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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

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.

Weather

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 2020 property listings offer a large selection of 1,219 vacation rentals around Chicago. From 756 condo and apartment rentals to 236 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 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: 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 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:

  • Wrigley Field: 1,118 vacation rentals
  • Grant Park: 698 vacation rentals
  • Chicago Water Tower: 1,112 vacation rentals
  • McCormick Place: 771 vacation rentals
  • Navy Pier: 643 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 Condos/Apartments in Chicago?

Yes, of course. Vrbo has 756 Condos/Apartments in Chicago. Our other popular types of vacation rentals in Chicago include:

  • Houses: 236 rentals available
  • Studios: 733 rentals available
  • Townhouses: 30 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 180 vacation rentals with pool available in Chicago. Please use our search bar to access the selection of vacation rentals available.

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