Holiday Rentals in Chicago, IL

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Chicago, IL holiday rentals
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13982 Holiday rentals and Airbnb in Chicago, IL

Best family friendly Chicago, IL holiday rentals

Among the 13982 accommodations in Chicago, IL, here are the 4 best family friendly rentals

Mccormick Place Huge 2br Cozy Loft Suite With Optional Parking Sleeps 8 Near Soldier Field And Grant Park - Chicago, IL
9.3 12 reviews

Mccormick Place Huge 2br Cozy Loft Suite With Optional Parking Sleeps 8 Near Soldier Field And Grant Park

apartment, Chicago
This Chicago McCormick Place loft is situated near the Museum Campus, approximately 2.4 kilometres from the Field Museum and 2.9 kilometres from the Art Institute of Chicago.
This spacious two-bedroom, two-bathroom apartment, offering 102 square metres of floor area, sleeps up to eight guests and boasts amenities including free Wi-Fi, on-site parking, and a fully equipped kitchen; nearby attractions include DePaul University and the Chicago Symphony Orchestra.
Prime 4 Br Sleeps 13, Chef Kitchen, 8 Blks To Wrigley, 15min Train To Mag Mile - Chicago, IL
9.8 33 reviews

Prime 4 Br Sleeps 13, Chef Kitchen, 8 Blks To Wrigley, 15min Train To Mag Mile

apartment, Chicago
This North Center family-friendly home, a 232 square metre property, is situated within 3.2 kilometres of Wrigley Field, Lincoln Park, and Lake Michigan, offering convenient access to Addison and Paulina stations.
The four-bedroom, three-bathroom dwelling sleeps thirteen guests and boasts amenities including free Wi-Fi, a fireplace, a fully equipped kitchen with dishwasher, and on-site parking, plus a playground and books for guests' enjoyment.
Modern Loft W/fast Wifi & Smart Tvs - Chicago, IL
9.5 23 reviews

Modern Loft W/fast Wifi & Smart Tvs

apartment, Chicago
This South Loop flat is situated a 10-minute walk from McCormick Place and a 5-minute Uber to Soldier Field, offering excellent access to Chicago's attractions.
This family-friendly flat provides three bedrooms, two bathrooms, and sleeps up to six guests, featuring a modern kitchen, air conditioning, and 250 Mbps Wi-Fi, with the option for responsible indoor smoking.
Modern Condo  Safe Chicago Stay Near Ohare - Chicago, IL
10 1 review

Modern Condo Safe Chicago Stay Near Ohare

apartment, Chicago
This Cook County flat offers convenient access to O'Hare International Airport and the Blue Line, placing you within 1.6 kilometres of Parkway Bank Park Entertainment District, Rosemont Theatre, and Rivers Casino.
This two-bedroom flat accommodates up to four guests, featuring a full kitchen with high-end appliances, complimentary Wi-Fi, air conditioning, and free private parking, with pets welcome subject to registration and potential fees.

Best Chicago, IL holiday rentals with parking

Modern 1-bedroom W/ Off-street Parking Space - Chicago, IL
9.9 130 reviews

Modern 1-bedroom W/ Off-street Parking Space

apartment, Chicago
This one-bedroom flat is located in the Logan Square neighbourhood, just 1.1 kilometres from both the Belmont and Logan Square Blue line stations, making it easy to explore the city. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
The flat is ideal for a group of three and comes with a fully-equipped kitchen including a fridge, freezer, microwave oven, and dishwasher. Guests can enjoy modern amenities such as in-unit laundry, high-speed internet, and air conditioning, as well as a peaceful garden.
Spacious Roscoe Village Getaway - Chicago, IL
9.8 8 reviews

Spacious Roscoe Village Getaway

house, Chicago
This Roscoe Village detached house is situated within easy walking distance of numerous eateries, shops, and a Starbucks, with the Brown Line train station a mere 500-meter stroll away for convenient access to downtown Chicago.
This residence offers two floors of living space, accommodating up to six guests with flexible bedding, and boasts a chef's kitchen, a spacious deck, and a grass yard complete with a full-size barbecue.
Walk To Train L Near Attractions And Ord L Free Parking L Patio - Chicago, IL
8.8 9 reviews

