Discover a selection of 214 vacation rentals in Old Town, Chicago that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and parking. Prices start at $50 per night, and condos and houses are popular options for a stay in Old Town. Either way, you'll find a rental for everyone's needs.
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Destination guide

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, Vrbo has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities

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)
Natural features

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)
How to get there

Traveling to and around Old Town

The nearest airport is in Chicago, IL (MDW-Midway Intl.), located 10 mi (16 km) from the city center. If you can't find a flight that works for your travel itinerary, you can also fly into Chicago, IL (ORD-O'Hare Intl.), which is 14.3 mi (23.1 km) away.

Catch a ride on the metro at Sedgwick Station to easily navigate the city.

How many vacation rentals are available around Old Town, Chicago?

Our 2020 property listings offer a large selection of 214 vacation rentals around Old Town. From 140 condo and apartment rentals to 26 house rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

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:

  • Near North Side: 571 vacation rentals
  • The Loop: 621 vacation rentals
  • West Town: 526 vacation rentals
  • Lakeview: 237 vacation rentals
  • Lincoln Park: 528 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:

  • Sedgwick Station: 1,409 vacation rentals
  • House of Glunz: 1,406 vacation rentals
  • Jackson Park: 1,148 vacation rentals
  • Garfield Park: 1,427 vacation rentals
  • United Center: 298 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 140 Condos/Apartments in Old Town. Our other popular types of vacation rentals in Old Town include:

  • Houses: 26 rentals available
  • Studios: 154 rentals available
  • Townhouses: 2 rentals available

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

Yes, you can select your preferred vacation rental with pool among our 43 vacation rentals with pool available in Old Town. Please use our search bar to access the selection of vacation rentals available.

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