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

Designer Apartment 10 Min Walk To Wrigley! - Chicago, IL
10 6 reviews

Designer Apartment 10 Min Walk To Wrigley!

apartment, Chicago
This two-bedroom flat is located in Chicago's Lakeview district, a 5-minute walk from Wrigley Field and a 12-minute journey to the city centre.
This 56 square metre apartment, suitable for four guests, offers a fully-equipped kitchen, air conditioning, a balcony, and in-unit laundry facilities, with high-speed WiFi ideal for remote working.
Cute & Cozy Chicago Basement - Chicago, IL
9.8 77 reviews

Cute & Cozy Chicago Basement

apartment, Chicago
This recently remodelled one-bedroom basement flat in Chicago is located approximately 16km from O'Hare International Airport and a 16km drive from the Blue Line, providing easy access to the city centre.
The 56-square-metre self-contained property offers a separate dining and living area (including a pull-out sofa bed), sleeping up to four guests, and boasts a fully equipped kitchen, private entrance, garden, parking, and excellent guest reviews.
Livn Millennium Park Downtown Chicago Superior 1br - Chicago, IL
No reviews

Livn Millennium Park Downtown Chicago Superior 1br

apartment, Chicago
This newly renovated one-bedroom flat offers a prime downtown Chicago location, just 100 metres from Millennium Park and Michigan Avenue's shopping and dining.
This family-friendly apartment sleeps two and features a fully equipped kitchen, air conditioning, a terrace, and in-unit laundry, with key code elevator access and proximity to the Theater District and Chicago's public transport network.
Fun 3br Apt With Games 10 Min Downtown W King Bed - Chicago, IL
9.6 157 reviews

Fun 3br Apt With Games 10 Min Downtown W King Bed

apartment, Chicago
This spacious Chicago apartment, ideal for families or large groups, is situated in a residential area approximately 5.6km from the city centre, a short drive from Millennium Park and Soldier Field, and close to Guaranteed Rate Field.
The 88 square metre property sleeps 8-10 guests and boasts three bedrooms, one bathroom, a fully equipped kitchen, free high-speed Wi-Fi, and entertainment features including four smart TVs and classic arcade games.

Best Chicago, IL holiday apartments with a balcony

2br Near Riverwalk + Downtown Access - Chicago, IL
10 3 reviews

2br Near Riverwalk + Downtown Access

apartment, Chicago
This Magnificent Mile apartment in downtown Chicago offers a luxurious stay close to Washington Square Park, Jane Byrne Plaza, and the Museum of Contemporary Art.
The 117 m² dwelling boasts two bedrooms, two bathrooms, sleeps up to seven guests, and includes a fully equipped kitchen with high-end appliances, a balcony with city views, and access to a building with a heated pool, hot tub, and fitness centre.
Luxury Designer Penthouse 3801 | Pool | Gold Coast - Chicago, IL
9.8 16 reviews

Luxury Designer Penthouse 3801 | Pool | Gold Coast

apartment, Chicago
This luxurious 3-bedroom penthouse apartment is situated in Chicago's Gold Coast district, a short distance from Michigan Avenue and close to cultural attractions such as the Chicago Theatre and Art Institute of Chicago.
The 139-square-metre (1496-square-foot) property boasts a chef's kitchen, rooftop pool access, parking, and sleeps up to 10 guests, making it ideal for families or large groups visiting the city.
South Loop 2br Corner Unit With Natural Light, Optional Parking And Guest Access Near Downtown Chica - Chicago, IL
No reviews

South Loop 2br Corner Unit With Natural Light, Optional Parking And Guest Access Near Downtown Chica

apartment, Chicago
Accommodation. You will be located in Chicago.
Facilities and services include air conditioning, an elevator and a fridge. Take advantage of the gym in this apartment.
West Loop Scenic Views + Private Balcony Retreat - Chicago, IL
9.6 5 reviews

West Loop Scenic Views + Private Balcony Retreat

apartment, Chicago
This spacious West Loop apartment, near Mary Bartelme Park and within easy reach of the WNDR Museum and Credit Union 1 Arena, offers convenient access to Chicago's public transport network.
The 93-square-metre flat features two queen bedrooms, two bathrooms, a balcony, and sleeps five guests, boasting high-end kitchen appliances, a 75” TV, Sonos sound system, and access to building amenities including a sky lounge and fitness centre.

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.
  • What are the best apartments in Chicago, IL?

  • 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?

  • What makes Chicago, IL unique or famous?

    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.

