Vacation 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

5 Bedroom Huge House In Best Location Parking Fireplace Back Yard - Chicago, IL
9.6 269 reviews
Chicago, IL
05/11 – 06/11
A$1534/nightfor 1 night

5 Bedroom Huge House In Best Location Parking Fireplace Back Yard

5 2
house , Chicago
This five-bedroom home is located in Chicago's Old Town district, a short walk from North Avenue Beach, Oak Street Beach, and Lincoln Park Zoo. The property has received excellent ratings for location, cleanliness, and user experience.
This spacious dwelling covers 279 square metres and offers a range of amenities, including a fully-equipped kitchen, a private terrace, a garden, a spa, a restaurant, a fitness centre, and free parking.
Inner-city Experience, Next Stop! - Chicago, IL
10 104 reviews
Chicago, IL
17/09 – 21/09
A$404/nighttotal: A$1616 (4 )

Inner-city Experience, Next Stop!

1 4
apartment , Chicago
This three-bedroom Chicago apartment is situated in the North Park neighbourhood, conveniently located near the Kedzie Brown Line station offering easy access to other areas of the city.
The property boasts a spacious layout sleeping five guests, includes a private backyard patio with grill, garage parking (suitable for vehicles under 5.5 metres), and a workspace with dual monitors – ideal for families or remote workers.
Modern 4br Pilsen Retreat Near Illinois Medical District & Chicago Downtown - Chicago, IL
10 2 reviews
Chicago, IL
23/06 – 25/06
A$889/nighttotal: A$1778 (2 )

Modern 4br Pilsen Retreat Near Illinois Medical District & Chicago Downtown

4 10
apartment , Chicago
This 4-bedroom flat in Pilsen is situated 3.9 kilometres from Union Station, providing straightforward access to the Illinois Medical District and downtown Chicago.
This family-friendly property offers 10 square metres of floor area, accommodates up to 19 guests, and includes a kitchen with a dishwasher, a fitness room, a garden, and parking.
Lincoln Park Gem - Chicago, IL
9.7 205 reviews
Chicago, IL
17/12 – 22/12
A$323/nighttotal: A$1615 (5 )

Lincoln Park Gem

3 2
apartment , Chicago
This Lincoln Park flat is ideally situated in Chicago, approximately 2.4 kilometres from Wrigley Field and Lincoln Park Zoo, and a similar distance from Fullerton and North Avenue Beaches.
The three-bedroom, one-bathroom property boasts a balcony with garden views, a fully equipped kitchen, free Wi-Fi, and access to on-site amenities including a tennis court, children's play areas, and a snack bar; parking is also available.

Best Chicago, IL holiday rentals with parking

Avondale Condo Near Classic Bars, Eateries, And More! Condo - Chicago, IL
Chicago, IL
23/07 – 27/07
A$494/nighttotal: A$1976 (4 )

Avondale Condo Near Classic Bars, Eateries, And More! Condo

3 2
apartment , Chicago
This Avondale flat offers a Chicago stay, situated 3 kilometres from Wrigley Field and 4.4 kilometres from Lincoln Park Zoo.
This 102 square metre, three-bedroom condominium accommodates up to nine guests and features a fully equipped kitchen, private entrance, on-site garden and free WiFi.
Chic 2 Br 1 Parking Sleeps 6 - Chicago, IL
9.8 7 reviews
Chicago, IL
28/07 – 03/08
A$1081/nighttotal: A$6486 (6 )

Chic 2 Br 1 Parking Sleeps 6

2 5
apartment , Chicago
This Chicago apartment near the United Centre offers convenient access to Union Station, DePaul University, and attractions such as Cloud Gate and the Willis Tower, all within a few kilometres.
The 106-square-metre property features two bedrooms, two bathrooms, sleeps up to six guests, and includes a fully equipped kitchen, private patio, and free Wi-Fi.
Jeffjack Heated Pool Penthouse In Chicago's West Loop - Chicago, IL
9.6 145 reviews
Chicago, IL
27/06 – 30/06
A$1529/nighttotal: A$4587 (3 )

Jeffjack Heated Pool Penthouse In Chicago's West Loop

2 2
apartment , Chicago
This penthouse apartment is conveniently located in the centre of Chicago, within easy walking distance of Union Station, Willis Tower, and CIBC Theatre. The apartment consistently receives excellent ratings for its location, cleanliness, and overall experience, making it a popular choice for travellers.
The apartment has two bedrooms, comfortably accommodating up to six guests. Enjoy a range of amenities including a rooftop pool, fitness centre, and private parking, as well as a fully equipped kitchen and balcony with stunning city views.
Chicago Charm - Chicago, IL
9.8 71 reviews
Chicago, IL
05/07 – 10/07
A$383/nighttotal: A$1915 (5 )

Chicago Charm

3 2
apartment , Chicago
This Chicago apartment is conveniently located near Loyola University, approximately 6.4 kilometres from Wrigley Field, offering easy access to other city attractions.
This three-bedroom, two-bathroom flat boasts 125 square metres of space, sleeping up to 11 guests and featuring free private parking, Wi-Fi, and a fully equipped kitchen with a dishwasher; outdoor seating is also available.

