Compare Vacation Rentals & Airbnb in Chicago, IL

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Chicago, IL vacation rentals
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13982 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

Lux Logan 3000 Sq Ft, Sleeps 12, Garage & Roofdeck - Chicago, IL
10 75 reviews

Lux Logan 3000 Sq Ft, Sleeps 12, Garage & Roofdeck

apartment, Chicago
This five-bedroom, four-bathroom house, ideal for large families or groups, is located in Chicago's Logan Square neighbourhood, offering easy access to local restaurants, coffee shops, and the elevated train line.
Sleeping up to twelve guests, the property boasts a rooftop deck with city views, a fully equipped kitchen including a dishwasher, two ground-floor bedrooms suitable for guests with mobility issues, and a two-car garage; a crib and wheelchair ramp are available on request.
Group-friendly 2br With Optional Parking And Gym Access Near Mccormick Place And Soldier Field - Chicago, IL
8.5 10 reviews

Group-friendly 2br With Optional Parking And Gym Access Near Mccormick Place And Soldier Field

apartment, Chicago
This Chicago apartment is conveniently located near the Field Museum (2.3 km), the Art Institute of Chicago (2.9 km), and the Chicago Symphony Orchestra (2.9 km).
The 74-square-metre two-bedroom, two-bathroom flat sleeps up to eight guests and offers free Wi-Fi, a fully equipped kitchen, on-site parking, a fitness centre, and a patio with city views.
Livn Millennium Park Downtown Chicago 1 Br - Chicago, IL
10 82 reviews

Livn Millennium Park Downtown Chicago 1 Br

apartment, Chicago
This newly renovated one-bedroom flat is located in the downtown district of Chicago, a mere 100 metres from Millennium Park and the shopping on Michigan Avenue.
This stylish apartment offers accommodation for two guests and includes a fully equipped kitchen, in-unit laundry, and comfortable furnishings throughout, with key code elevator access for convenience.
Up-scale Wicker Park 4bd/3.5ba Home (+Garage) - Chicago, IL
9.4 18 reviews

Up-scale Wicker Park 4bd/3.5ba Home (+Garage)

apartment, Chicago
This Wicker Park apartment, a 10-minute walk from the Blue Line CTA station and close to numerous Chicago attractions, offers a prime location near Division Street.
This 300 square metre dwelling boasts four bedrooms, four bathrooms, and sleeps twelve, featuring a chef's kitchen, attached garage, and private patio.

Best Chicago, IL vacation rentals with parking

Vintage Ukrainian Village Apartment - Chicago, IL
9.9 185 reviews

Vintage Ukrainian Village Apartment

apartment, Chicago
This first-floor flat is situated in a hip Chicago neighbourhood, offering easy access to the city centre via public transport.
The two-bedroom, one-bathroom apartment sleeps four, features a private balcony, dedicated workspace, and is well-equipped with modern conveniences including a fridge, microwave, and parking.
Sleek Avondale Condo Spa Bath Kng+qn Beds +Garage - Chicago, IL
9.9 34 reviews

Sleek Avondale Condo Spa Bath Kng+qn Beds +Garage

apartment, Chicago
This newly remodelled, modern two-bedroom flat is situated in Chicago's Avondale district, offering convenient access to local eateries and the Blue Line transit, which is 1.2 kilometres away for travel to the city centre and airport.
This stylish accommodation for up to four guests features a fully equipped kitchen with a breakfast bar, a spa-like bathroom with a walk-in rain shower and soaking tub, in-unit laundry, and a private garage parking space, with two smart televisions provided for entertainment.
Modern Downtown Home With 5 Baths & Private Garage - Chicago, IL
9.5 154 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.
Designer Hideaway Private Patio Near Wicker Park - Chicago, IL
9.3 3 reviews

Designer Hideaway Private Patio Near Wicker Park

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.

Frequently Asked Questions about vacation rentals in Chicago, IL

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

    You can't miss the iconic Willis Tower, formerly known as the Sears Tower, for stunning views of the city. A visit to Millennium Park, with its famous Cloud Gate sculpture, affectionately known as 'The Bean', is a must. And no trip to Chicago is complete without a stroll along the Magnificent Mile, a bustling stretch of shops and restaurants.
  • What are the best Airbnb and vacation rentals in Chicago, IL?

    52nd Floor Magmile Penthouse Views Fireplace Pool, 2bd/2ba Mag Mile Masterpiece (+Rooftop) and Kasa | Walk To Lincoln Park Zoo | Chicago are the most popular Airbnb and vacation rentals in Chicago, IL among travelers.

  • 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 River North. It's close to many attractions, including the Art Institute of Chicago and the Chicago Riverwalk. If you prefer a more relaxed atmosphere, Lincoln Park is a lovely option with its beautiful green spaces and proximity to the zoo.
  • 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 range of animals and exhibits. The Shedd Aquarium is another popular choice, especially with its impressive Oceanarium. For a more interactive experience, the Museum of Science and Industry is a great option, with hands-on exhibits for all ages.
  • 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 the crowds and higher prices, book your vacation rental in the shoulder seasons, from April to May or September to October. Summer can be hot and busy, while winter can be cold and snowy, but you can find great deals if you're willing to brave the elements.
  • 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 Taste of Chicago in July is a popular food festival, while the Chicago Blues Festival in June celebrates the city's rich musical heritage. For a unique experience, check out the Chicago Air & 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 stroll along the Chicago Riverwalk, enjoying the views and the city's unique architecture. Visit the free museums, including the Art Institute of Chicago and the Field Museum. And don't forget to check out the free concerts and events held in Millennium Park throughout the year.
  • What are the best restaurants with local dishes in Chicago, IL?

