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

The Neighborhood Hotel-little Italy - Chicago, IL
9.6 265 reviews
Chicago, IL
25/06 – 28/06
SG$509/nighttotal: SG$1527 (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 South Loop Chicago - Chicago, IL
9.4 3084 reviews
Chicago, IL
06/07 – 10/07
SG$375/nighttotal: SG$1500 (4 )

Kasa South Loop Chicago

1 1
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
18/07 – 15/08
SG$411/nighttotal: SG$11508 (28 )

Kasa Magnificent Mile Chicago

1 1
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 River North Chicago - Chicago, IL
9.4 351 reviews
Chicago, IL
10/07 – 24/07
SG$1105/nighttotal: SG$15470 (14 )

Kasa River North Chicago

2 4
hotel , 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

Mccormick 4br Huge Unit W/ Pool Table | Sleeps 10 - Chicago, IL
8.0 1 review
Chicago, IL
12/10 – 14/10
SG$1294/nighttotal: SG$2588 (2 )

Mccormick 4br Huge Unit W/ Pool Table | Sleeps 10

4 4
apartment , Chicago
This spacious four-bedroom flat in the McCormick district offers convenient access to Chicago's key attractions, situated between 1.6 and 3.2 kilometres of the Field Museum, Grant Park, DePaul University, the Art Institute of Chicago, the Chicago Symphony Orchestra, and the CIBC Theatre.
This accommodation for up to 10 guests features a fully equipped kitchen with a dishwasher and kettle, air conditioning, free WiFi, a private entrance, and two bathrooms, one with a hot tub, alongside a full-sized pool table for entertainment.
Bright Modern Flat With Free Garage Parking - Chicago, IL
10 66 reviews
Chicago, IL
06/07 – 12/07
SG$511/nighttotal: SG$3066 (6 )

Bright Modern Flat With Free Garage Parking

1 5
apartment , Chicago
This three-bedroom apartment is situated in Chicago's Logan Square neighbourhood, offering easy access to the city's attractions.
The 3-bedroom flat sleeps six guests comfortably, boasting a spacious open-plan living/dining area, fully equipped kitchen with dishwasher, Jacuzzi, in-unit entertainment, and parking; nearby activities include exploring the Logan Square Farmers Market.
Private Room In Norwood Park - Chicago, IL
9.9 35 reviews
Chicago, IL
21/06 – 26/06
SG$66/nighttotal: SG$330 (5 )

Private Room In Norwood Park

1 1
apartment , Chicago
This Chicago guest house is located in Norwood Park, 5km from O'Hare International Airport and 19km from Chicago's city centre.
The self-contained unit offers a private bedroom with a semi-walk-in closet, a shared living area with Chromecast, and access to a kitchen equipped with a fridge, freezer, microwave, and dishwasher; it sleeps one guest and includes a jacuzzi.
Spacious 3br 420-friendly | Mccormick & Uic Campus - Chicago, IL
Chicago, IL
30/07 – 03/08
SG$2216/nighttotal: SG$8864 (4 )

Spacious 3br 420-friendly | Mccormick & Uic Campus

3 7
apartment , Chicago
This three-bedroom flat in Chicago's Near West Side is situated within 3.2 kilometres of Grant Park, the Art Institute of Chicago, and the Willis Tower, and is conveniently close to the McCormick Place and UIC campuses.
This accommodation offers a hot tub, air conditioning, complimentary WiFi, and a fully equipped kitchen, sleeping up to 13 guests with a 11:00 AM check-out time.

