Vacation Rentals in Chicago, IL

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Chicago, IL vacation rentals
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10119 Vacation rentals and Airbnb in Chicago, IL

Best family friendly Chicago, IL vacation rentals

Among the 10119 accommodations in Chicago, IL, here are the 4 best family friendly rentals

Spacious 2br Group Retreat Near Mccormick Place - Chicago, IL
10 1 review
Chicago, IL
07/10 – 14/10
₹66957/nighttotal: ₹468699 (7 )

Spacious 2br Group Retreat Near Mccormick Place

2 3
apartment , Chicago
This Near South Side Chicago flat is conveniently located a short walk from State Street and McCormick Place, and within 3.2km of Soldier Field and Lake Michigan.
The 84 square metre property offers three bedrooms, two bathrooms, sleeps six, and includes a fully equipped kitchen, private patio, free Wi-Fi, on-site fitness centre, and parking.
Stylish Friendly 3br Suite Near Mccormick - Chicago, IL
Chicago, IL
29/07 – 03/08
₹122434/nighttotal: ₹612170 (5 )

Stylish Friendly 3br Suite Near Mccormick

3 1
apartment , Chicago
This South Loop flat offers a prime Chicago location, just a short walk to McCormick Place and Grant Park, and a quick Uber to Museum Campus and Soldier Field.
This spacious 86-square-metre residence features three bedrooms and two bathrooms, accommodating up to six guests with amenities including in-unit laundry, fast Wi-Fi, and 4K Roku Smart TVs.
420 Friendly 3br/2ba Heaven With Optional Parking And Sleeps 8 - Chicago, IL
10 2 reviews
Chicago, IL
24/07 – 27/07
₹85945/nighttotal: ₹257835 (3 )

420 Friendly 3br/2ba Heaven With Optional Parking And Sleeps 8

3 8
apartment , Chicago
This Near South Side Chicago flat is a short walk from Wintrust Arena and McCormick Place, and within 1.6km of Soldier Field and Lake Michigan.
The 102 square metre property sleeps eight, boasts three bedrooms, two bathrooms, a fully equipped kitchen including dishwasher, in-unit laundry, and free Wi-Fi; housekeeping is available on request.
Large, Sunny 3 Bedroom Apartment Two Blocks From Down Town Oak Park. - Chicago, IL
9.9 336 reviews
Chicago, IL
02/07 – 03/07
₹45190/nightfor 1 night

Large, Sunny 3 Bedroom Apartment Two Blocks From Down Town Oak Park.

1 5
apartment , Oak Park
This apartment in Oak Park is conveniently situated just two blocks from the Frank Lloyd Wright district, offering easy access to the area's architectural gems and a short walk to shops, restaurants, and parks. It has consistently received excellent ratings for location, cleanliness, and user experience.
The three-bedroom flat, which spans 130 square metres, comfortably accommodates up to eight guests. It features a fully equipped kitchen, a private deck overlooking a landscaped garden, a private entrance, and a modern bathroom with laundry facilities.

Best Chicago, IL holiday rentals with parking

Windy City Getaway - 3br 2ba Chicago Townhouse Home - Chicago, IL
9.5 2 reviews
Chicago, IL
24/07 – 27/07
₹77774/nighttotal: ₹233322 (3 )

Windy City Getaway - 3br 2ba Chicago Townhouse Home

3 8
house , Chicago
This Chicago townhouse, situated approximately 8-13 kilometres from Wrigley Field, Lincoln Park Zoo, and the United Centre, offers convenient access to major attractions.
Sleeping up to 17 guests, this three-bedroom, three-bathroom property boasts a fully equipped kitchen, in-unit laundry, free Wi-Fi, private parking, a fireplace, and a terrace/balcony; nearby activities include exploring Lincoln Park Zoo and catching a Cubs game at Wrigley Field.
Stunning, Spacious, & Sun-soaked 2br Uptown Condo By Allset Turnover - Chicago, IL
9.8 237 reviews
Chicago, IL
17/07 – 19/07
₹42908/nighttotal: ₹85816 (2 )

Stunning, Spacious, & Sun-soaked 2br Uptown Condo By Allset Turnover

2 2
apartment , Chicago
This one-bedroom flat is situated in Chicago's Uptown neighbourhood, just a short walk from the lakefront and Montrose Beach, and a six-minute walk from the Wilson Red Line station. The apartment has received excellent ratings for its location, cleanliness, and overall user experience.
The flat is ideal for up to four guests, and comes with a dedicated workspace, a fully equipped kitchen, and a spacious sunroom with a sofa bed. Guests can enjoy a bright and inviting atmosphere, and benefit from 24/7 customer assistance and accidental damage protection.
Cozy Estate 20 Minutes From Downtown And Lakefront - Chicago, IL
9.6 17 reviews
Chicago, IL
02/07 – 03/07
₹37092/nightfor 1 night

Cozy Estate 20 Minutes From Downtown And Lakefront

1 5
apartment , Willow Springs
This two-bedroom flat in Willow Springs is located just 160 metres from the Forrest Preserve, offering convenient access to extensive hiking and biking trails, with downtown and lakefront beaches a 20-minute drive away.
This pet-friendly apartment accommodates up to five guests and features a kitchen, air conditioning, and parking, providing a peaceful base for outdoor recreation and city exploration.
United Center Compound W/rooftop, Hot Tub, Sauna - Chicago, IL
9.8 91 reviews
Chicago, IL
28/08 – 30/08
₹257880/nighttotal: ₹515760 (2 )

United Center Compound W/rooftop, Hot Tub, Sauna

1 10
apartment , Chicago
This spacious four-bedroom Chicago home, near the United Centre in the West Loop, offers easy access to local attractions.
Sleeping nine in total across four bedrooms and three bathrooms, this mid-century modern property boasts a chef's kitchen, multiple entertainment areas including a rooftop deck and a large heated private garage (111.5 m²).

