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 private pools. Prices start at $115 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.
Top rated rentals — Chicago
Destination guide

Experience Chicago from vacation home rentals

With acclaimed architecture and a legendary food scene, Chicago is one of America's most iconic cities. Spend your time admiring public artworks, ticking off world-class museums and devouring deep-dish pizza. Wash it all down with sleek rooftop bars, hip microbreweries and elaborate craft cocktails. You'll also be just steps from some of North America's best urban beaches, so don't forget to pack a swimsuit. Feeling swept away by the Windy City? From sleek downtown condos, to trendy River North lofts, you'll find Chicago vacation rentals across the city.

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 O'Hare Intl. Airport (ORD), the closest airport, located 15.7 mi (25.3 km) from the city center. If you're unable to find a flight that fits your schedule, you could also fly into Chicago Midway Airport (MDW), which is 8.6 mi (13.9 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 city. It's easy to get around Chicago by jumping on the metro at Monroe Station (Red Line), Monroe Station (Blue Line) 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 2022 property listings offer a large selection of 1,548 vacation rentals around Chicago. From 266 house rentals to 1,178 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:

  • River North: 628 vacation rentals
  • Lakeview: 387 vacation rentals
  • The Loop: 817 vacation rentals
  • Logan Square: 547 vacation rentals
  • West Town: 944 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:

  • John Hancock Center: 2,090 vacation rentals
  • Willis Tower: 2,086 vacation rentals
  • Marina City: 2,088 vacation rentals
  • Pump It Up Party Zone: 2,101 vacation rentals
  • Cyrus McCormick Mansion: 2,090 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 266 Houses in Chicago. Our other popular types of vacation rentals in Chicago include:

  • Condos/Apartments: 1,178 rentals available
  • Townhouses: 28 rentals available
  • Cabins: 8 rentals available

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

Can I find a vacation rental with pool in Chicago?

Yes, you can select your preferred vacation rental with pool among our 342 vacation rentals with pool available in Chicago. Please use our search bar to access the selection of vacation rentals available.

Explore destinations around Chicago

River North
628 vacation rentals
387 vacation rentals
The Loop
817 vacation rentals
Logan Square
547 vacation rentals
West Town
944 vacation rentals
Near North Side
753 vacation rentals
Rush and Division
371 vacation rentals
Rogers Park
97 vacation rentals
404 vacation rentals
Lake View East
214 vacation rentals
Near South Side
933 vacation rentals
Goose Island
1,952 vacation rentals
Old Town Chicago
345 vacation rentals
424 vacation rentals
Theatre District
385 vacation rentals
Pulaski Park
181 vacation rentals
Old Town Triangle
87 vacation rentals
Gold Coast
363 vacation rentals
University Village / Little Italy
113 vacation rentals
Roscoe Village
252 vacation rentals