Find short term rentals in Chicago, IL at the best prices

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

The Neighborhood Hotel-little Italy - Chicago, IL
9.6 327 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 Lake Shore Chicago - Chicago, IL
8.2 30 reviews

Kasa Lake Shore Chicago

aparthotel, Chicago
This 4-star aparthotel in Downtown Chicago offers a prime location, situated a short walk from Ohio Street Beach, Michigan Avenue, and Lake Michigan, with Grant Park and Navy Pier within 1.5 kilometres.
Each apartment provides a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, alongside an in-room washer/dryer, and the property features a rooftop terrace with city views.
Kasa South Loop Chicago - Chicago, IL
9.4 3284 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.
Kasa Magnificent Mile Chicago - Chicago, IL
9.2 1582 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 1br | Steps To Mag Mile & Chicago River - Chicago, IL
10 1 review

Luxury 1br | Steps To Mag Mile & Chicago River

apartment, Chicago
This one-bedroom flat is located in the Streeterville district of Chicago, offering direct elevator access to a Whole Foods and being a mere 2-minute walk from the Magnificent Mile, 3 minutes from the Riverwalk, and 8 minutes from Navy Pier, with the L train just 100 metres away for easy city exploration.
This accommodation for up to four guests features floor-to-ceiling windows with city views, a king-size bed, a queen sofa bed, an air mattress, an in-unit washer/dryer, and access to resort-style amenities including indoor and outdoor heated swimming pools, a fitness centre, steam room, putting green, and golf simulator.
New Modern 3br • Gym • Workspace • Quiet Location - Chicago, IL
9.5 4 reviews

New Modern 3br • Gym • Workspace • Quiet Location

apartment, Dunning
This modern three-bedroom house is located in Chicago, approximately 6 kilometres from O'Hare International Airport and within a 16-21 kilometre radius of attractions such as Wrigley Field, Lincoln Park Zoo, the United Center, and Loyola University.
The 929-square-metre property offers ample space for up to eight guests, boasting a fully equipped kitchen, a jacuzzi, a fitness centre, and free Wi-Fi; its proximity to major Chicago landmarks makes it ideal for exploring the city.
West Loop 2br With Skyline Views + Prime Location - Chicago, IL
10 5 reviews

West Loop 2br With Skyline Views + Prime Location

apartment, Chicago
This three-bedroom, two-bathroom Chicago apartment offers excellent guest accommodation in Downtown Chicago, within 1.6km of Milwaukee Avenue and the Merchandise Mart, and under 3.2km from the Chicago Riverwalk and Michigan Avenue.
The 6-guest property includes a fully equipped kitchen, in-unit laundry, a garden, and access to a fitness centre, all within a smoke-free building conveniently located near Grand and Clinton public transport stations.
Prime 2br Retreat: Urban Vibes + Views Await - Chicago, IL
9.8 6 reviews

Prime 2br Retreat: Urban Vibes + Views Await

apartment, Chicago
This two-bedroom, two-bathroom apartment in Chicago's prime Downtown area is situated less than 0.8 km from the Merchandise Mart and State Street, offering easy access to the Clark-Lake and Washington-Wells public transport stations.
The 4-guest dwelling boasts a fully equipped kitchen, including a dishwasher, in-unit laundry, and access to an on-site swimming pool and fitness centre; nearby attractions include the Chicago Theatre and Willis Tower, both within a 1-km radius.

Frequently Asked Questions about short term rentals in Chicago, IL

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

    You definitely want to check out the iconic Willis Tower, formerly known as the Sears Tower. It's the tallest building in Chicago, and the views from the top are incredible. You should also visit Millennium Park, where you can see the famous Cloud Gate sculpture, nicknamed 'The Bean', and the Crown Fountain. And no trip to Chicago is complete without a stroll along the Magnificent Mile, a stretch of North Michigan Avenue known for its high-end shopping and dining.
  • 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. Summers are warm and humid, with temperatures averaging around 25 degrees Celsius. Winters are cold and snowy, with temperatures often dropping below freezing. Spring and autumn are mild, with pleasant temperatures and beautiful foliage in the fall. You'll want to pack layers for all seasons, as the weather can change quickly.
  • 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 has a vibrant festival scene. The Chicago Blues Festival is a must-see for music lovers, and the Taste of Chicago is a great way to sample the city's diverse culinary offerings. If you're visiting in the summer, you can catch the Chicago Air and Water Show, a spectacular display of aviation and watercraft. And for the holidays, the Christkindlmarket in Daley Plaza is a festive tradition.
  • 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 city of sports fans. Wrigley Field, home to the Chicago Cubs baseball team, is a historic landmark and a must-visit for any baseball enthusiast. The United Center is home to the Chicago Bulls basketball team and the Chicago Blackhawks hockey team. And Soldier Field is the home of the Chicago Bears football team.
  • What are the best short term rentals for families and kids in Chicago, IL?

    The best short term rentals for families and kids in Chicago, IL are 2bd/2ba Mag Mile Masterpiece (+Rooftop), Kasa South Loop Chicago and Sonder South Wabash.

  • What notable natural landmarks are near Chicago, IL?

