Vacation Rentals in Chicago, IL

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Chicago, IL vacation rentals
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13982 Vacation rentals and Airbnb in Chicago, IL

Best family friendly Chicago, IL vacation rentals

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

Stylish Cozy Boho  10 Min To Downtown  Sleeps 5 - Chicago, IL
9.7 82 reviews

Stylish Cozy Boho 10 Min To Downtown Sleeps 5

apartment, Chicago
This Chicago apartment rental is located in Little Village, a 10-minute drive (approx. 4.8km) from the city centre, 4.8km from Little Italy and Chinatown, and a 15-minute drive (approx. 11.2km) from Millennium Park and Soldier Field.
The one-bedroom flat sleeps five guests comfortably, offering a full kitchen, washer/dryer, in-unit entertainment (two smart TVs, Pac-Man arcade game, board games), a mini-patio with grill, and enhanced security features including keyless entry.
Modern Loft W/fast Wifi & Smart Tvs - Chicago, IL
9.5 23 reviews

Modern Loft W/fast Wifi & Smart Tvs

apartment, Chicago
This South Loop flat is situated a 10-minute walk from McCormick Place and a 5-minute Uber to Soldier Field, offering excellent access to Chicago's attractions.
This family-friendly flat provides three bedrooms, two bathrooms, and sleeps up to six guests, featuring a modern kitchen, air conditioning, and 250 Mbps Wi-Fi, with the option for responsible indoor smoking.
A Comfortable Stay While You Are Away In Oak Park - Chicago, IL
9.8 104 reviews

A Comfortable Stay While You Are Away In Oak Park

apartment, Oak Park
This charming three-bedroom flat is located in Oak Park, Illinois, just a short distance from major expressways and downtown Chicago, offering easy access to the city and its attractions. The property has received excellent ratings for location, cleanliness, and user experience, making it a popular choice for travellers.
The flat is ideal for families or groups of up to six people, with a dedicated living room, a large kitchen, and a private bathroom. Guests can enjoy a beautiful backyard patio, perfect for relaxing or enjoying a meal outdoors, as well as access to a well-equipped kitchen, a desk, and ample storage space.
Downtown 2bd Gym Near Park Lake Museums #6 - Chicago, IL
No reviews

Downtown 2bd Gym Near Park Lake Museums #6

apartment, Chicago
This two-bedroom flat is located in downtown Chicago, a 10-minute walk from Grant Park and 1.9 kilometres from the city centre, placing it close to DePaul University and the Art Institute of Chicago.
This 63 square metre apartment offers accommodation for up to seven guests, featuring air conditioning, complimentary WiFi, and a kitchen equipped with a fridge and microwave, with an on-site fitness centre available for use.

Best Chicago, IL holiday rentals with parking

3br Modern Apt • Gym • Workspace • Quiet Location - Chicago, IL
No reviews

3br Modern Apt • Gym • Workspace • Quiet Location

apartment, Dunning
This Chicago condo is situated 6 kilometres from O'Hare International Airport, offering easy access to Wrigley Field (16 kilometres) and Lincoln Park Zoo (18 kilometres).
The 929 square metre property boasts three bedrooms, two bathrooms, and sleeps nine guests, featuring a fully equipped kitchen, in-unit laundry, free Wi-Fi, and on-site amenities including a 24-hour reception and luggage storage.
The Hotel & Athletic Club At Midtown - Chicago, IL
8.9 1364 reviews

The Hotel & Athletic Club At Midtown

resort, Chicago
The Hotel & Athletic Club at Midtown is conveniently located in Chicago's Midtown neighbourhood, just a short distance from popular attractions like Wrigley Field, Lincoln Park Zoo, and United Center. The hotel consistently receives high ratings for its cleanliness, location, and overall experience, making it a popular choice for travellers.
The hotel offers a range of comfortable and modern rooms, each equipped with amenities such as air conditioning, flat-screen TVs, and private bathrooms. Guests have access to a wide array of facilities including indoor and outdoor swimming pools, a spa, a fitness centre, tennis courts, and a variety of fitness classes, making it a great choice for those seeking a wellness-focused getaway.
Gorgeous Penthouse With Stunning Views From Private Rooftop - Chicago, IL
9.8 316 reviews

