Holiday Rentals in Chicago

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Chicago holiday rentals
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Chicago holiday rentals: compare the best deals

Best family friendly Chicago holiday rentals

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

New! 10-min To Downtown - Chicago
10 2 reviews

New! 10-min To Downtown

apartment, Oak Park
This Oak Park flat is conveniently situated for exploring the area's historic architecture and cultural sites, being a 4-minute drive from the Frank Lloyd Wright Historic District and a 5-minute drive from the Ernest Hemingway Museum and House, with Austin Metro Station just 500 metres away for wider Chicago exploration.
This family-friendly four-bedroom, two-bathroom apartment accommodates up to eight guests, offering amenities such as Wi-Fi, air conditioning, a fully equipped kitchen, and in-unit laundry, alongside outdoor space with a garden and balcony, plus covered parking.
Livn Millennium Park Downtown Chicago 2br - Chicago
No reviews

Livn Millennium Park Downtown Chicago 2br

apartment, Chicago
This newly renovated two-bedroom flat is located in central Chicago, just 100 metres from Millennium Park and Michigan Avenue.
This family-friendly apartment sleeps four guests and features a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, alongside air conditioning and an in-unit washer and dryer.
Nine-bedrooms In Wrigleyville - Chicago
No reviews

Nine-bedrooms In Wrigleyville

house, Chicago
This Wrigleyville property is centrally located in Chicago's entertainment district, offering proximity to nightlife, restaurants, and the iconic Wrigley Field, approximately 1.5 kilometers from the nearest Underground station.
This detached residence comprises three self-contained apartments, accommodating up to 22 guests with nine bedrooms and three bathrooms, featuring a shared rear deck and essential amenities including Wi-Fi and air conditioning, with optional street parking permits available.
Blueground | Greektown, Bbq, Gym, Nr Willis Tower - Chicago
10 1 review

Blueground | Greektown, Bbq, Gym, Nr Willis Tower

apartment, Chicago
This one-bedroom flat is situated in Chicago's Greektown district, offering city views from its balcony.
This flat accommodates two guests and includes a fully equipped kitchen, in-apartment laundry, air conditioning, and building amenities such as a BBQ area and fitness centre.

Best Chicago holiday rentals with parking

The Greenhouse - Chic 2br Flat Near Fulton Market - Chicago
9.9 89 reviews

The Greenhouse - Chic 2br Flat Near Fulton Market

apartment, Chicago
This West Loop flat is ideally situated in Chicago's West Loop neighbourhood, offering easy access to the city's attractions.
The 2-bedroom, 1-bathroom apartment sleeps 4 guests and boasts a newly renovated kitchen, in-unit laundry, a private balcony, and access to a large garden; free street parking is available but not guaranteed.
Welcome To Nancy's Pad! - Chicago
9.7 358 reviews

Welcome To Nancy's Pad!

apartment, Chicago
This Lakeview flat, near Wrigley Field and Southport's nightlife, offers easy access to downtown Chicago.
Sleeping up to six guests, this two-bedroom, one-bathroom apartment includes a garden, parking, free laundry facilities, and a private patio; amenities such as a fridge, microwave, and air conditioning are also provided.
Space&style New Rehab, First Flr + Bsmt Of Duplex, Driveway Prkng, Walk To Train - Chicago
10 17 reviews

Space&style New Rehab, First Flr + Bsmt Of Duplex, Driveway Prkng, Walk To Train

apartment, Oak Park
This Oak Park apartment is situated a 15-minute walk from the Frank Lloyd Wright Historic District and Concordia University Chicago, and within 9.6km of both the Walt Disney House and Loyola University Medical Centre.
The three-bedroom, three-bathroom property sleeps seven guests and boasts a private patio, fully equipped kitchen, free Wi-Fi, on-site parking, a spa, and a shared garden with an arcade/games room.
Sleep 25 - Huge Downtown Vintage Lofts - Chicago
9.5 1044 reviews

Sleep 25 - Huge Downtown Vintage Lofts

apartment, Chicago
This penthouse flat is located in downtown Chicago, just a short walk from Millennium Park, Grant Park, the Skydeck, Shedd Aquarium, and Adler Planetarium. The property has received excellent ratings for location, cleanliness, and overall user experience.
The apartment features a spacious loft design with high ceilings, offering a sense of openness and grandeur. Guests can enjoy a well-equipped kitchen, a private balcony with city views, a fitness centre, a tennis court, and parking facilities.

