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

Our Favorite Luxury Short-Term Rentals in Chicago

Live in the heart of the Gold Coast or Streeterville in rentals featuring floor-to-ceiling windows and high-end finishes. These units place you steps from the Magnificent Mile and Michelin-starred dining in the West Loop.

The Neighborhood Hotel-little Italy - Chicago
9.6 265 reviews
Chicago
07/21 – 07/26
$424/nighttotal: $2120 (5 )

The Neighborhood Hotel-little Italy

1 2
aparthotel , Chicago
This 3.5-star Chicago Near West Side apartment hotel is located less than a mile from Rush University Medical Center and within three miles of the United Center and Millennium Park, offering easy access to public transportation.
Each apartment features a kitchenette with a refrigerator, stovetop, microwave, and dishwasher, plus a smart TV with satellite channels, a sitting area, and coffee/tea maker; on-site laundry facilities are also available.
Kasa River North Chicago - Chicago
9.4 351 reviews
Chicago
10/09 – 10/13
$669/nighttotal: $2676 (4 )

Kasa River North Chicago

1 2
hotel , Chicago
The Kasa River North Chicago is located in the River North district, a short walk from Oak Street Beach and within a mile and a half of Ohio and North Avenue Beaches, offering easy access to restaurants, bars, and shopping. This hotel has excellent user, location, and cleanliness ratings, making it a popular choice for travelers.
The Kasa River North Chicago offers modern apartment-style accommodations with a variety of amenities. Guests can enjoy a seasonal outdoor pool, a terrace, a fitness center, free Wi-Fi, and comfortable beds.
Kasa South Loop Chicago - Chicago
9.4 3084 reviews
Chicago
07/07 – 07/24
$326/nighttotal: $5542 (17 )

Kasa South Loop Chicago

1 3
aparthotel , Chicago
Kasa South Loop Chicago is located in the South Loop neighborhood, just a short walk from DePaul University and a quick drive from attractions like Willis Tower and the Art Institute of Chicago. The aparthotel has excellent ratings for location, cleanliness, and overall user experience.
The apartments are spacious and well-equipped with kitchens, seating areas, and private bathrooms. Guests can enjoy amenities like a swimming pool, fitness center, and a sun terrace, along with free Wi-Fi and a business center.
Kasa Magnificent Mile Chicago - Chicago
9.2 1379 reviews
Chicago
06/27 – 07/06
$283/nighttotal: $2547 (9 )

Kasa Magnificent Mile Chicago

1 2
aparthotel , Chicago
Kasa Magnificent Mile Chicago is located on the Magnificent Mile, a bustling shopping and dining district, just a short walk from the Shops at Northbridge, CIBC Theatre, and Millennium Station. This aparthotel boasts excellent user ratings for its location, cleanliness, and overall experience.
The apartment features modern amenities like a flat-screen TV, air conditioning, and a private bathroom. Guests can enjoy a terrace or balcony, a garden, a fitness center, and a restaurant.

Best Chicago Short term rentals with a jacuzzi

Among the 9542 accommodations in Chicago, here are the 4 best rentals with a jacuzzi

Cozy Smoke Ok 3br City Retreat Near Mccormick - Chicago
Chicago
09/10 – 09/17
$376/nighttotal: $2632 (7 )

Cozy Smoke Ok 3br City Retreat Near Mccormick

1 2
apartment , Chicago
This Chicago condo is located near McCormick Place, offering proximity to DePaul University (1.6 miles), Grant Park (1.7 miles), the Art Institute of Chicago (1.9 miles), and the Field Museum of Natural History (1.5 miles).
This air-conditioned apartment accommodates up to 13 guests with one bedroom and one bathroom, featuring a fully equipped kitchen, complimentary WiFi, and a relaxing hot tub.
The Jackpot | Hot Tub · Cinema · Bar · Sleeps 14 - Chicago
10 15 reviews
Chicago
07/31 – 08/05
$2262/nighttotal: $11310 (5 )

The Jackpot | Hot Tub · Cinema · Bar · Sleeps 14

6 13
apartment , Chicago
This 6-bedroom, 3-bathroom Chicago rental home offers excellent access to the city, with a 9-minute walk to the Blue Line providing a 13-mile drive to O'Hare Airport and a 16-mile drive to downtown, plus it's a 15-mile drive to Wrigley Field.
This spacious vacation rental accommodates 14 guests and features a backyard oasis with a hot tub and fire pit, a game room with ping pong and foosball, a 120-inch 4K home theater, a sunroom, and a fully equipped kitchen, complemented by free garage parking for two vehicles.
The Bernardin Gold Coast Luxury Apartments Near Magnificent Mile - Chicago
9.1 68 reviews
Chicago
07/04 – 07/07
$1379/nighttotal: $4137 (3 )

