Chicago, IL Short term rentals

9542 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 3083 reviews
Chicago, IL
02/10 – 05/10
A$616/nighttotal: A$1848 (3 )

Kasa South Loop Chicago

1 4
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 River North Chicago - Chicago, IL
9.5 439 reviews
Chicago, IL
01/07 – 05/07
A$1226/nighttotal: A$4904 (4 )

Kasa River North Chicago

3 5
aparthotel , Chicago
Kasa River North Chicago is situated in the River North district, a short walk from Oak Street Beach and the Shops at Northbridge, offering easy access to Chicago's attractions and vibrant nightlife. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The hotel offers a range of modern apartments with amenities such as air conditioning, a fridge, a dishwasher, and a coffee machine. Guests can enjoy the seasonal outdoor swimming pool, terrace, and fitness centre, or simply relax in the garden and take advantage of the concierge service.
Kasa Magnificent Mile Chicago - Chicago, IL
9.2 1381 reviews
Chicago, IL
02/10 – 05/10
A$1058/nighttotal: A$3174 (3 )

Kasa Magnificent Mile Chicago

2 4
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.
The Neighborhood Hotel-little Italy - Chicago, IL
9.6 265 reviews
Chicago, IL
13/09 – 16/09
A$644/nighttotal: A$1932 (3 )

The Neighborhood Hotel-little Italy

1 2
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.

Best Chicago, IL Short term rentals with a jacuzzi

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

Luxe Home 20 Min From Downtown Chicago ,Heated Indoor Pool, Spa Bath, Tree House - Chicago, IL
9.2 7 reviews
Chicago, IL
01/01 – 31/01
A$1515/nighttotal: A$45450 (30 )

Luxe Home 20 Min From Downtown Chicago ,Heated Indoor Pool, Spa Bath, Tree House

4 6
apartment , Skokie
This Skokie treehouse rental, a 7-minute (11 km) drive from Lake Michigan and a 12-minute (19 km) drive from Wrigley Field, offers convenient access to Chicago's attractions.
Sleeping up to nine guests, this four-bedroom, five-bathroom property boasts a fully equipped kitchen with dishwasher and microwave, a swimming pool, jacuzzi, Wi-Fi, and on-site parking.
Checkerboard Studio, Private Outdoor Hot Tub, Yard - Chicago, IL
9.7 520 reviews
Chicago, IL
11/09 – 13/09
A$375/nighttotal: A$750 (2 )

Checkerboard Studio, Private Outdoor Hot Tub, Yard

1 2
apartment , Chicago
This studio apartment is situated in a residential neighbourhood in Chicago, just a short distance from local landmarks and with easy access to street parking.
The studio features a king-size bed, a spacious couch, and a well-equipped kitchen, making it ideal for a couple seeking a comfortable and convenient base for exploring the city.
Jungle Chicago Private Room - Chicago, IL
9.8 128 reviews
Chicago, IL
23/06 – 25/07
A$103/nighttotal: A$3296 (32 )

Jungle Chicago Private Room

1 1
apartment , Chicago
This charming guesthouse is situated on the northwest side of Chicago, just a short distance from the city's vibrant attractions, offering a peaceful suburban retreat. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
The guesthouse features a comfortable bedroom with a queen-size bed, a private bathroom, and a shared kitchen, dining room, and living room, perfect for couples looking for a relaxing stay. Guests can enjoy a large garden and deck, a Jacuzzi, and the option of renting a car for exploring the city.
Spacious 2bdm Unit 15min To Dwtn - Chicago, IL
8.6 40 reviews
Chicago, IL
17/07 – 19/07
A$341/nighttotal: A$682 (2 )

Spacious 2bdm Unit 15min To Dwtn

1 4
apartment , Chicago
This Chicago apartment, registration number R20000054504, is unfortunately lacking precise location details, preventing a description of its proximity to specific landmarks.
The two-bedroom, one-bathroom flat sleeps four, offering a kitchen with fridge and microwave, air conditioning, a jacuzzi, garden, parking, and excellent guest and location ratings; further details on interior design and nearby activities are unavailable.

