Holiday Rentals in Chicago, IL

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Chicago, IL holiday rentals
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10119 Holiday Rentals and Airbnb in Chicago, IL

Best family friendly Chicago, IL holiday rentals

Among the 10119 accommodations in Chicago, IL, here are the 4 best family friendly rentals

Comfortable And Trendy Design 1br In Lincoln Square - Chicago, IL
9.0 9 reviews
Chicago, IL
31/07 – 12/08
NZ$722/nighttotal: NZ$8664 (12 )

Comfortable And Trendy Design 1br In Lincoln Square

1 1
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.
Spacious 5br Luxury Suite Perfect For Group Sleeps 12 Near Mccormick Place, Grant Park And Soldier Field - Chicago, IL
Chicago, IL
14/08 – 16/08
NZ$2331/nighttotal: NZ$4662 (2 )

Spacious 5br Luxury Suite Perfect For Group Sleeps 12 Near Mccormick Place, Grant Park And Soldier Field

5 9
apartment , Chicago
This luxury Chicago apartment, situated approximately 2.4 kilometres from the Field Museum and within 3.2 kilometres of the Art Institute of Chicago and the Chicago Symphony Orchestra, offers easy access to the city's cultural attractions.
The 214-square-metre property boasts a spacious five-bedroom, four-bathroom layout sleeping up to 12 guests, complete with a fully equipped kitchen, fitness centre access, free Wi-Fi, and a patio offering city views.
Chic Suite/mins To L Train /Laundry/free Parking - Chicago, IL
9.4 148 reviews
Chicago, IL
25/06 – 27/06
NZ$324/nighttotal: NZ$648 (2 )

Chic Suite/mins To L Train /Laundry/free Parking

1 1
apartment , Oak Park
This Oak Park studio apartment is situated near the ‘L’ train, offering convenient access to Chicago city centre and is within walking distance of the Frank Lloyd Wright Home and Studio and the Ernest Hemingway Museum.
The self-contained apartment sleeps up to five guests in a queen bed, sofa bed and roll-away bed, boasting a fully equipped kitchen, ultra-fast Wi-Fi, in-unit laundry, and a 4K Smart TV with streaming services; free parking is also available.
The Penthouse At Grand Plaza - Chicago, IL
9.7 358 reviews
Chicago, IL
10/07 – 14/07
NZ$1097/nighttotal: NZ$4388 (4 )

The Penthouse At Grand Plaza

1 4
aparthotel , Chicago
This 4-star serviced apartment is located in downtown Chicago, just a short walk from the Magnificent Mile, Navy Pier, and Millennium Park. It has received excellent user ratings for its location, cleanliness, and overall experience.
The apartment features two bedrooms, three bathrooms, a fully equipped kitchen, and a spacious living area. Guests can enjoy a range of amenities including a rooftop swimming pool, a fitness centre, and a basketball court.

Best Chicago, IL holiday rentals with parking

The Banksy-king Bed-firepit-rooftop-united Center - Chicago, IL
10 5 reviews
Chicago, IL
01/07 – 06/07
NZ$1770/nighttotal: NZ$8850 (5 )

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

4 11
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.
Cozy 2br/1ba Garden Apartment Near Lincoln Square - Chicago, IL
9.3 338 reviews
Chicago, IL
04/12 – 09/12
NZ$293/nighttotal: NZ$1465 (5 )

Cozy 2br/1ba Garden Apartment Near Lincoln Square

2 2
apartment , Chicago
This garden-level flat is situated near Lincoln Square, a lively neighbourhood in Chicago, with a 5-minute walk to the Brown Line and easy access to local attractions. The property has received excellent ratings for location, cleanliness, and overall user experience.
This two-bedroom home comfortably accommodates up to five guests and features a spacious living/dining area, a sunroom, and a fully equipped kitchen. The flat offers a shared laundry, free street parking, and Apple TV access, ensuring a comfortable and convenient stay.
Walk To Wrigley/ Boystown -Chicago 3br/2ba Duplex-paid Parking Available! - Chicago, IL
9.0 132 reviews
Chicago, IL
02/10 – 04/10
NZ$1008/nighttotal: NZ$2016 (2 )

Walk To Wrigley/ Boystown -Chicago 3br/2ba Duplex-paid Parking Available!

