Best apartment offers in Chicago, IL

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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

Secret Gallery On The Park - 2bd/1ba - Chicago, IL
8.0 1 review

Secret Gallery On The Park - 2bd/1ba

apartment, Chicago
This two-bedroom flat is located 1.4 kilometres from the city centre, offering a 18-minute walk to Oak Street Beach and convenient access to attractions such as Water Tower Chicago and the Chicago Museum of Contemporary Art.
This apartment, covering 80 square metres and accommodating up to six guests, features a fully equipped kitchen with a fridge and microwave, air conditioning, a private balcony, and complimentary WiFi, with a washing machine also provided for guest use.
Business Ready 2br Apartment In South Loop With Skyline View, Optional Parking & Gym Access Close To Mccormick, Downtown & Cta - Chicago, IL
8.4 6 reviews

Business Ready 2br Apartment In South Loop With Skyline View, Optional Parking & Gym Access Close To Mccormick, Downtown & Cta

apartment, Chicago
This family-friendly apartment near Chicago's Museum Campus is conveniently located approximately 2.25 kilometres from the Field Museum and within 3.2 kilometres of Grant Park and the Art Institute of Chicago.
The 74-square-metre property boasts a spacious two-bedroom, two-bathroom layout sleeping up to eight guests, complete with a fully equipped kitchen, free Wi-Fi, on-site parking, a fitness centre, and a private patio offering skyline views.
Bronzeville Hidden Oasis - Chicago, IL
10 188 reviews

Bronzeville Hidden Oasis

apartment, Chicago
This family-friendly Chicago apartment, ideally located near the University of Chicago and Illinois Institute of Technology, offers easy access to Guaranteed Rate Field (3.9 km), the lakefront (8 km), and various museums, all within a 9.6 km radius.
The 4-bedroom, 2-bathroom property sleeps up to 10 guests and features a fully equipped kitchen, garden, parking, and excellent internet access; exterior security cameras enhance safety and security.
Modern Studio Near Mccormick *Gym & Rooftop - Chicago, IL
9.2 16 reviews

Modern Studio Near Mccormick *Gym & Rooftop

apartment, Chicago
This studio flat is situated just outside Chicago's city centre, offering a 5-minute drive to McCormick Place and a 10-15 minute drive to The Loop, with easy access to Museum Campus, Soldier Field, and the lakefront.
This family-friendly flat accommodates up to four guests and features a fully equipped kitchen, air conditioning, internet, a fitness centre, and a rooftop deck, with complimentary parking and 24/7 virtual concierge support.

Best Chicago, IL holiday apartments with a balcony

Modern 2br In South Loop Near Soldier Field, Grant Park, Downtown, & Lakefront Trail - Chicago, IL
8.8 42 reviews

Modern 2br In South Loop Near Soldier Field, Grant Park, Downtown, & Lakefront Trail

apartment, Chicago
This Chicago apartment, near McCormick Place and the Museum Campus, is conveniently located approximately 2.4-3.2km from the Field Museum, Art Institute of Chicago, and the Chicago Symphony Orchestra.
The 88 square metre property features a two-bedroom, two-bathroom layout sleeping up to six guests, offering a private patio, fitness centre access, and free Wi-Fi; parking is available.
Chicago Charm! Quiet And Inviting ! - Chicago, IL
10 38 reviews

Chicago Charm! Quiet And Inviting !

apartment, Chicago
This comfortable apartment is located in the West Ridge neighbourhood of Chicago, just 5 kilometres from Lake Michigan and 5 kilometres from the Aragon Ballroom. It has received excellent reviews from previous guests.
This three-bedroom, two-bathroom property offers 125 square metres of space, comfortably accommodating up to six guests. It features a well-equipped kitchen, a jacuzzi, a terrace, and a garden, as well as a washer and dryer, a high chair, a crib, and games and toys for children.
Live Like A Local. 10min Walk To Train. Rooftop+garage. 3-level Spacious Retreat - Chicago, IL
9.8 35 reviews

Live Like A Local. 10min Walk To Train. Rooftop+garage. 3-level Spacious Retreat

apartment, Chicago
This train is located in the West Town neighbourhood of Chicago, just 800 metres from Humboldt Park and 1.3 kilometres from Milwaukee Avenue. It has been rated excellent by previous guests.
The train offers 372 square metres of space with five bedrooms, four bathrooms, and a capacity of 20 guests. Amenities include a fully equipped kitchen, a hot tub, a garden, a terrace, parking, and Wi-Fi.
Top Floor Views + Central Comfort - Chicago, IL
10 103 reviews

Top Floor Views + Central Comfort

apartment, Chicago
This top-floor flat in Chicago offers exceptional city views and is situated just 400 metres from Union Station and 800 metres from the Willis Tower.
This modern apartment accommodates up to six guests with two bedrooms and two bathrooms, featuring a designer kitchen with premium appliances, a 75-inch television, and access to building amenities including a fitness centre, game room, and an outdoor sky terrace with grills and firepits.