    For a taste of Chicago's famous deep-dish pizza, try Lou Malnati's or Pizzeria Bebu. For a more casual experience, try the Italian beef sandwiches at Al's Beef or Mr. Beef. If you're looking for something a little more upscale, try the award-winning seafood at RPM Steak.
  • What are the best walking or cycling routes in Chicago, IL?

    The Lakefront Trail offers stunning views of Lake Michigan and is perfect for a leisurely walk or bike ride. For a more urban experience, try the 606, a former railway line transformed into a raised park and trail. And don't forget to check out the Chicago Riverwalk, which offers scenic views of the city's architecture.
  • Are there pet-friendly attractions in Chicago, IL?

    Yes, many attractions in Chicago are pet-friendly. The Lincoln Park Zoo welcomes dogs on leash, and many restaurants and cafes have outdoor seating areas where you can enjoy a meal with your furry friend. The Chicago Riverwalk is also a great place to take a stroll with your dog.
  • What are the benefits of choosing a vacation rental in Chicago, IL?

    Vacation rentals offer more space and privacy than hotels. They often come with kitchens, allowing you to prepare your own meals and save money. You can also find rentals in different neighbourhoods, giving you a more local experience.
  • What are the top sports attractions and facilities in Chicago, IL?

    Chicago is home to the iconic Wrigley Field, home of the Chicago Cubs baseball team. The United Center is home to the Chicago Bulls basketball team and the Chicago Blackhawks hockey team. Soldier Field hosts the Chicago Bears football team.

Popular destinations

Best Chicago, IL vacation rentals with a balcony

Flexhome Ukrainian Village • 2br • Walkable + Private Balcony · Sleeps 6 - Chicago, IL
8.1 30 reviews

Flexhome Ukrainian Village • 2br • Walkable + Private Balcony · Sleeps 6

apartment, Chicago
Flexhome Ukrainian Village 2BR D2 is situated in Chicago's Ukrainian Village neighbourhood, 2.1km from the United Centre and 4.5km from Water Tower Place.
This two-bedroom apartment, offering 55 square metres of space, sleeps nine guests and includes a fully equipped kitchen with dishwasher, in-unit laundry, air conditioning, a balcony, and free Wi-Fi.
Flexhome Ukrainian Village 2br - Private Balcony & Walkable Location - Chicago, IL
9.5 2 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.
Premier Penthouses And Apartment With Captivating Views Of Millennium Park - Chicago, IL
9.1 10 reviews

Premier Penthouses And Apartment With Captivating Views Of Millennium Park

apartment, Chicago
This luxurious Chicago penthouse flat is situated in the downtown area, less than 0.4km from Millennium Park and offers stunning views of Cloud Gate ("The Bean").
The 246 square metre property boasts three bathrooms, a fully equipped kitchen, private parking (a rare downtown Chicago amenity), and access to a swimming pool, jacuzzi, and on-site bar; sleeping arrangements are not specified.
Large 3br /2ba Duplex King  Parking - Chicago, IL
10 8 reviews

Large 3br /2ba Duplex King Parking

apartment, Chicago
This four-bedroom apartment is located in the Avondale neighbourhood of Chicago, a short 5-minute walk from Milwaukee Avenue and a 5-minute drive to Humboldt Park. It is rated excellent by previous guests.
The apartment comfortably accommodates eight guests and features a fully equipped kitchen with modern appliances, a washer and dryer, and a private garden with a hot tub. It also offers a range of amenities including Wi-Fi, a smart TV, and on-site parking.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL vacation rentals with air conditioning

Amazing Studio! Excellent Amenities In The Loop - Chicago, IL
10 2 reviews

Amazing Studio! Excellent Amenities In The Loop

resort, Chicago
This Chicago Loop studio apartment offers easy access to the Theatre District, River North, Millennium Park, and the Magnificent Mile, all within comfortable walking distance.
The self-contained apartment, sleeping two guests, features a contemporary kitchen, in-unit laundry, high-speed internet, and access to a rooftop pool, games room, and fitness centre; a 32-night minimum stay applies.
Stylish Northside Retreat - Chicago, IL
9.8 73 reviews

Stylish Northside Retreat

apartment, Chicago
This two-bedroom Chicago apartment is situated on the North Side, offering convenient access to local shops and public transport.
The 4-guest flat features a fully equipped kitchen, high-speed Wi-Fi, and free street parking, ensuring a comfortable stay.
Central | Bbq Deck | Family-friendly Pueblo Magíco - Chicago, IL
9.4 144 reviews

Central | Bbq Deck | Family-friendly Pueblo Magíco

apartment, Chicago
This spacious duplex is located in a residential area of Chicago, just 15 kilometres from the city centre, Chinatown, and the beach. The property has received excellent ratings for its cleanliness, location, and overall experience.
The duplex spans 186 square metres and comfortably accommodates 12 guests across five bedrooms and two bathrooms. It boasts a fully equipped kitchen, a private garden, a Jacuzzi, and a dedicated entertainment room with foosball and board games, providing plenty of space and activities for families and groups.
Cozy Bright Quiet Boho-chic House In Bridgeport - Chicago, IL
9.9 210 reviews

Cozy Bright Quiet Boho-chic House In Bridgeport

apartment, Chicago
This Bridgeport coach house, near Halsted Street in Chicago, offers easy walking access to numerous bakeries, restaurants, and breweries.
Sleeping up to five guests, this well-equipped apartment boasts a kitchen with fridge, freezer, microwave, and dishwasher, plus air conditioning, parking, and excellent guest ratings; modern amenities are also included.
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