3 6
apartment , Chicago
This Lakeview, Chicago flat is a short walk from Wrigley Field and offers easy access to Boystown, Southport Corridor, and public transport.
The three-bedroom, two-bathroom duplex sleeps eight, features keyless entry, Wi-Fi, a smart TV, and a garden, plus nearby access to Lake Michigan, Millennium Park (accessible via public transport), and various water sports.
Comfortable Living, Within Reach! - Chicago, IL
Chicago, IL
18/09 – 19/09
NZ$1542/nightfor 1 night

Comfortable Living, Within Reach!

2 2
apartment , Oak Park
This Oak Park flat is located 8.5 kilometres from the United Centre, providing easy access to downtown Chicago landmarks within an 8.5-kilometre radius and is 9.9 kilometres from Midway International Airport.
This one-bedroom flat offers accommodation for up to 11 guests, featuring air conditioning, complimentary Wi-Fi, a fully equipped kitchen with a dishwasher and oven, and an in-unit washing machine, with parking available and pets permitted.

Frequently asked questions about holiday rentals in Chicago, IL

  • What should a first-time visitor not miss in Chicago, IL?

    You've got to see the iconic Willis Tower, take a boat trip on the Chicago River, and wander around Millennium Park, where you'll find the famous Cloud Gate sculpture, nicknamed 'The Bean'.
  • What are the best Airbnb and holiday rentals in Chicago, IL?

  • What kind of vacation rentals can you find in Chicago?

    There's a wide range of vacation rental choices in Chicago to choose from, from houses to downtown apartments and penthouses.
  • Which neighborhood in Chicago, IL should you consider for a vacation rental?

    For a vibrant atmosphere, try Wicker Park or Bucktown. If you prefer a more relaxed vibe, Lincoln Park or Lakeview are great choices. You'll find plenty of options in each of these neighbourhoods.
  • What are the most popular Airbnbs in Chicago, IL?

  • What's the best one-day itinerary for Chicago?

    Kick things off Ferris Bueller style at the Art Institute of Chicago for some culture before heading over to "The Bean" at Millennium Park, making sure you leave the park via the BP Bridge, which will give you stunning views of the city's skyline. On the corner of Michigan Avenue and Randolph street, make sure you check out the Chicago Cultural Center for the stunning interior alone (the largest Tiffany stained-glass dome in the world is so worth it!). Cross through Grant Park and visit the Buckingham Fountain before heading south to the amazing Museum Campus, home to the Field Museum, Shedd Aquarium, and Adler Planetarium. Head up the Skydeck at Willis Tower (one of the world's tallest buildings) and if you dare, step on the ledge. Head over to the Chicago Riverwalk to find something to eat before hitting one of the famous jazz and blues clubs.
  • What are the top family-friendly attractions in Chicago, IL?

    The Shedd Aquarium is a must-see, especially for kids. Lincoln Park Zoo is free and has a variety of animals, and the Museum of Science and Industry is always a hit with families.
  • What are the best holiday rentals with a pool in Chicago, IL?

  • Where should you book a vacation rental in Chicago?

    It really depends on what you want. If you're want to be in the heart of the action, or it's your first visit to the Windy City, then book an apartment or a studio in the Chicago Loop downtown. However, some of the most popular places to book are Lincoln Park and Hyde Park when it comes to vacation rentals.
  • When is the best time to book a vacation rental in Chicago, IL?

    Summer is the peak season, so booking in advance is essential. You can often find good deals in the shoulder seasons, like spring or autumn, when the weather is still pleasant but crowds are smaller.
  • What are the best rentals for families and kids in Chicago, IL?