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

Architect-designed Logan Square Loft | 15 Ceiling - Chicago, IL
9.8 421 reviews

Architect-designed Logan Square Loft | 15 Ceiling

apartment, Chicago
This Logan Square apartment is conveniently located near Palmer Square Park, offering easy walking access to local coffee shops, restaurants, and galleries.
The open-plan studio flat features a queen-size bed in a loft area, a full kitchen with gas range, espresso machine, and fridge, accommodates up to three guests, and includes high-speed Wi-Fi and access to a shared laundry.
Luxury Designer Penthouse 3804 | Pool | Gold Coast - Chicago, IL
9.4 16 reviews

Luxury Designer Penthouse 3804 | Pool | Gold Coast

apartment, Chicago
This luxurious Gold Coast penthouse apartment in downtown Chicago boasts stunning Lake Michigan and cityscape views from its 38th-floor location, a short walk from Michigan Avenue and its many shops and restaurants.
The 167 square metre (1798 square foot) property features three bedrooms, two bathrooms, sleeps up to twelve guests, and includes a fully equipped chef's kitchen, rooftop pool access, and free high-speed internet with streaming services.
Home In Forest Park Downstairs. - Chicago, IL
9.7 412 reviews

Home In Forest Park Downstairs.

apartment, Forest Park
This ground floor flat is located in Forest Park, just 12 kilometres from downtown Chicago and 24 kilometres from O'Hara International Airport, making it a convenient base for exploring the city and its surroundings. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
The flat has two bedrooms and one bathroom, comfortably accommodating up to four guests. You'll enjoy a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, as well as air conditioning, a garden, parking, and fast internet access.
3br/2ba + Pull Out Sofa Bed + No Stairs + Backyard - Chicago, IL
9.9 56 reviews

3br/2ba + Pull Out Sofa Bed + No Stairs + Backyard

apartment, Worth
This family-friendly house in Worth sleeps eight guests across three bedrooms and two bathrooms, boasting a fully equipped kitchen with dishwasher and a garden with parking.
The property offers air conditioning, internet access, and is pet-friendly, with further details on its precise location in Worth and nearby attractions to be confirmed.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday apartments with air conditioning

Pets Ok | Walk Score 95 | Desk | 1,750ft² |W/d - Chicago, IL
10 675 reviews

Pets Ok | Walk Score 95 | Desk | 1,750ft² |W/d

apartment, Chicago
This spacious two-bedroom, two-bathroom apartment is located near Lincoln Park in Chicago, a 10-minute drive (approx. 16km) from the city centre and a 30-minute drive (approx. 48km) from O'Hare International Airport.
The 167 sq m flat boasts high ceilings, exposed brick, a fully equipped kitchen, laundry facilities, keyless entry, and sleeps up to six guests comfortably, thanks to a king-size bed, queen bed, queen-size sofa bed, and double day bed; free on-street parking is provided with a permit.
Lovely 2-bedroom Apartment In Pilsen - Chicago, IL
9.7 177 reviews

Lovely 2-bedroom Apartment In Pilsen

apartment, Chicago
This two-bedroom apartment is situated in Chicago's Pilsen neighbourhood, a short walk from the Pink Line 'L' train offering easy access to the city centre (approximately 1.6km).
The flat, sleeping up to four guests, boasts a kitchen with fridge, freezer and microwave, air conditioning, a jacuzzi, garden, parking, and is near the Mexican Museum of Art.
Cozy 2br Haus Inn Pilsen With Patio And Fire Pit - Chicago, IL
9.5 135 reviews

Cozy 2br Haus Inn Pilsen With Patio And Fire Pit

apartment, Chicago
This two-bedroom flat is ideally located in a lively neighbourhood, just 8 kilometres from the UIC Pavilion, 15 kilometres from McCormick Place and 15 kilometres from downtown Chicago. It has consistently received excellent ratings for location, cleanliness and overall experience.
The flat is spacious and serene, perfect for a relaxing stay. It features a garden, a terrace, a fireplace and parking, making it ideal for families and groups.
Charming Wrigleyville Home Close To The Cubs! - Chicago, IL
9.4 68 reviews

Charming Wrigleyville Home Close To The Cubs!

apartment, Chicago
This Wrigleyville apartment, situated in Lakeview, Chicago, offers convenient access to Wrigley Field and is a short drive from downtown Chicago's attractions.
The 56-square-metre (603-square-foot) self-catering flat features two bedrooms, one bathroom, sleeps four guests, and includes a kitchenette, free parking (before 6pm), and Wi-Fi.
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