The Bernardin Gold Coast Luxury Apartments Near Magnificent Mile

2 1
apartment , Chicago
This apartment is located in the heart of the Magnificent Mile, a short walk from Oak Street Beach and Ohio Street Beach, making it ideal for exploring Chicago's vibrant downtown and relaxing by the lake. The apartment has excellent ratings for location, cleanliness, and user experience, ensuring a comfortable and enjoyable stay.
The apartment is fully furnished and equipped with a kitchen, making it perfect for families or groups. Amenities include a rooftop pool, free Wi-Fi, and private parking, offering a range of options for relaxation and entertainment.
Harvey House Bed & Breakfast - Chicago
9.8 156 reviews
Chicago
08/06 – 08/09
$321/nighttotal: $963 (3 )

Harvey House Bed & Breakfast

1 2
B&B , Oak Park
Harvey House Bed and Breakfast is conveniently located in Oak Park, just a short walk from the CTA Green Line and a quick drive from O'Hare Airport. It's situated in a charming neighborhood known for its historic architecture and vibrant atmosphere. Guests consistently rate the B&B highly for its location, cleanliness, and overall experience.
Each suite at Harvey House is uniquely decorated and can accommodate up to two guests. Amenities include flat-screen TVs, refrigerators, private bathrooms, and a delicious breakfast served every morning. Enjoy relaxing by the fireplace in the common area, taking a dip in the Jacuzzi, or exploring the beautiful garden.

Frequently Asked Questions about short term rentals in Chicago

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

    You definitely want to check out the iconic Willis Tower, formerly known as Sears Tower, for panoramic city views. The Art Institute of Chicago is a must-see for art lovers, and Millennium Park is home to the famous Cloud Gate sculpture, affectionately known as 'The Bean.'
  • What are the best short term rentals in Chicago?

  • What's the best district to book a short term rental in Chicago?

    For short-term rentals in Chicago, the best district would be the Loop. It's the downtown area and offers proximity to major business centers, theaters, and cultural institutions.
  • What kind of weather can travelers expect in Chicago, IL?

    Chicago has four distinct seasons. Summers are hot and humid, with temperatures often reaching the 80s. Winters are cold and snowy, with temperatures often below freezing. Spring and fall are mild and pleasant, with temperatures in the 50s and 60s.
  • What are the best short term rentals with a pool in Chicago?

  • What are the most affordable attractions to visit in Chicago?

    The most affordable attractions to visit in Chicago include exploring Millennium Park, visiting the Art Institute of Chicago on free admission days, and enjoying the scenic views from Navy Pier.
  • What are the most popular festivals and events in Chicago, IL?

    Chicago is known for its vibrant festival scene. The Chicago Blues Festival is a major event, and the Taste of Chicago is a great way to sample the city's diverse culinary offerings. The Lollapalooza music festival is a huge draw for music fans.
  • What are the best short term rentals with a jacuzzi in Chicago?

  • How accessible are attractions and amenities for families with strollers or wheelchairs in Chicago?

    Most attractions and amenities in Chicago are accessible for families with strollers or wheelchairs.
  • Are there any famous stadiums or sports arenas in Chicago, IL?

    Chicago is a major sports city. Wrigley Field is home to the Chicago Cubs baseball team, and Guaranteed Rate Field is home to the Chicago White Sox. The United Center is home to the Chicago Bulls basketball team and the Chicago Blackhawks hockey team.
  • What are the best short term rentals for families and kids in Chicago?

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

  • Are popular attractions more affordable in off-peak season in Chicago?

    Popular attractions in Chicago may be more affordable in the off-peak season, which is typically during the winter months.
  • What notable natural landmarks are near Chicago, IL?

    The Indiana Dunes National Park is a short drive from Chicago and offers beautiful beaches, hiking trails, and scenic views of Lake Michigan. The Morton Arboretum is a great place to explore different types of trees and plants.
  • What are the top nightlife spots and party destinations in Chicago?

    For the best party travel experience in Chicago, head to River North for its upscale nightclubs and trendy bars. Wicker Park and Logan Square are also fantastic for a more laid-back, hipster vibe with plenty of dive bars and live music venues.
  • What part of Chicago, IL is ideal for finding lodging?

    The River North neighborhood is a popular choice for its trendy restaurants, bars, and art galleries. The Magnificent Mile is another great option, with its upscale shopping and dining. If you're looking for a more budget-friendly option, consider staying in the Wicker Park or Bucktown neighborhoods.
  • What are the most popular festivals and events in Chicago for party lovers?

    For party lovers, Lollapalooza is a must-attend music festival held every summer in Grant Park. Chicago Pride Parade and Northalsted Market Days in Boystown are also huge events that draw lively crowds and offer a fantastic party atmosphere.
  • Are there any outdoor sports activities that one can participate in while visiting Chicago?

    While visiting Chicago, you can enjoy outdoor sports activities like kayaking on the Chicago River, biking along Lake Michigan, or playing beach volleyball at North Avenue Beach.

Destinations nearby

Find the Best Family-Friendly Lodgings in Chicago

Stay near Millennium Park or the Shedd Aquarium for easy access to world-class museums. These apartments offer extra bedrooms and full kitchens, making logistics simple near the Lakefront Trail and Navy Pier.