Walk To Train L Near Attractions And Ord L Free Parking L Patio

apartment, Chicago
This Chicago apartment is conveniently located near public transport, a short walk from a train station, and approximately 7.4 kilometres from Wrigley Field.
The 9-square-metre flat offers two bedrooms, one bathroom, sleeps seven guests, and includes a fully equipped kitchen, private patio, in-unit laundry, free Wi-Fi, and on-site parking and bar.
Lovely Near Loyola - Enjoy The Wonderful Outdoor Space And Sun Room - Room For The Whole Crew Apts - Chicago, IL
9.8 338 reviews

Lovely Near Loyola - Enjoy The Wonderful Outdoor Space And Sun Room - Room For The Whole Crew Apts

apartment, Chicago
This three-bedroom flat is conveniently located just a few blocks from Loyola University in Chicago, within easy walking distance of Lake Michigan and a wide range of restaurants. The property has consistently received excellent ratings for its cleanliness, location and overall guest experience.
The flat is fully furnished and sleeps up to seven guests, with a queen bed, two double beds and a pull-out futon. Amenities include a fully equipped kitchen, a sunroom with a backyard, three televisions, Wi-Fi, cable TV and a parking permit for one car.

Frequently asked questions about holiday rentals in Chicago, IL

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

    You can't go wrong with a visit to Millennium Park, where you'll find the iconic Cloud Gate sculpture, affectionately known as 'The Bean'. A trip to Navy Pier is a must, with its Ferris wheel, shops, and restaurants. And no trip to Chicago is complete without a deep-dish pizza experience.
  • What are the best Airbnb and holiday 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, the Chicago River, and many restaurants and bars. If you prefer a more residential and quiet vibe, Lincoln Park is a great option, with its beautiful park 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 attraction, popular with families, and the Shedd Aquarium is a great option for marine life enthusiasts. The Field Museum is also a favourite, with its dinosaur exhibits and other natural history displays.
  • What are the best holiday 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?

    Booking your vacation rental in advance is always a good idea, especially during peak season, which runs from May to September. If you're looking for a more affordable option, consider visiting during the shoulder seasons, April-May and September-October, when the weather is still pleasant.
  • 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 events scene. The Taste of Chicago, a massive food festival, takes place in July. The Chicago Blues Festival in June is a popular event, and the Lollapalooza music festival in August attracts crowds from all over.
  • 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?

    Chicago has many free and affordable activities. A stroll along the Lakefront Trail offers stunning views. You can enjoy free concerts at Millennium Park's Pritzker Pavilion. And exploring the many diverse neighbourhoods is a great way to experience the city's character.
  • What are the best restaurants with local dishes in Chicago, IL?

    Chicago is a foodie's paradise. For a classic deep-dish pizza experience, Lou Malnati's is a must-try. For authentic Italian, try Tufano's Vernon Park Tap. And for a taste of Chicago's Polish heritage, visit Smak Tak.
  • What are the best walking or cycling routes in Chicago, IL?

    The Lakefront Trail is a popular choice for both walking and cycling, offering stunning views of Lake Michigan. The 606, a former railway line transformed into a park, is a great option for a more urban cycling experience.
  • Are there pet-friendly attractions in Chicago, IL?

    Chicago is a pet-friendly city. The Lincoln Park Zoo welcomes well-behaved dogs on leash. Many parks, such as Millennium Park, have designated areas for dogs. And many restaurants have outdoor patios where you can enjoy a meal with your furry friend.
  • What are the benefits of choosing a vacation rental in Chicago, IL?

    Vacation rentals offer more space and privacy compared to hotels. They often come with amenities like kitchens, which allow you to prepare your own meals and save money. And they can be a great option for families or groups travelling together.

