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
13/09 – 16/09
SG$582/nighttotal: SG$1746 (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 Magnificent Mile Chicago - Chicago, IL
9.2 1381 reviews
Chicago, IL
14/07 – 18/07
SG$973/nighttotal: SG$3892 (4 )

Kasa Magnificent Mile Chicago

2 5
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 South Loop Chicago - Chicago, IL
9.4 3083 reviews
Chicago, IL
01/01 – 31/01
SG$444/nighttotal: SG$13320 (30 )

Kasa South Loop Chicago

2 6
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 River North Chicago - Chicago, IL
9.5 439 reviews
Chicago, IL
01/07 – 05/07
SG$1108/nighttotal: SG$4432 (4 )

Kasa River North Chicago

3 5
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

Sentral Premium 2br Apt South Loop Chicago - Chicago, IL
9.4 353 reviews
Chicago, IL
09/08 – 11/08
SG$647/nighttotal: SG$1294 (2 )

Sentral Premium 2br Apt South Loop Chicago

2 4
apartment , Chicago
This apartment is situated in the Grant Park neighbourhood, just a short walk from Millennium Park and the Art Institute of Chicago, offering easy access to the city's cultural highlights. The apartment enjoys excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The apartment features two bedrooms and two bathrooms, comfortably accommodating up to four guests. Guests can enjoy a range of amenities, including a swimming pool, jacuzzi, fitness centre, and on-site services such as dry cleaning and a bistro.
Business Leisure Smoke Ok 3br Suite Near Mccormick - Chicago, IL
Chicago, IL
10/09 – 14/09
SG$543/nighttotal: SG$2172 (4 )

Business Leisure Smoke Ok 3br Suite Near Mccormick

3 2
apartment , Chicago
This 3-bedroom flat in Chicago is located within 3.2 kilometres of DePaul University, 2.7 kilometres of Grant Park, and 3 kilometres of the Art Institute of Chicago, with a private entrance and 13 guest capacity.
This accommodation offers air conditioning, Wi-Fi, a kitchen with a fridge, microwave oven, and dishwasher, two bathrooms (one with a hot tub), and is situated 13 kilometres from Midway International Airport.
Vintage Chicago Gem: The Rockwell Retreat\n - Chicago, IL
Chicago, IL
23/06 – 25/07
SG$4187/nighttotal: SG$133984 (32 )

Vintage Chicago Gem: The Rockwell Retreat\n

3 1
apartment , Chicago
This Chicago apartment is located in the West Ridge neighbourhood, just 3 kilometres from Lake Michigan and 4 kilometres from Lincoln Park, offering a peaceful residential setting close to the city's attractions. The apartment is ideal for a solo traveller, featuring three bedrooms and two bathrooms. The apartment offers a fully equipped kitchen, a jacuzzi, internet access, and a washing machine and dryer, perfect for a comfortable and convenient stay.
Spacious 3br 2ba Haven City Views Steps To Magmile - Chicago, IL
9.3 3 reviews
Chicago, IL
24/06 – 28/06
SG$1687/nighttotal: SG$6748 (4 )

Spacious 3br 2ba Haven City Views Steps To Magmile

3 5
apartment , Chicago
This spacious three-bedroom flat is located in Chicago's Loop district, offering skyline views and a 15-minute walk to Millennium Park, with Navy Pier a 20-minute walk away. Guests can enjoy a fully-equipped kitchen, an indoor-outdoor pool, a fitness centre, and a 24-hour doorman, accommodating up to seven people with three queen-sized beds and a rollaway.

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

Downtown 9bd - Sleep 18 - (4 Units, Same Floor) - Chicago, IL
Chicago, IL
21/07 – 04/08
SG$4835/nighttotal: SG$67690 (14 )

Downtown 9bd - Sleep 18 - (4 Units, Same Floor)

9 6
apartment , Chicago
This spacious nine-bedroom flat is located in downtown Chicago, a 1.26-kilometre walk from the Field Museum of Natural History and a 0.9-kilometre walk from Grant Park, placing it near the Art Institute of Chicago and the Chicago Symphony Orchestra.
This apartment offers a generous 264 square metres of living space, accommodating up to 30 guests with five bathrooms, a fully equipped kitchen, air conditioning, free WiFi, and a fitness centre, making it suitable for large groups and families.
Welcoming 3-bedroom House In Vibrant Chicago - Chicago, IL
Chicago, IL
27/06 – 04/07
SG$1066/nighttotal: SG$7462 (7 )

Welcoming 3-bedroom House In Vibrant Chicago

3 2
apartment , Chicago
This Ukrainian Village flat, situated in Chicago's West Town district, is a short 800-metre walk to the United Centre and offers convenient access to downtown attractions, Millennium Park, and Lake Michigan.
This three-bedroom, two-bathroom apartment accommodates up to eight guests, featuring a kitchen with a fridge, microwave, and dishwasher, air conditioning, Wi-Fi, and a patio, with free street parking available.
Floresitas Oasis, Your Home In Chicago - Chicago, IL
9.9 85 reviews
Chicago, IL
25/06 – 28/06
SG$322/nighttotal: SG$966 (3 )

