Best apartment offers in Chicago, IL

13595 available apartment offers

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Chicago, IL apartments
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13595 Holiday apartments Chicago, IL

Best family friendly Chicago, IL Holiday Apartments and Self Catering Accommodations

Among the 13595 accommodations in Chicago, IL, here are the 4 best family friendly holiday apartments

Classy Apt/comfy Beds/25mins To Ord>mdw>dt>hosp - Chicago, IL
9.4 40 reviews

Classy Apt/comfy Beds/25mins To Ord>mdw>dt>hosp

apartment, Berwyn
This two-bedroom flat is situated in Berwyn, just a short drive from the Chicago Zoo, Oak Park, and Little Village, making it a great base for exploring the area. The property has an excellent user rating, so you can be sure of a comfortable stay.
The flat is ideal for families or groups of up to six people. It comes equipped with a kitchen, air conditioning, and a spa, as well as free parking and fast Wi-Fi. You can enjoy easy access to local amenities, including restaurants, public transport, and gambling slots, as well as attractions like Wrigley Field and McCormick Place.
Cozy Nest In Chicago's Vibrant Lincoln Square - Chicago, IL
9.9 281 reviews

Cozy Nest In Chicago's Vibrant Lincoln Square

apartment, Chicago
This three-bedroom duplex is situated near the Brown Line train station, providing easy access to the city's vibrant attractions and diverse neighbourhoods. The property enjoys excellent ratings for its location, cleanliness, and user experience.
The spacious apartment is perfect for families or groups of up to five guests, with a dedicated dining room, game room, and a pack 'n play for younger children. Guests can enjoy a fully equipped kitchen, a dedicated workspace, entertainment options including a Roku-equipped TV, board games, and an air hockey and foosball table, as well as a private outdoor table and grill for warmer months.
Modern, 2-bedroom Apt., 15 Minute Drive To Lake Michigan, Free Parking Spot. - Chicago, IL
9.2 29 reviews

Modern, 2-bedroom Apt., 15 Minute Drive To Lake Michigan, Free Parking Spot.

apartment, Chicago
This two-bedroom Chicago apartment rental is situated in the West Ridge neighbourhood, offering convenient access to Lake Michigan and Millennium Park, although precise distances aren't specified.
The family-friendly flat, sleeping four, includes a fully equipped kitchen, designated workspace with high-speed internet, private parking, and on-site host support; nearby attractions include the Field Museum and Wrigley Field.
3br Spacious Home Away From Home. Coziest Neighborhood In Chicago. - Chicago, IL
9.9 155 reviews

3br Spacious Home Away From Home. Coziest Neighborhood In Chicago.

apartment, Chicago
This three-bedroom flat is situated in a neighbourhood close to the lakefront, offering easy access to the lake and nearby parks. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The property spans 111 square metres and comfortably accommodates up to six guests. Amenities include a fully equipped kitchen, a private back porch, and a range of extras such as coffee, toiletries, and plenty of towels and crockery.

Best Chicago, IL holiday apartments with a balcony

Skyline 2br On 20th Floor Near Grant Park With Paid Parking - Chicago, IL
10 1 review

Skyline 2br On 20th Floor Near Grant Park With Paid Parking

apartment, Chicago
This 2-bedroom flat is situated in downtown Chicago, a mere 1.9 kilometres from the city centre and a 10-minute walk from DePaul University, offering convenient access to Grant Park and the Art Institute of Chicago.
This 112 square metre residence accommodates up to 15 guests, boasting a private balcony with city views on the 20th floor, an equipped kitchen, two bathrooms, complimentary Wi-Fi, and on-site fitness and entertainment facilities.
Historic Oak Park Home - Chicago, IL
9.2 21 reviews

Historic Oak Park Home

apartment, Oak Park
This apartment is located in the historic district of Oak Park, offering convenient access to local attractions.
This family-friendly flat provides complimentary internet, on-site parking, air conditioning, and a balcony, with a tennis court and garden also available for guests.
Chic Little Italy 4br Stay With Optional Parking - Chicago, IL
10 1 review

