This Uptown Chicago flat, located two blocks from the Aragon Ballroom, Riviera Theatre, and Green Mill Cocktail Lounge, and a 2.4 kilometre walk from Lake Michigan, offers easy access to the CTA Red Line. The four-bedroom, 1.5-bathroom property, sleeping up to eight guests, includes a kitchen with fridge, freezer, microwave, and dishwasher, plus air conditioning, parking, and internet access; nearby activities include exploring Lake Michigan and visiting Wrigley Field.
9.8 326 reviews
Chicago, IL
09/07 – 13/07
SG$328/nighttotal: SG$1312 (4 )
Logan Square Modern Vintage Garden
2 2
apartment , Chicago
This ground-floor flat is situated in Logan Square, Chicago, offering easy access to local amenities and convenient proximity to Chicago's attractions. The two-bedroom, one-bathroom apartment sleeps three guests and features a newly renovated kitchen and bathroom, a shared backyard with a Weber grill, free on-street parking (permit provided), and shared laundry facilities and WiFi.
9.7 22 reviews
Chicago, IL
05/07 – 11/07
SG$787/nighttotal: SG$4722 (6 )
The Cubs Dugout | 2 Level Retreat
4 8
apartment , Chicago
This four-bedroom, two-bathroom flat is situated in Chicago's Wrigleyville district, merely steps from the historic Wrigley Field, offering excellent access to the city's entertainment and transit networks, with the CTA 'El' train just metres away for convenient journeys to downtown attractions such as Millennium Park and the Magnificent Mile. This spacious accommodation for up to nine guests boasts a private patio, a fully equipped kitchen with a fridge, microwave oven, and dishwasher, complimentary high-speed Wi-Fi, and entertainment options including a 70-inch Smart TV and a Golden Tee arcade game, all within a short distance of popular Wrigleyville dining and drinking establishments.
9.9 77 reviews
Chicago, IL
14/07 – 21/07
SG$312/nighttotal: SG$2184 (7 )
The Modern Woodlawn 2 Bed 2 Bath
1 2
apartment , Chicago
This Woodlawn flat is ideally situated within 1.6km of the University of Chicago and under 3.2km from Jackson Park and the forthcoming Obama Presidential Centre. The two-bedroom, two-bathroom apartment sleeps four, boasting a fully equipped kitchen (fridge, freezer, microwave, dishwasher), air conditioning, a garden, parking, and excellent guest reviews; nearby attractions include the Museum of Science and Industry and South Shore Cultural Centre.
9.9 107 reviews
Chicago, IL
30/06 – 05/07
SG$1083/nighttotal: SG$5415 (5 )
Lux 5br Near Downtown | Rooftop +Garage + Spa Bath
1 10
apartment , Chicago
This luxurious four-storey house is located in Humboldt Park, Chicago, approximately 8 kilometres from the city centre. The 370 sqm property boasts five ensuite bedrooms, sleeping up to 16 guests, and features a chef's kitchen, rooftop deck with Chicago skyline views, a games room, and ample outdoor space.
9.9 113 reviews
Chicago, IL
17/09 – 21/09
SG$199/nighttotal: SG$796 (4 )
The Colorful Little Apartment
1 2
apartment , Chicago
This Logan Square garden flat is situated approximately 2.4km from the 606 Trail and 4km from the Logan Square Farmers' Market, offering easy access to local amenities and public transport. The newly renovated one-bedroom apartment sleeps four, featuring a full kitchen with appliances, in-unit laundry, a dedicated workspace, and two exits for enhanced safety; guests can enjoy nearby restaurants and boutiques.
9.4 16 reviews
Chicago, IL
31/07 – 03/08
SG$1833/nighttotal: SG$5499 (3 )
*Comfortable & Spacious Home Close To Downtown*
4 8
apartment , Chicago
This apartment is located in West Town, a neighbourhood in Chicago, just a few blocks from Humboldt Park and within walking distance of restaurants, cafes, and bars. It has received excellent user ratings, making it a popular choice for travellers. The apartment has four bedrooms and three bathrooms, comfortably accommodating up to eight guests. Amenities include a fully equipped kitchen, in-unit laundry, air conditioning, and access to a spa, parking, and the internet.
