Holiday Rentals in Chicago, IL

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Chicago, IL holiday rentals
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13982 Holiday Rentals and Airbnb in Chicago, IL

Best family friendly Chicago, IL holiday rentals

Among the 13982 accommodations in Chicago, IL, here are the 4 best family friendly rentals

Skyline 2br On 20th Floor Near Grant Park With Paid Parking - Chicago, IL
No reviews

Skyline 2br On 20th Floor Near Grant Park With Paid Parking

apartment, Chicago
This 2-bedroom flat is situated in downtown Chicago, a mere 1.9 kilometres from the city centre and a 10-minute walk from DePaul University, offering convenient access to Grant Park and the Art Institute of Chicago.
This 112 square metre residence accommodates up to 15 guests, boasting a private balcony with city views on the 20th floor, an equipped kitchen, two bathrooms, complimentary Wi-Fi, and on-site fitness and entertainment facilities.
Bright Upper-level 3br Chicago  King  Walkable - Chicago, IL
9.9 81 reviews

Bright Upper-level 3br Chicago King Walkable

apartment, Chicago
This apartment is conveniently located in a neighbourhood with easy access to public transport, just a short walk from the bus and train, making it ideal for exploring all that Chicago has to offer. The property has consistently received excellent ratings from guests for its cleanliness, location, and overall experience.
The apartment is spacious and can comfortably accommodate up to 5 guests, with 3 bedrooms and 1 bathroom. It is fully equipped with modern amenities, including a printer, garage, a spacious kitchen, central heating and air conditioning, a porch veranda, Wi-Fi, and Roku for entertainment. Guests can also enjoy a private backyard with a hammock, fire pit, and multiple grilling options, as well as fresh produce from the shared garden.
Luxe Vintage Loft, 10min To Downtown, Retro Movie Theatre - 15% Discount Applied - Chicago, IL
8.8 11 reviews

Luxe Vintage Loft, 10min To Downtown, Retro Movie Theatre - 15% Discount Applied

apartment, Chicago
This spacious Chicago apartment, ideal for families or groups, is situated in New City, offering easy access to Lake Michigan, Grant Park, and major museums such as the Art Institute of Chicago and the Field Museum (distances unspecified).
Sleeping 8-12 guests, the three-bedroom, three-bathroom property boasts a fully equipped kitchen, themed rooms (including a retro cinema and galaxy kids' room), smart TVs, high-speed Wi-Fi, and family-friendly amenities like cribs and high chairs, alongside a garden, spa and parking.
Giant 5-bedroom Home W/ Pool Table, 15 Min To Wrigley & Downtown - Chicago, IL
9.6 4 reviews

Giant 5-bedroom Home W/ Pool Table, 15 Min To Wrigley & Downtown

apartment, Chicago
This spacious 223 square metre five-bedroom, three-bathroom residence in Chicago's Irving Park district offers a classic early-1900s Craftsman Foursquare design and is a 3.2 to 4 kilometre Uber journey from landmarks including Wrigley Field, the city centre, and Soldier Field.
This family-friendly apartment accommodates up to 14 guests and features a fully-equipped chef's kitchen, a dedicated games room with a pool table and 75" smart TV, high-speed Wi-Fi, air conditioning, and parking, with a check-out time of 10:00 AM.

Best Chicago, IL holiday rentals with parking

Spacious 1br - Free Parking, Golf & Midway Access - Chicago, IL
10 2 reviews

Spacious 1br - Free Parking, Golf & Midway Access

apartment, Chicago
This one-bedroom flat in Chicago's Gage Park district offers convenient access to Midway Airport, located just 3.2 kilometres away, and the Orange Line, providing a direct route to the city centre.
This accommodation accommodates up to 4 guests with a queen bed and sofa bed, featuring a full kitchen, complimentary on-site parking, and is within reach of attractions such as Michigan Avenue and the Museum of Science and Industry.
Walk To Wrigley/ Boystown -Chicago 3br/2ba Duplex-paid Parking Available! - Chicago, IL
9.0 147 reviews

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

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.
Near Parks & Eats! Elegant Southwest Chicago Home - Chicago, IL
No reviews

Near Parks & Eats! Elegant Southwest Chicago Home

apartment, Chicago
This Ashburn flat offers a refined retreat in Chicago, situated in a quiet suburban neighbourhood just 15 kilometres from Downtown Chicago and less than 1.6 kilometres from Dan Ryan Woods, with convenient access to public transport at the Wrightwood station.
This spacious 184 square metre, single-level residence accommodates up to 9 guests with 5 bedrooms and 2 bathrooms, featuring a fully equipped kitchen with a fridge and microwave, air conditioning, a fireplace, Smart TVs, an outdoor patio with a grill, and driveway parking for 2 vehicles.
The Dakin Estate: A Refined 4br Art Deco Speakeasy Duplex In Wrigleyville. Featuring Curated Interiors, Elevated Finishes, And A Private Entertainment Lounge Just Minutes From Wrigley Field, Dining, Nightlife, And Chicagos Iconic Attractions. - Chicago, IL
10 2 reviews

The Dakin Estate: A Refined 4br Art Deco Speakeasy Duplex In Wrigleyville. Featuring Curated Interiors, Elevated Finishes, And A Private Entertainment Lounge Just Minutes From Wrigley Field, Dining, Nightlife, And Chicagos Iconic Attractions.

apartment, Chicago
This five-bedroom flat in Chicago's Lakeview district is just a 5-minute walk from Wrigley Field and a 2-minute walk from the Sheridan Red Line station, offering excellent transport links to the Magnificent Mile and the Loop.
This two-level Art Deco Jazz sanctuary provides 2200 square meters of living space, accommodating up to 12 guests with a fireplace, pool table, onsite garage parking, and close proximity to dining, nightlife, and Lake Michigan's shoreline.

