Chicago, IL Short term rentals

13281 available short term rental offers

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Chicago, IL short term rentals
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Best Short term and Weekly rentals in Chicago, IL

Best Chicago, IL luxury short term rentals

Kasa South Loop Chicago - Chicago, IL
9.4 3254 reviews

Kasa South Loop Chicago

aparthotel, Chicago
Kasa South Loop Chicago is situated in the South Loop, a short walk from DePaul University and within a mile of the CIBC Theatre, offering easy access to the city's vibrant attractions. This aparthotel has consistently received excellent ratings for its location, cleanliness, and overall user experience.
The accommodation features modern, comfortable apartments with fully equipped kitchens, including a dishwasher, and a separate living area with a flat-screen TV. Guests can enjoy a range of amenities, such as a swimming pool, a fitness centre, a garden, and a terrace, as well as a business centre and a restaurant.
The Neighborhood Hotel-little Italy - Chicago, IL
9.6 307 reviews

The Neighborhood Hotel-little Italy

aparthotel, Chicago
This Near West Side serviced apartment is situated less than 1.6km from Rush University Medical Centre and within 4.8km of both the United Centre and Millennium Park.
The self-catering apartments feature kitchenettes with fridges, microwaves, and dishwashers, smart TVs with satellite channels, and free Wi-Fi in public areas; guests also benefit from proximity to public transport links, including Polk and Racine train stations.
Kasa Magnificent Mile Chicago - Chicago, IL
9.2 1546 reviews

Kasa Magnificent Mile Chicago

aparthotel, Chicago
Kasa Magnificent Mile Chicago is situated on the Magnificent Mile, a short walk from the Shops at Northbridge and just over a mile from North Avenue Beach, making it ideal for exploring Chicago's attractions and enjoying the lakefront. This aparthotel consistently receives excellent ratings for its location, cleanliness, and overall experience.
The accommodation offers spacious rooms with desks, comfortable furnishings, and private bathrooms. Amenities include a kitchen with a fridge, freezer, microwave oven, and dishwasher, as well as air conditioning, a terrace or balcony, a garden, a concierge, a restaurant, a fitness centre, and parking.

Best Chicago, IL Short term rentals with a jacuzzi

Among the 13281 accommodations in Chicago, IL, here are the 4 best rentals with a jacuzzi

Luxury Penthouse: Iconic Views + Exclusive Comfort - Chicago, IL
10 7 reviews

Luxury Penthouse: Iconic Views + Exclusive Comfort

apartment, Chicago
This luxurious Chicago penthouse, situated on the 21st floor directly opposite Millennium Park and Cloud Gate ("The Bean") in the city centre, offers unparalleled access to downtown attractions.
This 258 square metre dwelling boasts four bedrooms, four bathrooms, sleeping up to nine guests, and includes a gourmet kitchen, private parking (subject to availability), and access to a private amenity floor with a swimming pool, fitness centre, and sky lounge; the 'All-inclusive Chicago Penthouse' experience also features a pre-stocked grocery service, daily cleaning, and a private Uber Black service.
Iconic Downtown Penthouses Getaway + City Views - Chicago, IL
No reviews

Iconic Downtown Penthouses Getaway + City Views

apartment, Chicago
This luxury duplex apartment in Chicago's Central Loop offers unparalleled access, being just 200 metres from Millennium Park and 'The Bean', with Michigan Avenue's premier shopping a 5-minute walk away.
This family-friendly residence accommodates up to 15 guests across seven bedrooms and seven bathrooms, boasting a fully-equipped chef's kitchen, a balcony with park views, and access to extensive building amenities including indoor and outdoor swimming pools and a fitness centre.
Skyline View Duo For Groups: Unmatched Luxury Stay - Chicago, IL
No reviews

Skyline View Duo For Groups: Unmatched Luxury Stay

apartment, Chicago
This six-bedroom, six-bathroom penthouse apartment in Chicago's River West district is just 800 metres from Logan Square and 1.3 kilometres from Fulton Market, offering spacious city living with excellent transport links.
Accommodating up to 14 guests, this residence boasts a chef's kitchen, Smart TVs, Sonos sound systems, and access to building amenities including a gym, yoga studio, outdoor swimming pool, and hot tub, with a Pack 'n Play available on request.
Chicago Spacious 3br Smoke Ok Near Mccormick Place - Chicago, IL
No reviews

