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 features

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)
How to get there

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 property listings offer a large selection of 1,240 vacation rentals near Uptown. From 135 Houses to 1,055 Condos/Apartments, 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: 743 vacation rentals
  • Wrigleyville: 404 vacation rentals
  • Lincoln Park: 654 vacation rentals
  • River North: 490 vacation rentals
  • Magnificent Mile: 543 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: 1,645 vacation rentals
  • Louis A. Weiss Memorial Hospital: 1,660 vacation rentals
  • Aragon Entertainment Center: 1,659 vacation rentals
  • About Face Theater: 1,662 vacation rentals
  • Montrose Harbor: 1,647 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 Houses in Uptown?

Yes, of course. HomeAway has 135 Houses in Uptown. Our other popular types of vacation rentals in Uptown include:

  • Condos/Apartments: 1,055 rentals available
  • Townhouses: 15 rentals available
  • Studios: 899 rentals available

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

Can I find a vacation rental with pool in Uptown?

Yes, you can select your preferred vacation rental with pool among our 130 vacation rentals with pool available in Uptown. Please use our search bar to access the selection of vacation rentals available.

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