Discover a selection of 1,500 vacation rentals in Chicago, IL 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 WiFi. Prices start at $137 per night, and houses and condos are popular options for a stay in Chicago. Either way, you'll find a rental for everyone's needs.
Destination guide

Relax in a lake rental in Chicago

Situated on Lake Michigan, Chicago is an ideal vacation spot for lake rentals in Illinois. Travelers will enjoy spending the day boating, fishing, and swimming in one of the region's lakes, or you can mix things up a bit and head into the city to get the most of your vacation. The children will enjoy a visit to the Chicago Children's Museum and have a blast spending the day on the rides at Navy Pier. Nature lovers can visit the Lincoln Park Conservatory or the Lurie Garden to learn about local flora. Stroll the Chicago Riverwalk before retreating back to your lakeside cabin for a relaxing evening by the campfire.

Things to do

Tourist attractions near Chicago vacation rentals

Chicago is an art lover's nirvana, with a host of galleries to explore. You can check out Impressionist paintings at the Art Institute, get lost in kaleidoscopic colors at the Museum of Mexican Art and discover "outsider art" at the INTUIT gallery. Kids will love the Field Museum of Natural History, which is home to Sue, the world's largest Tyrannosaurus Rex skeleton. Perched on the lake, Navy Pier is another family favorite. Gear up for carnival rides, ice cream parlors, an IMAX theater, fireworks and more. Traveling with little ones? With spacious living areas and private kitchens, Chicago vacation rentals provide an ideal setting for family getaways to the Windy City.


Activities near Chicago vacation homes

Chicago serves up one of the country's best street scenes, with buskers, food trucks and public art on every corner. Don't miss Cloud Gate, a gleaming stainless-steel pod that's been famously nicknamed "The Bean" by locals. Chicago is also a champion for contemporary architecture. As you walk around the city you can admire Frank Gehry's futuristic Pritzker Pavilion, peer through the stained-glass windows of Frank Lloyd Wright's Robie House and gaze over the city from the Skydeck of Willis Tower.


Best time to travel to Chicago vacation homes

Summer is high season in Chicago, when the city enjoys long days and plenty of sunshine. You can also catch summer events like Blues Fest, which lures over half a million music lovers to Millennium Park. Late spring and early fall can be a great time to visit, with thinner crowds and every chance of beach weather. Chicago is home to multiple professional sports teams, with crowds flocking to big games. Whether you're watching the Cubs bat at Wrigley Field, the Bears score touchdowns at Soldier Field, or the Bulls shoot hoops at United Center, Chicago vacation rentals have you covered.

Natural features

Get lost in Chicago's Millennium Park

From public parks to sandy beaches, Chicago doesn't scrimp on open space. Millennium Park is the undisputed showpiece, with public art, bubbling fountains and an enormous outdoor band pavilion. Not to mention an ice rink, botanic garden and enormous Great Lawn. Head down to the waterfront and you'll find over 25 beaches lacing the shore of Lake Michigan. You'll also see locals soaking up the sun in Lincoln Park, Chicago's biggest green space. It covers a 1200-acre footprint and is dotted with meadows, ponds, playing fields and the famous Lincoln Park Zoo.

How to get there

How to get to and around Chicago

Fly into Chicago, IL (MDW-Midway Intl.), the closest airport, located 8.6 mi (13.9 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 15.7 mi (25.3 km) away.

If you're traveling by train, Millennium Station, Chicago Van Buren Street Station and Chicago Union Station are the main stations in the area. You can get around Chicago by jumping on the metro at Monroe Station, Monroe Station or Adams-Wabash Station.

Food and drink

Regional specialties in Chicago

Chicago has plenty of regional specialties derived from the city’s working-class roots. In addition to the world-famous deep-dish pizza, popular dishes included thin-crust pizza, Chicago-style hot dogs, Italian beef sandwiches, the francheezie hot dog variation, and gyros. You can also find unique dishes from hidden gems in the city, all within reach of your vacation rental.

Good for couples

Romantic vacation rentals in Chicago

Chicago offers the perfect setting for a couple’s retreat. Romantic vacation homes can be found near places like the Lincoln Park Conservatory, a domed garden space with vibrant wildflowers and exotic plants, and the Chicago Theatre, a baroque-style auditorium with national musical and comedy acts. The North Avenue Beach, a popular lakeside beach with dining and shopping, is also great for couples.

How many vacation rentals are available around Chicago, IL?

Our 2021 property listings offer a large selection of 1,540 vacation rentals around Chicago. From 259 house rentals to 1,179 condo and apartment 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 Chicago?

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 Chicago:

  • Near North Side: 688 vacation rentals
  • The Loop: 764 vacation rentals
  • West Town: 650 vacation rentals
  • Lakeview: 204 vacation rentals
  • Lincoln Park: 591 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 Chicago?

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

  • Jackson Park: 1,474 vacation rentals
  • Garfield Park: 1,528 vacation rentals
  • United Center: 1,523 vacation rentals
  • Wrigley Field: 1,513 vacation rentals
  • Chicago's Mercury Theater: 1,511 vacation rentals

But there are many other points of interest around Chicago 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 Houses in Chicago?

Yes, of course. Vrbo has 259 Houses in Chicago. Our other popular types of vacation rentals in Chicago include:

  • Condos/Apartments: 1,179 rentals available
  • Townhouses: 20 rentals available
  • Studios: 1,061 rentals available

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

Can I find a vacation rental with pool in Chicago?

Yes, you can select your preferred vacation rental with pool among our 223 vacation rentals with pool available in Chicago. Please use our search bar to access the selection of vacation rentals available.

    Explore destinations around Chicago

    Near North Side
    688 vacation rentals
    The Loop
    764 vacation rentals
    West Town
    650 vacation rentals
    204 vacation rentals
    Lincoln Park
    591 vacation rentals
    Near South Side
    824 vacation rentals
    Logan Square
    334 vacation rentals
    1,055 vacation rentals
    North Center
    112 vacation rentals
    West Loop
    701 vacation rentals
    52 vacation rentals
    Rogers Park
    55 vacation rentals
    213 vacation rentals
    54 vacation rentals
    Grand Boulevard
    33 vacation rentals
    Hyde Park
    43 vacation rentals
    47 vacation rentals
    Lower West Side
    36 vacation rentals
    Irving Park
    36 vacation rentals
    Washington Park
    19 vacation rentals