Frequently asked questions about short term rentals in Chicago, IL

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

    You can't visit Chicago without seeing the iconic Willis Tower, formerly known as the Sears Tower. It's the tallest building in the city and offers breathtaking views. The Magnificent Mile, a stretch of North Michigan Avenue, is also a must-see, filled with shops, restaurants, and art galleries. And of course, no trip to Chicago is complete without a visit to Millennium Park, home to the Cloud Gate sculpture, affectionately nicknamed 'The Bean', and Crown Fountain, an interactive fountain that displays faces of Chicagoans.
  • 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, so pack accordingly! Summers are hot and humid, with temperatures reaching around 27°C. Winters are cold and snowy, with average temperatures around -3°C. Spring and autumn can be unpredictable, with temperatures fluctuating between cool and warm. It's always a good idea to check the forecast before you go.
  • 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 known for its vibrant festival scene. The Chicago Blues Festival, held in June, is a must-see for music lovers. For something a bit different, the Taste of Chicago, held in July, showcases the city's diverse culinary scene. And if you're a film buff, the Chicago International Film Festival in October is a great way to experience some of the best independent and foreign films.
  • 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 huge sports city! Wrigley Field, home to the Chicago Cubs baseball team, is a historic landmark. Soldier Field, home to the Chicago Bears, is also a popular destination for football fans. And United Center is where you can catch 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 Chicago, you'll find Indiana Dunes National Park, a stunning stretch of sand dunes along the shores of Lake Michigan. The park offers hiking trails, beaches, and scenic overlooks. If you're looking for something a little closer to the city, the Morton Arboretum, a sprawling botanical garden, is a great option.
  • What part of Chicago, IL is ideal for finding lodging?

    The River North neighbourhood is a great option for travellers, with its trendy restaurants, art galleries, and proximity to the Magnificent Mile. If you're looking for something more budget-friendly, the Wicker Park and Bucktown neighbourhoods offer a vibrant atmosphere with plenty of bars, cafes, and shops.

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

New Luxurious 5bd-2ba Duplex-free Wine-2car Parking - Chicago, IL
9.2 22 reviews
Chicago, IL
03/07 – 05/07
SG$586/nighttotal: SG$1172 (2 )

New Luxurious 5bd-2ba Duplex-free Wine-2car Parking

5 5
apartment , Chicago
This luxurious five-bedroom Chicago apartment is situated approximately 6.3 km from the Museum of Science and Industry, offering easy access to other attractions such as Guaranteed Rate Field (14.5 km), the Field Museum (16 km), and the Adler Planetarium (16 km).
The 158 square metre property features a spacious five-bedroom, two-bathroom layout sleeping up to 19 guests, complete with a fully equipped kitchen, free Wi-Fi, private parking, and complimentary wine or champagne on arrival.
Wrigleyville Condo, Sleeps 10, 1/2 Block From Wrigley Field - Chicago, IL
10 117 reviews
Chicago, IL
08/07 – 10/07
SG$857/nighttotal: SG$1714 (2 )

Wrigleyville Condo, Sleeps 10, 1/2 Block From Wrigley Field

3 8
apartment , Chicago
This Wrigleyville apartment is located just half a kilometre from Wrigley Field and Clark Street, in the heart of Lakeview, a lively neighbourhood known for its vibrant atmosphere and proximity to public transport. It has received excellent user ratings, making it a popular choice for travellers.
The three-bedroom apartment spans 102 square metres and comfortably sleeps six guests. It boasts a range of modern amenities, including a fully equipped kitchen, a jacuzzi, a garden, and parking, as well as multiple living spaces for families or groups.
Cozy, Comfortable And Convenient Apartment. Close To Everything! - Chicago, IL
9.8 175 reviews
Chicago, IL
19/07 – 20/07
SG$749/nightfor 1 night

Cozy, Comfortable And Convenient Apartment. Close To Everything!

