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

Fully Furnished Extended Stay Work Or Insurance In Chicago - Chicago, IL
8.5 14 reviews
Chicago, IL
19/09 – 05/10
NZ$268/nighttotal: NZ$4288 (16 )

Fully Furnished Extended Stay Work Or Insurance In Chicago

2 4
apartment , Chicago
This flat is located in a Chicago neighbourhood, approximately 9.2 kilometres from the United Centre and 12.6 kilometres from Willis Tower.
This 28 square metre flat offers two bedrooms, a living room, and a kitchen equipped with a fridge and microwave, accommodating up to seven guests with free on-site parking and complimentary WiFi.
Uptown Gem - Chicago, IL
9.7 29 reviews
Chicago, IL
12/09 – 14/09
NZ$807/nighttotal: NZ$1614 (2 )

Uptown Gem

1 2
apartment , Chicago
The Uptown Gem apartment is situated in Chicago's Uptown neighbourhood, a short walk from Montrose Beach and Foster Beach, offering easy access to both the city and the lakefront. This apartment has consistently received excellent ratings for location, cleanliness, and user experience, ensuring a comfortable and enjoyable stay.
The apartment comes with one bedroom and one bathroom, spanning 42 square metres, providing ample space for a comfortable stay. It offers a range of amenities, including a fully equipped kitchen, a balcony with city views, a swimming pool, a fitness centre, and a restaurant, making it ideal for a relaxing and enjoyable trip to Chicago.
Giant 5br W/ Pool Table, 15 Min To Cubs & Mag Mile - Chicago, IL
10 6 reviews
Chicago, IL
24/07 – 26/07
NZ$2490/nighttotal: NZ$4980 (2 )

Giant 5br W/ Pool Table, 15 Min To Cubs & Mag Mile

1 14
apartment , Chicago
This substantial five-bedroom residence in Chicago's Irving Park district offers convenient access to major attractions, situated a 15-25 minute Uber journey from landmarks such as Wrigley Field, the city centre, The Bean sculpture, Soldier Field, the United Center, and the Riverwalk.
This early 1900s Craftsman Foursquare property accommodates up to 14 guests with its five bedrooms featuring hotel-quality bedding, three bathrooms, a fully equipped kitchen with a large peninsula, and a dedicated games room complete with a pool table and a 75-inch smart television, all supported by high-speed Wi-Fi.
Level One Bedroom Suite | Fulton Market - Chicago, IL
9.3 31 reviews
Chicago, IL
24/12 – 26/12
NZ$525/nighttotal: NZ$1050 (2 )

Level One Bedroom Suite | Fulton Market

1 2
apartment , Chicago
This West Loop studio apartment is ideally situated in Chicago's Fulton Market district, offering easy access to the city's many attractions.
The self-catering apartment sleeps three guests and boasts a fully equipped kitchen (fridge, freezer, microwave, dishwasher), a private bathroom, plus access to a swimming pool, Jacuzzi, fitness centre, and parking (additional nightly fees apply).

Best Chicago, IL holiday rentals with parking

Cozy 2bd 2ba Apt! Steps To Lake With Gym & Parking - Chicago, IL
Chicago, IL
27/06 – 04/07
NZ$590/nighttotal: NZ$4130 (7 )

Cozy 2bd 2ba Apt! Steps To Lake With Gym & Parking

2 2
apartment , Chicago
This flat is situated in Chicago's Edgewater district, offering convenient access to the Granville Red Line, Loyola University, lakefront attractions, and parks, with Lake Michigan and its beaches approximately 0.5 kilometres away.
This 93 square metre residence accommodates up to four guests in two bedrooms and features a fully equipped kitchen, in-unit laundry, air conditioning, and a complimentary garage parking spot, with the CTA Red Line just a short walk away for easy travel.
1911 Home For Beautiful Family Moments! - Chicago, IL
9.5 53 reviews
Chicago, IL
28/08 – 02/09
NZ$1099/nighttotal: NZ$5495 (5 )

1911 Home For Beautiful Family Moments!

1 13
apartment , Maywood
This spacious Maywood house, sleeping 14, offers four bedrooms with six queen-size beds and two bathrooms, plus a large basement recreation area; ample parking is available.
The property boasts a well-equipped kitchen, a private backyard, and convenient access points, making it ideal for large families or groups visiting Maywood.
West Loop - City Views With In & Out Parking 6 - Chicago, IL
9.7 4 reviews
Chicago, IL
02/08 – 03/08
NZ$1395/nightfor 1 night

West Loop - City Views With In & Out Parking 6

1 2
apartment , Chicago
This West Loop flat offers expansive city views and is situated a 15-minute walk from the Willis Tower, 1.9 kilometres from DePaul University, and 2.1 kilometres from the CIBC Theatre.
This 125-square-metre residence features four bedrooms, four bathrooms, a fully equipped kitchen, and complimentary WiFi, accommodating up to fifteen guests with on-site parking available.
1 #33 - 4 Bedroom / 2 Bath Condo Near Mccormick Place, Wintrust Arena, Chinatown - Chicago, IL
10 16 reviews
Chicago, IL
09/10 – 12/10
NZ$1117/nighttotal: NZ$3351 (3 )

1 #33 - 4 Bedroom / 2 Bath Condo Near Mccormick Place, Wintrust Arena, Chinatown

4 2
apartment , Chicago
This four-bedroom apartment is situated in Chicago's Chinatown district, just a short distance from the city centre, McCormick Place and popular attractions such as the Art Institute of Chicago.
This spacious apartment sleeps up to 20 guests and features a fully equipped kitchen, in-unit laundry facilities, a 55-inch flat-screen TV and high-speed Wi-Fi, ideal for both families and groups of friends.

