Discover a selection of 250 holiday home rentals in Old Town, Chicago that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Stayz holiday homes have the best amenities for hanging out with the people that matter most, including pool and parking. Prices start at AU$ 80 per night, and flats & apartments and holiday houses are popular options for a stay in Old Town. Either way, you'll find holiday accommodation 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 well known for its bars, zoo and restaurants. John Hancock Center and Millennium Park 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, Stayz 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 holiday home and experience everything that makes Old Town a fun place to get away to. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • 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 highlights

Exploring the natural landscape of Old Town

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

  • 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

Travelling to and around Old Town

The nearest airport is in Chicago, IL (MDW-Midway Intl.), located 10 mi (16 km) from the city centre. 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 holiday accommodation are available around Old Town?

Our 2021 accommodation listings offer a large selection of 250 holiday rentals around Old Town. From 176 flats & apartments to 29 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 Old Town is on Stayz.

Can I rent Condos/Apartments in Old Town?

Yes, of course. Stayz offers 176 Condos/Apartments in Old Town. Our other popular types of Old Town holiday rentals include:

  • Houses: 29 holiday houses
  • Studios: 186 holiday houses
  • House: 29 holiday houses

Can I find a holiday accommodation with pool in Old Town?

Yes, you can select your preferred holiday accommodation with pool among our 48 holiday homes with pool available in Old Town. Please use our search bar to access the selection of holiday rentals available.