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

The Bright Retreat In Andersonville - Chicago, IL
9.4 7 reviews

The Bright Retreat In Andersonville

apartment, Chicago
This Andersonville apartment in Chicago is situated near Foster Beach (2.9km) and Montrose Beach (2.3km), also close to Loyola University Chicago (3.2km).
This one-bedroom, one-bathroom flat sleeps seven guests and offers free Wi-Fi, private parking, a fully equipped kitchen, and air conditioning; nearby attractions include Lincoln Park Zoo (8.4km) and Wrigley Field (3.7km).
Shared Rooftop Deck And Fully Stocked Kitchen - Luxury Oasis - Chicago, IL
No reviews

Shared Rooftop Deck And Fully Stocked Kitchen - Luxury Oasis

apartment, Chicago
This luxury suite is situated in Goose Island, a district north of central Chicago, offering convenient street parking and proximity to the city's attractions.
This family-friendly apartment accommodates up to 9 guests with two bedrooms, featuring a fully stocked kitchen with stainless steel appliances, complimentary hotel-like amenities, and high-speed Wi-Fi, all within a short distance of Chicago's landmarks.
Clean & Sunny, 2bd, Private Deck, 15min To Wrigley! - Chicago, IL
10 27 reviews

Clean & Sunny, 2bd, Private Deck, 15min To Wrigley!

apartment, Chicago
This Irving Park, Chicago flat is a short walk from Addison and Irving Park buses, a 15-minute walk (approx. 1.2km) from the train, and a 15-minute bus ride or free shuttle to Wrigley Field.
The 84-square-metre (904 sq ft) two-bedroom apartment sleeps six, boasting a fully equipped kitchen, in-unit laundry, a private porch, access to a shared garden, and is close to Horner Park and numerous restaurants and bars.
Vintage Library Museum Retreat Near Cta Brown Line - Chicago, IL
10 40 reviews

Vintage Library Museum Retreat Near Cta Brown Line

apartment, Chicago
This private flat is located in a Chicago district offering excellent public transport links, mere metres from the CTA Brown Line and seconds from the Montrose 78 bus line, facilitating exploration of the city.
This two-bedroom dwelling accommodates up to four guests and features a kitchen with a fridge, freezer, and microwave, air conditioning, a garden, parking, and a bathroom with both a bathtub and a full-sized shower, offering a museum-like ambience.

Best Chicago, IL holiday apartments with a balcony

Mccormick Oasis With Balcony, Optional Parking, Patio And Gym Sleeps 6 Near Mccormick Place, Grant Park, Soldier Field & Museum Campus - Chicago, IL
9.2 8 reviews

Mccormick Oasis With Balcony, Optional Parking, Patio And Gym Sleeps 6 Near Mccormick Place, Grant Park, Soldier Field & Museum Campus

apartment, Chicago
This Chicago apartment, near the city's Museum Campus, is 2.4 kilometres from the Field Museum and under 3.2 kilometres from both the Art Institute of Chicago and the Chicago Symphony Orchestra.
The 84-square-metre, two-bedroom flat sleeps up to six guests and boasts a fully equipped kitchen, balcony, private parking (optional), and on-site fitness centre; it's allergy-free and non-smoking.
Group Lux In Old Town 4bd/3ba (+Rooftop/parking) - Chicago, IL
9.7 612 reviews

Group Lux In Old Town 4bd/3ba (+Rooftop/parking)

apartment, Chicago
This Old Town Chicago flat, moments from Wells Street's restaurants and a 0.8 km walk from the Red Line, offers easy access to the city's attractions.
The two-bedroom, two-bathroom property boasts a private rooftop deck with a Weber grill, a state-of-the-art kitchen with a built-in bar, and in-unit laundry facilities; parking is available.
Walk To Wrigley Field/monthly Discounts Available - Chicago, IL
9.8 207 reviews

Walk To Wrigley Field/monthly Discounts Available

apartment, Chicago
This apartment is located in Lakeview, a lively neighbourhood just a short walk from Wrigley Field and across the street from the Metro, with easy access to the city's attractions. It has been highly rated by previous guests for its comfortable accommodation and excellent location.
The apartment has three bedrooms and one bathroom, comfortably accommodating up to six guests. The kitchen is equipped with a fridge, microwave oven, and dishwasher, and the property also offers a terrace/balcony, garden, parking, and air conditioning.
3br Luxury Suite W/gym And Balcony - Chicago, IL
9.6 35 reviews

3br Luxury Suite W/gym And Balcony

apartment, Chicago
This three-bedroom Chicago apartment, located in the downtown area within 1.6km of State Street, Michigan Avenue, and Water Tower Place, offers easy access to major attractions and public transport.
The 139 square metre dwelling boasts three bathrooms, sleeps eight guests, and includes a fully equipped kitchen, in-unit laundry, and access to a fitness centre; nearby activities include exploring Lake Michigan and the Chicago Riverwalk (within 3.2km).