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, for stunning views of the city. The Art Institute of Chicago is a must-visit for art lovers, with masterpieces like Grant Wood's 'American Gothic'. And no trip to Chicago is complete without a stroll along Navy Pier, with its Ferris wheel, shops, and restaurants.
  • 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 hot and humid, with temperatures often reaching over 30 degrees Celsius. Winters are cold and snowy, with average temperatures around -5 degrees Celsius. Spring and autumn are mild and pleasant, with temperatures ranging from 10 to 20 degrees Celsius.
  • 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 a city that loves its festivals! The Chicago Blues Festival in June is a huge celebration of blues music, while the Taste of Chicago in July offers a chance to sample food from all over the city. The Chicago Air and Water Show in August is a spectacular display of aerial acrobatics.
  • 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 big sports city! Wrigley Field, home to the Chicago Cubs baseball team, is a must-see for any baseball fan. Soldier Field, home of the Chicago Bears football team, is another popular destination. And if you're a hockey fan, you can catch a game at the United Center, home to both the Chicago Blackhawks and Chicago Bulls.
  • 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 Mag Mile Mega Entire Floor 4bd\/4ba+parking&rooftop, Kasa South Loop Chicago and Sonder South Wabash.

  • What notable natural landmarks are near Chicago, IL?

    Just a short drive from Chicago, you'll find the Indiana Dunes National Park, with its beautiful beaches and towering sand dunes. For a different kind of natural beauty, head to the Morton Arboretum, a sprawling arboretum with over 17,000 trees and plants.
  • What part of Chicago, IL is ideal for finding lodging?

    The Magnificent Mile, along Michigan Avenue, is a popular spot for luxury hotels and high-end shops. For something more budget-friendly, consider staying in the River North or Wicker Park neighbourhoods. If you're looking for a more authentic Chicago experience, try the Lincoln Park or Lakeview neighbourhoods.

Destinations nearby

Best family friendly Chicago, IL Short term rentals

Among the 9542 accommodations in Chicago, IL, here are the 4 best family friendly rentals

Cheltenham 8br Combo - Chicago, IL
9.8 301 reviews
Chicago, IL
16/09 – 23/09
A$1139/nighttotal: A$7973 (7 )

Cheltenham 8br Combo

1 14
apartment , Chicago
This apartment is situated in a historic neighbourhood close to Lake Shore Drive, approximately 32 kilometres from the city centre and within easy reach of attractions such as Soldier Field, the Shedd Aquarium and the Field Museum.
The property offers a choice of two apartments, each equipped with a kitchen, a garden and free on-site parking, making it ideal for families or groups of friends.
Oak Park 3000 Sq Ft Sleep 16 Birthday Anniversary - Chicago, IL
9.9 83 reviews
Chicago, IL
24/07 – 27/07
A$1696/nighttotal: A$5088 (3 )

Oak Park 3000 Sq Ft Sleep 16 Birthday Anniversary

1 14
apartment , Oak Park
This luxurious Airbnb in Oak Park, Illinois, offers easy access to the Frank Lloyd Wright Home and Studio and Ernest Hemingway's birthplace, though precise distances aren't specified.
Sleeping up to 16 guests, this newly renovated six-bedroom, 3.5-bathroom house boasts a fully equipped kitchen, landscaped garden, parking, and excellent guest reviews; it is perfect for large families or groups visiting the area.
Aloha 2.0 | Patio, 2 Parking, Sleeps 23 - Chicago, IL
10 106 reviews
Chicago, IL
13/07 – 15/07
A$647/nighttotal: A$1294 (2 )