Popular destinations

Best Chicago, IL holiday rentals with a balcony

Peaceful Boho Retreat Free Private Parking - Chicago, IL
10 1 review

Peaceful Boho Retreat Free Private Parking

apartment, Chicago
This one-bedroom flat in Chicago is conveniently located an 18-minute walk from the United Center and 3.9 kilometres from Union Station, offering easy access to attractions such as Water Tower Chicago and Willis Tower.
This pet-friendly apartment provides complimentary Wi-Fi, private parking, a fully equipped kitchen, and a private balcony, accommodating up to 15 guests with a check-out between 10:00 AM and 11:00 AM.
High-end West Loop 2br + City Views & Walkability - Chicago, IL
10 2 reviews

High-end West Loop 2br + City Views & Walkability

apartment, Chicago
This three-bedroom, two-bathroom apartment in Chicago's prime downtown area is less than 1.6km from the Willis Tower and the University of Illinois Chicago, and within 3.2km of the United Centre and the Art Institute of Chicago.
The 5-guest property boasts a fully equipped kitchen, balcony, in-unit TV, fitness centre access, and is conveniently located near public transport links, making it ideal for exploring the city.
2-car Parking, Pingpong, Arcade, 3 Floors! - Chicago, IL
10 2 reviews

2-car Parking, Pingpong, Arcade, 3 Floors!

apartment, Chicago
This West Town apartment, a 130 square metre (1400 square foot) property, is situated in Chicago's West Town district, conveniently located within a 24-32 km radius of the city centre, O'Hare International Airport, Navy Pier, Millennium Park, the Field Museum, and the Art Institute of Chicago.
The spacious dwelling boasts three bedrooms, two bathrooms, and sleeps up to 14 guests comfortably, offering a fully equipped kitchen, a games room with a pool table and arcade machine, two free on-site parking spaces, and in-unit laundry facilities.
Chic 2br Apartment In Edgewater: Gym & Parking - Chicago, IL
No reviews

Chic 2br Apartment In Edgewater: Gym & Parking

apartment, Chicago
This two-bedroom flat in Chicago's Edgewater district is situated a mere 500 metres from the Lake Michigan shoreline, providing convenient access to Loyola University and the Granville Red Line station.
This family-friendly apartment accommodates up to four guests with its two bedrooms, a fully equipped kitchen, in-unit laundry, and access to a communal fitness centre, with a complimentary garage parking spot also included.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday rentals with air conditioning

A Dash Of Panache In Lincoln Square - 1 Br/1 Ba - Chicago, IL
9.6 71 reviews

A Dash Of Panache In Lincoln Square - 1 Br/1 Ba

apartment, Chicago
This ground-floor apartment in Chicago's Bowmanville/Budlong Woods neighbourhood, a 2.4km walk from Lincoln Square and Andersonville, offers convenient access to public transport and diverse culinary options.
The 74-square-metre flat features a king-size bed, two Roku TVs, a fully equipped kitchen (minus a dishwasher), on-site laundry, and parking, comfortably sleeping two guests.
Lovely Studio, 3min Walk To Train For Downtown/ord - Chicago, IL
9.7 166 reviews

Lovely Studio, 3min Walk To Train For Downtown/ord

apartment, Chicago
This Logan Square studio apartment is situated a short 0.5km walk from the train station, offering easy access to Chicago's city centre and O'Hare International Airport.
The self-contained unit sleeps two guests and includes a kitchenette with fridge, freezer and microwave, air conditioning, and access to a shared laundry room; nearby amenities include numerous restaurants and bars.
Stylish 2br Chicago/suburbs Home, Fully Equipped. - Chicago, IL
9.7 137 reviews

Stylish 2br Chicago/suburbs Home, Fully Equipped.

house, Chicago
This comfortable home is located near the border of Chicago and Oak Park, just a short distance from Hemingway's birthplace and a few minutes from several nearby suburbs. The property has received excellent user, location, and cleanliness ratings, ensuring a pleasant stay.
The house has two bedrooms and one bathroom, accommodating up to six guests. Amenities include a fully equipped kitchen, air conditioning, a garden, parking, and internet access, allowing for a relaxing and enjoyable stay.
Private 3 Bedroom Garden Apartment In Lincoln Square Chicago - Chicago, IL
10 3 reviews

Private 3 Bedroom Garden Apartment In Lincoln Square Chicago

apartment, Chicago
This Lincoln Square flat is situated a short 2.4 kilometre drive from Wrigleyville Cubs Stadium and a 3.2 kilometre drive from O'Hare International Airport, offering convenient access to Northeastern University and local amenities.
This furnished three-bedroom flat, accommodating up to four guests, provides 93 square metres of living space with a kitchen, central heating, air conditioning, free WiFi, shared laundry facilities, and a patio backyard for relaxation.
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