Chicago Spacious 3br Smoke Ok Near Mccormick Place

apartment, Chicago
This three-bedroom flat in Chicago is conveniently located for McCormick Place, with Grant Park just 2.7 kilometres away and the Art Institute of Chicago 3 kilometres distant.
This accommodation offers air conditioning, free Wi-Fi, and a kitchen equipped with a fridge, microwave, and dishwasher, plus a bathroom with a hot tub, accommodating up to 11 guests.

Frequently asked questions about short term rentals in Chicago, IL

  • Which top landmarks you shouldn't miss in Chicago, IL?

    You can't visit Chicago without seeing the iconic Willis Tower, formerly known as the Sears Tower. It's the tallest building in the city and offers breathtaking views. The Magnificent Mile, a stretch of North Michigan Avenue, is also a must-see, filled with shops, restaurants, and art galleries. And of course, no trip to Chicago is complete without a visit to Millennium Park, home to the Cloud Gate sculpture, affectionately nicknamed 'The Bean', and Crown Fountain, an interactive fountain that displays faces of Chicagoans.
  • What are the best short term rentals in Chicago, IL?

  • What kind of weather can travelers expect in Chicago, IL?

    Chicago has four distinct seasons, so pack accordingly! Summers are hot and humid, with temperatures reaching around 27°C. Winters are cold and snowy, with average temperatures around -3°C. Spring and autumn can be unpredictable, with temperatures fluctuating between cool and warm. It's always a good idea to check the forecast before you go.
  • What are the best short term rentals with a pool in Chicago, IL?

  • What are the most popular festivals and events in Chicago, IL?

    Chicago is known for its vibrant festival scene. The Chicago Blues Festival, held in June, is a must-see for music lovers. For something a bit different, the Taste of Chicago, held in July, showcases the city's diverse culinary scene. And if you're a film buff, the Chicago International Film Festival in October is a great way to experience some of the best independent and foreign films.
  • What are the best short term rentals with a jacuzzi in Chicago, IL?

  • Are there any famous stadiums or sports arenas in Chicago, IL?

    Chicago is a huge sports city! Wrigley Field, home to the Chicago Cubs baseball team, is a historic landmark. Soldier Field, home to the Chicago Bears, is also a popular destination for football fans. And United Center is where you can catch the Chicago Bulls basketball team and the Chicago Blackhawks hockey team.
  • What are the best short term rentals for families and kids in Chicago, IL?

  • What notable natural landmarks are near Chicago, IL?

    Just a short drive from Chicago, you'll find Indiana Dunes National Park, a stunning stretch of sand dunes along the shores of Lake Michigan. The park offers hiking trails, beaches, and scenic overlooks. If you're looking for something a little closer to the city, the Morton Arboretum, a sprawling botanical garden, is a great option.
  • What part of Chicago, IL is ideal for finding lodging?

    The River North neighbourhood is a great option for travellers, with its trendy restaurants, art galleries, and proximity to the Magnificent Mile. If you're looking for something more budget-friendly, the Wicker Park and Bucktown neighbourhoods offer a vibrant atmosphere with plenty of bars, cafes, and shops.

Popular destinations

Best family friendly Chicago, IL Short term rentals

Among the 13281 accommodations in Chicago, IL, here are the 4 best family friendly rentals

Family Friendly Spacious 3br Suite Sleeps Up To 10 Guests With Optional Parking And Gym Access Near Mccormick Place And Soldier Field - Chicago, IL
8.5 2 reviews

Family Friendly Spacious 3br Suite Sleeps Up To 10 Guests With Optional Parking And Gym Access Near Mccormick Place And Soldier Field

apartment, Chicago
This three-bedroom Chicago apartment, near McCormick Place, is conveniently located approximately 2.4 kilometres from the Field Museum and 2.9 kilometres from the Art Institute of Chicago.
The 111 square metre property sleeps up to 10 guests and boasts a fully equipped kitchen, free Wi-Fi, a fitness centre, and on-site parking; it also benefits from a garden and is allergy-free.
The Penthouse, Lux Stay Near Downtown, Uofc & Lake - Chicago, IL
9.4 40 reviews