Popular destinations

Best Chicago, IL holiday apartments with parking

Sloth Apt  King Bed  Parking  Walk 2 Blue Line - Chicago, IL
10 103 reviews

Sloth Apt King Bed Parking Walk 2 Blue Line

apartment, Chicago
This Old Irving Park flat offers convenient access to Chicago's Blue Line, providing a quick 25-minute journey to downtown attractions such as the Loop, Art Institute of Chicago, Willis Tower, Millennium Park, and Navy Pier.
The recently renovated one-bedroom apartment sleeps two, features Samsung appliances, a 65” LG OLED TV with Netflix, 300mbps WiFi, in-unit laundry, dedicated parking, and a unique Michigan pine beam ceiling.
Bright Colorful Boho-chic Studio In Lincoln Square - Chicago, IL
9.9 169 reviews

Bright Colorful Boho-chic Studio In Lincoln Square

apartment, Chicago
This modern studio flat is located in Lincoln Square, Chicago, on Foster Avenue, near Winnemac Park and within easy walking distance of local restaurants and shops.
The 15-foot-high-ceilinged apartment sleeps up to five guests, featuring two queen-size beds and a sofa bed, a fully equipped kitchen with dishwasher, and a privacy screen separating sleeping and living areas; nearby attractions include Winnemac Park, perfect for outdoor activities.
Treetop Sunny Large 1- Bedroom In Lincoln Square - Chicago, IL
10 4 reviews

Treetop Sunny Large 1- Bedroom In Lincoln Square

apartment, Chicago
This top-floor Chicago flat is situated in a peaceful, tree-lined neighbourhood near a River Park, offering easy access to the Chicago River and its trails; the precise distance isn't specified.
The spacious one-bedroom apartment sleeps two, features a fully equipped kitchen, air conditioning, parking, and boasts excellent user, location, and cleanliness ratings.
Sunny Northside Duplex With Free Parking - Chicago, IL
10 25 reviews

Sunny Northside Duplex With Free Parking

apartment, Chicago
This Edgewater flat is located on a quiet, tree-lined street, offering convenient walking access to the Metra, Loyola University, and the CTA Red Line, all within 500 metres.
This two-floor residence accommodates two guests, featuring a well-equipped kitchen with a fridge, freezer, and microwave, air conditioning, internet, parking, and a 65-inch television, with no neighbours above or below.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday apartments with air conditioning

Chic Chicago Retreat (2-bedroom Home) By Redawning - Chicago, IL
8.4 5 reviews

Chic Chicago Retreat (2-bedroom Home) By Redawning

apartment, Chicago
This Little Village flat is centrally located in Chicago, offering easy access to attractions such as Millennium Park and Lake Michigan, with the United Center and McCormick Place also within a reasonable distance (distances unspecified).
The two-bedroom, one-bathroom apartment sleeps six, features a fully equipped kitchen with fridge and microwave, free Wi-Fi, air conditioning, and a garden; guests can explore nearby cultural attractions including the Chicago Theatre and Art Institute of Chicago.
Stylish River North Suites Luxe Comfort Near Chicagos Best Shopping & Nightlife - Chicago, IL
10 2 reviews

Stylish River North Suites Luxe Comfort Near Chicagos Best Shopping & Nightlife

apartment, Chicago
This Level River North apartment, a stylish flat in Chicago's River North district, is minutes from the Magnificent Mile and across the river from the Loop.
The 56 square metre (602 square foot) studio suite sleeps four, offering a fully equipped kitchen, in-suite laundry, complimentary Wi-Fi, and access to a swimming pool, sauna, and parking; nearby attractions include the Chicago Theatre and Art Institute of Chicago.
Luxury Soho Styled Two-level Townhouse - Old Town - Chicago, IL
9.9 153 reviews

Luxury Soho Styled Two-level Townhouse - Old Town

apartment, Chicago
This luxurious Old Town duplex townhouse, a five-minute walk from the beach and adjacent to Second City and Lincoln Park, offers a prime Chicago location.
The 268 square metre property boasts a spacious open-plan layout, sleeping up to twelve guests, and includes three bedrooms, three bathrooms, a chef's kitchen with Gaggenau appliances, and convenient parking options.
Chicago Gem Near Downtown Steps From La Catedral Café : Family And Pet Friendly - Chicago, IL
No reviews

Chicago Gem Near Downtown Steps From La Catedral Café : Family And Pet Friendly

apartment, Chicago
This Lawndale flat offers convenient access to downtown Chicago, situated near the popular La Catedral Café and providing direct Pink Line train access to the Loop, approximately 8 kilometres away.
This two-bedroom dwelling accommodates up to seven guests and features a fully equipped kitchen with a Nespresso coffee station, a dining and game table, and pet-friendly amenities, with Grant Park and Millennium Park accessible within a short journey.
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