Discover a selection of 1,000 holiday rentals in Uptown, Chicago that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo holiday homes have the best amenities for hanging out with the people that matter most, including pool and private pool. Prices start at £ 51 per night, and flats & apartments and houses are popular options for a stay in Uptown. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Uptown
Destination guide

The vibrant city of Uptown awaits you

Enjoy the area's theatre scene, live music and opera with a rental holiday home in Uptown. Revered 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-see attractions in the area. If you're looking for accommodation options 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 holiday rental, you'll want to experience everything that makes Uptown a fun place to get away to. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • 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 centre:

  • 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

Transport 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 centre. 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 travelling 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 holiday rentals are available around Uptown?

Our 2020 accommodation listings offer a large selection of 913 holiday lettings around Uptown. From 747 flats & apartments to 121 houses, find unique self catering accommodation for you to enjoy a memorable stay with your family and friends for a long holiday or a weekend break.

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:

  • The Loop: 592 holiday homes
  • Near North Side: 538 holiday homes
  • West Town: 491 holiday homes
  • Bucktown: 49 holiday homes
  • Irving Park: 37 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?

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

  • Pegasus Players: 1,347 holiday lettings
  • Louis A. Weiss Memorial Hospital: 1,345 holiday lettings
  • Montrose Harbor: 1,308 holiday lettings
  • Wilson Station: 1,347 holiday lettings
  • Lawrence Station: 1,336 holiday lettings

But there are many other points of interest around Uptown listed on Vrbo UK 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 Flats in Uptown?

Yes, of course. Vrbo UK offers 747 Flats in Uptown. Our other popular types of Uptown holiday rentals include:

  • Houses: 121 self catering accommodations
  • Townhouses: 13 self catering accommodations
  • Studios: 663 self catering accommodations

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

Can I find a holiday accommodation with pool in Uptown?

Yes, you can select your preferred holiday accommodation with pool among our 214 holiday homes with pool available in Uptown. Please use our search bar to access the selection of holiday rentals available.

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