Chicago vacation rentals
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Top-rated vacation rentals in Chicago
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- Entire rental unit
- Bridgeport
Please make sure to review "Getting Around" details within the "Neighborhood" section. Nearest building intersection is 28th Place & Canal St to map transit options Newly remodeled 1br with modern finishes, smart tech & security, in a hip, central neighborhood minutes from downtown Chicago & steps from all that trendy Bridgeport has to offer. Managed by a seasoned team specializing in monthly furnished rentals Per the City of Chicago ordinances, 31 night minimum on all stays
- Entire rental unit
- Lower West Side
Please make sure to review "Getting Around" details within the "Neighborhood" section. Nearest building intersection is 23rd St. & Leavitt St. to map transit options Newly remodeled two-bedroom apartment with modern finishes, smart tech & security, in a hip, central neighborhood minutes from downtown Chicago and part of all that trendy Pilsen has to offer. Managed by a seasoned team specializing in monthly furnished rentals. Per the City of Chicago ordinances, 31 night minimum on all stays
- Private room
- Little Italy
Private, VERY CLEAN room 5 minutes to downtown with FREE PARKING, GREEN TEA & ALOE memory foam mattress, and an EARLY check-in (11 a.m.). You will have your own door code and may arrive at ANY time and as late as you wish, EASY self check-in guaranteed. I allow LUGGAGE DROP OFF! You can store your luggage in the closet before check-in and after check-out times, you can drop it off and pick it up as early and as late as you would like. The neighborhood is extremely safe even at night :)
Popular amenities for Chicago vacation rentals
Downtown Chicago vacation rentals
Chicago summer vacation rentals
Chicago holiday vacation rentals
Your guide to Chicago
All About Chicago
Settled along the banks of Lake Michigan, the Windy City of Chicago offers world-class dining, exciting architecture, a top performing arts scene, and plenty of excellent museums. With more than 200 neighborhoods calling this city home, there’s a unique aura found in each.
You’ll find historic mansions and upscale shopping in Gold Coast, Gothic-style university buildings in Hyde Park, cool cocktail bars and quirky shops in hip Logan Square, and incredible comedy clubs in Old Town. Enjoy time outside lounging on the city beaches, catch a baseball game at Wrigley Field, shop along the Magnificent Mile, or sample the celebrated dining scene in this dynamic city, the third-largest metropolis in the United States.
When is the best time to stay in a vacation rental in Chicago?
Chicago’s summers are warm and sunny, which means the rooftops and patios are buzzing, and the days are filled with music and food festivals. This is also when the city's lakeside beaches are at their best, so it’s a popular time for booking Chicago vacation rentals. Fall is chilly but pleasant. Winters are downright cold, and you can expect plenty of snow between the months of December and April, but there’s also plenty of opportunity for ice skating in rinks and snowshoeing and sledding down hills in city parks. There are also wonderful Christmas lights at Navy Pier and throughout the city. Expect relatively cool temperatures and a decent amount of rainfall in spring, and pack your waterproof layers.
What are the top things to do in Chicago?
The Art Institute of Chicago
The Art Institute is one of the best museums in the United States with more than 300,000 permanent artworks and many traveling exhibits. Take shelter from the city’s infamous wind and check out world-famous paintings from French Impressionists and modern American masterpieces. Cafes and restaurants are on-site for coffee breaks and leisurely lunches, and the museum also hosts regular lectures and events.
Willis Tower
The tallest building in the world for almost 25 years, the Willis Tower is a 110-story skyscraper that’s now the second-tallest building in the U.S. For a view that can reach Wisconsin and Michigan on a clear day, visit The Willis Tower observation deck. It’s located on the 103rd floor of the building, and you can even step inside glass observation boxes that extend four feet over the street below.
Millennium Park
Located across from the Art Institute, this city park is one of the most recognizable areas in Chicago thanks to the iconic Cloud Gate sculpture, lovingly known as “The Bean.” Rotating sculpture exhibitions and the naturalistic Lurie Garden make for lovely visits in spring and fall. During the summer months, the park comes alive with outdoor concerts, film screenings, dance performances, and even public yoga classes.