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

Kasa Lake Shore Chicago - Chicago, IL
8.4 25 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 Magnificent Mile Chicago - Chicago, IL
9.2 1572 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.
The Neighborhood Hotel-little Italy - Chicago, IL
9.6 322 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 South Loop Chicago - Chicago, IL
9.4 3281 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

Exclusive 3br With Views, Ideal For Tourists - Chicago, IL
10 6 reviews

Exclusive 3br With Views, Ideal For Tourists

apartment, Chicago
This Chicago apartment, situated in the downtown area a short distance from Millennium Park and the Chicago Riverwalk, offers easy access to major attractions such as Grant Park and the Art Institute of Chicago.
The 65 square metre (700 square foot) three-bedroom, two-bathroom dwelling sleeps six, and includes a fully equipped kitchen, air conditioning, and private bathrooms with showers; nearby activities include events at the United Center and Soldier Field.
6 Luxe Apts, Perfect Group Solution, Sleeps 30 - Chicago, IL
10 2 reviews

6 Luxe Apts, Perfect Group Solution, Sleeps 30

apartment, Chicago
This expansive apartment in Chicago's West Loop is situated just 2 minutes on foot from Union Park and within 1.6 kilometres of Fulton Market's dining and shopping district.
This property offers accommodation for up to 32 guests across 13 bedrooms, featuring 12 bathrooms, a swimming pool, fitness centre, and a dedicated gathering space with city skyline views, ideal for corporate offsites and group getaways.
Chicago Oasis | Spa Bath, Patio & Fireplace - Chicago, IL
10 21 reviews

Chicago Oasis | Spa Bath, Patio & Fireplace

apartment, Chicago
This apartment is located in downtown Chicago, just a short walk from Navy Pier and Michigan Avenue, making it easy to explore the city’s attractions and vibrant nightlife. It has received excellent reviews from previous guests.
The one-bedroom apartment spans 88 square metres and comfortably accommodates up to four guests. It boasts a fully equipped kitchen, a spa bathroom with a jetted tub and a rain shower, and a terrace where you can relax and enjoy the city views.
Scenic 3br Ph For Tourism + Prime Location - Chicago, IL
10 2 reviews

Scenic 3br Ph For Tourism + Prime Location

apartment, Chicago
This River West penthouse apartment, located in West Town, Chicago, offers easy access to Logan Square and Fulton Market, and is near the Chicago Academy for the Arts and Ogden International High School.
This 178 square metre three-bedroom, three-bathroom dwelling boasts two balconies with city views, a 75-inch TV, Sonos sound system, and access to a 24-hour gym, yoga studio, outdoor pool, and hot tub within the building, sleeping up to seven guests.

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-see for art lovers, with works by Monet, Picasso, and Van Gogh. And no trip to Chicago is complete without a visit to Millennium Park, home to the famous Cloud Gate sculpture, affectionately 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 a humid continental climate, so you'll experience all four seasons. Summers are hot and humid, with average temperatures around 25°C. Winters are cold and snowy, with average temperatures around -5°C. Spring and autumn are generally mild, but can be unpredictable.
  • 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 a good festival! You'll find something for everyone, from the massive Lollapalooza music festival in the summer to the Taste of Chicago food festival in July. The Chicago Air and Water Show in August is always a crowd-pleaser, and the Chicago Marathon in October is a major sporting event.
  • What are the best short term rentals with a jacuzzi in Chicago, IL?

    The best short term rentals with a jacuzzi in Chicago, IL are Sentral Michigan Avenue, The Neighborhood Hotel Lincoln Park and Level Chicago – Old Town.

  • Are there any famous stadiums or sports arenas in Chicago, IL?

    Chicago is a sports town! 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 home to both 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?

    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 the city, you can find Indiana Dunes National Park, with its beautiful beaches and towering sand dunes. The Morton Arboretum is a great place to escape the city and enjoy a peaceful walk among the trees. And if you're looking for some outdoor adventure, the Chain O'Lakes State Park offers boating, fishing, and hiking.
  • What part of Chicago, IL is ideal for finding lodging?

    It depends on what you're looking for! If you want to be in the heart of the action, the Magnificent Mile is a great option, with plenty of hotels and restaurants. For a more relaxed experience, consider staying in the Lincoln Park neighbourhood, with its beautiful park and museums. And if you're on a budget, the River North neighbourhood is a good choice.

