Find the best place to stay — Uptown

Where to stay around Uptown?

Our 2018 property listings offer a large selection of 92 vacation rentals near Uptown. From 46 apartments to 24 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: 143 vacation rentals
  • Wrigleyville: 107 vacation rentals
  • Lakeview: 202 vacation rentals
  • Gold Coast: 149 vacation rentals
  • Wicker Park: 100 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: 882 vacation rentals
  • Montrose Harbor: 879 vacation rentals
  • Louis A. Weiss Memorial Hospital: 884 vacation rentals
  • Aragon Entertainment Center: 884 vacation rentals
  • About Face Theater: 888 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 46 apartments in Uptown. Our other popular types of vacation rentals in Uptown include:

  • Condos: 24 rentals available
  • Houses: 14 rentals available
  • Studios: 5 rentals available

Can I rent golf rentals in Uptown?

Absolutely, HomeAway has 26 golf rentals in Uptown. You have also many other possibilities in Uptown area, including:

  • Downtown rentals: 13 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.

    Head to the Exciting City of Uptown

    Come and experience Uptown and its entertainment, live music and opera. This city is scenic and cosmopolitan, recognized for its bird watching, theaters and lake. The area has so much to see with top attractions like Wrigley Field, John Hancock Center and Millennium Park. With a vacation rental, you get a home away from home—many rentals offer full kitchens and outdoor grills for some home cooking.

    Attractions In and Around Uptown

    First time in Uptown and looking for places to see? Some of the area's family-friendly draws for travelers include Skydeck Ledge, Lincoln Park Zoo and Navy Pier. Don't miss cultural highlights like Aragon Entertainment Center, About Face Theater and Neo-Futurists. To appreciate the outdoor scene, make time for beaches like Montrose Beach and Kathy Osterman Beach and green spaces such as Millennium Park and Lincoln Park. Plan to attend a game or event? Get tickets for Wrigley Field or United Center. To discover the region's top popular attractions, head to John Hancock Center, Willis Tower and McCormick Place during your stay. You might also want to add other must-see places in the region like Chicago Water Tower, Tribune Tower or Merchandise Mart to your agenda.