Discover a selection of 108 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 kitchens. Prices start at $144 per night, and condos and hotels are popular options for a stay in Old Town. Either way, you'll find a rental for everyone's needs.
AsyncDestinationUrgency
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
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, HomeAway 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 108 vacation rentals around Old Town. From 83 condo and apartment rentals to 2 hotel 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: 251 vacation rentals
  • Chicago Loop: 247 vacation rentals
  • Lake View: 205 vacation rentals
  • Lincoln Park: 351 vacation rentals
  • Logan Square: 262 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: 1,113 vacation rentals
  • House of Glunz: 1,111 vacation rentals
  • Wrigley Field: 1,118 vacation rentals
  • Grant Park: 698 vacation rentals
  • Chicago Water Tower: 1,112 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 83 Condos/Apartments in Old Town. Our other popular types of vacation rentals in Old Town include:

  • Hotels: 2 rentals available
  • Houses: 13 rentals available
  • Studios: 42 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 preferred vacation rental with pool among our 36 vacation rentals with pool available in Old Town. Please use our search bar to access the selection of vacation rentals available.

    Explore destinations around Old Town

    Evanston
    604 vacation rentals
    Forest Park
    868 vacation rentals
    Oak Park
    852 vacation rentals
    Hammond
    139 vacation rentals
    Northbrook
    162 vacation rentals
    Des Plaines
    338 vacation rentals
    Lincolnshire
    82 vacation rentals
    Oak Brook
    235 vacation rentals
    Wheeling
    168 vacation rentals
    Downers Grove Township
    274 vacation rentals
    Deerfield
    93 vacation rentals
    Glenview
    342 vacation rentals
    Elmwood Park
    835 vacation rentals
    Skokie
    652 vacation rentals
    Highland Park
    574 vacation rentals
    Orland Park
    72 vacation rentals
    Wilmette
    353 vacation rentals
    Homer Glen
    49 vacation rentals
    Burr Ridge
    205 vacation rentals
    Gary
    150 vacation rentals