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

Sophisticated Urban Haven With Modern Luxury - Elegant Retreat - Chicago, IL
No reviews

Sophisticated Urban Haven With Modern Luxury - Elegant Retreat

apartment, Chicago
This luxury flat in Chicago's historic Bronzeville district is located approximately 5 kilometres from downtown Chicago and Lake Michigan, with close proximity to McCormick Place and the IIT campus.
This 3-bedroom, 2-bathroom residence accommodates up to 6 guests and offers essential amenities including air conditioning, Wi-Fi, and a fully equipped kitchen, with free street parking available.
Wicker Park Home: Movie Room, Piano - Chicago, IL
9.9 45 reviews

Wicker Park Home: Movie Room, Piano

apartment, Chicago
This Wicker Park apartment, ideally situated in Chicago's West Town neighbourhood, offers easy access to public transport and is within walking distance of Humboldt Park.
The four-bedroom, three-and-a-half-bathroom dwelling sleeps up to 12 guests, boasting an electric baby grand piano, a dedicated movie room with an 85-inch smart TV, and a private back deck; nearby attractions include Wicker Park's diverse culinary scene and numerous live music venues.
Remodeled Boho Avondale Getaway - Sleeps 6 - Chicago, IL
No reviews

Remodeled Boho Avondale Getaway - Sleeps 6

apartment, Chicago
This 65 square meter garden flat is situated in Chicago's Avondale district, a developing area approximately 15 minutes by public transport from the city centre.
The property offers a modern boho-style decor, accommodates up to six guests with two queen beds, a sleeper sofa, and two twin air mattresses, and includes an in-unit washer/dryer, free street parking, and a shared garden, with entertainment provided by a classic arcade machine and wall-mounted games.
Bright 3br Stylish Apartment Near North Ave Shops - Chicago, IL
9.9 31 reviews

Bright 3br Stylish Apartment Near North Ave Shops

apartment, Chicago
This newly designed luxury 3-bedroom B&B is located in downtown Chicago, providing easy access to premier dining, shopping, and attractions, with excellent public transport links within 500 meters.
This family-friendly accommodation offers private access to the entire unit, sleeping up to 8 guests with a fully equipped kitchen, high-speed internet, air conditioning, and spectacular city views from large windows.

Best Chicago, IL vacation rentals with parking

New Apartment W/patio & Backyard - Chicago, IL
9.9 33 reviews

New Apartment W/patio & Backyard

apartment, Chicago
This Jefferson Park flat is situated approximately 0.5km from the CTA Blue Line and Mariano's grocery store, offering easy access to I-90 & I-94 for a 20-30 minute commute to Chicago's city centre.
The two-bedroom, one-bathroom apartment sleeps four guests and boasts a spacious kitchen with a centre island, private balcony, rare backyard access, and fast Wi-Fi.
Beautiful Garden Unit In Logan Square! - Chicago, IL
9.8 174 reviews

Beautiful Garden Unit In Logan Square!

apartment, Chicago
This Logan Square flat is situated a block from Kosciuszko Park, 0.6 km from the Healy Metra Station and 1.6 km from the CTA Blue Line, offering easy access to the 606 Bloomingdale Trail.
The one-bedroom, one-bathroom apartment sleeps four, features a large walk-in closet, open-plan living/dining area, and a garden, and is close to restaurants, bars and a cinema.
Rustic Retreat Near Hosp - Chicago, IL
9.2 51 reviews

Rustic Retreat Near Hosp

apartment, Berwyn
This Berwyn apartment is ideally situated a short walk from restaurants and the BNSF Metra station, offering easy access to Oak Park and Chicago city centre by car or train.
The one-bedroom flat sleeps four guests and features a fully equipped kitchen, 50" Smart TV, free street parking, and shared laundry facilities within the building; keyless entry is provided.
Lincoln Park Apt: Walk To Beach, Shops & Dining! - Chicago, IL
9.4 37 reviews

Lincoln Park Apt: Walk To Beach, Shops & Dining!

apartment, Chicago
This Lincoln Park flat is a mere 1.5 kilometres from Millennium Park and the Art Institute of Chicago, offering excellent access to the Magnificent Mile.
This one-bedroom flat accommodates up to three guests and features a fireplace, a furnished patio, a fully equipped kitchen, in-unit laundry, a workspace, and garage parking for one car.

