Chicago vacation rentals
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Top-rated vacation rentals in Chicago
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- Private room
Welcoming and Cozy home for up to 2 guests. City Living! Located in the University of Chicago area. EASILY ACCESSIBLE to EVERYWHERE in the Chicago! 5-10 minutes from UC, 15 minutes from South Loop and downtown Chicago . Use the kitchen and its appliances, your own personal bathroom, TV, hi-speed Wifi, laundry & parking. Meaningful conversation (if you want it).
- Private room
Recently renovated, enjoy the comfort of staying on a brand new home with everything brand new. Brand new mattress, comforters, sheets, towels and everything else! Each room is equipped with Smart TV with Netflix included, expensive luxury mattresses with 4 layers sheets & comforters bed setup, air conditioning with air humidifier, high speed internet and so much more! Convenient location close to downtown Chicago, Chinatown, White Sox, Pilsen, South Loop & McCormick Convention Center.
- Private room
- West Town
The apartment is wonderfully spacious, bright, and airy with soaring seven-foot windows that have an amazing view of downtown. The place is kept clean, tidy, and organized. All the amenities for a comfortable stay are provided (see list). This “Shared Listing” is a value option where you save costs by sharing common area space with other guests staying in separate lockable bedrooms. Also, the building is conveniently located near the train station giving easy access to other areas of Chicagoland
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.
How do I get around Chicago?
Both of Chicago’s international airports, O’Hare (ORD) and Chicago Midway (MDW), have excellent public transit links. O’Hare is 18 miles from the city center, and the CTA train leaves directly from the airport and takes about 50 minutes to reach centrally-located vacation homes in Chicago. Chicago Midway is about 13 miles from the city center, and the CTA train leaves directly from the airport and takes about 30 minutes. Shuttles, taxis and rideshares are also available from either airport, but traffic is often congested, making the trains a bit more convenient.
Once you arrive, Chicago is a walkable city with one of the country’s best public transit systems, so you can easily take advantage of the trains and buses. Cabs and ride-hailing services are also plentiful around town.
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.
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.
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.