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 Magnificent Milestone (Rooftop Deck  Gym) - Chicago, IL
9.5 470 reviews

The Magnificent Milestone (Rooftop Deck Gym)

apartment, Chicago
This two-bedroom Chicago apartment boasts an exceptional downtown location, within walking distance of Millennium Park, Navy Pier, and the Riverwalk, and just a short distance from an 'L' train station, offering easy access to the city's many attractions.
The spacious flat features two queen beds, a sofa bed, and an air mattress, accommodating multiple guests, alongside a fully equipped kitchen (fridge, freezer, microwave, dishwasher), high-speed Wi-Fi, Roku, and access to building amenities including a fitness centre and parking.
Newly Updated Vintage 6 Bedroom Single Family Home - Chicago, IL
9.2 23 reviews

Newly Updated Vintage 6 Bedroom Single Family Home

apartment, Chicago
This Near West Side flat, a 10-minute (1.6km) drive from Chicago's city centre and close to Little Italy, offers easy access to the West Loop/Fulton Market district and major attractions such as Millennium Park and the Art Institute of Chicago.
The 167 square metre property sleeps twelve guests in six bedrooms, two bathrooms, and boasts a fully equipped kitchen, private parking, a terrace, and a garden.
Large 4br/3ba Unit Near Field Museum & Mccormick - Chicago, IL
9.5 11 reviews

Large 4br/3ba Unit Near Field Museum & Mccormick

apartment, Chicago
This four-bedroom flat in Chicago's South Loop offers excellent access to downtown attractions, being 1.3 to 1.6 kilometres from McCormick Place and close to the Museum Campus.
This spacious residence accommodates ten guests with four private bedrooms, three bathrooms, a fully equipped kitchen, and in-unit laundry, plus building amenities including a fitness centre and Wi-Fi.
Sunflower Apt 10 Min From Downtown Chicago - Sleeps Up To 6 - Chicago, IL
8.6 21 reviews

Sunflower Apt 10 Min From Downtown Chicago - Sleeps Up To 6

apartment, Chicago
This Chicago apartment rental is situated in Brighton Park, a residential neighbourhood on the city's Far South Side, approximately 5 kilometres from Little Italy, Chinatown, and the city centre.
The 60 square metre flat comprises two bedrooms, one bathroom, and sleeps six guests, offering a full kitchen, laundry facilities, two smart TVs, and free high-speed Wi-Fi; nearby attractions include Sox Park and, slightly further afield, Millennium Park and Soldier Field.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday apartments with air conditioning

Private Logan Square Garden Apt - Chicago, IL
9.9 118 reviews

Private Logan Square Garden Apt

house, Chicago
This Chicago garden flat is located in the West Logan Square neighbourhood, three blocks (approximately 0.24 kilometres) from the western entrance to the 606 Trail.
The self-contained unit, sleeping two guests, features a queen-size bed, well-equipped kitchen with full-sized appliances, a private garden, parking, and fast Wi-Fi; nearby attractions include North and Pulaski avenues' restaurants and cafes.
Guest Nest Oak Park 321_1 - Chicago, IL
9.8 71 reviews

Guest Nest Oak Park 321_1

apartment, Oak Park
This stylish flat is located in a mid-century building in Oak Park, just a short walk from the town centre, Forest Park and the Oak Park Historical Districts. The property has excellent ratings for location, cleanliness and user experience.
The two-bedroom apartment is 70 square metres and comes with a fully equipped kitchen, a private patio, a garden and free parking. Guests can enjoy a range of amenities including free Wi-Fi, air conditioning and a shared laundry.
Inspiring Stone Grotto Sleeps 10-20 & Free Parking - Chicago, IL
9.9 265 reviews

Inspiring Stone Grotto Sleeps 10-20 & Free Parking

apartment, Chicago
This spacious four-bedroom apartment is situated in East Lakeview, just two blocks from Lake Michigan and Lincoln Park, offering easy access to the city's attractions and public transport. It has consistently received excellent ratings for location, cleanliness and overall experience.
The property is a unique blend of modern amenities and historical charm, housed in a historic 1893 building. Guests can enjoy the fully equipped kitchen, large TV, Wi-Fi, a private garage, and a spacious backyard, perfect for relaxing or enjoying outdoor activities.
2br Fitness Pad  Private Gym  Sleeps 7 - Chicago, IL
8.6 7 reviews

2br Fitness Pad Private Gym Sleeps 7

apartment, Chicago
This Irving Park flat offers convenient access to Michigan Avenue and State Street for shopping, and is a short distance from Lake Michigan and Millennium Park, approximately 6.4 kilometres away.
This pet-friendly two-bedroom flat accommodates up to seven guests, featuring a fully equipped kitchen, free Wi-Fi, central air conditioning, an on-site washer and dryer, and a dedicated indoor gym with various equipment.
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