Gorgeous Penthouse With Stunning Views From Private Rooftop

apartment, Chicago
This Wicker Park flat is situated near the Division Blue Line station, providing easy access to O'Hare Airport and neighbourhoods such as Ukrainian Village (within walking distance) and Bucktown (a short cycle ride away).
The top-floor condo offers a private roof terrace with neighbourhood views, two bedrooms, two bathrooms, and a full kitchen; it sleeps five guests and includes central air conditioning, free nearby street parking, and is within easy reach of diverse dining and nightlife options.
2br On Great Block In Pilsen - Chicago, IL
9.3 3 reviews

2br On Great Block In Pilsen

apartment, Chicago
This two-bedroom flat in Chicago's Pilsen district, on Oakley Avenue, is located in the "Heart of Italy" area, placing it adjacent to three Italian restaurants and 800 metres from public transport and the train station, with downtown Chicago 4.8 kilometres away.
This residence for four guests offers keyless entry, a dedicated workspace, a kitchen with granite countertops and a peninsula bar, and window air conditioning units, with shared laundry facilities in the basement.

Frequently asked questions about holiday rentals in Chicago, IL

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

    You absolutely must see the iconic Willis Tower (formerly Sears Tower) for breathtaking city views. A trip to Millennium Park is essential, with the Cloud Gate sculpture (affectionately known as 'The Bean') and Crown Fountain being must-sees. No visit to Chicago is complete without a stroll along Navy Pier, enjoying the Ferris wheel and the vibrant atmosphere.
  • What are the best Airbnb and vacation 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 and central location, consider staying in the River North neighbourhood. It's close to the Magnificent Mile, with plenty of shops, restaurants, and nightlife. If you prefer a more relaxed atmosphere, Lincoln Park is a great choice, with beautiful parks, museums, and a thriving local scene.
  • 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 option, with a wide variety of animals. The Shedd Aquarium is a must-visit for marine life enthusiasts, and the Field Museum offers engaging exhibits on dinosaurs and other natural history topics. For a fun day out, head to Navy Pier, where you can enjoy rides, games, and a carousel.
  • What are the best vacation 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 avoid peak crowds and high prices, booking your vacation rental in the shoulder seasons, like spring (April-May) or autumn (September-October), is a good idea. You'll still experience pleasant weather and fewer crowds. However, if you want to enjoy the city's festivals and events, summer (June-August) is a popular time, but be prepared for higher prices and larger crowds.
  • 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 vibrant festival scene. The Chicago Blues Festival in June is a must-see for music lovers. The Taste of Chicago in July offers a culinary journey through the city's diverse food scene. For a unique experience, check out the Chicago Air and Water Show in August.
  • 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 walk or cycle along the Lakefront Trail for stunning views of Lake Michigan. Explore the free museums, like the Art Institute of Chicago or the Museum of Contemporary Art. Enjoy a picnic in Millennium Park or Grant Park, soaking up the city's energy.
  • What are the best restaurants with local dishes in Chicago, IL?

    For a classic Chicago hot dog, head to Portillo's. If you're looking for deep dish pizza, Lou Malnati's is a local favourite. For a taste of the city's Polish heritage, try the pierogies at the famous Old Town Sausage and Deli.
  • What are the best walking or cycling routes in Chicago, IL?

    The Lakefront Trail offers a scenic route along Lake Michigan, stretching for 18.5 km. For a more urban experience, explore the 606 Bloomingdale Trail, a former railway line transformed into a greenway. You can also cycle along the Chicago Riverwalk, enjoying the city's architecture.
  • Are there pet-friendly attractions in Chicago, IL?

    Many parks in Chicago are dog-friendly, including Millennium Park and Grant Park. You can also find dog-friendly restaurants and cafes throughout the city. The Lincoln Park Zoo is also pet-friendly, allowing well-behaved dogs on leashes.
  • What are the benefits of choosing a vacation rental in Chicago, IL?

    Vacation rentals offer more space and privacy compared to hotels. You can enjoy a home-like environment with amenities like a kitchen, allowing you to prepare your own meals. They often come with unique features and character, giving you a more authentic local experience.
  • What are the top sports attractions and facilities in Chicago, IL?

    Chicago is a major sports city, home to the Chicago Cubs (baseball), Chicago White Sox (baseball), Chicago Bulls (basketball), Chicago Blackhawks (ice hockey), and Chicago Bears (American football). You can catch a game at Wrigley Field, Guaranteed Rate Field, United Center, or Soldier Field.