Floresitas Oasis, Your Home In Chicago

1 2
apartment , Chicago
This Pilsen flat is conveniently located in Chicago, within an 8km radius of the city centre, McCormick Place, and various major sporting venues, including the United Center and Soldier Field, and 2km from the National Museum of Mexican Art.
Sleeping up to six guests in three bedrooms with a king, queen, double and single bed, this family-friendly Chicago apartment boasts two bathrooms, a fully equipped kitchen including a dishwasher, air conditioning, a garden, parking, and excellent guest reviews.
* Extended Stay* Oak Lawn Fhs Rental - Chicago, IL
Chicago, IL
24/07 – 27/07
SG$1027/nighttotal: SG$3081 (3 )

* Extended Stay* Oak Lawn Fhs Rental

1 14
apartment , Oak Lawn
This spacious four-bedroom apartment is situated in Oak Lawn, just a short distance from Midway Airport and the suburbs of Tinley Park and Orland Park. It offers a convenient location for travellers exploring the area.
The apartment is ideal for families or groups of friends, comfortably accommodating up to 14 guests. It is fully equipped with a range of amenities including a well-stocked kitchen, entertainment options like an arcade cabinet, pool table, and board games, as well as a garden and parking.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL short term rentals with parking

Group-friendly 6br Luxury Suite In Prime South Loop Location With Optional Parking And Gym Access Near Mccormick Place, Soldier Field And Grant Park - Chicago, IL
10 1 review
Chicago, IL
07/08 – 09/08
SG$1855/nighttotal: SG$3710 (2 )

Group-friendly 6br Luxury Suite In Prime South Loop Location With Optional Parking And Gym Access Near Mccormick Place, Soldier Field And Grant Park

6 12
apartment , Chicago
This luxurious Chicago apartment, near the Museum Campus, is situated 2.4 kilometres from the Field Museum and under 3.2 kilometres from the Art Institute of Chicago.
The 253-square-metre property boasts six bedrooms, three bathrooms, sleeps up to twelve guests, and includes a fully equipped kitchen, fitness centre, garden, parking, and free Wi-Fi.
Luxe 2br Unit With Skyline View South Loop Near Mccormick Place & Soldier Field - Chicago, IL
Chicago, IL
03/07 – 11/07
SG$475/nighttotal: SG$3800 (8 )

Luxe 2br Unit With Skyline View South Loop Near Mccormick Place & Soldier Field

2 8
apartment , Chicago
This Near South Side Chicago flat is located a 9-minute walk from McCormick Place, with easy access to Soldier Field (5 minutes by Uber), the Museum Campus (7 minutes by Uber), and the city centre (8 minutes by Uber).
This 74-square-metre (797 sq ft) two-bedroom, two-bathroom apartment sleeps eight guests comfortably, offering a fully equipped kitchen, on-site gym, 24/7 security, and EV charging stations; optional parking costs £24 per day.
53 \/ 54ο όροφο Magmile ρετιρέ - θεα, τζάκι, γυμναστήριο, μπαλκόνι - Chicago, IL
10 213 reviews
Chicago, IL
21/07 – 04/08
SG$1820/nighttotal: SG$25480 (14 )

53 \/ 54ο όροφο Magmile ρετιρέ - θεα, τζάκι, γυμναστήριο, μπαλκόνι

2 6
aparthotel , Chicago
This aparthotel is located in Chicago's River North District, just a short walk from North Michigan Avenue and offering stunning views of Lake Michigan. It consistently receives excellent reviews from guests, praising its luxurious amenities and prime location.
The spacious apartment features two bedrooms, three bathrooms, and a generous 215 square metres of living space, comfortably accommodating up to eight guests. This modern apartment offers a fully equipped kitchen, a fireplace, a private terrace, and access to a swimming pool, Jacuzzi, sauna, and spa, ensuring a comfortable and enjoyable stay.
Lovely 5bd|3br|parking |Sleeps 16|andersonville - Chicago, IL
10 79 reviews
Chicago, IL
05/07 – 11/07
SG$1051/nighttotal: SG$6306 (6 )

Lovely 5bd|3br|parking |Sleeps 16|andersonville

1 8
apartment , Chicago
This spacious home is located in the Uptown/Andersonville neighbourhood of Chicago, just a short walk (under 4 km) from popular attractions like the Green Mill, Aragon Ballroom, and Riviera Theatre. The apartment has received excellent reviews for its location, cleanliness, and overall experience.
The property offers 5 bedrooms and 3 bathrooms, comfortably accommodating up to 14 guests. It is equipped with modern amenities including a fully equipped kitchen, laundry facilities, a workspace, and a garden, making it ideal for families or groups of friends.
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