Destination guide

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

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)
Natural highlights

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)
Transport

Transportation to and around Uptown

Fly into Chicago, IL (ORD-O'Hare Intl.), the closest airport, located 12.9 mi (20.8 km) from the city center. If you can't find a flight that's convenient for your trip, you can also fly into Chicago, IL (MDW-Midway Intl.), which is 13 mi (21 km) away.

If you're traveling by train, the main station is Chicago Ravenswood Station. You can see more of Uptown by catching a ride on the metro at Wilson Station, Lawrence Station or Argyle Station.

Where to stay around Uptown?

Our 2019 accommodation listings offer a large selection of 913 holiday lettings near Uptown. From 139 Houses to 577 Studios, find unique self catering accommodation for you to enjoy a memorable stay with your family and friends. The best place to stay near Uptown for a long holiday or a weekend break is on HomeAway.

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

Whether you are travelling solo or with family and friends, here are the areas with the largest selection of holiday accommodations for a long holiday or just a weekend break in Uptown:

  • Wicker Park: 529 holiday homes
  • Near West Side: 275 holiday homes
  • West Rogers Park: 44 holiday homes
  • Bronzeville: 52 holiday homes
  • South Loop: 99 holiday homes

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

What are the most popular points of interest and landmarks to stay near when travelling to Uptown?

HomeAway offers a large selection of holiday accommodations near great places in Uptown. From HomeAway travellers, the most popular points of interest to stay near are:

  • About Face Theater: 1,133 holiday lettings
  • Montrose Harbor: 1,216 holiday lettings
  • Louis A. Weiss Memorial Hospital: 1,208 holiday lettings
  • Aragon Entertainment Center: 1,108 holiday lettings
  • Montrose Beach: 1,221 holiday lettings

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 holiday rentals available near the point of interest of your choice.

Can I rent Houses in Uptown?

Yes, of course. HomeAway offers 139 Houses in Uptown. Our other popular types of Uptown holiday rentals include:

  • Studios: 577 self catering accommodations
  • Condos/Apartments: 733 self catering accommodations
  • Townhouses: 15 self catering accommodations

But you can also enjoy a great stay in one of our other holiday rentals including Guest houses and more.

Can I find a holiday accommodation with pool in Uptown?

Yes, you can select your preferred holiday accommodation with pool among our 72 holiday homes with pool available in Uptown. Please use our search bar to access the selection of holiday rentals available.