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

Spacious Brookfield Home Near Zoo  Sleeps 10. Walk To Metra - Chicago, IL
8.8 3 reviews
Chicago, IL
14/08 – 16/08
A$743/nighttotal: A$1486 (2 )

Spacious Brookfield Home Near Zoo Sleeps 10. Walk To Metra

4 10
apartment , Brookfield
This Brookfield residence is situated in the town centre, a short distance from Brookfield Zoo and 30 minutes from downtown Chicago, with convenient access to the Metra station.
This four-bedroom flat, spanning 186 square metres, accommodates up to 12 guests and features a fully equipped kitchen, a private outdoor space with a grill, and is located near walking trails and a golf course.
Comfy Bed/free Parking&wifi /Nearhosp/ord/mdw/dt - Chicago, IL
9.4 21 reviews
Chicago, IL
27/06 – 04/07
A$277/nighttotal: A$1939 (7 )

Comfy Bed/free Parking&wifi /Nearhosp/ord/mdw/dt

1 2
apartment , Oak Park
This one-bedroom flat is located just 5 kilometres from Oak Park, offering easy access to its charming downtown, Frank Lloyd Wright's homes, and the Hemingway District. The property has received excellent user ratings, highlighting its appeal to travellers.
The flat is ideal for families or groups of up to 5 people, with a comfortable living area and a fully equipped kitchen. Amenities include air conditioning, parking, internet access, and a range of entertainment options, ensuring a comfortable and enjoyable stay.
Sweet Home Oak Park - Chicago, IL
9.7 60 reviews
Chicago, IL
02/07 – 03/07
A$625/nightfor 1 night

Sweet Home Oak Park

1 5
apartment , Oak Park
This Oak Park apartment rental is conveniently located near Oak Park train station, offering easy access to Chicago city centre.
The three-bedroom, two-bathroom property sleeps six, includes in-unit laundry, free parking, and a private porch and yard, all within walking distance of local pubs and coffee shops.
Boho House - A Chic, 1903 Chicago Workers Cottage - Chicago, IL
10 20 reviews
Chicago, IL
02/08 – 14/08
A$831/nighttotal: A$9972 (12 )

Boho House - A Chic, 1903 Chicago Workers Cottage

3 3
apartment , Chicago
This charming three-bedroom cottage is located in Avondale, a neighbourhood just 10 minutes from downtown Chicago, offering easy access to the city's attractions and amenities. It has consistently received excellent reviews from previous guests.
The cottage is perfect for families or groups of up to eight people, with a private backyard and a cosy fireplace for relaxing evenings. Guests can enjoy free coffee, fast internet, and parking for two vehicles, as well as a fully equipped kitchen and a peaceful garden.

Best Chicago, IL holiday rentals with parking

The Urban Oasis | Outdoor Lounge • Sleeps 10+ - Chicago, IL
9.9 164 reviews
Chicago, IL
19/08 – 23/08
A$1355/nighttotal: A$5420 (4 )

The Urban Oasis | Outdoor Lounge • Sleeps 10+

1 10
apartment , Chicago
This modern four-bedroom apartment in Pilsen is a 5-minute drive from downtown Chicago, close to attractions like Millennium Park and the United Center, and within easy walking distance of Chinatown and Little Italy. The apartment has received excellent ratings for location, cleanliness and overall experience.
The spacious home is ideal for large groups of up to 12 guests, with two bathrooms and a fully equipped kitchen. The apartment has a garden, free on-street parking, and amenities such as air conditioning, laundry facilities, and high-speed internet.
Mccormick 2br With Skyline View Near Soldier Field & Museum Campus - Chicago, IL
9.4 6 reviews
Chicago, IL
14/07 – 18/07
A$827/nighttotal: A$3308 (4 )

Mccormick 2br With Skyline View Near Soldier Field & Museum Campus

2 5
apartment , Chicago
This South Loop apartment, a short walk from McCormick Place and a short Uber ride from the Museum Campus and the city centre, offers easy access to Chicago's key attractions.
The 74-square-metre (800 sq ft) property boasts a modern layout, sleeping up to eight guests with two queen beds, a sofa bed, and an air mattress, and includes a fully equipped kitchen, two bathrooms, and a terrace.
Heart Of East Village 2-bed 2-bath Peaceful Oasis Condo - Chicago, IL
Chicago, IL
31/07 – 12/08
A$674/nighttotal: A$8088 (12 )

Heart Of East Village 2-bed 2-bath Peaceful Oasis Condo

2 1
apartment , Chicago
This two-bedroom flat is situated in Chicago's East Village district, offering 2.9 kilometres to the United Center and within 3.9 kilometres of Water Tower Chicago and Union Station.
This 102 square metre apartment accommodates up to seven guests, featuring on-site parking, complimentary WiFi, a fully equipped kitchen, and a washing machine.
Cozy 1br Retreat Near Transit, Dining And Parking - Chicago, IL
9.4 8 reviews
Chicago, IL
27/06 – 01/07
A$245/nighttotal: A$980 (4 )

Cozy 1br Retreat Near Transit, Dining And Parking

1 2
apartment , Chicago
This Chicago apartment, near Loyola University Chicago, is a 15-minute walk from the university and within 7km of Wrigley Field, Lincoln Park Zoo, and the city centre.
The 84-square-metre one-bedroom flat offers free Wi-Fi, private parking, a fully equipped kitchen, and sleeps up to seven guests.

