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

The Neighborhood Hotel-little Italy - Chicago, IL
9.6 288 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 1517 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.
Kasa Lake Shore Chicago - Chicago, IL
9.4 3 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 3242 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.

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

Stylish 2br Retreat In Fulton Market For Getaways - Chicago, IL
10 2 reviews

Stylish 2br Retreat In Fulton Market For Getaways

apartment, Chicago
This stylish two-bedroom apartment, situated in Chicago's Fulton Market district, is a 7-minute walk from Union Park and a 10-minute walk from Google's headquarters.
The 107-square-metre (1150 sq ft) property boasts a chef's kitchen, private balcony, and access to a 2800 sq m amenity space with a pool, spa, and fitness centre; it sleeps five guests and offers a rollaway bed and crib.
Vital Urban: Spa Inspired Retreat - Chicago, IL
10 13 reviews

Vital Urban: Spa Inspired Retreat

apartment, Chicago
This two-bedroom, three-bathroom apartment in Chicago's Wicker Park neighbourhood is a five-minute walk from the Damen Blue Line station, offering easy access to other areas of the city and attractions such as the Chicago Theatre and the Art Institute of Chicago.
The 2-bedroom apartment sleeps six guests and boasts a jacuzzi, sauna, private steam room, and terrace, plus a fully equipped kitchen including a dishwasher, all within a West Town location.
Jeffjack Heated Pool Penthouse In Chicago's West Loop - Chicago, IL
9.6 148 reviews

Jeffjack Heated Pool Penthouse In Chicago's West Loop

apartment, Chicago
This penthouse apartment is conveniently located in the centre of Chicago, within easy walking distance of Union Station, Willis Tower, and CIBC Theatre. The apartment consistently receives excellent ratings for its location, cleanliness, and overall experience, making it a popular choice for travellers.
The apartment has two bedrooms, comfortably accommodating up to six guests. Enjoy a range of amenities including a rooftop pool, fitness centre, and private parking, as well as a fully equipped kitchen and balcony with stunning city views.
Modern Comfort In Roscoe Village - Chicago, IL
9.7 31 reviews

Modern Comfort In Roscoe Village

apartment, Chicago
This Roscoe Village flat offers a peaceful neighbourhood feel, with quick access to Wrigleyville and downtown Chicago via public transport, approximately 6 kilometres away.
This modern two-bedroom flat accommodates up to four guests and features air conditioning, internet, and a fully equipped kitchen, with complimentary street parking and ground-floor access simplifying your stay.

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.

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

Eco Stay By Uchicago, Lakefront & Hyde Park! - Chicago, IL
9.4 7 reviews

Eco Stay By Uchicago, Lakefront & Hyde Park!

apartment, Chicago
This Hyde Park flat is conveniently located near the University of Chicago, 4.2 km from the Museum of Science and Industry, and within 13 km of Buckingham Fountain and Chicago's city centre.
The 74 square metre self-catering property offers two bedrooms, one bathroom, sleeps five, and includes a fully equipped kitchen, private garden, free on-site parking, and air conditioning.
Two 2br Apts For Business & Leisure Groups - Chicago, IL
No reviews

Two 2br Apts For Business & Leisure Groups

apartment, Chicago
This four-bedroom flat is situated in Chicago's West Loop, 500 metres from Fulton Market and 600 metres from Union Park, offering convenient access to the city's attractions.
This spacious accommodation for ten guests boasts a top-floor unit with private balconies, city views, four Queen bedrooms, four bathrooms, and access to building amenities including a fitness centre, game room, and outdoor sky terrace with grills and firepits.
1br Near O'hare W/ Private Parking  Safe Location - Chicago, IL
No reviews

1br Near O'hare W/ Private Parking Safe Location

apartment, Chicago
This one-bedroom flat is located in Chicago's River North district, a mere 500 metres from the Magnificent Mile and the Chicago Riverwalk.
The apartment, managed by LuxuryLodgingSTR and suitable for four guests, offers air conditioning, internet, and parking, with a kitchen equipped with a fridge, freezer, and microwave oven.
Modern Apartment With Private Rooftop Patio & Free Parking In Downtown Chicago - Chicago, IL
9.8 201 reviews

Modern Apartment With Private Rooftop Patio & Free Parking In Downtown Chicago

apartment, Chicago
This apartment is situated in a central Chicago neighbourhood, just a short walk from the L-transit system and within 1.6 km of the city centre. The apartment has received excellent ratings for cleanliness, location, and user experience.
The apartment offers 232 square metres of living space with three bedrooms, comfortably accommodating up to 10 guests. Amenities include a fully equipped kitchen, two outdoor spaces, a private rooftop deck with a fire pit, and free parking.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL short term rentals with parking

Great Suburban Location! Perfect For Solo Or Couple Travelers - Chicago, IL
9.5 141 reviews

Great Suburban Location! Perfect For Solo Or Couple Travelers

apartment, Hickory Hills
This one-bedroom flat is situated in a suburban area of Hickory Hills, just a short walk from restaurants, shops, and other amenities on 95th Street. It has received excellent ratings for location, cleanliness, and overall user experience.
The flat is ideal for couples, offering a comfortable living area with a kitchenette, a king-size bed, and a 70-inch TV. Guests can enjoy modern amenities such as air conditioning, a spa, and parking, as well as a relaxing retreat with blackout curtains and comfortable furnishings.
The Palmer Street House - Logan Square - Chicago, IL
9.2 59 reviews

The Palmer Street House - Logan Square

apartment, Chicago
This Logan Square duplex, a 15-minute drive (approx. 24km) from Chicago's city centre and near the 606 trail, offers easy access to public transport.
The spacious 150m² three-bedroom, two-bathroom property sleeps up to seven guests and includes a private patio, fully equipped kitchen, in-unit laundry, and family-friendly amenities such as a cot and high chair.
Great Location In Oak Park! - Chicago, IL
10 8 reviews

Great Location In Oak Park!

apartment, Oak Park
This Oak Park garden flat is conveniently located a few blocks from the Interstate 290, approximately 13 kilometres from Chicago's city centre, offering easy access to the Green and Blue 'L' lines.
The self-contained apartment sleeps up to five guests and features a California king bed, double futon, efficiency kitchen with dishwasher and beverage fridge, a smart TV, poker table, and access to a shared patio with gas grill; nearby amenities include shops, restaurants, parks, and a hospital.
Gorgeous Room #2 - Chicago, IL
9.7 319 reviews

Gorgeous Room #2

apartment, Franklin Park
This charming bed and breakfast is situated in a peaceful area of Franklin Park, just a short distance from downtown Chicago, Naperville, Brookfield Zoo, and O'Hare Airport. The property has received excellent ratings for its cleanliness, location, and overall guest experience.
The guest house has a shared kitchen, making it ideal for couples or solo travellers. Guests can enjoy a peaceful garden, use the free Wi-Fi, and benefit from the convenient parking facilities.
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