This Lakeview apartment in Chicago is situated a short walk from Wrigley Field and approximately 3km from Lincoln Park Zoo. The 37 square metre flat offers two bedrooms, one bathroom, sleeps six guests, and includes a fully equipped kitchen with dishwasher, in-unit laundry, and free Wi-Fi.
9.5 30 reviews
Chicago, IL
02/07 – 06/07
SG$184/nighttotal: SG$736 (4 )
1st Floor Condo Apartment Close To Midway Airport
1 2
apartment , Chicago
This Chicago apartment, near Midway International Airport and a short drive (approximately 16km) from the city centre, offers convenient access to both airport and downtown attractions. The first-floor flat features a queen-size bed, sofa bed, and two massage chairs, accommodating up to three guests, and includes a fully equipped kitchen, in-unit laundry, high-speed Wi-Fi, and smart TV.
9.4 364 reviews
Chicago, IL
28/06 – 29/06
SG$309/nightfor 1 night
Close2city 3 Bedroom With Private Parking (Mdw)
1 4
apartment , Cicero
This Cicero apartment is conveniently located near Midway Airport and Interstate 55, providing easy access to Chicago. Sleeping up to seven guests, this three-bedroom property boasts a large kitchen with an eight-seat table, private rear parking, and two entrances, alongside self check-in and excellent guest reviews.
9.2 22 reviews
Chicago, IL
25/06 – 26/06
SG$453/nightfor 1 night
Cozy & Furnished 2br Unit
2 1
apartment , Chicago
This Ravenswood flat is situated near Wrigley Field (6.4 km drive) and Lake Michigan (9.7 km drive), with easy access to the Brown Line at Western (0.5 km walk) and Damen (1.3 km walk) stations. The two-bedroom, one-bathroom apartment sleeps four guests and includes Wi-Fi, a fully equipped kitchen with dishwasher, a washer/dryer, and bathroom amenities; nearby attractions include the Merchandise Mart, Willis Tower, and the Field Museum.
10 5 reviews
Chicago, IL
01/01 – 31/12
SG$13/nighttotal: SG$4732 (364 )
Lux River North 1br W/ Gym, W/d, Bbq, Pool, Near Mag Mile, By Blueground
1 2
apartment , Chicago
This one-bedroom flat is ideally located in River North, just a short walk from the Chicago River and a quick drive to Millennium Park and Navy Pier. It has received excellent ratings for location, cleanliness, and overall experience. The apartment features a modern design with a fully equipped kitchen and a spacious living room offering city views. Residents have access to a range of amenities, including a gym, swimming pool, lounge, parking, and a BBQ area, ensuring a comfortable and enjoyable stay.
9.6 49 reviews
Chicago, IL
04/09 – 05/09
SG$370/nightfor 1 night
Friendly Abbey Road Retreat
1 4
apartment , Berwyn
This Beatles-themed flat in Berwyn's Friendly Music Community offers convenient access to the Frank Lloyd Wright Home and Studio and Ernest Hemingway's birthplace, with easy train links to Chicago's Magnificent Mile. The two-bedroom, one-bathroom apartment sleeps six, boasting a fridge, freezer, microwave, air conditioning, garden, parking, and on-site amenities including a bar and coffee lounge; music lessons at the Friendly Music School are also available.
10 198 reviews
Chicago, IL
31/07 – 03/08
SG$677/nighttotal: SG$2031 (3 )
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.
9.8 46 reviews
Chicago, IL
12/07 – 17/07
SG$479/nighttotal: SG$2395 (5 )
Loop 2br W/city Views | Walk To Millennium Park
1 2
apartment , Chicago
This luxury two-bedroom flat is located in a prime downtown Chicago district, offering immediate walking access to Millennium Park, Navy Pier, and Soldier Field, with an 'L' train stop just 100 metres away for city-wide exploration. This accommodation sleeps seven with two queen beds, a pull-out couch, and an air mattress, featuring a private washer/dryer, high-speed Wi-Fi, and access to building amenities including a lounge, business centre, and recreation area.
9.8 144 reviews
Chicago, IL
28/10 – 05/11
SG$266/nighttotal: SG$2128 (8 )
Stylish Avondale 3bed 2 Bath With Parking
1 5
apartment , Chicago
This three-bedroom, two-bathroom Chicago apartment is situated in Avondale, a neighbourhood close to the Blue Line ‘L’ train and easily accessible to Logan Square, Bucktown, and Wicker Park. The 6-guest property boasts a well-equipped kitchen, two televisions, and a large dining table; nearby attractions include numerous bars and restaurants, plus easy access to Chicago's brewing and distilling scene.