    Just a short drive from Chicago, you can find the Indiana Dunes National Park. It's a beautiful area with rolling sand dunes, beaches, and forests. It's a great place to hike, bike, or simply relax and enjoy the scenery.
  • What part of Chicago, IL is ideal for finding lodging?

    The best area for lodging really depends on your preferences and budget. For easy access to the city's main attractions, the Magnificent Mile is a good choice. For a more affordable option, consider staying in the River North or West Loop neighborhoods. If you're looking for a quieter experience, the Lincoln Park or Lakeview neighborhoods are good options.

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

Stunning 3 Br In Prime Chicago Location! - Chicago, IL
9.7 241 reviews

Stunning 3 Br In Prime Chicago Location!

apartment, Chicago
This three-bedroom Lincoln Park condo offers easy access to Chicago's attractions, being within 8km of Wrigley Field, Navy Pier, and the Art Institute of Chicago.
The 3-bathroom apartment sleeps six, features a fully equipped kitchen, private patio, shared garden, parking, and high-speed internet, ensuring a comfortable stay.
Chicago Lakefront Vacation Rental · Fire Pit Patio · Loyola Beach - Chicago, IL
8.0 2 reviews

Chicago Lakefront Vacation Rental · Fire Pit Patio · Loyola Beach

apartment, Chicago
This Rogers Park flat is situated directly opposite Lake Michigan, a short 350-metre stroll from Loyola Park and Leone Beach Park, offering convenient access to the 147 express bus route and the Loyola 'L' Red Line station for travel into downtown Chicago.
This fully renovated one-bedroom flat accommodates up to five guests with a queen bed, full-size bed, and sofa bed, and includes complimentary in-building laundry, high-speed WiFi, a private patio with lake views, fire pit, and garden, plus proximity to Divvy Bike Share for exploring the 30-kilometre Lakefront Trail.
Susie's Space. 2br Easy Parking & Pet Friendly - Chicago, IL
9.8 393 reviews

Susie's Space. 2br Easy Parking & Pet Friendly

apartment, Chicago
This Avondale flat is conveniently located near the Green Exchange/Greenhouse Loft in Chicago.
The two-bedroom apartment, sleeping up to five guests, boasts a private fenced backyard with fire pit and grill, a fully equipped kitchen, free Wi-Fi, and a laundry room; street parking permits are provided.
Luxe Vintage Loft, 10min To Downtown, Retro Movie Theatre - 15% Discount Applied - Chicago, IL
8.8 13 reviews

Luxe Vintage Loft, 10min To Downtown, Retro Movie Theatre - 15% Discount Applied

apartment, Chicago
This spacious Chicago apartment, ideal for families or groups, is situated in New City, offering easy access to Lake Michigan, Grant Park, and major museums such as the Art Institute of Chicago and the Field Museum (distances unspecified).
Sleeping 8-12 guests, the three-bedroom, three-bathroom property boasts a fully equipped kitchen, themed rooms (including a retro cinema and galaxy kids' room), smart TVs, high-speed Wi-Fi, and family-friendly amenities like cribs and high chairs, alongside a garden, spa and parking.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL lodging with parking

50th Floor Mag Mile Views, Balcony, Pool, Gym - Chicago, IL
10 43 reviews

50th Floor Mag Mile Views, Balcony, Pool, Gym

apartment, Chicago
This Downtown Chicago penthouse, situated between North Michigan Avenue and the River North district, offers easy access to Millennium Park and the Art Institute of Chicago.
The 68-square-metre (732 sq ft) apartment features one bedroom, one bathroom, and sleeps two guests, boasting a terrace, swimming pool, and on-site parking, alongside stunning 50th-floor city views.
Large 5br Retreat. Perfect For Long Stays & Groups - Chicago, IL
8.4 14 reviews

Large 5br Retreat. Perfect For Long Stays & Groups

apartment, Chicago
This Chicago holiday home, situated in the Avalon Park neighbourhood, offers convenient access to attractions such as the Museum of Science and Industry and the Field Museum, although precise distances aren't provided.
Sleeping up to 10 guests, this five-bedroom, three-bathroom property boasts a fully equipped kitchen (fridge, microwave, dishwasher), WiFi, laundry facilities, air conditioning, and parking; responsive hosts ensure a comfortable stay.
Sleeps 4 • New Modern 1br • Private Workspace - Chicago, IL
No reviews

Sleeps 4 • New Modern 1br • Private Workspace

apartment, Chicago
This Chicago apartment, situated 17.7km from O'Hare International Airport, provides easy access to the city.
The 92-square-metre property offers a one-bedroom layout sleeping seven guests, complete with a fully equipped kitchen (including dishwasher and microwave), in-unit laundry, free Wi-Fi, and a stylish workspace.
Wrigleyville Inn. Historic Greystone, Free Parking - Chicago, IL
10 144 reviews

Wrigleyville Inn. Historic Greystone, Free Parking

apartment, Chicago
This three-bedroom, two-bathroom Chicago apartment is situated in a historic greystone building near Wrigleyville, a five-minute walk (0.8 km) from Wrigley Field and two minutes (0.3 km) from Clark and Halsted Streets, offering easy access to public transport.
The completely refurbished condo features a new kitchen and bathrooms, a private back porch, free parking, and accommodates up to six guests, making it ideal for families or groups visiting this iconic Chicago neighbourhood.
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