Frequently asked questions about holiday rentals in Chicago

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

    You've got to see the iconic Willis Tower, stroll along Navy Pier, and catch a show in the historic Chicago Theatre. These are must-dos for any first-time visitor.
  • What are the best Airbnb and vacation rentals in Chicago?

  • Which neighborhood in Chicago, IL should you consider for a vacation rental?

    For a vibrant and central location, you could look at Lincoln Park. It's close to the lakefront, museums, and has great restaurants and shops. Wicker Park is also trendy with a cool vibe and plenty of independent businesses.
  • What are the most popular Airbnbs in Chicago?

  • What are the top family-friendly attractions in Chicago, IL?

    The Lincoln Park Zoo is a free attraction with lots to see, and the Shedd Aquarium is a great place for kids to learn about marine life. The Field Museum is also a hit with families, especially the Sue the T-Rex exhibit.
  • What are the best vacation rentals with a pool in Chicago?

  • When is the best time to book a vacation rental in Chicago, IL?

    You'll want to book your vacation rental in advance, especially if you're travelling during peak season, which is typically from May to October. You can find good deals outside of these months, but you might miss out on some of the best weather.
  • What are the best rentals for families and kids in Chicago?

  • What events or festivals should visitors check out in and around Chicago, IL?

    Chicago has a great festival scene. The Taste of Chicago in July is a must-see for foodies, and the Chicago Blues Festival in June is a great way to experience the city's musical heritage. The Air and Water Show in August is also a popular event.
  • What are the best rentals or Airbnbs with a jacuzzi in Chicago?

  • What are the best budget-friendly activities in Chicago, IL?

    You can explore the city for free by walking or cycling along the Lakefront Trail. Visiting the free museums like the Art Institute of Chicago on Tuesdays after 5pm is a great way to save money. The Millennium Park is a great place to spend a sunny afternoon and soak up the atmosphere.
  • What are the best restaurants with local dishes in Chicago, IL?

    For a taste of Chicago's famous deep-dish pizza, head to Lou Malnati's or Pizzeria Bebu. For a more casual experience, try a Chicago-style hot dog from Portillo's. If you're looking for something more upscale, try Alinea, which offers a modern take on American cuisine.
  • What are the best walking or cycling routes in Chicago, IL?

    The Lakefront Trail is a great option for both walking and cycling, offering stunning views of Lake Michigan. The 606 is a popular elevated trail that winds through the city's diverse neighbourhoods. For a more scenic route, try the North Shore Channel Trail, which follows a historic canal.
  • Are there pet-friendly attractions in Chicago, IL?

    Yes, there are lots of pet-friendly places in Chicago! You can walk your dog along the Lakefront Trail, or visit the dog-friendly restaurants and cafes in the city. The Lincoln Park Zoo is also pet-friendly, as are many of the parks and green spaces.
  • What are the benefits of choosing a vacation rental in Chicago, IL?

    Vacation rentals offer more space and privacy than a hotel room, and are often a more affordable option for families or groups. 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 a great sports city! You can catch a baseball game at Wrigley Field, a basketball game at the United Center, or a football game at Soldier Field. The city also has a number of other sporting facilities, including golf courses, tennis courts, and swimming pools.