  • What are Chicago's special dishes you should try?

    You can't come to Chicago without trying some deep-dish pizza, a Chicago icon. However, there's plenty else to chow down on. Chicago had a large Italian community, so you can try some great Italian-American dishes. If you want something quick to go, grab a spicy Italian beef sandwich from a local street food joint.
  • What events or festivals should visitors check out in and around Chicago, IL?

    The Chicago Blues Festival in June is a great time to experience the city's musical heritage. The Taste of Chicago in July offers a chance to sample local cuisine, and Lollapalooza in August is a huge music festival.
  • What are the best rentals or Airbnbs with a jacuzzi in Chicago, IL?

  • What is sites are there to see in Chicago?

    There's plenty to keep you on your feet on your next trip to Chicago. If you're an art lover, make sure you pay a visit to the Art Institute of Chicago, which is home to more than 300,000 artworks! But if you want a view that's more than paintings, then get yourself to the top of 360 Chicago for panoramas over the city from this 1000-ft-high observation deck. Millennium Park with its futuristic-looking Cloud Gate (AKA the Bean), is great place to explore. And that's just to get you started!
  • What are the best budget-friendly activities in Chicago, IL?

    Take a stroll along the Lakefront Trail, visit the free museums on the Museum Campus, or explore the diverse neighbourhoods like Chinatown or Little Italy. These are all great ways to experience the city without breaking the bank.
  • What are the best restaurants with local dishes in Chicago, IL?

    For deep-dish pizza, try Lou Malnati's or Pizzeria Bebu. For Chicago-style hot dogs, try Portillo's or Superdawg. These are all classic Chicago eateries.
  • What are the best walking or cycling routes in Chicago, IL?

    The Lakefront Trail is a popular choice for both walking and cycling, offering stunning views of Lake Michigan. The 606, a former railway line, is now a great place for a scenic walk or bike ride through the city.
  • Are there pet-friendly attractions in Chicago, IL?

    Lincoln Park Zoo is very pet-friendly, allowing dogs on leashes in designated areas. Many restaurants and cafes also have outdoor seating that welcomes dogs.
  • What are the benefits of choosing a vacation rental in Chicago, IL?

    Vacation rentals often offer more space and privacy than hotels, and you can usually cook your own meals, saving money. They also tend to be located in more residential neighbourhoods, giving you a more authentic feel of the city.
  • What are the top sports attractions and facilities in Chicago, IL?

    Wrigley Field, home to the Chicago Cubs, is a must-visit for baseball fans. Soldier Field is home to the Chicago Bears, and the United Center hosts the Chicago Bulls and Blackhawks.

Destinations nearby

Best Chicago, IL holiday rentals with a balcony

Bucktown Condo Just Two Blocks From The L By Allset Turnover - Chicago, IL
10 14 reviews
Chicago, IL
07/10 – 14/10
NZ$1289/nighttotal: NZ$9023 (7 )

Bucktown Condo Just Two Blocks From The L By Allset Turnover

2 3
apartment , Chicago
This West Town flat is conveniently located near Damen Station, less than 3.2km from Humboldt Park and within 5km of both The Salt Shed and the United Centre.
The two-bedroom, one-bathroom apartment sleeps four guests and boasts a balcony, in-unit laundry, parking, and a fully equipped kitchen including a dishwasher; enjoy nearby Steppenwolf Theatre.
Bucktown Private Condo - Chicago, IL
9.3 41 reviews
Chicago, IL
22/07 – 25/07
NZ$942/nighttotal: NZ$2826 (3 )

