Where to stay around Old Town, Chicago?

Our 2018 property listings offer a large selection of 238 vacation rentals near Old Town. From 153 Condos/Apartments to 83 Studios, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Old Town for a holiday or a weekend are on VRBO.

What is the best area to stay when traveling to Old Town?

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 Old Town:

  • Lakeview: 283 vacation rentals
  • Chicago Loop: 706 vacation rentals
  • Streeterville: 206 vacation rentals
  • Wrigleyville: 315 vacation rentals
  • Wicker Park: 562 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular point of interests near where I can stay when traveling to Old Town?

VRBO offers a large selection of vacation rentals near lovely places in Old Town. From VRBO travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Royal George Theater: 1,998 vacation rentals
  • Steppenwolf Theatre: 2,008 vacation rentals
  • Legacy Motors Automotive Art Gallery: 1,973 vacation rentals
  • Wrigley Field: 2,296 vacation rentals
  • Millennium Park: 941 vacation rentals

But there are many other points of interest around Old Town 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 Condos/Apartments in Old Town?

Yes, of course. VRBO has 153 Condos/Apartments in Old Town. Our other popular types of vacation rentals in Old Town include:

  • Studios: 83 rentals available
  • Hotels: 50 rentals available
  • Houses: 28 rentals available

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

Can I find a vacation rental with pool in Old Town?

Yes, you can select your prefered vacation rental with pool among our 63 vacation rentals with pool available in Old Town. Please use our search bar to access the selection of vacation rentals available.

    Why people love visiting friendly Old Town

    Enjoy the museums and other features of Old Town. This welcoming and walkable city is known for its bars, zoo and restaurants. John Hancock Center and Millennium Park are just a couple of the must-sees in the area. If you're looking for accommodations 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.

    Sightseeing in and around Old Town

    Are you hoping to find attractions to see while you're in town? Venture out of your vacation home and experience everything that makes Old Town a fun place to get away. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

    • Skydeck Ledge (2.3 mi / 3.7 km)
    • Lincoln Park Zoo (0.8 mi / 1.2 km)
    • Navy Pier (2.1 mi / 3.4 km)
    • John G. Shedd Aquarium (3.4 mi / 5.5 km)
    • Adler Planetarium and Astronomy Museum (3.6 mi / 5.7 km)
    • Brookfield Zoo (11.3 mi / 18.1 km)

    Exploring the natural landscape of Old Town

    Whether you're an adventurous traveler or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Old Town. Here are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city center:

    • Millennium Park (2.2 mi / 3.5 km)
    • Lincoln Park (2.7 mi / 4.3 km)
    • Grant Park (2.8 mi / 4.6 km)
    • North Avenue Beach (0.8 mi / 1.3 km)
    • Oak Street Beach (1.1 mi / 1.8 km)
    • Chicago Riverwalk (1.8 mi / 2.9 km)