9.6 551 reviews
Chicago, IL
17/07 – 19/07
SG$411/nighttotal: SG$822 (2 )
Cozy Apartment With Free On-site Parking
1 4
apartment , Chicago
This three-bedroom Chicago apartment is situated two blocks (approximately 0.32 km) from the Brown Line, providing easy access to the city centre and other neighbourhoods. The spacious flat offers free on-site parking, laundry facilities, an outdoor seating area, and sleeps five guests comfortably, with all essential amenities included.
9.4 19 reviews
Chicago, IL
24/07 – 26/07
SG$469/nighttotal: SG$938 (2 )
Lovely 2 Bedroom Apartment
1 5
apartment , Chicago
This two-bedroom Chicago apartment, ideally located for exploring the city, is approximately 24km from O'Hare International Airport and Downtown Chicago. The property sleeps six guests and boasts a fully equipped kitchen with fridge, freezer, microwave, and dishwasher, plus air conditioning, a garden, parking, and excellent guest reviews.
9.7 869 reviews
Chicago, IL
28/06 – 28/07
SG$375/nighttotal: SG$11250 (30 )
Chi-town Comfort | 1pbr | Bucktown | Wicker Pk
1 4
apartment , Chicago
This Chicago guesthouse is situated in Wicker Park, offering easy access to Chicago's public transport network via a nearby train station. The three-bedroom apartment, sleeping up to six guests, features a fully equipped kitchen, including fridge, freezer and microwave, plus a garden and on-site parking.
Chicago, IL
04/07 – 16/08
SG$183/nighttotal: SG$7869 (43 )
Walk To Train & Bus: Updated Chicago Apartment
2 1
apartment , Chicago
This two-bedroom Chicago apartment is located in the Ashburn neighbourhood, approximately 8 kilometres from Midway International Airport and 14-15 kilometres from the city centre, offering easy access to Lake Michigan (14.5km) and the Illinois Medical District (16km). The 130 square metre self-catering flat features a well-equipped kitchen, a balcony, and parking, comfortably sleeping four guests and situated near Pete's Fresh Market and The Original Rainbow Cone.
9.6 152 reviews
Chicago, IL
05/09 – 10/09
SG$1404/nighttotal: SG$7020 (5 )
Take The Whole Crew Out To The Ballgame! Four Bedrooms And Only 1 Mile From Wrigley By Allset Turnover
4 8
apartment , Chicago
This Chicago apartment is located in the Lakeview neighbourhood, just a short walk from the lively Southport Corridor and a mile from Wrigley Field. It has consistently received excellent ratings for cleanliness, location, and user experience. This four-bedroom property is ideal for large groups, accommodating up to eight guests comfortably within its 223 square metres of space. The apartment is fully equipped with modern amenities, including a well-stocked kitchen, air conditioning, and high-speed internet, making it a perfect base for exploring the city.
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
10 30 reviews
Chicago, IL
28/06 – 28/07
SG$284/nighttotal: SG$8520 (30 )
Two Bedroom - Tranquil Retreat
1 4
apartment , Chicago
This Logan Square flat, in Chicago, offers convenient access to the city's attractions and is ideally situated near the trendy shops and restaurants of the neighbourhood. The two-bedroom, one-bathroom apartment sleeps four guests and features a fully equipped kitchen, shared laundry facilities with laundry pods, and designated parking; a combined shower/bathtub is in the modern bathroom.
9.8 195 reviews
Chicago, IL
28/07 – 31/07
SG$834/nighttotal: SG$2502 (3 )
Boho House | Chic, 1903 Chicago Workers Cottage
1 7
apartment , Chicago
This three-bedroom Chicago cottage, sleeping eight, is situated in a neighbourhood near popular bars and restaurants, approximately 16km from O'Hare International Airport and 8km from Chicago's city centre. The property boasts a redesigned kitchen with stainless steel appliances, a private fenced backyard with a fire pit and deck, high-speed WiFi (800+ Mbps), and secure parking for two cars; wellness services are also available nearby.