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

1 Garage Parking/skyline Rooftop/pingpong/balcony - Chicago, IL
10 2 reviews
Chicago, IL
21/06 – 24/06
NZ$1037/nighttotal: NZ$3111 (3 )

1 Garage Parking/skyline Rooftop/pingpong/balcony

2 6
apartment , Chicago
This West Loop apartment is ideally situated 0.5km from Fulton Market and within 1.3-1.6km of Chicago's Millennium Park and Navy Pier.
This 111 square metre Chicago flat boasts two bedrooms, two bathrooms, sleeps eight guests, and includes a fully equipped kitchen, in-unit laundry, and a private balcony with stunning city views; heated garage parking is also provided.
Modern Home Near Rosemont Allstate Arena O'hare Home - Chicago, IL
Chicago, IL
03/08 – 12/08
NZ$572/nighttotal: NZ$5148 (9 )

Modern Home Near Rosemont Allstate Arena O'hare Home

3 2
house , Des Plaines
This modern three-bedroom holiday home in Des Plaines is situated just 966 metres from Chicago O'Hare International Airport, offering convenient access to Chicago city centre attractions including Loyola University Chicago (19 kilometres) and Wrigley Field (21 kilometres).
This spacious 102 square metre property comfortably accommodates up to 11 guests, boasting a fully equipped kitchen with a dishwasher, complimentary WiFi, air conditioning, a garden, and on-site yoga classes.
Sleep 25 - Huge Downtown Vintage Lofts - Chicago, IL
9.5 998 reviews
Chicago, IL
30/07 – 13/08
NZ$5854/nighttotal: NZ$81956 (14 )

Sleep 25 - Huge Downtown Vintage Lofts

5 2
apartment , Chicago
This penthouse flat is located in downtown Chicago, just a short walk from Millennium Park, Grant Park, the Skydeck, Shedd Aquarium, and Adler Planetarium. The property has received excellent ratings for location, cleanliness, and overall user experience.
The apartment features a spacious loft design with high ceilings, offering a sense of openness and grandeur. Guests can enjoy a well-equipped kitchen, a private balcony with city views, a fitness centre, a tennis court, and parking facilities.
Irving Park/avondale Updated Vintage Top Unit In 2-flat - Chicago, IL
9.4 3 reviews
Chicago, IL
05/07 – 10/07
NZ$417/nighttotal: NZ$2085 (5 )

Irving Park/avondale Updated Vintage Top Unit In 2-flat

2 2
apartment , Chicago
This Irving Park flat is situated 2.4 kilometres from Milwaukee Avenue, offering easy access to the Addison and Irving Park Blue Line stations and is within 9.6 kilometres of Wrigley Field and the Walt Disney House.
The two-bedroom, one-bathroom apartment sleeps six, features a terrace, fully equipped kitchen including a dishwasher, free Wi-Fi, and on-site barbecue facilities.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday rentals with air conditioning

Stylish Avondale 3bed 2 Bath With Parking - Chicago, IL
9.8 144 reviews
Chicago, IL
02/07 – 06/07
NZ$632/nighttotal: NZ$2528 (4 )

Stylish Avondale 3bed 2 Bath With Parking

1 5
apartment , Chicago
This three-bedroom, two-bathroom Chicago apartment is situated in Avondale, a neighbourhood close to the Blue Line ‘L’ train and easily accessible to Logan Square, Bucktown, and Wicker Park.
The 6-guest property boasts a well-equipped kitchen, two televisions, and a large dining table; nearby attractions include numerous bars and restaurants, plus easy access to Chicago's brewing and distilling scene.
2br Apt Near Rosemont & O'hare, Private Deck - Chicago, IL
10 26 reviews
Chicago, IL
27/08 – 30/08
NZ$376/nighttotal: NZ$1128 (3 )

2br Apt Near Rosemont & O'hare, Private Deck

1 1
apartment , Chicago
This Norwood Park apartment, situated in Chicago's Northwest Side with easy access to O'Hare International Airport and Park Ridge, offers convenient transport links to the city centre.
The two-bedroom, one-bathroom flat sleeps four, boasts a private patio with barbecue, a Peloton bike, and is equipped with a fridge, freezer, microwave, and dishwasher.
Bucktown Brick Cottage Apartment - Chicago, IL
9.9 148 reviews
Chicago, IL
25/11 – 29/11
NZ$354/nighttotal: NZ$1416 (4 )

Bucktown Brick Cottage Apartment

1 4
apartment , Chicago
This Bucktown apartment, a 1.6km walk from the Blue Line 'L' train offering easy access to the Chicago Loop, is conveniently located near parks, a public pool, and numerous bars and restaurants.
The one-bedroom flat sleeps four comfortably, featuring a California King-size bed, a pull-out sofa bed, a fully equipped kitchen including fridge, freezer and microwave, and free internet access; nearby grocery stores ensure convenience.
Chic 2 Br, 1 Parking, Sleeps 6! - Chicago, IL
9.8 57 reviews
Chicago, IL
03/07 – 05/07
NZ$745/nighttotal: NZ$1490 (2 )

Chic 2 Br, 1 Parking, Sleeps 6!

1 4
apartment , Chicago
This West Loop apartment, a five-minute walk from the West Loop neighbourhood and within 1.6 to 2.4km of attractions such as Millennium Park, offers a convenient base for exploring Chicago.
This two-bedroom, two-bathroom flat sleeps six guests comfortably, boasting a fully equipped kitchen with a Keurig coffee machine, in-unit laundry, smart TVs, private parking, and a patio; nearby activities include visiting the Art Institute of Chicago, Navy Pier, and the Field Museum.
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