoo (3.3 mi / 5.4 km)
    • Navy Pier (5.6 mi / 9 km)
    • John G. Shedd Aquarium (7.2 mi / 11.5 km)
    • Adler Planetarium and Astronomy Museum (7.3 mi / 11.7 km)
    • Brookfield Zoo (12.9 mi / 20.8 km)

    Exploring the natural features in Uptown

    Whether you're looking for fun outdoor activities or just want to take in the scenery, Uptown is a great place to spend some time outside. These are some of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city center:

    • Millennium Park (6 mi / 9.6 km)
    • Lincoln Park (1.3 mi / 2.1 km)
    • Grant Park (6.6 mi / 10.7 km)
    • Montrose Beach (0.8 mi / 1.3 km)
    • Kathy Osterman Beach (1.5 mi / 2.4 km)
    • North Avenue Beach (3.7 mi / 6 km)