Chicago, IL
14/08 – 16/08
SG$1148/nighttotal: SG$2296 (2 )
Chicago 4br 3ba South Getaway Near Mccormick Place
4 9
apartment , Chicago
This four-bedroom flat is situated in Chicago, 2.6 kilometres from Guaranteed Rate Field and 3.2 kilometres from the Field Museum of Natural History, with convenient access to McCormick Place. This family-friendly residence offers 74 square metres of living space, accommodating up to 19 guests with four bedrooms, three bathrooms, a full kitchen including a dishwasher, and on-site parking, all accessible via a lift.
This renovated flat is located in a peaceful, family-friendly neighbourhood in northwest Chicago, just a short distance from downtown attractions like Navy Pier and Michigan Avenue. The property enjoys excellent user ratings and is a popular choice for travellers seeking a comfortable and convenient base for exploring the city. The three-bedroom apartment spans 93 square metres and can comfortably accommodate up to 10 guests. A range of amenities are provided, including free Wi-Fi, a well-equipped kitchen, a Jacuzzi, a garden, and a spa, ensuring a relaxing and enjoyable stay.
Best Chicago, IL holiday apartments with a balcony
9.5 998 reviews
Chicago, IL
11/10 – 17/10
SG$5362/nighttotal: SG$32172 (6 )
Sleep 25 - Huge Downtown Vintage Lofts
5 1
apartment , Chicago
This penthouse flat is located in downtown Chicago, just a short walk from Millennium Park, Grant Park, the Skydeck, Shedd Aquarium, and Adler Planetarium. The property has received excellent ratings for location, cleanliness, and overall user experience. The apartment features a spacious loft design with high ceilings, offering a sense of openness and grandeur. Guests can enjoy a well-equipped kitchen, a private balcony with city views, a fitness centre, a tennis court, and parking facilities.
9.0 3 reviews
Chicago, IL
14/08 – 19/08
SG$459/nighttotal: SG$2295 (5 )
Mccormick Place 2br Suite With Patio, Skyline View And Optional Parking Sleeps 6 Near Soldier Field And Grant Park
2 1
apartment , Chicago
This McCormick Patio apartment is situated near Chicago's Museum Campus, approximately 2.3 kilometres from the Field Museum and within 3.2 kilometres of Grant Park and the Art Institute of Chicago. This 88-square-metre, two-bedroom, two-bathroom flat sleeps up to six guests and boasts a balcony, fully equipped kitchen, free Wi-Fi, on-site parking, and access to a fitness centre; Midway International Airport is 15 kilometres away.
Chicago, IL
01/09 – 31/10
SG$347/nighttotal: SG$20820 (60 )
Cute Gold Coast 2br W/ Outdoor Terrace, Nr Beach & L, By Blueground
2 2
apartment , Chicago
This Rush & Division apartment in Chicago's downtown area offers a 97 square metre (1044 square foot) two-bedroom, two-bathroom dwelling, conveniently located near Lake Michigan and Millennium Park, within easy walking distance. The self-catering flat, sleeping four guests comfortably in king and queen-sized beds, boasts a fully equipped kitchen, in-apartment laundry, and access to building amenities including a fitness centre, BBQ area, and game room; pet-friendly (with restrictions).
Chicago, IL
06/07 – 10/07
SG$389/nighttotal: SG$1556 (4 )
South Loop 2br Oasis W/ Patio & Gym Near Mccormick Place And Soldier Field
2 2
apartment , Chicago
This two-bedroom flat is situated in Chicago's South Loop district, a short 500-meter walk from McCormick Place and a few minutes from Michigan Avenue and downtown attractions. This spacious corner suite accommodates up to six guests and features a fully equipped kitchen, high-speed Wi-Fi, and building amenities including a fitness centre and a rooftop patio with city views, with optional on-site parking available.
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
9.5 261 reviews
Chicago, IL
26/08 – 30/08
SG$615/nighttotal: SG$2460 (4 )
Modern Luxury In Old Town - Sleeps 4
2 2
apartment , Chicago
This two-bedroom, two-bathroom apartment is situated in Chicago's Old Town neighbourhood, a 1.6km walk from North Avenue Beach and a 3.2km train journey from the Loop. The spacious top-floor condo, sleeping four guests, boasts a fully equipped kitchen including a dishwasher, air conditioning, parking, and internet access; nearby attractions include Michelin-starred restaurants and a renowned rib house.