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

The Upscale Getaway Near Downtown - Chicago, IL
9.8 95 reviews
Chicago, IL
09/09 – 14/09
A$614/nighttotal: A$3070 (5 )

The Upscale Getaway Near Downtown

2 3
apartment , Chicago
This Chicago apartment rental is situated in Little Italy/UIC, a short walk from the Western Blue Line station, offering easy access to the city centre, West Loop, and River North.
The 111-square-metre (1194 square feet) flat features two bedrooms, two bathrooms, three queen-size beds (including a sofa bed), and accommodates up to six guests, with amenities including a well-equipped kitchen, gated parking, and an Amazon Echo.
New! Large/beautiful Home With 6bds/4bth + Garage! - Chicago, IL
10 9 reviews
Chicago, IL
02/07 – 06/07
A$1933/nighttotal: A$7732 (4 )

New! Large/beautiful Home With 6bds/4bth + Garage!

5 10
apartment , Chicago
This five-bedroom, four-bathroom Chicago house, located in Belmont Cragin, is 1.8km from the Walt Disney House and 4.3km from Portage Park, offering easy access to Wrigley Field and the United Center (within 9.6km).
Sleeping twelve guests, this property boasts a fully equipped kitchen, in-unit laundry, a private patio, and parking, ideal for families or groups exploring Chicago's attractions.
Blueground River North Pool Wd Nr Mile Chi-1194 - Chicago, IL
Chicago, IL
01/08 – 30/09
A$325/nighttotal: A$19500 (60 )

Blueground River North Pool Wd Nr Mile Chi-1194

1 2
apartment , Chicago
This one-bedroom flat is located in Chicago's River North district, 1.8 kilometres from Oak Street Beach and an eleven-minute walk to The Shops at Northbridge, placing it close to Water Tower Chicago, 360 Chicago, and the Chicago Museum of Contemporary Art.
This 77-square-metre apartment accommodates up to three guests and features air conditioning, a private balcony, a fully equipped kitchen with a dishwasher and microwave, and on-site amenities including a sauna and free Wi-Fi.
4br Modern Urban Escape, Walk To Zoo, Lakefront & Red Line - Chicago, IL
Chicago, IL
10/07 – 12/07
A$1690/nighttotal: A$3380 (2 )

4br Modern Urban Escape, Walk To Zoo, Lakefront & Red Line

4 5
apartment , Chicago
This four-bedroom corporate apartment in Chicago's Near North Side offers prime access to Old Town, Lincoln Park, and the Clybourn Corridor, situated just 500 meters from New City shopping plaza and a short walk from the Second City Theater, with the North Branch Trail leading to the lakefront and multiple public transport options including the Red Line train for direct routes downtown.
The 112 square meter dwelling accommodates up to ten guests with four bedrooms, including two en-suite suites, a fully equipped kitchen featuring stainless steel appliances, and in-unit laundry, all complemented by spectacular city views and high-speed internet.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday rentals with air conditioning

Avondale Oasis 
Beautiful + Bright 
Condo - Chicago, IL
9.9 92 reviews
Chicago, IL
19/09 – 05/10
A$391/nighttotal: A$6256 (16 )

Avondale Oasis Beautiful + Bright Condo

2 4
apartment , Chicago
This Avondale, Chicago flat is ideally located near CTA bus routes and the 'L' train, providing easy access to the city's attractions.
The two-bedroom, one-bathroom apartment offers a spacious open-plan living/dining area, a fully equipped kitchen, private deck, and shared garden, sleeping up to five guests and including on-site laundry facilities.
Comfortable And Cozy Apartment - Chicago, IL
9.9 129 reviews
Chicago, IL
21/09 – 28/09
A$183/nighttotal: A$1281 (7 )

Comfortable And Cozy Apartment

1 2
apartment , Chicago
This two-bedroom Chicago apartment, registered as R23000106118, enjoys a convenient location near the Orange Line CTA station, offering easy access to the city centre (approximately 10 km) and Midway Airport (approximately 6 km).
The self-catering flat sleeps three guests and includes a fridge, microwave, air conditioning, parking, and is within walking distance of shops including Walgreens, Aldi, and Target, plus numerous restaurants.
Mccormick 4br Huge Unit With Pool Table 2010 South Wabash Ave - 3r - Chicago, IL
8.0 1 review
Chicago, IL
11/09 – 13/09
A$1178/nighttotal: A$2356 (2 )

Mccormick 4br Huge Unit With Pool Table 2010 South Wabash Ave - 3r

4 11
apartment , Chicago
This spacious four-bedroom flat in the McCormick district offers convenient access to Chicago's key attractions, situated between 1.6 and 3.2 kilometres of the Field Museum, Grant Park, DePaul University, the Art Institute of Chicago, the Chicago Symphony Orchestra, and the CIBC Theatre.
This accommodation for up to 10 guests features a fully equipped kitchen with a dishwasher and kettle, air conditioning, free WiFi, a private entrance, and two bathrooms, one with a hot tub, alongside a full-sized pool table for entertainment.
Montrose Gardens - Chicago, IL
9.8 94 reviews
Chicago, IL
25/11 – 29/11
A$172/nighttotal: A$688 (4 )

Montrose Gardens

1 2
apartment , Chicago
This Chicago apartment is situated in a diverse neighbourhood, a short distance from the Blue Line ‘L’ train, providing easy access to Lake Michigan (approximately 3.2km away), the city centre, United Center, and Wrigley Field (all within a 3.2km radius).
The one-bedroom flat offers a full kitchen, bathroom, and a pull-out sofa bed, accommodating up to four guests; on-site parking and a private outdoor space are also available.
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