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

Modern 3br South Loop Living Family Unit Near Adler Planetarium & Mccormick Convention Center - Chicago, IL
No reviews

Modern 3br South Loop Living Family Unit Near Adler Planetarium & Mccormick Convention Center

apartment, Chicago
This three-bedroom Chicago apartment, near the Museum Campus, is 2.3km from the Field Museum and under 3.2km from Grant Park and the Art Institute of Chicago.
The 88-square-metre property boasts two bathrooms, sleeps eight guests, includes free Wi-Fi, private parking (optional), a fitness centre, and a patio with city views; a fully equipped kitchen and family-friendly features are also available.
2 Bed Apartment | Convenient Access To Downtown - Chicago, IL
9.7 240 reviews

2 Bed Apartment | Convenient Access To Downtown

apartment, Forest Park
This Forest Park apartment, near the highway, provides easy access to Chicago city centre (approx. 32km) and both O'Hare and Midway airports (approx. 48km).
The two-bedroom property, sleeping up to four guests, offers a fully equipped kitchen, fast Wi-Fi, Netflix, and a private patio with backyard access; a cot is available.
Beach Side In The City - Chicago [Near Nwu] [Near Red Line] - Chicago, IL
10 4 reviews

Beach Side In The City - Chicago [Near Nwu] [Near Red Line]

apartment, Chicago
This five-bedroom flat in Chicago's Rogers Park district provides excellent access to attractions such as the Chicago Theatre, the Art Institute of Chicago, Michigan Avenue shopping, and Wrigley Field entertainment, with the latter being approximately 10 kilometres away.
This residence accommodates up to eleven guests and features a microwave oven, air conditioning, heating, and parking, with a 11:00 AM check-out time.
Great Location-beautiful Friendly Andersonville Neighborhood - Chicago, IL
10 283 reviews

Great Location-beautiful Friendly Andersonville Neighborhood

apartment, Chicago
This charming apartment is located in the Andersonville neighbourhood on Chicago's north side, just under 0.3 kilometres west of Clark Street, a lively area with a diverse range of restaurants, bars, and shops. The apartment receives excellent ratings for user experience, location, and cleanliness.
This three-bedroom flat provides 92 square metres of space and comfortably accommodates up to four guests. The apartment offers a range of amenities, including a private patio, a front porch, and a shared laundry area, as well as garage parking.

Best Chicago, IL holiday apartments with a balcony

Luxury Downtown Penthouse With Private Rooftop! - Chicago, IL
9.2 32 reviews

Luxury Downtown Penthouse With Private Rooftop!

apartment, Chicago
This Downtown Chicago flat is conveniently located within a 1.6km walk of State Street and Michigan Avenue, and less than 1.6km from Lake Michigan and the Merchandise Mart.
The 111 square metre apartment boasts two bedrooms, two bathrooms, parking, and a balcony, comfortably accommodating up to 10 guests and offering amenities including Wi-Fi, a fully equipped kitchen and a washing machine.
Promo 10% Weekly And 15% Monthly! Jacuzzi, King Beds, Easy Access To Dt Chicago! - Chicago, IL
9.6 21 reviews

Promo 10% Weekly And 15% Monthly! Jacuzzi, King Beds, Easy Access To Dt Chicago!

apartment, Westchester
This four-bedroom house is located in Westchester, a suburb just west of Downtown Chicago, making it easy to reach the city centre. The property has received excellent ratings from previous guests.
The apartment spans 186 square metres and comfortably accommodates up to 10 guests. It offers a range of amenities, including a jacuzzi, a spacious garden, and a games room, ensuring a relaxing and enjoyable stay for all.
3br Spacious Home Away From Home. Coziest Neighborhood In Chicago. - Chicago, IL
9.9 151 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.
Walk To Stores & Parks! Stylish Chicago Apartment - Chicago, IL
No reviews

Walk To Stores & Parks! Stylish Chicago Apartment

apartment, Chicago
This Chicago flat in Cook County is located 24 kilometres from downtown landmarks such as Millennium Park and the Willis Tower, with convenient access to Dan Ryan Woods.
This 93 square metre, single-storey residence accommodates up to five guests and features a private deck with seating and a barbecue, four Smart TVs, an on-site bar, and gated surface lot 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