9.4 21 reviews
Chicago, IL
03/09 – 07/09
SG$489/nighttotal: SG$1956 (4 )
Oak Park, Il, Entire House, Short Walk To Train.
3 2
apartment , Chicago
This train is located in Oak Park, a suburb of Chicago, just minutes from the expressway, train station, and downtown Chicago. It has received excellent user ratings, making it a popular choice for travellers. The train offers three bedrooms, one bathroom, and a floor area of 112 square metres, accommodating up to eight guests. It includes amenities such as a kitchen with a fridge and microwave, air conditioning, a garden, parking, and internet access.
Chicago, IL
01/08 – 30/06
SG$2677/nighttotal: SG$891441 (333 )
Spacious Family Size Home With Indoor Pool
3 1
apartment , Chicago
This spacious apartment is in Cook County, Chicago, close to Lake Michigan and Millennium Park, making it a great base for exploring the city. The apartment is ideal for large groups, with three bedrooms, each with a king-size bed, and a guest capacity of seven. There are two living rooms with TVs, a well-equipped kitchen, and a dining area, as well as a full bathroom on the top floor. The apartment also has a heated indoor pool, a games room, and a seating area with a TV in the basement, offering plenty of entertainment options.
9.4 191 reviews
Chicago, IL
13/08 – 14/08
SG$515/nightfor 1 night
Entire Modern 2 Bedroom Apartment
2 1
apartment , Chicago
This modern two-bedroom flat is located in Chicago, just 10km from the United Center and 11km from Wrigley Field. It has received excellent ratings for cleanliness, location and user experience. The apartment is 9 square metres and can accommodate up to four guests. The flat comes with free Wi-Fi, air conditioning, a fully equipped kitchen and private parking, as well as access to a garden.
Neighborhoods and points of interest in Chicago, IL
Best Chicago, IL holiday apartments with air conditioning
9.8 161 reviews
Chicago, IL
28/07 – 31/07
SG$498/nighttotal: SG$1494 (3 )
The Bagel Inn - Bright & Modern Wrigleyville 2 Bed
1 2
apartment , Chicago
This Southport Corridor flat is situated above Steingold's Delicatessen, next to the Music Box Theatre, and less than a kilometre from Wrigley Field. The two-bedroom, one-bathroom apartment sleeps six guests, offering a king-size bed, queen-size bed, sleeper sofa, a fully equipped kitchen including a Vita-mix blender, and complimentary bagels from the deli below; a 150 GBP pet fee applies for one pet.
8.3 7 reviews
Chicago, IL
27/06 – 04/07
SG$222/nighttotal: SG$1554 (7 )
A Sunny, Well-kept & Comfy Studio In Gold Coast
1 2
apartment , Chicago
This Gold Coast studio apartment is situated in a prime Chicago location, a short walk from Oak Street Beach, Michigan Avenue shopping, and the Art Institute. This pet-friendly flat offers a capacity for two guests, with a fully equipped kitchen (excluding a dishwasher) and air conditioning, located a 5-minute walk from the Red Line Subway at Clark/Division Station.
9.9 18 reviews
Chicago, IL
02/07 – 08/08
SG$131/nighttotal: SG$4847 (37 )
Remodel Clean One Bedroom W/parking & Laundry
1 2
apartment , Chicago
This one-bedroom apartment is located in a convenient neighbourhood close to public transport, a supermarket, shops, and restaurants. It has received excellent ratings for cleanliness, location, and user experience. The flat is suitable for two guests and includes a fully equipped kitchen with a fridge, microwave, and dishwasher. It also features a washer and dryer, a 50-inch TV, high-speed Wi-Fi, a dedicated workspace, and extra towels and bedding.
9.9 45 reviews
Chicago, IL
24/06 – 30/06
SG$258/nighttotal: SG$1548 (6 )
Spacious New Studio: Kitchenette, Laundry & Office
1 2
apartment , Chicago
This Chicago apartment, registration number R25000124541, offers comfortable accommodation for four guests and includes a fridge, freezer, microwave, air conditioning, parking, and internet access. The flat features one bathroom and its precise location within Chicago, and proximity to specific landmarks, remains undisclosed.
