Chicago is a great destination for a metropolitan getaway. For a more personalized experience and to get more bang for your buck, consider booking a vacation rental in Chicago. Choose from small studio apartments to spacious townhouses all throughout the city. If this is your first trip to Chicago, check out these tips for choosing the best rental.

Find A Place Near Your Favorite Sites

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Select vacation home rentals in Chicago that are close to the attractions and places you plan to frequent. Chicago is a large city, and you don’t want to spend most of your time and money traveling within the city. While the price tag on a vacation rental home in Des Plaines near the airport might sound convenient, you could spend 45 minutes to an hour just getting into the city.

Check Out Transportation and Parking Options


Like any major city, Chicago has a strong public transportation system. The L is the elevated rapid transit system that goes all through the city and makes stops in some of Chicago’s suburbs. Additionally, there are bus stops throughout the city to take you to all of the major attractions with ease. If you’re driving to Chicago, check what the parking options are for your vacation rental home. Parking is scarce in many parts of the city, and often comes at a premium. Homes with a place to park your car are a bonus.

Choose the Right Neighborhood

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When you’re planning a trip to Chicago, one of the top tips for finding the best Chicago vacation rentals is location. Of course you want to choose a rental with enough space for your crew, but you also want to stay in a neighborhood that suits you and is close to everything you want to see, do and experience. Whatever neighborhood you choose to call your temporary home, you just might find yourself never wanting to leave “The Windy City.”

  1. Hyde Park
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    If you’re into art or history, this South Side neighborhood is the ideal sport for vacation home rentals in Chicago. Hyde Park is one of Chicago’s most historic neighborhoods. This is where Chicago’s World Fair took place in 1893, introducing the country to two major advancements: the Ferris wheel and electricity. Popular attractions in the neighborhood include the Museum of Science and Industry, the Western Hemisphere’s biggest science museum. Other attractions include the architecture and scenery of the University of Chicago, Frank Lloyd Wright’s Robie House, the DuSable Museum of African American History and the Hyde Park Art Center.

  2. The Loop

    When you want to stay near all the downtown action, the Loop neighborhood is the place to be. You’ll be surrounded by skyscrapers and close to some top attractions. Just walking around and taking in the amazing architecture designed by greats like Louis Henri Sullivan and Ludwig Mies van der Rohe is a fun way to spend some time. Millennium Park is one of the neighborhood’s most popular hangouts, with its iconic features like Cloud Gate and a stunning amphitheater where concerts and events are held during nice weather.

  3. Gold Coast
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    This swanky neighborhood is just north of downtown, and it offers some of the most luxurious homes, shopping and attractions. Plus, its location along the shores of Lake Michigan make it one of the city’s most scenic neighborhoods to stay. The upscale shopping on Oak Street, which is just off the Magnificent Mile, is a favorite among serious shoppers. The neighborhood’s also home to several Michelin-star restaurants and plenty of nightlife located along Rush Street.

  4. Lincoln Park
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    For a great balance of natural beauty, outdoor recreation and independent eateries and boutiques, it’s hard to top the Lincoln Park neighborhood. Quiet, tree-lined streets mingle with busy business corridors, and you’ll find plenty of museums, theaters and clubs to choose from. Of course, at the heart of this dynamic, artsy neighborhood is its namesake park. In addition to roughly 1,200 acres of open green space, you’ll also have access to Lincoln Park’s free zoo, nature museum and its lakefront trail and beaches.

  5. Wrigleyville
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    Sports fans love the Wrigleyville neighborhood because it’s situated right in the shadow of Wrigley Field. When you book a vacation rental here, you’ll be in walking distance to baseball’s second oldest stadium along with shops, casual restaurants and some raucous nightlife.