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, formerly known as the Sears Tower, for incredible views of the city. A trip to Millennium Park is a must, with the Cloud Gate sculpture, affectionately known as 'The Bean', and the Crown Fountain. And don't forget to take a stroll along Navy Pier, enjoying the Ferris wheel and the bustling atmosphere.
  • 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, consider staying in the trendy Wicker Park or Bucktown neighbourhoods. If you prefer a quieter experience with easy access to the city centre, the Lincoln Park area is a good choice. For a more budget-friendly option, check out the Logan Square neighbourhood.
  • 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 Lincoln Park Zoo is a fantastic free attraction with a wide variety of animals. The Shedd Aquarium is a must-visit for families, with interactive exhibits and fascinating marine life. The Field Museum, with its dinosaur exhibits and cultural displays, is also a popular choice for 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?

    To secure the best deals and availability, it's best to book your vacation rental in Chicago at least 3-4 months in advance, particularly during peak season, which runs from May to September. If you're flexible with your travel dates, you might find better deals outside of peak season.
  • 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?

    Chicago is known for its lively events scene. The Chicago Blues Festival in June is a highlight for music lovers. The Taste of Chicago in July offers a culinary journey through the city's diverse food scene. The Lollapalooza music festival in August attracts crowds with its eclectic lineup of artists.
  • 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 free walking tour to explore the city's history and architecture. Visit the Art Institute of Chicago on Tuesdays, when admission is free after 5 pm. Enjoy a picnic in Millennium Park, taking in the views and the atmosphere.
  • What are the best restaurants with local dishes in Chicago, IL?

    For classic Chicago-style deep-dish pizza, try Lou Malnati's or Pizzeria Bebu. For a taste of the city's Polish heritage, visit the iconic Old Town Restaurant. If you're looking for a unique dining experience, try the Chicago-style hot dog at Portillo's.
  • What are the best walking or cycling routes in Chicago, IL?

    The Lakefront Trail offers stunning views of Lake Michigan and is perfect for both walking and cycling. The 606 Bloomingdale Trail, a former railway line transformed into a park, is a popular cycling route. For a scenic walk, explore the Lincoln Park Zoo and its surrounding area.
  • Are there pet-friendly attractions in Chicago, IL?

    Many parks and attractions in Chicago are pet-friendly. The Lincoln Park Zoo welcomes well-behaved dogs on a leash. Navy Pier also allows dogs in designated areas. Check the specific attraction's website for their pet policy.
  • What are the benefits of choosing a vacation rental in Chicago, IL?

    Vacation rentals offer more space and privacy compared to hotels. They often come with kitchen facilities, allowing you to prepare your own meals and save on dining costs. Many rentals also feature unique local charm and character.
  • What are the top sports attractions and facilities in Chicago, IL?

    Chicago is a sports city! Catch a game at Wrigley Field, home to the Chicago Cubs baseball team. The United Center is home to the Chicago Bulls basketball team and the Chicago Blackhawks hockey team. Soldier Field is the home of the Chicago Bears football team.

Destinations nearby

Best Chicago, IL holiday rentals with a balcony

Pilsen Art Center Family Friendly 3br Retreat With Free Parking Near Medical District, Douglas Park And University Illinois Chicago - Chicago, IL
10 1 review
Chicago, IL
12/08 – 05/09
A$491/nighttotal: A$11784 (24 )

Pilsen Art Center Family Friendly 3br Retreat With Free Parking Near Medical District, Douglas Park And University Illinois Chicago

3 2
apartment , Chicago
This three-bedroom apartment in Chicago's Pilsen neighbourhood is situated approximately 3.2 kilometres from the United Centre and 7.2 kilometres from Union Station, Grant Park, and the CIBC Theatre.
The 139-square-metre property features two bathrooms, a fully equipped kitchen, private parking, a terrace, garden, and accommodates up to 15 guests, offering free Wi-Fi and convenient access to public transport.
4br Old Town Chicago Loft | Walk To Wells St - Chicago, IL
10 121 reviews
Chicago, IL
02/07 – 05/07
A$1307/nighttotal: A$3921 (3 )