Chic Little Italy 4br Stay With Optional Parking

apartment, Chicago
This four-bedroom flat is located in Chicago's Little Italy, within 2 kilometres of Union Station, the United Centre, Willis Tower, and the Art Institute of Chicago.
This 130-square-metre residence offers a kitchen equipped with a fridge, microwave, and dishwasher, air conditioning, free WiFi, and a terrace or balcony, with optional parking and on-site washing facilities available.
Skyline 24th Floor Near Grant Park - Chicago, IL
No reviews

Skyline 24th Floor Near Grant Park

apartment, Chicago
This 24th-floor flat in Chicago's downtown offers prime city views and is a 12-minute walk from Grant Park, 0.8 miles from the Art Institute of Chicago, and a 10-minute walk from DePaul University.
This 112 square metre apartment accommodates 15 guests with 2 bedrooms and 2 bathrooms, featuring a kitchen with a fridge, microwave, and dishwasher, plus on-site amenities like a fitness centre, billiards, table tennis, an outdoor fireplace, and private parking.

Frequently asked questions about apartment rentals in Chicago, IL

  • What are the must-see attractions for a 2 days stay in Chicago, IL?

    You can't miss the iconic Willis Tower for its views of the city. A visit to Millennium Park is a must, with the Cloud Gate sculpture (aka 'The Bean') and Crown Fountain. And no trip to Chicago is complete without a walk along Navy Pier, especially at night when the Ferris wheel lights up.
  • What are the best apartments in Chicago, IL?

  • Which neighborhoods in Chicago, IL are best for renting an apartment?

    For a vibrant, trendy atmosphere, check out Wicker Park or Bucktown. If you prefer a more relaxed vibe with easy access to nature, consider Lincoln Park or Lakeview. And for a more budget-friendly option, Logan Square or Pilsen are popular choices.
  • What are the best apartments with a pool in Chicago, IL?

  • What are the top cultural and historical sites in Chicago, IL?

    The Art Institute of Chicago is a must-see for art lovers, with works from Monet, Picasso, and Van Gogh. For history buffs, the Field Museum houses dinosaur skeletons and ancient artifacts. And the Museum of Science and Industry offers interactive exhibits on everything from transportation to space exploration.
  • What are the best apartments with a jacuzzi in Chicago, IL?

  • What makes Chicago, IL unique or famous?

    Chicago is known for its stunning architecture, from the towering skyscrapers of the Loop to the charming brownstones of Lincoln Park. The city also boasts a world-class food scene, with deep-dish pizza, hot dogs, and Italian beef sandwiches being local favourites. And don't forget the vibrant music scene, with blues, jazz, and rock all having strong roots in the city.
  • 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 great place to find a mix of local crafts, produce, and street food vendors. For a more upscale experience, head to the Green City Market in Lincoln Park, which features local and organic produce, artisanal goods, and prepared foods. And for a taste of Mexican cuisine, check out the Pilsen Food Truck Festival.
  • What are the best pet friendly apartments in Chicago, IL?

  • How is the public transportation system in Chicago, IL?

    Chicago has a well-developed public transportation system, with the 'L' (elevated train) and buses covering most of the city. The 'L' is particularly convenient for getting around downtown and the surrounding neighbourhoods. You can purchase a Ventra card for easy 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?

    In the summer, the Chicago Blues Festival is a must-see, while the Taste of Chicago food festival is a great way to sample local cuisine. In the autumn, the Chicago Marathon draws crowds of runners and spectators. And in the winter, the Christkindlmarket brings a touch of European charm to the city with its festive decorations and traditional treats.
  • What amenities are typically included in apartments in Chicago, IL?

    Most apartments in Chicago come with basic amenities like central heating and air conditioning, in-building laundry facilities, and sometimes a fitness centre. Some high-end buildings may offer additional amenities like swimming pools, rooftop decks, and concierge services.