10 1 review
Chicago, IL
11/07 – 12/07
SG$397/nightfor 1 night
Downtown Elmhust 5 Min Away King,queen 3twin Beds
2 8
apartment , Elmhurst
This Elmhurst apartment boasts a central location, within walking distance of a grocery store, gym, Starbucks, and restaurants, and minutes from the expressway and Elmhurst's town centre. The two-bedroom, one-bathroom flat sleeps up to 10 guests and offers amenities including a fridge, freezer, microwave, dishwasher, air conditioning, parking, and internet access.
9.7 87 reviews
Chicago, IL
09/07 – 13/07
SG$359/nighttotal: SG$1436 (4 )
Avondale Chicago - 1 Of The World's Coolest Hoods
2 2
apartment , Chicago
This Avondale flat, in a neighbourhood cited as one of the world's coolest, is conveniently located between O'Hare International Airport and Chicago's Loop, offering easy access to public transport and major attractions. The two-bedroom, one-bathroom apartment sleeps four, features an eat-in kitchen with dishwasher and in-unit laundry, and is a short walk from the Sleeping Village music venue.
9.6 9 reviews
Chicago, IL
13/08 – 14/08
SG$1554/nightfor 1 night
Stylish River North Suites: Luxury Living Near Chicagos Best Shopping&nightlife
2 1
apartment , Chicago
This Level River North apartment, a two-bedroom suite offering 93 square metres of space, is situated in the River North district, minutes from the Magnificent Mile and the Loop. The flat boasts two bathrooms, sleeps six guests, includes a fully equipped kitchen, balcony, and access to a swimming pool, sauna, and parking, with nearby water activities such as motor boating on the Chicago River readily available.
Best family friendly Chicago, IL Holiday Apartments and Self Catering Accommodations
Among the 10028 accommodations in Chicago, IL, here are the 4 best family friendly holiday apartments
9.8 10 reviews
Chicago, IL
10/08 – 10/10
SG$342/nighttotal: SG$20862 (61 )
Secluded Lincoln Square / Ravenswood Escape!
1 2
apartment , Chicago
This two-bedroom Chicago flat is ideally situated between Lincoln Square and Ravenswood, an 8-minute walk (approximately 0.64 km) from Lincoln Square's centre. The ground-floor apartment, offering in-unit laundry and private garden access, comfortably sleeps four guests and benefits from nearby free parking (street cleaning restrictions apply) and easy access to public transport.
9.7 116 reviews
Chicago, IL
05/08 – 11/08
SG$690/nighttotal: SG$4140 (6 )
Old Town/gold Coast Masterpiece (+Private Terrace)
1 4
apartment , Chicago
This top-floor apartment in Chicago's Old Town district is located a 5-10 minute walk (0.8-1.6km) from the Red Line and steps from Wells Street's restaurants and entertainment. The two-bedroom, one-bathroom flat sleeps seven guests, boasts a fully equipped kitchen with stainless steel appliances, a private courtyard entrance, and a spacious rooftop deck with 360-degree city views; parking is also available.
10 169 reviews
Chicago, IL
12/10 – 14/10
SG$565/nighttotal: SG$1130 (2 )
Lakeview/lincolnpark 2br/1ba Updated Vintage Apartment In Walkable Neighborhood
2 4
apartment , Chicago
This Lakeview flat is situated less than 1.6km from Wrigley Field and Lake Michigan, offering easy access to Chicago's North Side attractions and public transport. The 93 square metre property comprises two bedrooms, one bathroom, and accommodates up to six guests, boasting a private garden, spa access, and parking, alongside a fully equipped kitchen and family-friendly amenities.
Chicago, IL
01/08 – 31/10
SG$161/nighttotal: SG$14651 (91 )
Blueground | The Loop, Elevator, Nr Willis Tower
1 1
apartment , Chicago
This studio flat is located in Chicago's Loop district, offering convenient access to the city's attractions. This modern studio apartment accommodates two guests and includes a fully equipped kitchen, in-apartment laundry, a smart TV, and premium wireless speaker, with flexible lease options available.
Best Chicago, IL holiday apartments with a balcony
10 7 reviews
Chicago, IL
17/10 – 23/10
SG$172/nighttotal: SG$1032 (6 )
Tranquil Library Near Brown Line 2 Bed 1 Bath Vintage Private Unit @ Solar Lodge
2 2
apartment , Chicago
This 2-bedroom flat in Chicago's Albany Park district offers convenient access, being a 720-metre walk to Kedzie and a 800-metre walk to Kimball subway stations, with Copernicus Center and Portage Park a 5-minute drive away. This accommodation for four guests includes a microwave, oven, stovetop, air conditioning, Wi-Fi, a television, and bathroom amenities, with proximity to attractions such as Michigan Avenue, Navy Pier, Lake Michigan, Millennium Park, Wrigley Field, and United Center.
