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

Foosball, Steps From Wrigley, Private Parking - Chicago, IL
9.8 180 reviews

Foosball, Steps From Wrigley, Private Parking

apartment, Chicago
This Chicago apartment rental is ideally situated near Wrigley Field and the Red Line, offering easy access to Chicago's North Side attractions.
The two-bedroom, two-bathroom flat sleeps five guests and includes a fully equipped kitchen, free on-site parking (a rarity in this area), and access to the entire condo.
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.
Architect-designed 3br Oak Park Flat - Chicago, IL
10 14 reviews

Architect-designed 3br Oak Park Flat

apartment, Oak Park
This newly renovated three-bedroom, two-bathroom flat in historic Oak Park offers excellent proximity to local cultural attractions and is just a short walk to the Green Line for convenient travel to Chicago.
This family-friendly apartment sleeps six and features air conditioning, Wi-Fi, a fully equipped galley kitchen, and a shared roof deck, situated within the architecturally significant Centennial building and close to amenities such as 3 Fold Bakery.
Livn Millennium Park Downtown Chicago 1 Br - Chicago, IL
10 1 review

Livn Millennium Park Downtown Chicago 1 Br

apartment, Chicago
This newly renovated one-bedroom flat at 19 S Wabash Avenue is located in the prime downtown Chicago district, a mere 100 metres from Millennium Park and within easy reach of Michigan Avenue's shopping and dining.
This 37 square metre apartment accommodates up to two guests and features a fully equipped kitchen, in-unit laundry facilities, and key code elevator access, offering convenient proximity to Chicago's Theatre District and public transport links.

Best Chicago, IL holiday rentals with parking

1 Open Parking | Chinatown | Close To Transit - Chicago, IL
10 5 reviews

1 Open Parking | Chinatown | Close To Transit

apartment, Chicago
This newly updated flat in a Chicago district provides excellent access to landmarks, with public transport just a short walk away, facilitating exploration of the city.
This residence, accommodating up to 10 guests, features two bathrooms, air conditioning, and a kitchen equipped with a fridge, freezer, and microwave, offering a comfortable base for both short and extended stays.
Mins To Dt & Frank Lloyd Wright - Chicago, IL
8.0 2 reviews

Mins To Dt & Frank Lloyd Wright

apartment, Oak Park
This one-bedroom flat in Oak Park offers a prime location, just 400 metres from the Frank Lloyd Wright Home and Studio and a 10-minute walk from Downtown Oak Park, with immediate access to popular eateries.
This pet-friendly apartment accommodates up to four guests, featuring a kitchen with a fridge and microwave, air conditioning, a garden, and parking, with flexible check-in/out options available.
Edgewater Andersonville-area Apt Close To Loyola Lake Ez Parking - Chicago, IL
9.5 7 reviews

Edgewater Andersonville-area Apt Close To Loyola Lake Ez Parking

apartment, Chicago
Edgwater Recharge is a family-friendly flat situated in Chicago's Edgewater district, a 14-minute walk from Loyola University Chicago and 2.9 kilometres from Foster Beach, offering convenient access to local amenities and the lakefront.
This air-conditioned, two-bedroom apartment spans 139 square metres, accommodates up to 11 guests, and features a fully equipped kitchen, on-site garden, complimentary Wi-Fi, and on-site parking.
Private Balcony, Parking, 5 Min To Uc - Chicago, IL
9.9 154 reviews

Private Balcony, Parking, 5 Min To Uc

apartment, Chicago
This spacious Chicago apartment, ideal for families, is centrally located, offering easy access to both the United Centre and McCormick Place, convenient for event attendees.
The 167 square metre property boasts two bedrooms, two bathrooms, sleeps six to eight guests, and features a chef's kitchen, private balcony with city views, in-unit laundry, and secure parking with EV charging.

