Uptown, Chicago holiday accommodation: flats & apartments & more

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Find the best place to stay — Uptown

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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

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 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 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 accommodation are available around Uptown?

Our 2020 accommodation listings offer a large selection of 979 holiday rentals around Uptown. From 798 flats & apartments to 127 holiday houses, find unique holiday homes for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay around Uptown is on Stayz.

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 rentals for a long holiday or just a weekend break in Uptown:

Chicago Loop: 249 holiday homes
West Loop: 269 holiday homes
Logan Square: 256 holiday homes
Printer's Row: 68 holiday homes
Near North Side: 251 holiday homes

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

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

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

Pegasus Players: 1,142 holiday rentals
Graceland Cemetery: 1,266 holiday rentals
Montrose Harbor: 1,087 holiday rentals
Wilson Station: 1,143 holiday rentals
Louis A. Weiss Memorial Hospital: 1,116 holiday rentals

But there are many other points of interest around Uptown listed on Stayz 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 Condos/Apartments in Uptown?

Yes, of course. Stayz offers 798 Condos/Apartments in Uptown. Our other popular types of Uptown holiday rentals include:

Houses: 127 holiday houses
Townhouses: 14 holiday houses
Studios: 687 holiday houses

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 221 holiday homes with pool available in Uptown. Please use our search bar to access the selection of holiday rentals available.