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.

Popular destinations

Best Chicago, IL holiday rentals with a balcony

Spacious Communal Areas And Cozy Balconies - Inviting Haven - Chicago, IL
No reviews

Spacious Communal Areas And Cozy Balconies - Inviting Haven

house, Chicago
This six-bedroom residence is situated in Chicago's Bronzeville district, a short walk from the lakefront and approximately 1.6 kilometres from the city centre.
This family-friendly house accommodates up to 12 guests, offering communal living spaces, a kitchen with a fridge, freezer, and microwave, air conditioning, multiple balconies, and is conveniently located 800 metres from Lake Michigan and within a 3.2 kilometre drive of McCormick Place Convention Centre and the University of Chicago.
Logan Sq 4br Duplex  Garage  Sleeps 8 - Chicago, IL
10 1 review

Logan Sq 4br Duplex Garage Sleeps 8

apartment, Chicago
This 4-bedroom flat is located in Chicago's Avondale district, offering proximity to Lake Michigan, the Art Institute of Chicago and Wrigley Field.
This well-equipped property accommodates up to 8 guests with 2 bathrooms, a kitchen featuring a microwave oven and dishwasher, and it also provides parking and a terrace.
High-end West Loop 2br + City Views & Walkability - Chicago, IL
10 2 reviews

High-end West Loop 2br + City Views & Walkability

apartment, Chicago
This three-bedroom, two-bathroom apartment in Chicago's prime downtown area is less than 1.6km from the Willis Tower and the University of Illinois Chicago, and within 3.2km of the United Centre and the Art Institute of Chicago.
The 5-guest property boasts a fully equipped kitchen, balcony, in-unit TV, fitness centre access, and is conveniently located near public transport links, making it ideal for exploring the city.
Luxury Home Theatre And Rooftop Oasis - Exquisite Architectural Masterpiece - Chicago, IL
No reviews

Luxury Home Theatre And Rooftop Oasis - Exquisite Architectural Masterpiece

house, Chicago
This substantial five-bedroom residence is located in Chicago's Wicker Park/Bucktown districts, offering direct access to the Damen and Division Blue Line 'L' train stations, facilitating travel to the city centre.
This 418-square-metre property accommodates up to 17 guests and features a private 140-square-metre rooftop terrace with city views, a Clive Christian kitchen with Sub-Zero and Wolf appliances, a home cinema, a games room with a pool table and ping pong, a sauna, and a hot tub.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday rentals with air conditioning

Chic & Spacious Bi-level Bucktown Condo - Sleeps 8 - Chicago, IL
9.7 109 reviews

Chic & Spacious Bi-level Bucktown Condo - Sleeps 8

apartment, Chicago
This Bucktown flat is ideally located near the 606 trail and a short distance from Milwaukee, Damen, and North Avenues, with Chicago's city centre a 19-kilometre drive away.
The self-catering property offers two bedrooms, a full bathroom, kitchen with fridge, microwave, and dishwasher, plus air conditioning and internet access; one pet is permitted for an extra £120 fee.
Experience Downtown Chicago At Millennium - Luxury Apartments In The Loop - Chicago, IL
8.5 100 reviews

Experience Downtown Chicago At Millennium - Luxury Apartments In The Loop

apartment, Chicago
This apartment is located in downtown Chicago, within half a mile of the city centre, close to attractions like the CIBC Theatre, Willis Tower, and DePaul University. The apartment has received excellent ratings for location, cleanliness, and overall experience.
The apartment is suitable for up to five guests and has a fully equipped kitchen. It also offers a range of amenities including a private terrace, a swimming pool, a jacuzzi, and free Wi-Fi.
Superior - Chicago, IL
9.6 199 reviews

Superior

apartment, Chicago
This Chicago apartment is conveniently located just a short distance from the United Center and Water Tower Chicago, offering easy access to both sporting events and historical landmarks. It has consistently received excellent ratings from previous guests, highlighting its cleanliness, location, and overall experience.
This spacious three-bedroom flat can comfortably accommodate up to eight guests, providing ample space for families or groups of friends. The apartment features a fully equipped kitchen, a private patio with city views, free parking, and a barbecue for outdoor dining, ensuring a comfortable and enjoyable stay.
King Bed| Near Downtown & United Ctr+walk To Train - Chicago, IL
9.9 24 reviews

King Bed| Near Downtown & United Ctr+walk To Train

apartment, Chicago
This two-bedroom Chicago apartment, ideally located near the United Centre, offers easy access to public transport, including the Green Line and Metra, and is within a 13-kilometre drive of the city centre and major hospitals.
The 2-bathroom flat sleeps six, boasts a fully equipped kitchen, in-unit laundry, a dedicated workspace, and a games area, complemented by free on-street parking nearby and dog-friendly amenities including a fenced yard.
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