Bucktown Private Condo

1 2
apartment , Chicago
This Bucktown condo, situated in Chicago's trendy Bucktown neighbourhood, is approximately 5km from Wrigley Field, 3.5km from Lincoln Park Zoo, and 4.5km from the United Centre.
The 106-square-metre property features two bedrooms, one bathroom, sleeps seven guests, and includes a fully equipped kitchen, terrace, garden, parking, and free Wi-Fi.
Quiet Comfort In The Big City, Just Steps To The Blue Line Apts - Chicago, IL
9.7 193 reviews
Chicago, IL
23/12 – 28/12
NZ$2390/nighttotal: NZ$11950 (5 )

Quiet Comfort In The Big City, Just Steps To The Blue Line Apts

2 2
apartment , Chicago
This two-bedroom flat is situated in Wicker Park, a trendy district just 1.6 kilometres from the bustling Milwaukee Avenue and Division Street, and a short walk from the Chicago Blue Line.
The property features an open plan living and kitchen area, a patio, a laundry room and can accommodate up to six guests, making it ideal for families or groups of friends.
Beautiful, Cozy, Stylish Bucktown, Wicker Park House, Perfect Chicago Location. - Chicago, IL
Chicago, IL
28/06 – 31/07
NZ$1482/nighttotal: NZ$48906 (33 )

Beautiful, Cozy, Stylish Bucktown, Wicker Park House, Perfect Chicago Location.

3 1
apartment , Chicago
This West Town family-friendly house, ideal for Chicago city breaks, is located less than 1.6km from The Salt Shed and Humboldt Park, and under 4.8km from both the United Centre and Michigan Avenue.
Sleeping up to 10 guests, this three-bedroom property boasts a fully equipped kitchen, balcony, garden, spa, concierge service, parking, and free Wi-Fi; nearby attractions include Damen and Division train stations.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday rentals with air conditioning

Cabin 104 By 747 Lofts - Chicago, IL
9.2 197 reviews
Chicago, IL
17/10 – 21/10
NZ$397/nighttotal: NZ$1588 (4 )

Cabin 104 By 747 Lofts

1 2
apartment , Chicago
This studio apartment is situated in Chicago's West Loop, just a short walk from Randolph Street's bustling restaurant scene and easily accessible to the city centre via the Blue Line "L" train. The studio enjoys excellent user, location and cleanliness ratings, making it a popular choice for travellers.
The apartment is ideal for couples or solo travellers and features a modern kitchen with a fridge and microwave oven. Guests can enjoy the convenience of in-unit laundry facilities, air conditioning, parking, and complimentary Wi-Fi.
Ace Properties - Chicago, IL
9.6 6 reviews
Chicago, IL
13/07 – 18/07
NZ$678/nighttotal: NZ$3390 (5 )

Ace Properties

2 4
apartment , Chicago
This Chicago apartment rental, near O'Hare International Airport, is conveniently located approximately 18 kilometres from the airport.
The 139-square-metre property boasts two bedrooms, two bathrooms, free private parking at Ace Properties, and comfortably sleeps up to 11 guests, featuring a fully equipped kitchen.
Best Of "Little Village" - Chicago, IL
9.5 162 reviews
Chicago, IL
09/09 – 12/09
NZ$267/nighttotal: NZ$801 (3 )

Best Of "Little Village"

1 2
apartment , Chicago
This Little Village flat is situated in a historic red-brick building in Chicago, offering easy access to the city's attractions, though precise distances require further information.
The one-bedroom, one-bathroom apartment sleeps two guests and features a newly renovated interior with a queen-size bed, full kitchen, in-unit laundry, and air conditioning.
Blueground | Streeterville, Pool & Gym, Nr Pier - Chicago, IL
10 1 review
Chicago, IL
24/06 – 24/12
NZ$297/nighttotal: NZ$54351 (183 )

Blueground | Streeterville, Pool & Gym, Nr Pier

1 2
apartment , Chicago
This Streeterville apartment in Chicago offers a central location, close to many attractions such as Navy Pier and Millennium Park.
The one-bedroom flat sleeps two, features a fully equipped kitchen, including a dishwasher, and boasts a swimming pool and fitness centre within the building, plus a smart TV and premium wireless speaker.
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