Popular destinations

Best Chicago, IL holiday rentals with a balcony

Modern Downtown Home With 5 Baths & Private Garage - Chicago, IL
9.5 157 reviews

Modern Downtown Home With 5 Baths & Private Garage

house, Chicago
This four-storey townhouse is located in Chicago's East Village, a short walk from the Milwaukee 'L' station and a 12-minute subway ride from the Loop, Michigan Avenue, and the Lakefront. It has consistently received excellent user ratings for location, cleanliness, and overall experience.
The property offers 223 square metres of living space, comprising four bedrooms and five bathrooms. Guests can enjoy a range of amenities, including a fully equipped kitchen, private terraces, a spa-like bathroom, a fireplace, games, and a Sonos sound system.
Luxe Home 20 Min From Downtown Chicago ,Heated Indoor Pool, Spa Bath, Tree House - Chicago, IL
9.0 9 reviews

Luxe Home 20 Min From Downtown Chicago ,Heated Indoor Pool, Spa Bath, Tree House

apartment, Skokie
This Skokie treehouse rental, a 7-minute (11 km) drive from Lake Michigan and a 12-minute (19 km) drive from Wrigley Field, offers convenient access to Chicago's attractions.
Sleeping up to nine guests, this four-bedroom, five-bathroom property boasts a fully equipped kitchen with dishwasher and microwave, a swimming pool, jacuzzi, Wi-Fi, and on-site parking.
The Upscale Getaway Near Downtown - Chicago, IL
8.6 7 reviews

The Upscale Getaway Near Downtown

apartment, Chicago
This family-friendly Chicago apartment, located in a residential area 1.8km from the United Centre and within a 6.4km radius of Union Station, the Willis Tower, and DePaul University, offers convenient access to major attractions.
The 111 square metre dwelling boasts two bedrooms, two bathrooms, sleeps eleven guests, and includes a fully equipped kitchen, balcony, fireplace, free parking, and Wi-Fi.
Desert Mirage Private Patio, Desk Parking - Chicago, IL
8.8 4 reviews

Desert Mirage Private Patio, Desk Parking

apartment, Chicago
This Chicago flat is situated 3.9 kilometres from the United Centre, providing easy access to downtown attractions within a 6.4 kilometre radius, including Union Station and Water Tower Chicago.
This 74 square metre flat accommodates up to nine guests, offering a fully equipped kitchen with a dishwasher and oven, free WiFi, air conditioning, on-site laundry, complimentary parking, and a private patio, all within a non-smoking environment.

Best Chicago, IL holiday rentals with air conditioning

Premium Queen Bed Non-smoking - Chicago, IL
9.3 55 reviews

Premium Queen Bed Non-smoking

apartment, Chicago
This studio flat is situated in the University of Chicago Hospitals Heliport area, placing it 4.6 kilometres from the Museum of Science and Industry and 7.7 kilometres from Guaranteed Rate Field.
Offering air conditioning, parking, and a 24-hour front desk, this 14 square metre studio accommodates up to two guests and is equipped with a desk and television.
Spacious Comfy 2br Near Highwaytrain Station - Chicago, IL
8.7 3 reviews

Spacious Comfy 2br Near Highwaytrain Station

apartment, Oak Park
This Oak Park flat is located 8.9 kilometres from the United Centre and 12 kilometres from Union Station, offering easy access to Chicago's transport networks and attractions.
This pet-friendly apartment accommodates up to 15 guests with two bathrooms, a fully equipped kitchen, air conditioning, and complimentary Wi-Fi, plus on-site parking.
Stunning 2 Floor Penthouse Downtown - Chicago, IL
8.6 14 reviews

Stunning 2 Floor Penthouse Downtown

apartment, Chicago
This West Town apartment in Chicago is situated 0.8km from The Salt Shed music venue, 4.8km from the United Centre, and 4.8km from Lake Michigan, offering easy access to the Blue Line at Chicago Station (7-minute walk).
This spacious 186 square metre flat boasts three bedrooms, three bathrooms, a balcony, parking, and accommodates up to 12 guests, with amenities including a full kitchen, washing machine, and internet access.
Garden Oasis - Chicago, IL
9.7 163 reviews

Garden Oasis

apartment, Chicago
This stylishly decorated two-bedroom garden flat is located in Chicago's North Center neighbourhood, 0.5km from public transport and a 20-minute walk from Wrigley Field.
The 4-guest apartment boasts a modern kitchen with dishwasher, in-unit laundry, a luxurious bathroom with underfloor heating, and a private patio; nearby attractions include Beagyle Brewery and numerous restaurants.
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