Hygge Hideaway - Chicago
10 37 reviews
Chicago
06/20 – 06/22
$534/nighttotal: $1068 (2 )

Hygge Hideaway

1 3
apartment , Chicago
This Ravenswood, Chicago apartment is conveniently located across from a grocery store, steps from a bakery and coffee shop, and within a ten-minute walk of the Brown Line 'L' station, offering easy access to public transportation and local amenities.
This two-bedroom rental sleeps eight guests and features a fully equipped kitchen with dishwasher, in-unit laundry, a shared backyard with a fire pit and hot tub, and free street parking nearby.
Artsy Pilsen Apartment - Chicago
10 9 reviews
Chicago
07/29 – 08/03
$486/nighttotal: $2430 (5 )

Artsy Pilsen Apartment

1 1
apartment , Chicago
This 3-bedroom, 1-bathroom apartment in Chicago's Pilsen neighborhood is located on 18th Street, a street recognized on TimeOut’s 2024 coolest streets in the world and within a Forbes 2018 coolest neighborhood, offering walking distance to live music venues like Thalia Hall and Honky Tonk BBQ.
This completely rehabbed 2024 rental sleeps 6 guests and features new GE appliances, hardwood floors, original art, a third bedroom with a customizable sleeping loft, and extensive complimentary family gear, with a park featuring a playground, sandbox, splash pad, and pool located 0.2 miles away.
Level - Studio In Fulton Market With Full Kitchen - Chicago
10 2 reviews
Chicago
06/24 – 07/31
$218/nighttotal: $8066 (37 )

Level - Studio In Fulton Market With Full Kitchen

1 2
apartment , Chicago
This Level Suite is located in Chicago's Fulton Market district, offering convenient access to dining and entertainment.
This apartment features a fully-equipped gourmet kitchen, private balconies with city views, an outdoor heated pool, a fitness center with a Peloton room, and in-suite laundry, accommodating up to 2 guests with 1 bathroom.
Hip East Lakeview/lincoln Park Designer Flat - Chicago
9.2 17 reviews
Chicago
09/29 – 10/02
$227/nighttotal: $681 (3 )

Hip East Lakeview/lincoln Park Designer Flat

1 2
apartment , Chicago
This Lakeview, Chicago apartment on Orchard Street offers a quiet retreat near Lake Michigan, providing easy access to kayaking, boating, and sailing, as well as major attractions like Michigan Avenue and Navy Pier.
This 410-square-foot unit features one bedroom, one bathroom, sleeps two guests, and includes a fully equipped eat-in kitchen, in-unit laundry, a private back deck, high-speed internet, and a smart TV.

Neighborhoods and points of interest in Chicago

Best Chicago lodging with parking

Sentral Michigan Avenue - Chicago
8.9 3214 reviews
Chicago
09/13 – 09/14
$2114/nightfor 1 night

Sentral Michigan Avenue

4 9
hotel , Chicago
Sentral Michigan Avenue is located in the South Loop neighborhood of Chicago, just a short walk from DePaul University, the Field Museum, and the Art Institute. The aparthotel has excellent ratings for location, cleanliness, and overall user experience.
Each apartment has a fully equipped kitchen with modern appliances, perfect for longer stays or those who prefer to cook their own meals. Guests can enjoy a variety of amenities including an indoor pool, hot tub, fitness center, and a shared lounge area.
Linea Luxury Living With Indoor Pool And Rooftop Views In The Loop - Chicago
8.5 56 reviews
Chicago
06/19 – 06/22
$1684/nighttotal: $5052 (3 )

Linea Luxury Living With Indoor Pool And Rooftop Views In The Loop

2 1
apartment , Chicago
This downtown Chicago apartment is located within 700 yards of the city center, close to CIBC Theatre, Millennium Station, and DePaul University, making it perfect for exploring the city's cultural attractions and vibrant nightlife. The apartment features a private entrance and modern amenities like a fully equipped kitchen with a dishwasher, oven, and microwave.
You can relax in the indoor pool or on the rooftop terrace, enjoying views of the city. The apartment also has air conditioning, a flat-screen TV, and a private bathroom with a hairdryer. Parking is available for an extra charge.
Ideal Spot Just Minutes From O’hare Airport | Lcp - Chicago
9.2 13 reviews
Chicago
06/19 – 06/21
$654/nighttotal: $1308 (2 )

Ideal Spot Just Minutes From O’hare Airport | Lcp

1 4
apartment , Northlake
This three-bedroom Northlake apartment rental is conveniently located minutes from O'Hare International Airport and near attractions like Dotty's Cafe and Cinemark Theatre.
The 1200+ square-foot property boasts a spacious layout with an oversized deck and large backyard, accommodating up to six guests with amenities including a fully equipped kitchen, in-unit laundry, and high-speed Wi-Fi.
Beverly Area- Home Away From Home, Free Parking - Chicago
9.7 34 reviews
Chicago
10/09 – 10/11
$600/nighttotal: $1200 (2 )

Beverly Area- Home Away From Home, Free Parking

1 4
apartment , Chicago
This Chicago home, located in a historic district near the Metra and CTA lines, offers easy access to expressways, schools, places of worship, parks, and shopping.
The four-bedroom, one-bathroom cottage comfortably sleeps eight guests and features a finished basement with laundry, a screened porch, outdoor dining area, and a dedicated study; plus nearby fitness center and lush gardens.
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