Chic Modern Loft Near United Center, Uic/imd & Downtown W/ Parking
2 8
apartment , Chicago
This pet-friendly Chicago apartment, located in the Near West Side, is a two-minute drive from the United Centre and five minutes from the Willis Tower, offering easy access to the Western subway station. The 147 square metre condo features two bedrooms, two bathrooms, and sleeps up to ten guests, boasting amenities including a garden, terrace, parking, and in-unit laundry facilities, with nearby kayaking and cycling trails.
10 198 reviews
Chicago, IL
03/10 – 09/10
SG$511/nighttotal: SG$3066 (6 )
New Luxury Condo With Patio Deck
1 2
apartment , Chicago
This apartment is located in West Town, a neighbourhood in Chicago, within easy reach of Navy Pier and Michigan Avenue. It has excellent user ratings and is a great choice for travellers looking for a comfortable and convenient stay. The property has one bedroom and two bathrooms, comfortably accommodating up to five guests. It offers a range of amenities, including a fully equipped kitchen, a private patio, a Jacuzzi, and secure parking, as well as access to nearby water activities like kayaking and motor boating.
10 214 reviews
Chicago, IL
12/09 – 15/09
SG$879/nighttotal: SG$2637 (3 )
New Luxury Penthouse Condo
2 7
apartment , Chicago
This penthouse apartment is situated in West Town, a lively neighbourhood just a few kilometres from popular attractions like Navy Pier, Millennium Park, and Wrigley Field. It has received excellent reviews from previous guests. The apartment comfortably accommodates up to nine guests in its two bedrooms and three bathrooms. It features a well-equipped kitchen, a rooftop terrace with stunning city views, and a spa-like bathroom with a jacuzzi.
9.2 614 reviews
Chicago, IL
01/07 – 03/07
SG$109/nighttotal: SG$218 (2 )
Comfortable Room Five Min Walk To Blue Line/ Rm 3
1 1
apartment , Chicago
This Irving Park guesthouse is a five-minute walk (0.8 km) from the Blue Line 'L' train and Kennedy Expressway, offering easy access to O'Hare International Airport, Chicago's city centre, Wrigleyville, and Logan Square/Wicker Park. The self-contained unit features one bedroom, two bathrooms, sleeps two guests, and includes a fully equipped kitchen with fridge, freezer, microwave, and dishwasher, plus shared amenities such as a living room with games.
9.7 115 reviews
Chicago, IL
25/06 – 26/06
SG$331/nightfor 1 night
Private Apt Near To Food/shops/highway/garage Park
1 3
apartment , Berwyn
This Berwyn apartment is conveniently located near Berwyn's shopping mall, Portillo's, and Starbucks, a 7-minute (approximately 11.2km) drive from Berwyn town centre via the highway. This two-bedroom flat sleeps four, features a king and queen-size bed, a garage parking space, and includes a fridge and microwave; guests can enjoy easy access to local eateries and shopping.
9.7 47 reviews
Chicago, IL
03/07 – 09/07
SG$473/nighttotal: SG$2838 (6 )
Bronzeville Tribe Palace Loft
1 5
apartment , Chicago
This Bronzeville apartment offers three bedrooms and two bathrooms, sleeping eight guests, and is situated in a historic Chicago neighbourhood, within 1.6km of McCormick Place and under 8km from the city centre. The self-catering property features a fully equipped kitchen with complimentary breakfast provisions, four 4K smart TVs, a shared garden, and on-site parking, alongside access to a fitness centre.
10 22 reviews
Chicago, IL
18/06 – 20/06
SG$327/nighttotal: SG$654 (2 )
Roomy And Comfortable Apartment With Everything Un
1 2
apartment , Chicago
This Hyde Park apartment is conveniently located near the University of Chicago Hospital and School, within easy reach of the Museum of Science and Industry and Midway Plaisance park. The two-bedroom, one-bathroom flat sleeps five, offering a fully equipped kitchen, air conditioning, internet access, and is suitable for both short and long-term lets, making it perfect for students, medical professionals, or tourists visiting Chicago.
Chicago, IL
19/06 – 21/06
SG$1065/nighttotal: SG$2130 (2 )
2br W/ Workspace - Coffee Bar - Near Transit
2 4
apartment , Chicago
This two-bedroom flat in Chicago's Belmont Cragin district offers convenient access to Millennium Park and Lake Michigan, located approximately 8.5 kilometres away, and is within easy reach of the Chicago Theatre and the Art Institute of Chicago. This pet-friendly apartment accommodates up to five guests and features a fully equipped kitchen, a living area with a 65-inch Smart TV, and shared outdoor space with a grill, with family-friendly amenities and on-site laundry facilities available.
10 81 reviews
Chicago, IL
03/09 – 07/09
SG$824/nighttotal: SG$3296 (4 )
Lovely 3/2.5 Duplex In Wicker Park Area
1 5
apartment , Chicago
This three-bedroom, two-bathroom duplex apartment is situated in a quiet West Loop neighbourhood, approximately 3.2 kilometres from The Loop, Millennium Park, and Michigan Avenue. The 3-bedroom Chicago apartment offers a spacious open-plan layout, sleeping up to seven guests and boasting two patios, a family room with fireplace and wet bar, secured parking, and proximity to the Blue Line and Division Street's shops and restaurants.
9.8 12 reviews
Chicago, IL
14/07 – 18/07
SG$589/nighttotal: SG$2356 (4 )
Spacious 3bd/3ba Apt In West Town - Next To Kasama
3 5
apartment , Chicago
This modern loft flat in Chicago's West Town district offers excellent access to downtown attractions, the Medical District, and the West Loop, being just a short drive from the United Center and Millennium Park. This spacious 3-bedroom, 3-bathroom abode accommodates up to six guests, featuring a fully equipped kitchen with stainless steel appliances, central air conditioning, complimentary high-speed Wi-Fi, and an in-unit washer and dryer.
9.6 579 reviews
Chicago, IL
28/06 – 01/07
SG$189/nighttotal: SG$567 (3 )
Relaxed Bucktown/wicker Park 1b Apt
1 2
apartment , Chicago
This Bucktown/Wicker Park flat is a five-minute walk (0.8 km) from the entertainment district and four blocks (0.4 km) from the CTA train, offering easy access to Chicago's public transport. The self-contained apartment sleeps three, features a king-sized bed, Arhaus sectional sofa, a fully stocked kitchenette, 60' HD SmartTV with premium channels, and access to shared laundry facilities and outdoor space.
9.5 1410 reviews
Chicago, IL
16/09 – 21/09
SG$209/nighttotal: SG$1045 (5 )
Dapper Uptown Studio Near The Lake
1 2
apartment , Chicago
This Uptown Chicago studio apartment is situated just 0.16 km from the Wilson Red Line station, providing easy access to Wrigley Field and Chicago's city centre. The self-contained apartment, sleeping two guests, features a queen-sized bed, in-unit laundry, a fully equipped kitchen including fridge-freezer and microwave, and a shared fitness centre and garden with BBQ.
Best Chicago, IL luxury short term rentals
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.
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.
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.
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
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.
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.
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.
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
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.
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.
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.
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
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.
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.
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.
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.