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 3084 reviews
Chicago, IL
24/08 – 26/08
344 €/nighttotal: 688 € (2 )

Kasa South Loop Chicago

1 3
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 1379 reviews
Chicago, IL
23/07 – 26/07
1619 €/nighttotal: 4857 € (3 )

Kasa Magnificent Mile Chicago

3 8
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
25/06 – 28/06
342 €/nighttotal: 1026 € (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.
Kasa River North Chicago - Chicago, IL
9.4 351 reviews
Chicago, IL
01/01 – 31/01
350 €/nighttotal: 10500 € (30 )

Kasa River North Chicago

3 6
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.

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

The Céline® Highrise - Stunning City Views, Gym - Chicago, IL
10 2 reviews
Chicago, IL
17/09 – 17/12
160 €/nighttotal: 14560 € (91 )

The Céline® Highrise - Stunning City Views, Gym

1 1
apartment , Chicago
This one-bedroom flat in a prime Chicago district offers excellent access to the city's attractions and business centres.
Guests can enjoy exclusive access to building amenities including a clubhouse with city views, a pool/jacuzzi, a private conference room, and a 24/7 fitness centre, with a fully stocked kitchen and high-speed WiFi catering to both leisure and business travellers.
United Center Compound W/rooftop, Hot Tub, Sauna - Chicago, IL
9.8 90 reviews
Chicago, IL
01/07 – 06/07
1035 €/nighttotal: 5175 € (5 )

United Center Compound W/rooftop, Hot Tub, Sauna

1 11
apartment , Chicago
This spacious four-bedroom Chicago home, near the United Centre in the West Loop, offers easy access to local attractions.
Sleeping nine in total across four bedrooms and three bathrooms, this mid-century modern property boasts a chef's kitchen, multiple entertainment areas including a rooftop deck and a large heated private garage (111.5 m²).
Luxe 3br, 2ba + Hot Tub - Chicago, IL
9.6 133 reviews
Chicago, IL
22/07 – 23/07
511 €/nightfor 1 night

Luxe 3br, 2ba + Hot Tub

1 8
apartment , Hillside
This raised ranch is ideally located in Hillside, just a short drive from the I-294 and I-88 motorways, making it easy to reach Elmhurst Hospital and downtown Chicago, which is 32 kilometres away. This property has consistently received excellent ratings for its location, cleanliness and overall experience.
This spacious three-bedroom house can comfortably accommodate up to eight guests. The house includes a well-equipped kitchen, a relaxing family room, a large garden with upper and lower decks, a hot tub, and a garage.
The Jackpot | Hot Tub · Cinema · Bar · Sleeps 14 - Chicago, IL
10 15 reviews
Chicago, IL
31/07 – 03/08
2100 €/nighttotal: 6300 € (3 )

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

6 11
apartment , Chicago
This Chicago flat offers convenient access, being a 9-minute walk to the Blue Line, 24 kilometres from O'Hare Airport and 25 kilometres from downtown, with Wrigley Field and Millennium Park within a 32 kilometre drive.
This spacious 6-bedroom, 3-bathroom property sleeps 14 guests and boasts a private 2-car garage, an all-season backyard with a hot tub, a game room, a 4K home theatre, and a sunroom.

Frequently asked questions about short term rentals in Chicago, IL

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

    You've got to see the iconic Willis Tower (formerly Sears Tower) for amazing views of the city. The Art Institute of Chicago is a must-visit for art lovers, and Millennium Park is perfect for a stroll with its famous Cloud Gate sculpture, nicknamed 'The Bean'.
  • 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°C. Winters are cold and snowy, with average temperatures around -5°C. Spring and autumn are beautiful, with mild temperatures and vibrant colours.
  • 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's got a festival for everyone! The Lollapalooza music festival is a big draw in the summer, and the Chicago Air & Water Show is a spectacular event in August. The Chicago Blues Festival in June is a fantastic celebration of music.
  • 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 sports city! Wrigley Field, home to the Chicago Cubs baseball team, is a historic landmark. Soldier Field is home to the Chicago Bears, and the United Center is where you'll find 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 the city, you'll find Indiana Dunes National Park. It has beautiful beaches, sand dunes, and forests, perfect for hiking, biking, and exploring nature.
  • What part of Chicago, IL is ideal for finding lodging?

    The Magnificent Mile, along Michigan Avenue, is a popular area with plenty of hotels. River North is another great option, with trendy restaurants and nightlife. For a quieter stay, consider the Gold Coast or Lincoln Park.

