Discover a selection of 1,000 vacation rentals in Uptown, Chicago that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $55 per night, and houses and condos are popular options for a stay in Uptown. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Uptown
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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, Vrbo 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.

How many vacation rentals are available around Uptown, Chicago?

Our 2021 property listings offer a large selection of 1,125 vacation rentals around Uptown. From 154 house rentals to 925 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

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:

  • Thorek Memorial Hospital: 1,547 vacation rentals
  • Aragon Ballroom: 1,547 vacation rentals
  • Louis A. Weiss Memorial Hospital: 1,544 vacation rentals
  • Montrose Harbor: 1,529 vacation rentals
  • Aragon Entertainment Center: 1,547 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 Houses in Uptown?

Yes, of course. Vrbo has 154 Houses in Uptown. Our other popular types of vacation rentals in Uptown include:

  • Condos/Apartments: 925 rentals available
  • Studios: 792 rentals available
  • Townhouses: 15 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 195 vacation rentals with pool available in Uptown. Please use our search bar to access the selection of vacation rentals available.