Aloha 2.0 | Patio, 2 Parking, Sleeps 23

1 6
apartment , Chicago
This five-bedroom property is situated in Wicker Park, a lively neighbourhood in Chicago, just a block from the Milwaukee/Damen/North Blue Line train station and 32 kilometres from O'Hare Airport. The accommodation has received excellent ratings for its location, cleanliness, and overall experience.
The property offers a unique tropical theme with flamingo, marlin, and shark decor, and can sleep up to 23 guests. It features a shared backyard with the neighbouring "ALOHA BANGTEL" penthouse, a fully equipped kitchen, air conditioning, a jacuzzi, a terrace, a garden, a fitness centre, and parking.
Villa D' Citta - Chicago, IL
9.3 191 reviews
Chicago, IL
17/10 – 23/10
A$587/nighttotal: A$3522 (6 )

Villa D' Citta

1 2
B&B , Chicago
This charming bed and breakfast is situated in the heart of Chicago's Lincoln Park, a short walk from the zoo and just a few miles from the Magnificent Mile. It has consistently received excellent ratings for its location, cleanliness and overall experience.
The guest rooms are beautifully decorated with an Italian-inspired theme and offer views of the neighbourhood. Guests can enjoy a range of amenities including a private grotto and garden with BBQ facilities, a hot tub, a gourmet kitchen and daily continental breakfast, plus a hot breakfast on weekends.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL short term rentals with parking

Flexhome Ukrainian Village 2br - Private Balcony & Walkable Location - Chicago, IL
Chicago, IL
28/07 – 05/08
A$754/nighttotal: A$6032 (8 )

Flexhome Ukrainian Village 2br - Private Balcony & Walkable Location

2 2
apartment , Chicago
This two-bedroom flat in Chicago's Ukrainian Village offers a walkable base with easy access to local attractions and dining.
This 55 square metre flat accommodates up to five guests, featuring air conditioning, a fully equipped kitchen with a dishwasher and microwave, and a balcony with outdoor seating, with free WiFi provided.
10 Min Walk To Stevenson Convention Center - Chicago, IL
8.0 12 reviews
Chicago, IL
26/06 – 28/06
A$546/nighttotal: A$1092 (2 )

10 Min Walk To Stevenson Convention Center

2 8
apartment , Rosemont
This two-bedroom apartment is situated in O'Hare, Rosemont, a short 10-minute walk from the Donald E. Stephens Convention & Conference Center and within a 10-minute drive of O'Hare Airport and Chicago's downtown. It has received excellent user ratings, making it a popular choice for travellers.
The 93 square metre apartment can comfortably accommodate up to eight guests. It features a fully equipped kitchen, air conditioning, a garden, parking, and internet access, making it ideal for families or groups looking for a comfortable and convenient stay.
1910 Charming Historic Flat - Walk To Beach & Loyola! - Chicago, IL
10 5 reviews
Chicago, IL
18/09 – 20/09
A$673/nighttotal: A$1346 (2 )

1910 Charming Historic Flat - Walk To Beach & Loyola!

3 2
apartment , Chicago
This historic craftsman-style apartment in Chicago's Rogers Park district offers excellent access to the city, situated just 3 blocks from Lake Michigan and 1 block from the El train, providing a 15-minute journey to Wrigley Field and an 18-minute trip to Michigan Avenue.
Spanning 149 square metres, this property accommodates up to 8 guests with 3 bedrooms, a fully equipped kitchen featuring a microwave and dishwasher, air conditioning throughout, and entertainment options including Apple TV, Netflix, an electric piano, and a guitar.
Charming 2-bed Garden Condo In Beautiful Chicago + Wifi, Ac, & Private Parking - Chicago, IL
Chicago, IL
01/09 – 31/10
A$158/nighttotal: A$9480 (60 )

Charming 2-bed Garden Condo In Beautiful Chicago + Wifi, Ac, & Private Parking

2 2
apartment , Chicago
This Bronzeville condo is situated in Chicago, near the Field Museum and Museum of Science and Industry, offering easy access to sporting events at Soldier Field and McCormick Place.
The two-bedroom, two-bathroom apartment sleeps three, features a terrace, garden, parking, and a kitchen with fridge, microwave, and dishwasher; queen-size beds are provided in each bedroom.
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