10 1 review
Chicago, IL
24/07 – 25/07
SG$675/nightfor 1 night
Sunny 2-bdrm Apt In-unit Lndry & Balcony Near Nu Hsptls
2 2
apartment , Evanston
This South Evanston flat offers convenient access to Lake Michigan, just a 4-minute drive away, and Wrigley Field, an 11-minute drive from your doorstep. This 93 square metre residence accommodates up to four guests with two bedrooms and one bathroom, featuring on-site parking, a fully equipped kitchen, complimentary Wi-Fi, and an in-unit washer and dryer.
9.6 9 reviews
Chicago, IL
25/06 – 26/06
SG$1054/nightfor 1 night
River North Private Deck With In And Out Parking
3 2
apartment , Chicago
This spacious Chicago city centre flat is ideally located within walking distance of the Chicago Theatre and Art Institute, a short drive from Millennium Park and Navy Pier. The 151 square metre three-bedroom property sleeps nine guests, boasting a private balcony, free parking nearby, and access to building amenities including a rooftop terrace, gym, and streaming services; a portable cot is also available.
9.0 2 reviews
Chicago, IL
23/06 – 25/06
SG$715/nighttotal: SG$1430 (2 )
Inspiring Grotto Sleeps 10-20 Free Tv & Parking
4 10
apartment , Chicago
This spacious Chicago apartment, located near Fullerton Beach (a 1.9km walk), Wrigley Field (1.9km), and Lincoln Park Zoo (2.7km), offers easy access to popular attractions. The 186 square metre property boasts four bedrooms, two bathrooms, sleeps 10-20 guests, and includes a private garden, tennis court, free parking, and an electric vehicle charging point.
Frequently asked questions about apartment rentals in Chicago, IL
What are the must-see attractions for a 2 days stay in Chicago, IL?
For a short trip, you'll want to see the iconic Willis Tower (formerly Sears Tower) for incredible views of the city, explore the Art Institute of Chicago with its impressive collection, and walk along the scenic Navy Pier with its Ferris wheel and shops.
Which neighborhoods in Chicago, IL are best for renting an apartment?
Lincoln Park is a popular choice for its parks, restaurants, and proximity to the lakefront. Wicker Park and Bucktown are trendy areas with cool shops and nightlife. For a more affordable option, check out Logan Square or Lakeview.
What are the best apartments with a pool in Chicago, IL?
What are the top cultural and historical sites in Chicago, IL?
The Field Museum is home to Sue the T-Rex and other fascinating exhibits. The Museum of Science and Industry offers interactive displays and the historic U-505 submarine. For architecture buffs, the Chicago Cultural Center is a must-visit, with its stunning Tiffany stained-glass dome.
What are the best apartments with a jacuzzi in Chicago, IL?
Chicago is known for its world-class architecture, particularly its skyscrapers like the Willis Tower and the John Hancock Center. It's also famous for its deep-dish pizza, its vibrant arts and culture scene, and its beautiful lakefront.
What are the best apartments for families and kids in Chicago, IL?
Where can you find the best local markets and street food in Chicago, IL?
The Maxwell Street Market is a lively open-air market with a mix of food stalls and vendors. The Wicker Park Farmers Market offers fresh produce and local crafts. For street food, head to Chinatown for dim sum and other Asian specialties.
What are the best pet friendly apartments in Chicago, IL?
How is the public transportation system in Chicago, IL?
Chicago has an extensive public transportation system, with the 'L' train, buses, and commuter trains. It's a reliable and affordable way to get around the city, especially for longer distances. You can purchase a Ventra card for convenient fare payments.
What are the best apartments with parking in Chicago, IL?
Which seasonal events or festivals should apartment renters look forward to in Chicago, IL?
Chicago is alive with festivals throughout the year. In the summer, the Taste of Chicago food festival is a must-do. In the winter, the Christkindlmarket offers a festive atmosphere with German-inspired food and crafts. And the Chicago Blues Festival in June is a celebration of music.
What amenities are typically included in apartments in Chicago, IL?
Apartments in Chicago usually include central heating and air conditioning. Many also have in-building laundry facilities, and some may offer additional features like a gym, a rooftop deck, or a swimming pool.
What leisure activities are available for relaxation in Chicago, IL?
The city offers plenty of opportunities for relaxation. Stroll along the lakefront path, enjoy a picnic in Millennium Park, or take a boat tour on Lake Michigan. For a more active experience, rent a Divvy bike and explore the city's bike paths.