The Banksy-king Bed-firepit-rooftop-united Center - Chicago, IL
10 5 reviews

The Banksy-king Bed-firepit-rooftop-united Center

apartment, Chicago
This apartment is situated in Chicago's Near West Side, a 13-minute walk from United Center and a 5-minute drive from Merchandise Mart, offering a convenient location for exploring the city. The apartment is within easy reach of major sporting events, cultural attractions, and public transport.
The property has four bedrooms and two bathrooms, providing ample space for up to 12 guests. The apartment is equipped with a modern kitchen, a private garden and terrace, a washer and dryer, and a range of other amenities perfect for a comfortable stay.
Bf - Bright And Cozy 1br Apartment In Logan Square! - Chicago, IL
9.8 279 reviews

Bf - Bright And Cozy 1br Apartment In Logan Square!

apartment, Chicago
This Logan Square flat is conveniently located in Chicago's trendy Logan Square neighbourhood, offering easy access to Chicago's attractions.
The 60-square-metre (646 sq ft) self-catering apartment features one bedroom, one bathroom, sleeps two guests, and includes amenities such as free Wi-Fi, parking, and a fully equipped kitchen.
Private Balcony, 1 Garage Parking, Sleeps 8! - Chicago, IL
10 2 reviews

Private Balcony, 1 Garage Parking, Sleeps 8!

apartment, Chicago
This West Loop apartment, a three-minute drive from Fulton Market and under 13km from both Millennium Park and Navy Pier, offers convenient access to Chicago's key attractions.
The 107 square metre property boasts a two-bedroom layout sleeping up to eight guests, featuring a king-size bed, double bed, bunk bed, a fully equipped kitchen with Keurig coffee maker, in-unit laundry, private balcony, and a heated garage parking space.
Comfortable And Trendy Design 1br In Lincoln Square - Chicago, IL
9.0 10 reviews

Comfortable And Trendy Design 1br In Lincoln Square

apartment, Chicago
This one-bedroom flat is located in Albany Park, a neighbourhood just a short walk from Lincoln Square, with easy access to the Brown Line for quick trips to Wrigleyville or downtown Chicago. The flat has an excellent user rating, with guests consistently praising its comfortable design and convenient location.
The flat is perfect for couples or solo travellers looking for a comfortable and well-equipped base in Chicago. It includes a kitchen with a fridge, microwave oven, and dishwasher, as well as air conditioning, parking, and internet access.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday apartments with air conditioning

Spacious Downtown 3br With Free Parking - Chicago, IL
9.8 154 reviews

Spacious Downtown 3br With Free Parking

apartment, Chicago
This three-bedroom Chicago apartment is centrally located in the Fulton Market district, offering easy access to public transport and renowned restaurants.
Sleeping up to 10 guests, the recently renovated property boasts a fully equipped kitchen, private porch with city views, free on-site parking, and a dedicated workspace; ideal for families or groups exploring Chicago.
Mccormick Place Modern 2br Loft In Downtown Chicago Michigan Avenue With Optional Parking Near Soldier Field - Chicago, IL
10 3 reviews

Mccormick Place Modern 2br Loft In Downtown Chicago Michigan Avenue With Optional Parking Near Soldier Field

apartment, Chicago
This apartment is situated on Michigan Avenue in Downtown Chicago, just 1.6 kilometres from the Field Museum of Natural History and 2.9 kilometres from the Art Institute of Chicago. It enjoys an excellent location rating, with very good user reviews for cleanliness and overall experience.
The two-bedroom flat comfortably sleeps up to six guests and offers a fully equipped kitchen with a dishwasher and oven, along with a fitness centre, a terrace, and on-site parking. You can also enjoy stunning city views from the apartment and benefit from free Wi-Fi access.
Stylish Luxe King Bed W/free Parkng Near Dt Oak Pk - Chicago, IL
9.5 131 reviews

Stylish Luxe King Bed W/free Parkng Near Dt Oak Pk

apartment, Oak Park
This Oak Park apartment, ideally located near Lake Street Theatre (approx. 9.6km) and Scoville Park (approx. 6.4km), provides easy access to downtown Chicago via public transport.
The two-bedroom, two-bathroom flat sleeps six guests, boasting a fully equipped kitchen, private parking, and luxury amenities including a 4K Smart TV and high-end toiletries, making it perfect for family stays.
Luxury 4br W/ Theater, Near Downtown & Mccormick - Chicago, IL
9.8 38 reviews

Luxury 4br W/ Theater, Near Downtown & Mccormick

apartment, Chicago
This four-bedroom, two-bathroom apartment in Chicago's East Pilsen neighbourhood is a 7-minute walk from Radius Chicago, and within a few kilometres of McCormick Place, the United Centre, and the University of Illinois at Chicago.
The 8-guest property boasts a home cinema, gourmet kitchen with high-end appliances, spa-like bathrooms with Bluetooth mirrors, free on-street parking, and is close to numerous museums and airports.
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