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

Mid Century Italian Suite With Large Patio - Charming Airy Oasis - Chicago, IL
No reviews

Mid Century Italian Suite With Large Patio - Charming Airy Oasis

apartment, Chicago
This Chicago flat is located in a district offering a private atmosphere yet close to key attractions, with the Magnificent Mile approximately 2.5 kilometres away.
This pet-friendly residence accommodates up to four guests in one bedroom and features a kitchenette with a Moccamaster coffee machine, a king bed, a queen sleeper sofa, a patio, and in-unit laundry.
Your Chicago Home Base  4br, 2ba, Sleeps 15, Ideal For Families & Groups! - Chicago, IL
9.8 16 reviews

Your Chicago Home Base 4br, 2ba, Sleeps 15, Ideal For Families & Groups!

apartment, Chicago
This Albany Park flat in Chicago offers a private room within a renovated three-bedroom, two-bathroom shared apartment, conveniently located for access to Lincoln Park Zoo and the Field Museum, though further from Michigan Avenue and Navy Pier.
The shared dwelling features a kitchen with a microwave and dishwasher, free parking, and accommodates two guests, with stylish common areas and proximity to Wrigley Field and the United Centre.
Flexhome Ukrainian Village  2br  Walkable + Private Balcony · Sleeps 6 - Chicago, IL
8.8 14 reviews

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

apartment, Chicago
This West Town apartment in Chicago offers convenient access to numerous parks, restaurants, and bars, with major attractions within easy reach.
The 55-square-metre (592-square-foot) flat features two queen-size beds, a sofa, one bathroom, in-unit laundry, and sleeps up to five guests, boasting a dedicated workspace and a smart TV with AirPlay.
New! Spacious Art Deco Modern 5 Bd/3ba Condo - Chicago, IL
8.5 2 reviews

New! Spacious Art Deco Modern 5 Bd/3ba Condo

apartment, Chicago
This spacious Chicago apartment, located near the United Center, Water Tower Place, and Union Station (all within a 3-5 km radius), offers easy access to major attractions.
The 279 square metre property boasts a five-bedroom, three-bathroom layout sleeping up to 27 guests, complete with a fully equipped kitchen, free Wi-Fi, private parking, and a terrace.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL vacation rentals with air conditioning

Bright 2br Luxury Corner Suite With Optional Parking Sleeps 6 Guests Near Mccormick Place And Soldier Field - Chicago, IL
9.1 232 reviews

Bright 2br Luxury Corner Suite With Optional Parking Sleeps 6 Guests Near Mccormick Place And Soldier Field

apartment, Chicago
This modern apartment is located in Chicago's McCormick Place district, just a short distance from the Field Museum of Natural History and the Art Institute of Chicago. The property has received excellent ratings for location, cleanliness, and overall user experience.
The apartment has two bedrooms and two bathrooms, comfortably accommodating up to six guests. It comes with a fully equipped kitchen, a fitness centre, a terrace, and on-site parking, making it perfect for families or groups of friends exploring the city.
Inspiring Stone Grotto Sleeps 10-20 & Free Parking - Chicago, IL
9.9 263 reviews

Inspiring Stone Grotto Sleeps 10-20 & Free Parking

apartment, Chicago
This spacious four-bedroom apartment is situated in East Lakeview, just two blocks from Lake Michigan and Lincoln Park, offering easy access to the city's attractions and public transport. It has consistently received excellent ratings for location, cleanliness and overall experience.
The property is a unique blend of modern amenities and historical charm, housed in a historic 1893 building. Guests can enjoy the fully equipped kitchen, large TV, Wi-Fi, a private garage, and a spacious backyard, perfect for relaxing or enjoying outdoor activities.
Kasa Lake Shore Chicago | One Bedroom Queen - Chicago, IL
9.3 9 reviews

Kasa Lake Shore Chicago | One Bedroom Queen

apartment, Chicago
This furnished one-bedroom flat is situated in Chicago's Streeterville district, just a short walk from Lake Michigan, Navy Pier, and the Magnificent Mile, offering convenient access to major attractions.
This accommodation provides space for up to four guests, featuring a full kitchen with a fridge, microwave, and dishwasher, air conditioning, on-site fitness centre, and allows pets for a nightly fee.
Chicago Oasis | Spa Bath, Patio & Fireplace - Chicago, IL
10 20 reviews

Chicago Oasis | Spa Bath, Patio & Fireplace

apartment, Chicago
This apartment is located in downtown Chicago, just a short walk from Navy Pier and Michigan Avenue, making it easy to explore the city’s attractions and vibrant nightlife. It has received excellent reviews from previous guests.
The one-bedroom apartment spans 88 square metres and comfortably accommodates up to four guests. It boasts a fully equipped kitchen, a spa bathroom with a jetted tub and a rain shower, and a terrace where you can relax and enjoy the city views.
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