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
18/07 – 23/07
SG$593/nighttotal: SG$2965 (5 )

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 Magnificent Mile Chicago - Chicago, IL
9.2 1379 reviews
Chicago, IL
20/06 – 27/06
SG$510/nighttotal: SG$3570 (7 )

Kasa Magnificent Mile Chicago

1 2
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
12/07 – 01/08
SG$548/nighttotal: SG$10960 (20 )

The Neighborhood Hotel-little Italy

1 1
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
08/07 – 12/07
SG$484/nighttotal: SG$1936 (4 )

Kasa River North Chicago

1 2
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

Designer Oasis - Sauna, Hot Tub, Patios, Game Room - Chicago, IL
9.8 78 reviews
Chicago, IL
01/08 – 08/08
SG$1956/nighttotal: SG$13692 (7 )

Designer Oasis - Sauna, Hot Tub, Patios, Game Room

1 10
apartment , Chicago
This Wicker Park house, in a central location within the neighbourhood, offers easy access to Chicago's shops, restaurants, and nightlife.
Sleeping sixteen guests, the five-bedroom, three-and-a-half-bathroom property boasts three patios, an entertainment basement with air hockey and foosball, a two-car garage, keyless entry, and a fully equipped kitchen including a dishwasher.
Luxury Condo!
30 E Huron St Chicago - Chicago, IL
Chicago, IL
24/08 – 30/09
SG$205/nighttotal: SG$7585 (37 )

Luxury Condo! 30 E Huron St Chicago

1 2
apartment , Chicago
This furnished 1-bedroom flat is situated in a luxury amenity building offering convenient access to Chicago's attractions, with the nearest Tube station 500 meters away and Millennium Park 1.5 kilometers distant.
This abode accommodates up to four guests and includes a fully equipped kitchen with a fridge, microwave, and dishwasher, alongside access to an outdoor swimming pool, fitness centre, and Wi-Fi.
Luxe Loft Vibe 4br/3ba Apt King Suite-11 Minutes From Downtown-families-groups - Chicago, IL
10 3 reviews
Chicago, IL
07/09 – 12/09
SG$707/nighttotal: SG$3535 (5 )

Luxe Loft Vibe 4br/3ba Apt King Suite-11 Minutes From Downtown-families-groups

4 2
apartment , Chicago
This spacious Chicago apartment, located in the Woodlawn neighbourhood, offers easy access to the lakefront, the University of Chicago, the Museum of Science and Industry, and the Obama Presidential Centre.
The 218 square metre property boasts a four-bedroom, three-bathroom layout, sleeping up to eight guests, and includes a fully equipped kitchen, in-unit laundry, and a terrace.
Luxury Penthouse W/ Hot Tub & Amazing Roof Deck - Chicago, IL
9.8 87 reviews
Chicago, IL
17/06 – 21/06
SG$2046/nighttotal: SG$8184 (4 )

Luxury Penthouse W/ Hot Tub & Amazing Roof Deck

1 8
apartment , Chicago
This Wicker Park flat is ideally located one block from the Division El station, offering swift access to Chicago's city centre in approximately 1.6 kilometres.
The three-bedroom, two-bathroom dwelling sleeps eight guests, boasting a rooftop hot tub with Chicago skyline views, a fully equipped kitchen including a dishwasher, and modern amenities such as smart TVs and high-speed internet; outdoor grilling facilities are also available.

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

Victorian Mansion In Garfield Park - Chicago, IL
9.7 50 reviews
Chicago, IL
19/08 – 24/08
SG$442/nighttotal: SG$2210 (5 )

Victorian Mansion In Garfield Park

3 2
house , Chicago
This three-bedroom house is situated in Chicago, just five miles from the city centre and a short distance from the United Center. The property has received excellent ratings for its cleanliness, location, and overall experience, making it a great choice for travellers.
The house provides 139 square metres of space, accommodating up to five guests. It features a fully equipped kitchen, a private patio and garden, air conditioning, and free Wi-Fi, ensuring a comfortable and enjoyable stay.
A Vintage Pink House In The Heart Of Chicago - Chicago, IL
9.9 487 reviews
Chicago, IL
25/07 – 27/07
SG$424/nighttotal: SG$848 (2 )

A Vintage Pink House In The Heart Of Chicago

2 2
apartment , Chicago
This East Village flat, a Victorian pink house with a Walk Score of 97, is situated in a residential area of Chicago, offering easy access to the Division Blue Line.
The two-bedroom, one-bathroom apartment sleeps three, features a Stearns & Foster queen-size bed, a gold glitter clawfoot bathtub, and a smart TV with streaming services, plus a garden and parking.
Mccormick Place City View 2br/2ba With Optional Parking For Up To 8 Guests - Chicago, IL
8.0 2 reviews
Chicago, IL
01/07 – 05/07
SG$588/nighttotal: SG$2352 (4 )