Popular destinations

Best Chicago, IL holiday apartments with parking

4 Br/3ba, Great For Large Groups, Garage Parking - Chicago, IL
9.8 67 reviews

4 Br/3ba, Great For Large Groups, Garage Parking

apartment, Chicago
This Humboldt Park apartment, situated in a trendy Chicago neighbourhood within easy reach of public transport, offers convenient access to local restaurants and the city's attractions.
This spacious 210 square metre duplex flat boasts four bedrooms sleeping up to ten guests, a dedicated recreation area with a 75-inch TV and games, plus a private balcony and free garage parking.
Spacious 3br Corner Family Oasis Near Mccormick Place & Soldier Field - Chicago, IL
9.4 8 reviews

Spacious 3br Corner Family Oasis Near Mccormick Place & Soldier Field

apartment, Chicago
This Near South Side Chicago flat is situated steps from McCormick Place convention centre, a short walk from a tube station, and a quick Uber ride from Soldier Field and the Museum Campus.
The 95 square metre (102 square meters = 95 square meters approximately) property boasts three bedrooms, two bathrooms, sleeps up to ten guests, and includes a fully equipped kitchen, in-unit laundry, and access to a building gym; EV charging is optionally available.
9 Entire Apt Near Downtown Chicago - Chicago, IL
No reviews

9 Entire Apt Near Downtown Chicago

apartment, Oak Park
This garden-level flat is located in a residential district of Oak Park, offering convenient access to local attractions.
This private unit accommodates up to five guests with a queen, full, and twin bed configuration, featuring in-unit WiFi, a TV, and a washer/dryer for a comfortable stay.
Classic Posh Home Chicago Roscoe Village+ Wrigley - Chicago, IL
9.9 110 reviews

Classic Posh Home Chicago Roscoe Village+ Wrigley

apartment, Chicago
This upscale Victorian-style flat is situated in a prime Chicago location, one block from excellent restaurants and shops, and within easy walking distance (approximately 0.8 kilometres) of Wrigley Field.
The one-bedroom, one-bathroom apartment sleeps two guests and boasts a chef's kitchen, marble steam bath, stained-glass windows, Bose music system, Smart TV, high-speed internet, and a well-stocked pantry; parking is also available.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday apartments with air conditioning

Fulton Market Loft | Rooftop Fire Pit | Parking - Chicago, IL
9.9 288 reviews

Fulton Market Loft | Rooftop Fire Pit | Parking

apartment, Chicago
This luxurious Chicago apartment, situated on Restaurant Row in the city centre, is minutes from the Chicago Theatre and Art Institute of Chicago.
The 177-square-metre (1907 sq ft) property boasts three bedrooms, sleeping up to eight guests, and features a modern kitchen, terrace, parking, and excellent proximity to major attractions including the Field Museum and Museum of Science and Industry.
Steps From Wrigley Field And Lake Michigan - Chicago, IL
9.5 4 reviews

Steps From Wrigley Field And Lake Michigan

apartment, Chicago
This Wrigleyville flat is located in Chicago, a short walk from Wrigley Field and 2.7 kilometres from Montrose Beach, offering air-conditioned accommodation with a patio and free WiFi.
This 167 square metre apartment accommodates up to 10 guests across 3 bedrooms and 2 bathrooms, featuring a fully equipped kitchen with a dishwasher and oven, plus an on-site casino and cycling opportunities nearby.
Chic 1 Br W Parking - Chicago, IL
9.8 118 reviews

Chic 1 Br W Parking

apartment, Chicago
This stylish West Loop apartment, a 5-minute walk from the West Loop neighbourhood, offers easy access to Chicago's attractions; Millennium Park and Navy Pier are both within a 1.6km Uber ride.
The 850 sq ft (79 sq m) flat features a king-size bed and sofa bed, sleeping up to four guests, and includes a fully equipped kitchen, in-unit laundry, two Smart TVs (75-inch and 65-inch), and a private patio.
Bee's Knees | Ritzy, 1924 Chicago Bungalow - Chicago, IL
9.9 115 reviews

Bee's Knees | Ritzy, 1924 Chicago Bungalow

apartment, Chicago
This four-bedroom house, ideal for families or large groups, is located in Chicago's Humboldt Park neighbourhood, approximately 40km from O'Hare International Airport and 16km from the city centre.
The property boasts a fully-fenced garden, secure private garage, high-speed Wi-Fi (800+ Mbps), and sleeps up to 10 guests, offering a comfortable stay with a fireplace and complimentary snacks.
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