Destination guide

Swept away by Chicago

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.

Activities

Art and architecture in Chicago

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

Cheer on Chicago's sports teams

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.

Transport

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.

Where to stay around Chicago?

Our 2019 property listings offer a large selection of 1,222 vacation rentals near Chicago. From 914 Condos/Apartments to 242 Houses, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Chicago for a holiday or a weekend are on HomeAway.

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:

  • Chicago Loop: 510 vacation rentals
  • Wrigleyville: 329 vacation rentals
  • Wicker Park: 530 vacation rentals
  • Lakeview: 309 vacation rentals
  • Gold Coast: 162 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular points of interest near where I can stay when traveling to Chicago?

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

  • Chicago Water Tower: 1,218 vacation rentals
  • Wrigley Field: 1,225 vacation rentals
  • McCormick Place: 1,019 vacation rentals
  • Navy Pier: 854 vacation rentals
  • Millennium Park: 878 vacation rentals

But there are many other points of interest around Chicago listed on HomeAway 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. HomeAway has 914 Condos/Apartments in Chicago. Our other popular types of vacation rentals in Chicago include:

  • Houses: 242 rentals available
  • Bungalows: 4 rentals available
  • Cottages: 4 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 90 vacation rentals with pool available in Chicago. Please use our search bar to access the selection of vacation rentals available.

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