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

Cozy 3br Free Parking & Games Near Dt - Chicago, IL
9.8 26 reviews

Cozy 3br Free Parking & Games Near Dt

apartment, Chicago
This three-bedroom Chicago apartment, ideal for families, is conveniently located approximately 13 kilometres from the city centre, offering easy access to Chicago's major attractions.
The 3-bedroom dwelling sleeps six guests and boasts a fully equipped kitchen, high-speed Wi-Fi, complimentary laundry facilities, designated parking, and a deck with a fire pit; a high chair and crib are available upon request.
Stay Near Family Or Close To Downtown, This Loft In Beverly Has It All! - Chicago, IL
9.2 17 reviews

Stay Near Family Or Close To Downtown, This Loft In Beverly Has It All!

apartment, Chicago
This two-bedroom Beverly apartment in Chicago is situated near the 99th and 95th Street stations, offering easy access to public transport and lies within 6km of Advocate Christ Medical Centre.
The 6-guest property features a fully equipped kitchen, free Wi-Fi, a Smart TV, and an on-site arcade, all within a short drive of Abbott Park and the Chicago Ridge Shopping Mall.
Six-bedrooms In Wrigleyville - Chicago, IL
9.6 4 reviews

Six-bedrooms In Wrigleyville

apartment, Chicago
This expansive six-bedroom, two-bathroom flat in Chicago's Wrigleyville district offers a combined living experience across two distinct units, ideal for groups of up to sixteen, and is situated a short walk from the iconic Wrigley Field and its surrounding amenities. Guests can enjoy the convenience of a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, air conditioning, and Wi-Fi, alongside shared outdoor decking and the option of arranging street parking permits.
2br/2ba Condo W/ Balcony & Garage - Near Hospitals - Chicago, IL
10 2 reviews

2br/2ba Condo W/ Balcony & Garage - Near Hospitals

apartment, Chicago
This 2-bedroom, 2-bathroom condo is located between Chicago's South Loop and Bronzeville districts, offering easy access to the city centre and the lakefront, with McCormick Place just a short walk away and Insight Hospital in the immediate vicinity.
This 119-square-metre flat, suitable for up to four guests, features a primary suite with a king-size bed and en-suite bathroom, a second bedroom with a queen-size bed and workspace, a fully equipped kitchen, in-unit laundry, and a private balcony, all within a secure, controlled-access building.

Best Chicago, IL lodging with parking

The Reset Space  A Minimalist 1br Oasis - Chicago, IL
9.8 13 reviews

The Reset Space A Minimalist 1br Oasis

apartment, Chicago
This Chicago flat is located in the Park Manor district, offering authentic neighbourhood character and convenient access to Hyde Park and the University of Chicago, approximately 1.6 kilometres away, with The Loop reachable by car in 16 to 32 kilometres.
This modern apartment, accommodating up to two guests, features a fully equipped kitchen with a fridge, freezer, and microwave, high-speed Wi-Fi for remote work, air conditioning, and a garden, situated near culinary attractions and offering excellent transport links to I-90/94 and the CTA Red Line.
Ravenswood Guest House Annex - Chicago, IL
9.9 501 reviews

Ravenswood Guest House Annex

apartment, Chicago
This charming garden flat is situated just north of Andersonville, a short walk from Lake Shore Drive, Evanston, and downtown Chicago. It boasts excellent user, location, and cleanliness ratings, making it a great choice for travellers seeking a comfortable and convenient stay.
The self-contained flat can accommodate up to four guests and features a well-equipped kitchen, a garden, and parking. Guests can enjoy the peaceful surroundings, explore the nearby Andersonville neighbourhood, or easily access other parts of the city using public transport.
Jeffjack Heated Pool Penthouse In Chicago's West Loop - Chicago, IL
9.7 152 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.
Studio In Chicago's Edgewater By Lakefront/lsd/cta - Chicago, IL
9.4 81 reviews

Studio In Chicago's Edgewater By Lakefront/lsd/cta

apartment, Chicago
This Chicago Edgewater basement studio is conveniently located one block from the Red Line 'L' train and a short walk (approx. 0.8km) from Lake Michigan beaches, offering easy access to the Magnificent Mile (approx. 7km drive) and Wrigley Field (approx. 5km drive).
The self-catering apartment features a 66" futon bed, sleeps four, includes a kitchen with fridge, freezer, microwave, and dishwasher, plus shared laundry facilities, and benefits from air conditioning and on-street parking.
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