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.

Destinations nearby

Best Chicago, IL holiday rentals with a balcony

Two-story Stunner In Iconic Old Town Chicago By Allset Turnover - Chicago, IL
9.6 134 reviews
Chicago, IL
07/10 – 14/10
₹134004/nighttotal: ₹938028 (7 )

Two-story Stunner In Iconic Old Town Chicago By Allset Turnover

2 8
apartment , Chicago
This Old Town Chicago condo is located blocks from the North and Wells intersection, offering easy access to the Second City comedy club and other attractions in the area.
The three-bedroom, three-bathroom property sleeps eight guests and features a fully equipped chef's kitchen, a living room, a dedicated workspace, and a terrace/balcony plus garden; street parking is available or can be pre-booked via apps such as SpotHero or ParkWhiz.
Charming 2 Br Apartment Near Lincoln Park Zoo In Historic Building - Chicago, IL
10 22 reviews
Chicago, IL
02/10 – 05/10
₹44013/nighttotal: ₹132039 (3 )

Charming 2 Br Apartment Near Lincoln Park Zoo In Historic Building

2 4
apartment , Chicago
This Lincoln Park flat is ideally located a 5-minute walk (approximately 0.8 km) from Lincoln Park Zoo, Lake Michigan, and numerous restaurants.
The two-bedroom apartment, sleeping five, boasts a private deck overlooking a courtyard, a fully equipped kitchen, and family-friendly amenities including a high chair and travel cot; nearby attractions include the Chicago Theatre, Art Institute of Chicago, Field Museum, and Museum of Science and Industry.
Irving Park/avondale Updated Vintage Top Unit In 2-flat - Chicago, IL
9.4 3 reviews
Chicago, IL
04/08 – 10/08
₹27364/nighttotal: ₹164184 (6 )

Irving Park/avondale Updated Vintage Top Unit In 2-flat

2 2
apartment , Chicago
This Irving Park flat is situated 2.4 kilometres from Milwaukee Avenue, offering easy access to the Addison and Irving Park Blue Line stations and is within 9.6 kilometres of Wrigley Field and the Walt Disney House.
The two-bedroom, one-bathroom apartment sleeps six, features a terrace, fully equipped kitchen including a dishwasher, free Wi-Fi, and on-site barbecue facilities.
Stylish River North Suites Luxe Comfort Near Chicagos Best Shopping & Nightlife - Chicago, IL
10 2 reviews
Chicago, IL
29/12 – 30/12
₹39463/nightfor 1 night

Stylish River North Suites Luxe Comfort Near Chicagos Best Shopping & Nightlife

1 4
apartment , Chicago
This Level River North apartment, a stylish flat in Chicago's River North district, is minutes from the Magnificent Mile and across the river from the Loop.
The 56 square metre (602 square foot) studio suite sleeps four, offering a fully equipped kitchen, in-suite laundry, complimentary Wi-Fi, and access to a swimming pool, sauna, and parking; nearby attractions include the Chicago Theatre and Art Institute of Chicago.

Best Chicago, IL holiday rentals with air conditioning

Charming 2br Retreat In Chicago! - Chicago, IL
9.0 16 reviews
Chicago, IL
19/07 – 31/07
₹40881/nighttotal: ₹490572 (12 )

Charming 2br Retreat In Chicago!

2 3
apartment , Chicago
This two-bedroom flat is situated in Humboldt Park, a lively neighbourhood in Chicago, just a short walk from the 606 Trail and a few kilometres from downtown Chicago. It has received excellent guest ratings, making it a popular choice for travellers.
The flat can comfortably accommodate up to five guests and comes equipped with a kitchen, air conditioning, a balcony and free parking. You can enjoy easy access to local shops, restaurants and parks, as well as the United Center and Wrigley Field, making it ideal for exploring the city and enjoying its vibrant culture.
Cozy Bright Quiet Boho-chic House In Bridgeport - Chicago, IL
9.9 200 reviews
Chicago, IL
30/07 – 02/08
₹57784/nighttotal: ₹173352 (3 )

Cozy Bright Quiet Boho-chic House In Bridgeport

1 3
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.
Modern 4br Gem - 15 Min To Downtown W/free Parking - Chicago, IL
9.4 50 reviews
Chicago, IL
28/07 – 06/08
₹48461/nighttotal: ₹436149 (9 )

Modern 4br Gem - 15 Min To Downtown W/free Parking

1 8
apartment , Chicago
This four-bedroom flat offers excellent access to Chicago's attractions, situated approximately a 15-minute drive from the city centre and within 11 kilometres of Millennium Park and Navy Pier, and 6 kilometres of the United Center.
This property accommodates up to nine guests, featuring four bedrooms with Queen beds, two kitchens, air conditioning, private parking, and a living area with a 55-inch Smart TV, making it ideal for groups seeking convenient Chicago city breaks.
Pet Friendly! Historic River West Neighborhood - Easy Access To O'hare Apts - Chicago, IL
9.4 243 reviews
Chicago, IL
10/08 – 13/08
₹30262/nighttotal: ₹90786 (3 )

Pet Friendly! Historic River West Neighborhood - Easy Access To O'hare Apts

3 3
apartment , Chicago
This three-bedroom River West apartment in Chicago offers easy access to the Loop and West Loop, situated close to a Blue Line station providing convenient transport links to O'Hare International Airport.
Sleeping up to six guests, this pet-friendly condo boasts two bathrooms, a fully equipped kitchen including a dishwasher, and high-speed internet access; nearby restaurants and bars in the West Loop offer additional dining and entertainment options.
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