2 4
apartment , Oak Park
This charming studio apartment is situated in Oak Park's Arts District, just a short walk from the Frank Lloyd Wright Home and Studio, and a mere 400 feet from the CTA Blue Line, making it easy to explore both Oak Park and downtown Chicago. The studio consistently receives excellent ratings for its location, cleanliness, and overall experience.
This comfortable apartment offers two bedrooms and one bathroom across 86 square metres. Guests can enjoy a fully equipped kitchen, a private garden, a spa, and parking, as well as keyless access and a patio with a grill for warm weather enjoyment.
Lovely 2bedroom  1bath  Apt And Outdoor Seating. - Chicago, IL
9.9 146 reviews
Chicago, IL
13/09 – 18/09
SG$242/nighttotal: SG$1210 (5 )

Lovely 2bedroom 1bath Apt And Outdoor Seating.

1 2
apartment , Chicago
This two-bedroom Chicago apartment, registration number R22000080636, is situated in a peaceful, family-friendly neighbourhood; precise location within Chicago and proximity to specific landmarks requires further clarification.
Sleeping up to five guests, this family-friendly flat offers a kitchen with fridge, freezer and microwave, air conditioning, a garden, parking and internet access; further details regarding the property's size, interior design and nearby attractions are unavailable.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL short term rentals with parking

Group-friendly 2br With Optional Parking And Gym Access Near Mccormick Place And Soldier Field - Chicago, IL
8.5 10 reviews
Chicago, IL
21/07 – 23/07
SG$441/nighttotal: SG$882 (2 )

Group-friendly 2br With Optional Parking And Gym Access Near Mccormick Place And Soldier Field

2 7
apartment , Chicago
This Chicago apartment is conveniently located near the Field Museum (2.3 km), the Art Institute of Chicago (2.9 km), and the Chicago Symphony Orchestra (2.9 km).
The 74-square-metre two-bedroom, two-bathroom flat sleeps up to eight guests and offers free Wi-Fi, a fully equipped kitchen, on-site parking, a fitness centre, and a patio with city views.
Mccormick Place 2b/2b Family Unit With Optional Parking For Up To 8 Guests - Chicago, IL
10 1 review
Chicago, IL
31/07 – 03/08
SG$1212/nighttotal: SG$3636 (3 )

Mccormick Place 2b/2b Family Unit With Optional Parking For Up To 8 Guests

2 8
apartment , Chicago
This Near South Side Chicago flat is conveniently located a short walk from State Street and Wintrust Arena, and within 1.6km of McCormick Place and Soldier Field.
The 88 square metre property boasts three bedrooms, two bathrooms, sleeps eight guests, and includes a fully equipped kitchen, private patio, free Wi-Fi, and access to a fitness centre and parking.
Cozy 1 Bedroom, 1 Min From Irving Park Blue Line, Free Parking - Chicago, IL
9.4 213 reviews
Chicago, IL
05/07 – 10/07
SG$217/nighttotal: SG$1085 (5 )

Cozy 1 Bedroom, 1 Min From Irving Park Blue Line, Free Parking

1 2
apartment , Chicago
This apartment is located in Chicago's Irving Park neighbourhood, a short 7km drive from Wrigley Field and 10km from Lincoln Park Zoo. It has received excellent ratings for location, cleanliness and user experience.
The apartment is a comfortable 28 square metre space with one bathroom. It offers a range of amenities, including free parking, a balcony, a garden, a spa, a tennis court and bicycle rentals.
Comfy 4 Bedroom Apartment In The Center Of Chicago! 15 Mins From Downtown! - Chicago, IL
9.1 70 reviews
Chicago, IL
25/11 – 29/11
SG$228/nighttotal: SG$912 (4 )

Comfy 4 Bedroom Apartment In The Center Of Chicago! 15 Mins From Downtown!

4 4
apartment , Chicago
This four-bedroom flat is located in a diverse area of Chicago, just under 5 kilometres from the expressway and 10 kilometres from Lake Shore Drive, offering easy access to the city centre. It has excellent user, location and cleanliness ratings, making it a popular choice for travellers.
The property has spacious rooms and comfortably sleeps up to eight guests. It is fully equipped with a kitchen, air conditioning, parking, Wi-Fi and other amenities for a comfortable stay.
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