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

Hamaline Luxury - Guest House - Chicago, IL
9.4 3 reviews
Chicago, IL
13/10 – 20/12
107 €/nighttotal: 7276 € (68 )

Hamaline Luxury - Guest House

3 2
apartment , Chicago
This Chicago guesthouse is located in the Douglas Park neighbourhood, offering convenient access to attractions such as the city centre, McCormick Place, and the lakefront.
The 93-square-metre, three-floor townhome sleeps five guests, boasting three bedrooms, one bathroom, a fully equipped kitchen with an air fryer and Keurig coffee maker, plus two massage chairs and automated check-in.
Private Lincoln Park Condo With 2 Parking Spots - Chicago, IL
9.9 131 reviews
Chicago, IL
27/06 – 30/06
612 €/nighttotal: 1836 € (3 )

Private Lincoln Park Condo With 2 Parking Spots

1 5
apartment , Chicago
This Lincoln Park flat, in a historically significant 1895 building, offers convenient access to Lincoln Park's attractions, within easy walking distance of many landmarks.
The two-bedroom, one-bathroom apartment sleeps six, boasting a fully-remodelled kitchen, a private balcony, two off-street parking spaces, a 75" 4K Smart TV, and high-speed fibre internet; a friendly black lab, Buck, may even greet you.
Fully Furnished Extended Stay Work Or Insurance In Chicago - Chicago, IL
8.5 14 reviews
Chicago, IL
09/12 – 26/12
106 €/nighttotal: 1802 € (17 )

Fully Furnished Extended Stay Work Or Insurance In Chicago

2 2
apartment , Chicago
This flat is located in a Chicago neighbourhood, approximately 9.2 kilometres from the United Centre and 12.6 kilometres from Willis Tower.
This 28 square metre flat offers two bedrooms, a living room, and a kitchen equipped with a fridge and microwave, accommodating up to seven guests with free on-site parking and complimentary WiFi.
The Hyde Park Hide-a-way - Chicago, IL
9.6 11 reviews
Chicago, IL
23/06 – 25/07
100 €/nighttotal: 3200 € (32 )

The Hyde Park Hide-a-way

1 1
apartment , Chicago
This Hyde Park flat is situated near the University of Chicago, Jackson Park, and the lakefront, offering easy access to Hyde Park's restaurants and attractions.
The three-bedroom, two-bathroom apartment sleeps six guests and includes a fully equipped kitchen, in-unit laundry, and free street parking; external security cameras provide added peace of mind.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL short term rentals with parking

Flexhome West Town - Spacious 2br Duplex - Chicago, IL
Chicago, IL
31/07 – 02/08
1395 €/nighttotal: 2790 € (2 )

Flexhome West Town - Spacious 2br Duplex

2 6
apartment , Chicago
This West Town flat is located in Chicago's West Town district, 3.2 kilometres from Union Station and 3.0 kilometres from Water Tower Chicago.
This 60 square metre residence accommodates up to 11 guests, featuring two bedrooms, two bathrooms, air conditioning, a fully equipped kitchen with a dishwasher, and complimentary WiFi.
1br Apartment - Walk To Shops - Downtown Oak Park - Chicago, IL
9.2 42 reviews
Chicago, IL
25/06 – 26/06
370 €/nightfor 1 night

1br Apartment - Walk To Shops - Downtown Oak Park

2 2
apartment , Oak Park
This one-bedroom flat in Oak Park offers a prime location in a district celebrated for its Frank Lloyd Wright architecture, placing guests within easy reach of local shops and restaurants, and just a 4-minute drive from the train station for access to Chicago.
This accommodation provides dedicated WiFi, two Smart TVs, and a fully equipped kitchen and bathroom, with a Pack 'n Play available for families, and is conveniently located a 2-minute drive from grocery stores and shopping centres, and a 20-minute drive to Downtown Chicago.
Spacious 5br Luxury Suite Perfect For Group Sleeps 12 Near Mccormick Place, Grant Park And Soldier Field - Chicago, IL
Chicago, IL
14/08 – 16/08
1176 €/nighttotal: 2352 € (2 )

Spacious 5br Luxury Suite Perfect For Group Sleeps 12 Near Mccormick Place, Grant Park And Soldier Field

5 10
apartment , Chicago
This luxury Chicago apartment, situated approximately 2.4 kilometres from the Field Museum and within 3.2 kilometres of the Art Institute of Chicago and the Chicago Symphony Orchestra, offers easy access to the city's cultural attractions.
The 214-square-metre property boasts a spacious five-bedroom, four-bathroom layout sleeping up to 12 guests, complete with a fully equipped kitchen, fitness centre access, free Wi-Fi, and a patio offering city views.
Spacious 2br South Loop Suite With Skyline View, Optional Parking And Gym Access Close To Mccormick Place, Grant Park, Museum Campus & Cta Lines - Chicago, IL
10 2 reviews
Chicago, IL
05/07 – 11/07
275 €/nighttotal: 1650 € (6 )

Spacious 2br South Loop Suite With Skyline View, Optional Parking And Gym Access Close To Mccormick Place, Grant Park, Museum Campus & Cta Lines

2 5
apartment , Chicago
This family-friendly apartment near Chicago's Museum Campus is conveniently located approximately 2.4 kilometres from the Field Museum and within 3.2 kilometres of the Art Institute of Chicago and the Chicago Symphony Orchestra.
The 74-square-metre dwelling boasts a spacious two-bedroom, two-bathroom layout sleeping up to eight guests, offering a private patio with skyline views, a fully equipped kitchen, free Wi-Fi, and access to an on-site fitness centre and parking.
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