Uptown, Chicago, IL, USA

Uptown, Chicago, IL, USA

We found 81 vacation rentals — enter your dates for availability

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Find the best place to stay — Uptown

Where to stay around Uptown?

Our 2018 property listings offer a large selection of 81 vacation rentals near Uptown. From 41 apartments to 23 condos, 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: 101 vacation rentals
  • Wrigleyville: 97 vacation rentals
  • Lakeview: 74 vacation rentals
  • Gold Coast: 21 vacation rentals
  • Wicker Park: 28 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: 853 vacation rentals
  • Louis A. Weiss Memorial Hospital: 855 vacation rentals
  • Montrose Harbor: 851 vacation rentals
  • Aragon Entertainment Center: 854 vacation rentals
  • About Face Theater: 857 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 apartments in Uptown?

Yes, of course. HomeAway has 41 apartments in Uptown. Our other popular types of vacation rentals in Uptown include:

  • Condos: 23 rentals available
  • Houses: 9 rentals available
  • Studios: 5 rentals available

Can I rent golf rentals in Uptown?

Absolutely, HomeAway has 27 golf rentals in Uptown. You have also many other possibilities in Uptown area, including:

  • Downtown rentals: 15 rentals
  • Lake rentals: 6 rentals
  • Beach rentals: 5 rentals

Please use our search bar to access the selection of vacation rentals.

Can I find a vacation rental with pool in Uptown?

Yes, you can select your preferred vacation rental with pool among our 5 vacation rentals with pool available in Uptown. Please use our search bar to access the selection of vacation rentals available.