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

Luxe Condo W/ Hot Tub And Amazing Roof Deck! - Chicago, IL
9.8 55 reviews

Luxe Condo W/ Hot Tub And Amazing Roof Deck!

apartment, Chicago
This three-bedroom Chicago apartment is ideally located in Wicker Park, a short 0.8 km walk from the Division El station offering easy access to the city centre.
The 3-bedroom property, sleeping up to eight guests, boasts a fully equipped kitchen, smart home technology, one garage parking space, and is within easy reach of Milwaukee Avenue's shops and restaurants.
West Loop Retreat | Indoor Pool + Rooftop Lounge - Chicago, IL
No reviews

West Loop Retreat | Indoor Pool + Rooftop Lounge

apartment, Chicago
This modern loft in Chicago's West Loop offers prime positioning, 600 metres from Fulton Market and within easy reach of Union Station and Michigan Avenue's shopping district.
This one-bedroom, one-bathroom flat accommodates up to four guests and features floor-to-ceiling windows with city views, a fully equipped kitchen, high-speed Wi-Fi, and access to building amenities including an indoor swimming pool and fitness centre.
Stylish 2br With Skyline Views Near Riverwalk - Chicago, IL
No reviews

Stylish 2br With Skyline Views Near Riverwalk

apartment, Chicago
This two-bedroom flat is located in Chicago's Loop district, a 15-minute walk from Millennium Park and a 20-minute walk from Navy Pier, offering easy access to the Lakefront Path and Michigan Avenue.
This family-friendly apartment accommodates four guests with two queen bedrooms and two bathrooms, featuring a fully equipped kitchen, air conditioning, a swimming pool, a jacuzzi, a terrace, a fitness centre, and parking, plus in-building entertainment like a Sky Lounge and Social Room.
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

Remodeled Splendid Flat In Bucktown +Back Porch, Ranked Guest Favorite! Pets Ok! - Chicago, IL
9.8 15 reviews

Remodeled Splendid Flat In Bucktown +Back Porch, Ranked Guest Favorite! Pets Ok!

apartment, Chicago
This Bucktown apartment in Chicago offers easy access to public transport, being a 0.8km walk from Chicago Clybourn Station and within 5km of attractions such as the United Centre, Lake Michigan, Wrigley Field, and Michigan Avenue.
The two-bedroom property sleeps six, features a fully equipped kitchen, private patio, garden access, and free Wi-Fi; housekeeping is available on request.
Mccormick Place Luxurious And Spacious 3br In Downtown Chicago With Optional Parking Sleeps 10 Guests - Chicago, IL
9.6 113 reviews

Mccormick Place Luxurious And Spacious 3br In Downtown Chicago With Optional Parking Sleeps 10 Guests

apartment, Chicago
This three-bedroom flat is situated in Downtown Chicago, just a short distance from renowned attractions like the Field Museum and the Art Institute of Chicago. The accommodation has received excellent reviews for its location, cleanliness, and overall experience.
The property comfortably sleeps eight guests and features a fully equipped kitchen with a dishwasher and oven. Guests can enjoy a range of amenities, including a fitness centre, a terrace, and on-site parking.
Entire Upstairs In Arts And Crafts Oak Park Home - Chicago, IL
9.8 536 reviews

Entire Upstairs In Arts And Crafts Oak Park Home

B&B, Oak Park
This charming property is situated in a friendly Oak Park neighbourhood, just a short walk from the CTA Blue Line and close to local amenities like coffee shops, restaurants, and parks. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
The home has two bedrooms, a futon, and a shared living area, comfortably accommodating up to four guests. Guests can enjoy a private backyard, free on-street parking, and a kitchen with a fridge, microwave, coffee maker, and kettle, perfect for preparing light meals and snacks.
Black Chicago Gallery Solar 2br Woodlawn Apartment - Chicago, IL
No reviews

Black Chicago Gallery Solar 2br Woodlawn Apartment

apartment, Chicago
This eco-luxury 2-bedroom suite is situated in Chicago, approximately 4 kilometres from the Museum of Science and Industry and close to the University of Chicago and the Obama Centre.
This air-conditioned flat offers 121 square metres of living space for up to 7 guests, featuring a fully equipped kitchen with a dishwasher, two bathrooms, and complimentary WiFi throughout.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL short term rentals with parking

2br • Newly Furnished Modern Apt • Near O'hare - Chicago, IL
No reviews

2br • Newly Furnished Modern Apt • Near O'hare

apartment, Chicago
This two-bedroom flat in Chicago is situated approximately 10 minutes by car from O'Hare International Airport and the Donald E. Stephens Convention Centre, and a 25-minute commute from Wrigley Field.
This family-friendly apartment offers accommodation for up to five guests, featuring a fully equipped kitchen with high-end appliances, air conditioning, free Wi-Fi, a dedicated workstation, and free street parking.
Cozy Queen Private Room | United Center & Downtown - Chicago, IL
9.6 55 reviews

Cozy Queen Private Room | United Center & Downtown

apartment, Chicago
This Chicago guest house is located in a developing neighbourhood, a 1.6km walk from a train station offering a swift 10-minute journey to the city centre, and a 5.6km drive from the United Center and UIC Medical District.
The one-bedroom, one-bathroom guesthouse sleeps two guests and features a fully equipped kitchen, garden, free on-street parking, and gated parking options; it also offers a designated workspace and modern bohemian décor.
Large 3br /2ba Duplex King  Parking - Chicago, IL
10 49 reviews

Large 3br /2ba Duplex King Parking

apartment, Chicago
This Chicago apartment rental, registration number R22000080347, is situated in the Avondale/Logan Square neighbourhood, offering convenient access to local restaurants and shops, although precise distances to specific landmarks are not provided.
The spacious four-bedroom, two-bathroom flat sleeps eight guests and boasts an open-plan living area with an 85-inch TV, a fully equipped kitchen including dishwasher, and a private garden with parking.
Bright Upper-level 3br Chicago  King  Walkable - Chicago, IL
9.9 81 reviews

Bright Upper-level 3br Chicago King Walkable

apartment, Chicago
This apartment is conveniently located in a neighbourhood with easy access to public transport, just a short walk from the bus and train, making it ideal for exploring all that Chicago has to offer. The property has consistently received excellent ratings from guests for its cleanliness, location, and overall experience.
The apartment is spacious and can comfortably accommodate up to 5 guests, with 3 bedrooms and 1 bathroom. It is fully equipped with modern amenities, including a printer, garage, a spacious kitchen, central heating and air conditioning, a porch veranda, Wi-Fi, and Roku for entertainment. Guests can also enjoy a private backyard with a hammock, fire pit, and multiple grilling options, as well as fresh produce from the shared garden.
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