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

Rooftop Skyline Views And Modern Comforts - Stylish Urban Retreat - Chicago, IL
No reviews

Rooftop Skyline Views And Modern Comforts - Stylish Urban Retreat

apartment, Chicago
This modern River North flat is situated a mere 200 metres from the CTA and 500 metres from the Magnificent Mile, offering convenient access to Chicago's dining, nightlife, and cultural attractions.
This family-friendly residence accommodates up to four guests, boasting two bedrooms and two bathrooms, with amenities including a fully equipped kitchen, 400mbps WiFi, an in-unit washer/dryer, and a stunning rooftop with panoramic skyline views.
Bright Upper-level 3br Chicago  King  Walkable - Chicago, IL
10 22 reviews

Bright Upper-level 3br Chicago King Walkable

apartment, Chicago
This comfortable apartment is situated in Avondale, a neighbourhood in Chicago, just a few kilometres from Lake Michigan. The area offers a relaxed atmosphere, with easy access to local restaurants and shops. Guests consistently rate this apartment as excellent.
The apartment has three bedrooms and one bathroom, offering enough space for up to five guests. The apartment also comes with a range of amenities, including a kitchen with a fridge, microwave oven, and dishwasher, as well as a garden, terrace, and parking.
Mccormick Place 2br Spacious Corner Unit With Optional Parking Sleeps 6 Guests Near Soldier Field An - Chicago, IL
No reviews

Mccormick Place 2br Spacious Corner Unit With Optional Parking Sleeps 6 Guests Near Soldier Field An

apartment, Chicago
Apartment rental listing. You will stay in Chicago.
Services and facilities include a fridge, free parking and an elevator. This apartment in Chicago is ideal for families.
Flexhome Ukrainian Village 2br - Private Balcony & Walkable Location - Chicago, IL
8.3 3 reviews

Flexhome Ukrainian Village 2br - Private Balcony & Walkable Location

apartment, Chicago
This two-bedroom flat in Chicago's Ukrainian Village offers a walkable base with easy access to local attractions and dining.
This 55 square metre flat accommodates up to five guests, featuring air conditioning, a fully equipped kitchen with a dishwasher and microwave, and a balcony with outdoor seating, with free WiFi provided.

Best Chicago, IL holiday rentals with air conditioning

Beautiful, Sunny 2nd Floor 3br/1ba W Free Parking - Chicago, IL
9.9 170 reviews

Beautiful, Sunny 2nd Floor 3br/1ba W Free Parking

apartment, Chicago
This Lincoln Square flat is situated near the Western Brown Line el station, a 3.2km walk from the Old Town School of Folk Music and 3.2km from Lake Michigan beaches, offering easy access to Wrigley Field (7 el stops away).
The three-bedroom, one-bathroom apartment sleeps six, features a fully equipped kitchen including a dishwasher, free parking, and original woodwork, plus is close to Lincoln Square's restaurants and shops.
Luxury Loft Collection Combo 01/03 | Terrace - Chicago, IL
9.6 4 reviews

Luxury Loft Collection Combo 01/03 | Terrace

apartment, Chicago
This luxurious River North apartment, ideally located in Chicago's downtown area, offers easy access to the Chicago Theatre and Art Institute of Chicago.
The 510 square metre dwelling comprises two adjoining lofts, sleeping up to 28 guests across six bedrooms and six bathrooms, and boasts a private terrace, secured parking, and high-end Gaggenau appliances.
River North | Rooftop With In & Out Parking | 5 - Chicago, IL
9.7 113 reviews

River North | Rooftop With In & Out Parking | 5

apartment, Chicago
This two-bedroom Chicago apartment, ideally located in the city centre, offers easy access to numerous downtown attractions.
The 93-square-metre (1000 sq ft) flat sleeps up to six guests, boasting a fully equipped kitchen, free parking, a rooftop patio with BBQ, and access to a fitness centre; Netflix, Hulu, Disney+, and Prime are included.
W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade - Chicago, IL
9.4 11 reviews

W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade

apartment, Chicago
This spacious three-bedroom apartment, sleeping 8-10, is situated in Brighton Park, Chicago, approximately 5km from Little Italy, Chinatown, and the city centre.
The 86 square metre property boasts a fully equipped kitchen, multiple smart TVs, free Wi-Fi, and a shared, fenced backyard, with family-friendly amenities including arcade games and a travel cot.
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