4br Old Town Chicago Loft | Walk To Wells St

4 2
apartment , Chicago
This four-bedroom apartment is situated in Chicago's SONO neighbourhood, just two blocks south of Chicago's "little Michigan Avenue" and within walking distance of the Magnificent Mile, Millennium Park, Navy Pier, and the city's finest museums.
This family-friendly apartment, with its 160 square metre floor area, offers a spacious open plan living area, a well-equipped kitchen, and a terrace, making it ideal for groups of up to 14 guests.
3-levels.11beds.sleeps 20. 10min Walk To Train. Rooftop+spa Bath+garage. - Chicago, IL
9.8 30 reviews
Chicago, IL
16/09 – 23/09
A$2587/nighttotal: A$18109 (7 )

3-levels.11beds.sleeps 20. 10min Walk To Train. Rooftop+spa Bath+garage.

5 14
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.
Lux Apts With Lake Views And Top Amenities - Chicago, IL
9.8 37 reviews
Chicago, IL
02/07 – 05/07
A$2101/nighttotal: A$6303 (3 )

Lux Apts With Lake Views And Top Amenities

2 2
apartment , Chicago
This Chicago apartment rental offers exclusive lake views and is centrally located near the Field Museum of Natural History, Grant Park, and DePaul University, approximately 16km from Midway International Airport.
The self-catering property features two bathrooms, a private terrace with a hot tub, a fully equipped kitchen, free Wi-Fi, air conditioning, and access to an indoor pool, jacuzzi, fitness centre, and parking including electric vehicle charging.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday rentals with air conditioning

New 2 Br/1 Bth, Free Parking, Near Lake & Loyola - Chicago, IL
9.9 109 reviews
Chicago, IL
04/08 – 10/08
A$446/nighttotal: A$2676 (6 )

New 2 Br/1 Bth, Free Parking, Near Lake & Loyola

1 3
apartment , Chicago
This brand new Rogers Park garden flat is located steps from Loyola University Chicago and a few blocks (approximately 0.8 km) from Lake Michigan beaches, offering easy access to downtown Chicago via the Red Line.
The 2-bedroom, 1-bathroom self-catering property sleeps six guests and features a well-equipped kitchen, keyless entry, free on-site parking, and a shared patio with a hammock; nearby activities include exploring the lakefront and visiting the university campus.
Beautiful Chicago Greystone - Chicago, IL
9.9 132 reviews
Chicago, IL
25/06 – 27/06
A$572/nighttotal: A$1144 (2 )

Beautiful Chicago Greystone

1 5
apartment , Chicago
This spacious four-bedroom Chicago apartment is situated in a prime West Side location, approximately 2.4km west of Chicago's city centre, close to the West Loop, Garfield Park Conservatory, and the United Centre.
The 4-bedroom condo, sleeping up to nine guests, features a fully equipped kitchen (fridge, freezer, microwave), a garden, on-site parking, and excellent guest reviews; access is via stairs only.
Lincoln Park Getaway Chicago Subwaythemed Unit 2 - Chicago, IL
9.3 55 reviews
Chicago, IL
09/10 – 11/10
A$701/nighttotal: A$1402 (2 )

Lincoln Park Getaway Chicago Subwaythemed Unit 2

1 1
apartment , Chicago
This Lincoln Park flat on Southport Avenue, Chicago, is 2.4km from Wrigleyville, 4.8km from Michigan Avenue, and 0.8km from DePaul University.
The one-bedroom apartment, sleeping up to eight guests (with additional fees), boasts a Chicago-themed interior, a two-player arcade machine, VIP access to the Broken Barrel restaurant, and free Wi-Fi with a Netflix-enabled Amazon Fire Stick.
Spacious Arcade Apt For 12 Guests 10 Min Downtown - Chicago, IL
9.6 49 reviews
Chicago, IL
03/08 – 08/08
A$317/nighttotal: A$1585 (5 )

Spacious Arcade Apt For 12 Guests 10 Min Downtown

3 5
apartment , Chicago
This 100-square-metre flat in Chicago is situated 5.6 kilometres southwest of the city centre, a 15-minute drive from Millennium Park and Soldier Field, and offers convenient access to public transport for exploring the city.
Accommodating up to 12 guests, this residence boasts three bedrooms, a fully equipped kitchen, in-unit laundry, and entertainment options including four Smart TVs and classic games, with a pac-n-play available for families with infants.
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