Mccormick Place City View 2br/2ba With Optional Parking For Up To 8 Guests

2 7
apartment , Chicago
This Near South Side Chicago flat is conveniently located a 3.2km walk from State Street and McCormick Place, and within 3.2km of Soldier Field and Lake Michigan.
This 88 square metre, three-bedroom, two-bathroom dwelling sleeps eight guests and boasts a fully equipped kitchen, private patio, free Wi-Fi, fitness centre, and parking.
Private Room Close To Iit, Mccormick Free Parking2 - Chicago, IL
9.6 506 reviews
Chicago, IL
01/08 – 07/08
SG$242/nighttotal: SG$1452 (6 )

Private Room Close To Iit, Mccormick Free Parking2

1 2
apartment , Chicago
This Chicago guesthouse is located in the historic Douglas neighbourhood, within 1.6km of the Green and Red Line stations, offering easy access to the Museum Campus and McCormick Place.
The self-catering apartment features a queen-size bed, a 32-inch smart TV, in-unit laundry facilities (small fee), and shared amenities including a rooftop terrace, accommodating two guests and providing 24/7 host support.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL short term rentals with parking

Sentral Michigan Avenue - Chicago, IL
8.9 3214 reviews
Chicago, IL
13/09 – 14/09
SG$2718/nightfor 1 night

Sentral Michigan Avenue

4 9
hotel , Chicago
Sentral Michigan Avenue is a short walk from Chicago’s downtown area, putting you within easy reach of DePaul University, the Field Museum of Natural History, and the Art Institute of Chicago. This aparthotel has received excellent ratings for its location, cleanliness, and overall experience.
The apartments include a kitchen with modern appliances, a seating area with a TV, and a private bathroom. Enjoy the on-site restaurant, relax in the hot tub, work out at the fitness centre, swim in the indoor pool, or take advantage of the garden, infinity pool, and barbecue facilities.
South Loop 2br Apt Near Soldier Field & Mccormick - Chicago, IL
9.7 153 reviews
Chicago, IL
25/11 – 29/11
SG$317/nighttotal: SG$1268 (4 )

South Loop 2br Apt Near Soldier Field & Mccormick

1 2
apartment , Chicago
This two-bedroom flat is situated in the South Loop district of Chicago, just a short walk from McCormick Place and within easy reach of other attractions. Guests have consistently rated this property excellent for location, cleanliness, and overall experience.
The 88 square metre flat comfortably sleeps up to six guests and features a fully equipped kitchen, two bathrooms, and a modern design. Amenities include a gym, parking (at an additional cost), and fast internet, making this a great choice for families or groups visiting Chicago.
Unique Home In Maywood | 5 Bedroom - Chicago, IL
9.8 21 reviews
Chicago, IL
11/09 – 13/09
SG$785/nighttotal: SG$1570 (2 )

Unique Home In Maywood | 5 Bedroom

1 11
apartment , Melrose Park
This five-bedroom, two-bathroom residence in Maywood offers a tranquil setting adjacent to Silver Creek stream, within a 3.2-kilometre drive of Maywood's dining and grocery amenities, 10.5 kilometres from Thatcher Woods for outdoor pursuits, 20.9 kilometres from Brookfield Zoo, 25.7 kilometres from O'Hare Airport, and 33.8 kilometres from Downtown Chicago.
This newly renovated 1950s home comfortably accommodates up to eleven guests, featuring air conditioning, internet, and a kitchen equipped with a fridge, freezer, microwave, and dishwasher, with on-site parking also provided.
Quiet 1br, Eat-in Kitchen, Close To Midway - Chicago, IL
8.0 14 reviews
Chicago, IL
08/07 – 12/07
SG$265/nighttotal: SG$1060 (4 )

Quiet 1br, Eat-in Kitchen, Close To Midway

1 2
apartment , Chicago
This one-bedroom Chicago apartment, near Midway International Airport, is conveniently located approximately 9.7 to 14.5 kilometres from attractions such as the Museum of Science and Industry, United Centre, and Guaranteed Rate Field.
The 70 square metre self-catering flat sleeps seven guests and offers a fully equipped kitchen, free Wi-Fi, a garden, fitness centre, parking, and access to nearby fishing and hiking opportunities.
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