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

Luxury 5bd Home: Sauna, Hot Tub, Rooftop, Game Rm - Chicago, IL
No reviews

Luxury 5bd Home: Sauna, Hot Tub, Rooftop, Game Rm

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.
Modern 2br Unit Near Mccormick & Chicago Downtown - Chicago, IL
9.5 176 reviews

Modern 2br Unit Near Mccormick & Chicago Downtown

apartment, Chicago
This apartment is located in the South Loop, a lively neighbourhood just a short walk from McCormick Place and within easy reach of downtown Chicago. It has received excellent ratings for location, cleanliness, and overall value.
The apartment has two bedrooms and two bathrooms, offering 88 square metres of space and comfortably accommodating up to six guests. A fully equipped kitchen, fast internet, a smart TV, and a fitness centre are just some of the amenities available.
Walk To Uc, No Stairs, Free Parking - Chicago, IL
10 184 reviews

Walk To Uc, No Stairs, Free Parking

apartment, Chicago
This spacious Chicago apartment, ideal for families or large groups, enjoys a central location offering easy access to both the United Centre and McCormick Place.
The 168 sq m property boasts two bedrooms, two bathrooms, two sofa beds, and a chef's kitchen, comfortably accommodating up to nine guests and featuring amenities such as a 65" 4K Roku TV and free parking (restrictions apply).
Mid-century Boho Oasis | Pet-friendly + Garage - Chicago, IL
9.6 5 reviews

Mid-century Boho Oasis | Pet-friendly + Garage

apartment, Chicago
This mid-century flat is situated in Chicago's historic Bronzeville district, a short walk or drive from landmarks such as the Victory Monument and Ida B. Wells Home, and less than 10 kilometres from Hyde Park and the Museum of Science and Industry.
This three-bedroom, two-bathroom residence accommodates up to seven guests and includes a private garage, a garden, air conditioning, Wi-Fi, a fully equipped kitchen, and Alexa smart-home technology, with flexible sleeping arrangements and dedicated workspaces.

Best Chicago, IL vacation rentals with parking

Studio With View Of Skyline In Heart Of Pilsen - Chicago, IL
9.4 192 reviews

Studio With View Of Skyline In Heart Of Pilsen

apartment, Chicago
This Pilsen studio flat boasts stunning Willis Tower views and is conveniently located near public transport, a Divvy bike station, and approximately 1.6 kilometres from downtown Chicago.
The open-plan studio, sleeping two guests, features a Roku TV, refrigerator, private entrance, and parking; enjoy exploring the nearby attractions of the Pilsen neighbourhood.
Woodlawn Oasis - Chicago, IL
9.2 15 reviews

Woodlawn Oasis

house, Chicago
Woodlawn Oasis, a three-bedroom, three-bathroom house in Chicago's Woodlawn neighbourhood, is located 2.4km from the Museum of Science and Industry and 2.6km from 63rd Street Beach, offering easy access to other attractions such as Guaranteed Rate Field (9km) and the Field Museum (11.5km).
This Chicago dwelling, boasting a 20 square metre floor area, comfortably sleeps 23 guests and includes a fully equipped kitchen, in-unit laundry, a garden, and free on-site parking.
Flexhome Wicker Park - Stylish 2br - Sleeps 6 - Chicago, IL
8.2 9 reviews

Flexhome Wicker Park - Stylish 2br - Sleeps 6

apartment, Chicago
Flexhome Wicker Park 2BR DV3 is a two-bedroom flat located in Chicago's Wicker Park district, situated 3.4 kilometres from the United Center and within a 5.3-kilometre radius of Union Station, 360 Chicago, and Water Tower Chicago.
This 102-square-metre flat accommodates up to nine guests and features a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, complimentary WiFi, and in-unit laundry facilities.
Garden Apartment In The Historic Heart Of The City - Chicago, IL
9.8 283 reviews

Garden Apartment In The Historic Heart Of The City

apartment, Chicago
This Chicago apartment, ideal for families, is situated on a quiet residential street within easy walking distance of the United Centre, Little Italy, and Greektown.
The one-bedroom flat offers a spacious open-plan living/kitchen area, a private garden with a rock garden and fountain, parking, and sleeps up to four guests; nearby attractions include Madison and Randolph Streets.