Destinations nearby
Best Chicago, IL holiday apartments with parking
9.8 28 reviews
Chicago, IL
19/07 – 31/07
SG$556/nighttotal: SG$6672 (12 )
Enjoy Our 2bd 2bd Condo With Parking In Tri Taylor
1 3
apartment , Chicago
This Chicago apartment rental, located in the Tri-Taylor neighbourhood, is minutes from the United Centre and the Illinois Medical District. The two-bedroom, two-bathroom flat offers a fully equipped kitchen, rooftop access with Chicago skyline views, and accommodates up to four guests.
10 4 reviews
Chicago, IL
03/07 – 12/07
SG$378/nighttotal: SG$3402 (9 )
Chicago 3br Oasis Near Downtown & United Center
3 7
apartment , Chicago
This Chicago West Side flat offers convenient access to the United Centre (12.9 kilometres), Rush University Medical Centre (12.9 kilometres), and Garfield Park Conservatory (16.1 kilometres), with quick access to UIC/Illinois Medical District and a short drive to downtown. This family-friendly apartment boasts three bedrooms, two bathrooms, a fully equipped kitchen, and a private balcony, accommodating up to eight guests with parking and internet provided.
10 1 review
Chicago, IL
09/10 – 12/10
SG$745/nighttotal: SG$2235 (3 )
Large Space With Garage
4 2
apartment , Chicago
This two-bedroom apartment is located in West Pullman, a neighbourhood in Calumet Park, around 32 kilometres south of downtown Chicago and a short drive from Lake Michigan. The area is quiet and residential, offering a peaceful retreat from the hustle and bustle of the city. This comfortable home sleeps up to four guests and has a well-equipped kitchen, a relaxing living room, and a private balcony. You can enjoy modern amenities like air conditioning, a jacuzzi, and free parking, making it an ideal base for exploring Chicago.
8.0 1 review
Chicago, IL
28/06 – 29/06
SG$545/nightfor 1 night
Mins To Dt & Frank Lloyd Wright
1 1
apartment , Oak Park
This one-bedroom flat in Oak Park offers a prime location, just 400 metres from the Frank Lloyd Wright Home and Studio and a 10-minute walk from Downtown Oak Park, with immediate access to popular eateries. This pet-friendly apartment accommodates up to four guests, featuring a kitchen with a fridge and microwave, air conditioning, a garden, and parking, with flexible check-in/out options available.
Neighborhoods and points of interest in Chicago, IL
Best Chicago, IL holiday apartments with air conditioning
9.8 375 reviews
Chicago, IL
12/10 – 14/10
SG$299/nighttotal: SG$598 (2 )
Tree Top 2nd Floor 3 Bedrm Apt
3 4
apartment , Chicago
This three-bedroom flat is located just 800 metres from the Blue Line train, providing easy access to downtown Chicago and O'Hare Airport, and sits in a neighbourhood with a variety of bars and restaurants. The apartment has received excellent ratings for its location, cleanliness, and overall experience. The flat is spacious and comfortably accommodates up to six guests. Amenities include free Wi-Fi, a fully equipped kitchen, a garden, and a sun porch with a view of the backyard, along with free on-street parking and access to a laundry room.
9.1 32 reviews
Chicago, IL
12/09 – 18/09
SG$269/nighttotal: SG$1614 (6 )
Modern Oasis | 4 Beds | Sleeps 7 | Mins To Loop
1 7
apartment , Chicago
This two-bedroom flat in Chicago offers excellent proximity to major attractions, situated just a few minutes from the city centre and The Loop, with convenient access to Chinatown and McCormick Place, placing it within 2 kilometres of Museum Campus and Union Station. This residence accommodates up to seven guests with two queen beds, a further queen bed, and a sofa bed, boasting a fully equipped kitchen, in-unit laundry, dedicated office space with Wi-Fi, and multiple Smart TVs, all within a property offering air conditioning and parking.
9.6 98 reviews
Chicago, IL
30/07 – 02/08
SG$729/nighttotal: SG$2187 (3 )
Two Bedroom Chicago Unit
1 3
apartment , Chicago
This two-bedroom flat is located near Clark Street, approximately 3.2 kilometres from downtown Chicago, with public transport options readily available. This well-appointed flat accommodates up to four guests and features air conditioning, parking, a microwave oven, and is ideal for exploring Chicago's attractions.
This four-bedroom, two-bathroom apartment is located in Chicago's Lincoln Square neighbourhood, 0.5 kilometres from Lincoln Avenue's restaurants and bars. The two-storey property offers a spacious open-plan living area, sleeps twelve guests, includes a fully equipped kitchen with dishwasher, and boasts a private patio (7 am–9 pm), plus designated parking and pet-friendly options (one pet, £100 fee).