The Penthouse, Lux Stay Near Downtown, Uofc & Lake

apartment, Chicago
This Chicago penthouse apartment, near the University of Chicago campus and approximately 8km from Downtown Chicago, offers easy access to Lake Michigan and Oakwood Beach (a 17-minute walk away).
The 135-square-metre (1453 sq ft) property boasts two bedrooms, two bathrooms, a fully equipped kitchen, and a terrace, accommodating up to seven guests and providing free Wi-Fi and toiletries.
Large 3br /2ba Duplex King  Parking - Chicago, IL
10 8 reviews

Large 3br /2ba Duplex King Parking

apartment, Chicago
This four-bedroom apartment is located in the Avondale neighbourhood of Chicago, a short 5-minute walk from Milwaukee Avenue and a 5-minute drive to Humboldt Park. It is rated excellent by previous guests.
The apartment comfortably accommodates eight guests and features a fully equipped kitchen with modern appliances, a washer and dryer, and a private garden with a hot tub. It also offers a range of amenities including Wi-Fi, a smart TV, and on-site parking.
Cambria Hotel Chicago Loop - Theatre District - Chicago, IL
8.8 4430 reviews

Cambria Hotel Chicago Loop - Theatre District

hotel, Chicago
The Cambria Hotel Chicago Loop/Theatre District is a 4-star hotel located in the heart of the Chicago Loop Theatre District, just a short walk from State Street and five blocks from Millennium Park. The hotel enjoys a very good user rating, making it a popular choice for travellers.
The hotel is housed in the historic Oriental Theatre building, giving it a unique character and a touch of old-world charm. Guests can enjoy a range of amenities, including a fitness centre, a games room, and a restaurant and bar serving local craft beer and fresh, local cuisine.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL short term rentals with parking

Spacious 3br Duplex W/ Garage - Chicago, IL
9.4 29 reviews

Spacious 3br Duplex W/ Garage

apartment, Chicago
This three-bedroom flat in Chicago offers excellent access to the city's attractions, situated minutes from prime areas and within immediate proximity to dining, shopping, and entertainment, with the Blue Line providing convenient transport.
This well-appointed flat accommodates up to eight guests and features air conditioning, a garden, and parking, alongside a kitchen equipped with a fridge, freezer, and microwave oven.
Vibrant Getaway In The Windy City Of Chicago - Chicago, IL
No reviews

Vibrant Getaway In The Windy City Of Chicago

apartment, Chicago
This three-bedroom flat in Chicago's East Garfield Park offers a residential base with a 12-minute commute to the city centre, providing convenient access to Millennium Park, Grant Park, the Field Museum of Natural History, and the Museum of Science and Industry.
This family-friendly dwelling accommodates up to six guests and features a kitchen with a fridge and microwave, air conditioning, Wi-Fi, a balcony, and parking, with opportunities for kayaking and swimming nearby, and hosts available for local advice.
Old Town Garden Getaway - Chicago, IL
9.8 163 reviews

Old Town Garden Getaway

apartment, Chicago
This Old Town flat is situated 0.6 km from the Clark/Division Red Line station and a short walk from Wells Street's restaurants, offering easy access to Chicago's attractions.
The two-bedroom apartment, sleeping four, boasts a fully equipped chef's kitchen, fireplace, washer/dryer, and free parking permits, alongside smart TVs and a workspace.
Remodeled Splendid Flat In Bucktown/wicker Park - Chicago, IL
9.5 174 reviews

Remodeled Splendid Flat In Bucktown/wicker Park

apartment, Chicago
This Bucktown flat is ideally situated in Chicago, 3.2 kilometres from both the city centre and Lincoln Park, offering easy access to the Blue Line for airport transfers and proximity to the 606 Trail.
The two-bedroom, one-bathroom apartment sleeps six, boasting a newly remodelled kitchen with LG appliances, a private back porch with fire pit overlooking a garden, in-unit laundry, 900mbps Wi-Fi, and accepts up to two pets.
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