Where to stay around Uptown?

Our 2018 property listings offer a large selection of 1,211 vacation rentals near Uptown. From 608 Condos/Apartments to 465 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 HomeAway.

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:

  • Chicago Loop: 620 vacation rentals
  • Wrigleyville: 262 vacation rentals
  • Lakeview: 266 vacation rentals
  • Gold Coast: 198 vacation rentals
  • Wicker Park: 486 vacation rentals

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

What are the popular points of interest near where I can stay when traveling to Uptown?

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

  • Montrose Beach: 2,314 vacation rentals
  • Montrose Harbor: 2,312 vacation rentals
  • Louis A. Weiss Memorial Hospital: 2,328 vacation rentals
  • Aragon Entertainment Center: 2,348 vacation rentals
  • About Face Theater: 2,359 vacation rentals

But there are many other points of interest around Uptown listed on HomeAway 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. HomeAway has 608 Condos/Apartments in Uptown. Our other popular types of vacation rentals in Uptown include:

  • Hotels: 465 rentals available
  • Studios: 444 rentals available
  • Houses: 102 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 preferred vacation rental with pool among our 262 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)