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

1br Near O'hare  Balcony  Workspace - Chicago, IL
No reviews

1br Near O'hare Balcony Workspace

apartment, Chicago
This one-bedroom flat in Cook County offers convenient access to O'Hare Airport, major motorways, and Rosemont, placing it within reach of entertainment and shopping districts.
This 56 square metre flat, suitable for up to three guests, features a private balcony, a dedicated workspace, a fully equipped galley kitchen with dining for four, in-building laundry, and one allocated parking space for a pet-friendly stay.
Level Studio Suite With Full Kitchen And Luxury Bath - Chicago, IL
10 2 reviews

Level Studio Suite With Full Kitchen And Luxury Bath

studio, Chicago
This River North studio apartment is centrally located in Chicago, minutes from the Magnificent Mile and a short distance across the river from the Loop.
The self-catering apartment, sleeping up to three guests, boasts a fully equipped kitchen, in-suite laundry, and access to a rooftop pool, fitness centre, and dog run, all within a large amenity space.
3 Prime 2br Units + Ideal Business Retreat - Chicago, IL
No reviews

3 Prime 2br Units + Ideal Business Retreat

apartment, Chicago
This six-bedroom, six-bathroom serviced apartment in Chicago's financial district offers direct access to Millennium Park, placing you within a 1.3-kilometre walk of the Art Institute and a 1-kilometre walk of Skydeck Chicago.
Accommodating up to fifteen guests, this property features three separate two-bedroom units, each with a chef's kitchen and Smart TV, and provides access to extensive building amenities including an outdoor swimming pool, 24-hour fitness centre, and BBQ area.
Relax In West Town - In-unit Laundry And Pet Friendly! By Allset Turnover - Chicago, IL
No reviews

Relax In West Town - In-unit Laundry And Pet Friendly! By Allset Turnover

apartment, Chicago
This West Town flat, a couple of kilometres from the Loop and Navy Pier, offers easy access to the Blue and Green 'L' lines and is conveniently located near Lake Michigan.
The one-bedroom apartment sleeps three, features a terrace, parking, and a kitchen with a fridge, microwave, and dishwasher, and is close to numerous restaurants and shops.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL vacation rentals with air conditioning

Luxury King Bed  Remodeled Safe Chicago Condo - Chicago, IL
10 1 review

Luxury King Bed Remodeled Safe Chicago Condo

apartment, Chicago
This studio flat in Cook County, Chicago, is situated near the airport and major motorways, offering direct access via the 'L' train to the Chicago Loop and the downtown Rosemont district, placing it within easy reach of shopping centres and entertainment venues.
The 38 square metre accommodation features a King Bed with an optional cot for up to three guests, a fully equipped kitchen including a Keurig coffee maker and Ninja Air Fryer, and is conveniently located 1.2 kilometres from the Fashion Outlets of Chicago and 5.8 kilometres from Wrigley Field, with a free parking spot provided.
Steps From Wrigley Field And Lake Michigan - Chicago, IL
9.5 4 reviews

Steps From Wrigley Field And Lake Michigan

apartment, Chicago
This Wrigleyville flat is located in Chicago, a short walk from Wrigley Field and 2.7 kilometres from Montrose Beach, offering air-conditioned accommodation with a patio and free WiFi.
This 167 square metre apartment accommodates up to 10 guests across 3 bedrooms and 2 bathrooms, featuring a fully equipped kitchen with a dishwasher and oven, plus an on-site casino and cycling opportunities nearby.
Elegant & Clean Cottage Apt 20 Minutes From Ohare - Chicago, IL
9.9 267 reviews

Elegant & Clean Cottage Apt 20 Minutes From Ohare

apartment, Chicago
This three-bedroom, two-bathroom apartment in Chicago's Jefferson Park neighbourhood is a five-minute walk from the CTA Blue Line and Metra stations, offering easy access to Chicago's city centre and O'Hare International Airport.
The ground-floor flat, sleeping up to six guests, boasts a full kitchen with dishwasher, two 55-inch smart TVs, free high-speed Wi-Fi, and free on-street parking; nearby amenities include restaurants, cafes, and parks.
Designer Oasis - Sauna, Hot Tub, Patios, Game Room - Chicago, IL
9.8 86 reviews

Designer Oasis - Sauna, Hot Tub, Patios, Game Room

apartment, Chicago
This Wicker Park house, in a central location within the neighbourhood, offers easy access to Chicago's shops, restaurants, and nightlife.
Sleeping sixteen guests, the five-bedroom, three-and-a-half-bathroom property boasts three patios, an entertainment basement with air hockey and foosball, a two-car garage, keyless entry, and a fully equipped kitchen including a dishwasher.
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