Popular destinations

Best Chicago holiday rentals with a balcony

Luxury Designer Penthouse 3802 | Pool | Gold Coast - Chicago
9.2 13 reviews

Luxury Designer Penthouse 3802 | Pool | Gold Coast

apartment, Chicago
This three-bedroom penthouse apartment is situated in Chicago's Gold Coast district, just a short walk from Michigan Avenue and Lake Michigan.
The 130 square metre property boasts stunning views of the Chicago skyline, a spacious open-plan living area and a fully equipped kitchen, comfortably sleeping up to ten guests.
Luxury 3br Penthouses + Group Comfort Awaits - Chicago
No reviews

Luxury 3br Penthouses + Group Comfort Awaits

apartment, Chicago
This six-bedroom, five-bathroom flat in Chicago's River West district offers excellent access, being just 2 minutes from downtown attractions and 5 minutes from the Riverwalk.
This spacious apartment accommodates up to 14 guests, featuring a chef's kitchen, 24-hour gym, outdoor pool, hot tub, and is conveniently located near Logan Square, Old Town, and Fulton Market.
Promo 10% Weekly And 15% Monthly! Jacuzzi, King Beds, Easy Access To Dt Chicago! - Chicago
9.4 23 reviews

Promo 10% Weekly And 15% Monthly! Jacuzzi, King Beds, Easy Access To Dt Chicago!

apartment, Westchester
This four-bedroom house is located in Westchester, a suburb just west of Downtown Chicago, making it easy to reach the city centre. The property has received excellent ratings from previous guests.
The apartment spans 186 square metres and comfortably accommodates up to 10 guests. It offers a range of amenities, including a jacuzzi, a spacious garden, and a games room, ensuring a relaxing and enjoyable stay for all.
Modern 2-bedroom Townhome In Chicago With Private Patio - Chicago
10 3 reviews

Modern 2-bedroom Townhome In Chicago With Private Patio

apartment, Chicago
This Bucktown townhouse, situated on a quiet corner block within easy walking distance of the Six Corners intersection of North, Milwaukee, and Damen Avenues, offers a convenient base for exploring Chicago.
This 167 square metre (1798 square foot) property sleeps up to nine guests, boasting two living rooms, three bathrooms, a fully equipped kitchen with coffee station, a private patio with fire pit, a game room with shuffleboard and Connect 4, and free street parking.

Best Chicago holiday rentals with air conditioning

Central Chicago Suite2 Access To Patio - Chicago
8.6 30 reviews

Central Chicago Suite2 Access To Patio

apartment, Chicago
This Chicago apartment, situated approximately 2.9-3.2km from the Water Tower Place, United Centre, and the Museum of Contemporary Art, offers convenient access to major attractions.
The 93 square metre dwelling boasts two bedrooms, one bathroom, sleeps sixteen guests, and includes a fully equipped kitchen, private patio, in-unit laundry, and free Wi-Fi.
Marvelous 3-bedroom Apartment With Ac In Vibrant Chicago - Chicago
No reviews

Marvelous 3-bedroom Apartment With Ac In Vibrant Chicago

apartment, Chicago
This Washington Heights flat in Chicago is conveniently located approximately 10 kilometres south of the city centre, offering easy access to Lake Michigan and Grant Park, as well as the Museum of Science and Industry and the Field Museum of Natural History.
This three-bedroom flat accommodates up to six guests and includes a dishwasher, air conditioning, and heating, with nearby access to McCormick Place and Soldier Field for events.
Flexhome East Village - Modern 2br - Quiet Street - Chicago
8.8 5 reviews

Flexhome East Village - Modern 2br - Quiet Street

apartment, Chicago
This East Village flat offers easy access to Chicago's attractions, being 2.7 kilometres from the United Center and 4.8 kilometres from the Willis Tower.
This two-bedroom flat, covering 102 square metres, sleeps up to nine guests and includes air conditioning, free WiFi, and a fully equipped kitchen with a dishwasher.
Penthouse Designer Loft 4w | Goldcoast/river North - Chicago
10 13 reviews

Penthouse Designer Loft 4w | Goldcoast/river North

apartment, Chicago
This luxury three-bedroom flat is located in Chicago's River North and Gold Coast districts, 100 metres from Michigan Avenue and 400 metres from Lake Michigan, placing it near numerous restaurants, shops, and nightlife.
This spacious accommodation, suitable for up to 12 guests, features a chef's kitchen with GE gas ranges, a restaurant-sized refrigerator, and a separate dining area, alongside convenient parking available a couple of blocks away.
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