Completely Remodeled Basement Apt Near The Airport
1 3
apartment , Chicago
This completely remodelled two-bedroom basement flat is situated in North-East Chicago, approximately 6.4 kilometres from O'Hare International Airport and offers easy access to public transport for the city centre. The self-catering apartment, sleeping up to six guests, boasts a well-equipped kitchen, air conditioning, parking, and complimentary toiletries; nearby attractions include the Fashion Outlets of Chicago and the Hippodrome Theatre.
9.9 229 reviews
Chicago, IL
04/09 – 07/09
SG$487/nighttotal: SG$1461 (3 )
Blue Brick Apartment In Bridgeport - Park For Free
1 3
apartment , Chicago
This two-bedroom Chicago flat, situated in a working-class neighbourhood, offers easy access to the city centre – a 24km train journey, 24km by bike, or a 24km drive. The 56-square-metre property boasts a fully equipped kitchen, private patio, on-site parking, and sleeps four guests, with a garden and bar within the building complex.
9.5 312 reviews
Chicago, IL
18/07 – 20/07
SG$197/nighttotal: SG$394 (2 )
Great Location Studio
1 2
apartment , Chicago
This Chicago studio apartment is ideally located in a central neighbourhood, within 0.8-1.6km of Oak Street Beach, the Magnificent Mile, and the Red and Brown Line 'L' train stations, offering easy access to the city's attractions including the Museum of Contemporary Art and Millennium Park. The self-contained apartment, sleeping up to two guests, features a kitchenette with fridge, freezer and microwave, air conditioning, parking, and excellent guest reviews; nearby activities include exploring the John Hancock Center and enjoying the city's iconic architecture.
8.7 75 reviews
Chicago, IL
10/07 – 31/08
SG$216/nighttotal: SG$11232 (52 )
Modern 4 Bedroom Greystone | White Sox
4 1
apartment , Chicago
This Greystone house is situated in a desirable Chicago neighbourhood, less than 1.6km from Guaranteed Rate Field, home of the Chicago White Sox. The four-bedroom property, sleeping up to nine guests, boasts a spacious three-storey layout with granite countertops, stainless steel appliances, and a private garden; free street parking is available.
9.8 24 reviews
Chicago, IL
03/08 – 05/08
SG$164/nighttotal: SG$328 (2 )
Cozy Apartment Near Logan Square/avondale
1 2
apartment , Chicago
This newly renovated garden flat in Chicago offers a peaceful base on a quiet, tree-lined street, just 1.1 kilometres from the Logan Square Blue Line station, providing direct access to the city centre and O'Hare International Airport. This one-bedroom, one-bathroom apartment accommodates up to two guests and includes a microwave, air conditioning, parking, and Wi-Fi, with the option of a queen-size air mattress or a pull-out couch for additional sleeping arrangements.
9.4 138 reviews
Chicago, IL
10/08 – 13/08
SG$407/nighttotal: SG$1221 (3 )
2 Bed Apt W/ Office, Free Parking, Near Wrigley
2 3
apartment , Chicago
This two-bedroom Chicago apartment is situated near Wrigleyville, a 15-minute walk from Wrigley Field, and within a 4.8-8 km radius of Lincoln Park Zoo, Water Tower Place, and the United Centre. The 111 square metre flat offers a fully equipped kitchen, free parking, and amenities including a fireplace and patio, sleeping up to four guests comfortably.
9.5 85 reviews
Chicago, IL
22/06 – 25/06
SG$267/nighttotal: SG$801 (3 )
Family Friendly Duplex/9 Min From Mdw/free Parking
1 7
apartment , Chicago
This spacious Chicago duplex apartment is ideally located, a 14.5km drive from Midway Airport and roughly 32km from Chicago's city centre. The three-bedroom property, sleeping seven guests, boasts a fully equipped kitchen, free on-street parking, a patio, and a cosy porch; self check-in is available after 4pm.
9.8 75 reviews
Chicago, IL
11/07 – 15/07
SG$234/nighttotal: SG$936 (4 )
Luxurious Cozy Boho 10 Min To Downtown Sleeps 5
1 3
apartment , Chicago
This Chicago apartment rental is located in Little Village, a 10-minute drive (approx. 4.8km) from the city centre, 4.8km from Little Italy and Chinatown, and a 15-minute drive (approx. 11.2km) from Millennium Park and Soldier Field. The one-bedroom flat sleeps five guests comfortably, offering a full kitchen, washer/dryer, in-unit entertainment (two smart TVs, Pac-Man arcade game, board games), a mini-patio with grill, and enhanced security features including keyless entry.
9.6 98 reviews
Chicago, IL
01/07 – 31/07
SG$171/nighttotal: SG$5130 (30 )
Top Notch 2 Bedroom Apt. Close To Downtown Chicago
1 2
apartment , Chicago
This Bronzeville Hyde Park flat is situated a short distance from Chicago's city centre, offering easy access to Lake Michigan and sporting venues such as Soldier Field and McCormick Place. The two-bedroom, one-bathroom apartment sleeps four guests and features a fully equipped kitchen with a microwave/grill oven, a 55" TV with 200+ cable channels, and reliable high-speed Wi-Fi.
9.8 131 reviews
Chicago, IL
14/07 – 18/07
SG$748/nighttotal: SG$2992 (4 )
The Executive's Escape (Fitness Center • Sauna)
1 4
apartment , Chicago
This Michigan Avenue apartment offers a prime downtown Chicago location, within walking distance of Millennium Park, Navy Pier, and the Riverwalk. The two-bedroom, two-bathroom flat sleeps six guests and boasts a king and queen bed, pull-out couch, private washer/dryer, Roku, high-speed Wi-Fi, and access to building amenities including a fitness centre, swimming pool, and a cinema.
9.7 38 reviews
Chicago, IL
20/07 – 27/07
SG$312/nighttotal: SG$2184 (7 )
Vibrant 1br Apartment
1 2
apartment , Chicago
This one-bedroom flat in Chicago offers convenient access to popular attractions, dining, and shopping, with a fully equipped kitchen featuring a fridge and microwave, air conditioning, and allowing pets. This accommodation is suitable for two guests and includes essential amenities such as internet and a modern bathroom, with potential for additional screening like a government-issued ID or security deposit.
9.6 341 reviews
Chicago, IL
27/08 – 30/08
SG$525/nighttotal: SG$1575 (3 )
Kasa | Elevate Your Stay, Premium 1bd | Chicago
1 2
apartment , Chicago
This Chicago apartment rental is ideally situated in the downtown area, a stone's throw from Oak Street Beach and a short walk (approximately 0.8 km) from Michigan Avenue and Millennium Park. The one-bedroom, one-bathroom flat offers self-check-in, sleeps three guests, includes a fully equipped kitchen with dishwasher and in-unit laundry, plus high-speed Wi-Fi, a Smart TV, and access to a fitness centre and garden; pets are welcome (with restrictions).
Best Chicago, IL luxury short term rentals
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.
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.
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.
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
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.
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.
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.
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
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.
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.
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.
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
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.
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.
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.
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.