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

Chic Cozy 2br Apartment Near Mccormick, Place Museum Campus And Soldier Field - Chicago
9.0 2 reviews

Chic Cozy 2br Apartment Near Mccormick, Place Museum Campus And Soldier Field

apartment, Chicago
This family-friendly Chicago apartment, situated approximately 2.4 kilometres from the Field Museum and within 3.2 kilometres of the Art Institute of Chicago and the Chicago Symphony Orchestra, offers easy access to major cultural attractions.
The 74-square-metre, two-bedroom, two-bathroom flat sleeps up to eight guests and includes a fully equipped kitchen, free Wi-Fi, a fitness centre, parking, and a patio with city views.
Irving Park/avondale Updated Vintage Top Unit - Chicago
9.9 105 reviews

Irving Park/avondale Updated Vintage Top Unit

apartment, Chicago
This Chicago apartment is conveniently located in a residential area, approximately 1.6km from Wrigley Field, 0.6km from the I-90/94 highway, and a short distance from the Blue Line.
The two-bedroom flat sleeps six guests, boasting a queen-size sofa bed, a private balcony, access to a shared backyard with a basketball court, and upcoming outdoor amenities including a pizza oven and space heater; free street parking is also available.
Luxury Penthouse Loft W/terrace  507 | River North - Chicago
9.9 27 reviews

Luxury Penthouse Loft W/terrace 507 | River North

apartment, Chicago
This brand new penthouse duplex loft in Chicago's River North district is situated 320 metres from Michigan Avenue and 960 metres from Lake Michigan, offering prime access to nightlife, restaurants, and shopping.
This spacious designer apartment accommodates up to 10 guests with two living areas, a chef's kitchen, a private terrace with city views, and secure parking nearby, making it ideal for families and pet owners seeking a comfortable stay.
Home Theater And Rooftop Decks - Exquisite Luxury Sanctuary - Chicago
No reviews

Home Theater And Rooftop Decks - Exquisite Luxury Sanctuary

house, Chicago
This detached house is located in Chicago's Wicker Park district, offering convenient access to the CTA Blue Line's Damen and Division stations, placing you approximately 8 kilometres from the city centre.
This family-friendly property accommodates up to 15 guests with four bedrooms, including a master suite and a bunk room, and features a private home theatre, two rooftop patios with skyline views, and garage parking.

Best Chicago holiday rentals with parking

Friendly Songbird Suite - Chicago
9.6 86 reviews

Friendly Songbird Suite

apartment, Oak Park
This Oak Park flat is situated above the Friendly Music Community, close to the Frank Lloyd Wright Home and Studio and the Ernest Hemingway Birthplace Museum.
The stylish apartment, sleeping up to three guests, features a vintage-style kitchen, a luxurious bathroom, a record player, Wi-Fi, a smart TV, and a private entrance; a community room is available for private bookings, and live music is performed downstairs.
Homey Studio Near Wrigley Field - Chicago
9.1 42 reviews

Homey Studio Near Wrigley Field

apartment, Chicago
This newly refurbished apartment in Chicago's Lakeview district is just 700 metres from Wrigley Field and Boys Town, offering excellent access to the brown line for travel into the city centre.
This studio, accommodating two guests, features a queen-size bed, a fully equipped kitchen with a dishwasher, air conditioning, Wi-Fi, and access to streaming services, with parking available.
Hear The Crowd Roar From A Condo Moments Away From Wrigley - Chicago
9.7 388 reviews

Hear The Crowd Roar From A Condo Moments Away From Wrigley

resort, Chicago
This three-bedroom Chicago apartment, located in Wrigleyville, is steps from Wrigley Field, offering unparalleled views and sounds of Cubs games.
Sleeping up to 10 guests, this recently renovated condo boasts a kitchen with fridge, freezer, microwave, and dishwasher, plus air conditioning, a garden, parking (on non-event days), and access to a shared patio and potential rooftop access overlooking Wrigley Field and downtown Chicago.
Perfect For A Hip And Romantic Getaway - This Chic Studio Offers The Best Of The City By Allset Turnover - Chicago
9.8 332 reviews

Perfect For A Hip And Romantic Getaway - This Chic Studio Offers The Best Of The City By Allset Turnover

studio, Chicago
This stylish studio apartment is located in Pilsen, a lively neighbourhood just 3 kilometres from the Loop and a short walk from historic Thalia Hall, making it a great base for exploring Chicago. The apartment has received excellent ratings for its cleanliness, location, and overall experience.
The apartment is bright and spacious, comfortably accommodating two guests. It has everything you need for a comfortable stay, including a fully equipped kitchen, air conditioning, and free parking.

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

Mccormick Place Modern 2br Loft In Downtown Chicago Michigan Avenue With Optional Parking Near Soldi - Chicago
10 1 review

Mccormick Place Modern 2br Loft In Downtown Chicago Michigan Avenue With Optional Parking Near Soldi

apartment, Chicago
Apartment to rent with an excellent rating of 100% based on 1 reviews. You will be based in Chicago.
Facilities and services: an elevator, an access for persons with reduced mobility and air conditioning.
Downtown Chicago 2br Getaway South Loop Comfort Near Mccormick Place, Soldier Field And Grant Park - Chicago
No reviews

Downtown Chicago 2br Getaway South Loop Comfort Near Mccormick Place, Soldier Field And Grant Park

apartment, Chicago
Apartment listing. You will be in Chicago.
Facilities and services include air conditioning, a kitchen and an iron. Take advantage of the terrace in this apartment in Chicago.
Charming One Bed With Office Near Chicago! - Chicago
No reviews

Charming One Bed With Office Near Chicago!

apartment, Forest Park
This Forest Park flat offers convenient access to the United Centre, approximately 19 kilometres away, and the Donald E. Stephens Convention Centre, 26 kilometres distant, with the Forest Park Transit Centre a mere 7-minute walk and Harlem-Forest Park Station a 14-minute walk.
This 74-square-metre apartment accommodates two guests with one bedroom and one bathroom, featuring air conditioning, Wi-Fi, a fully equipped kitchen including a fridge and microwave, and on-site laundry facilities.
Brand-new West Loop 3br + City Views For Families - Chicago
10 1 review

Brand-new West Loop 3br + City Views For Families

apartment, Chicago
This three-bedroom Chicago apartment, situated in the West Loop's Fulton Market District, is within walking distance of Union Park and Little Italy, and a short 0.8 km drive from Randolph Street Market.
The 3-bedroom dwelling boasts a full kitchen with dishwasher, in-unit Sonos sound system, balcony with city views, access to a building swimming pool and terrace, and sleeps up to seven guests; a rollaway bed and travel cot are available.

Best Chicago holiday rentals with air conditioning

Chic Little Italy 4br Stay With Optional Parking - Chicago
10 1 review

Chic Little Italy 4br Stay With Optional Parking

apartment, Chicago
This four-bedroom flat is located in Chicago's Little Italy, within 2 kilometres of Union Station, the United Centre, Willis Tower, and the Art Institute of Chicago.
This 130-square-metre residence offers a kitchen equipped with a fridge, microwave, and dishwasher, air conditioning, free WiFi, and a terrace or balcony, with optional parking and on-site washing facilities available.
Sleeps 15  Game Room  Theater  Gym - Chicago
10 1 review

Sleeps 15 Game Room Theater Gym

apartment, Chicago
This spacious seven-bedroom flat in Chicago offers ample room for up to 15 guests, featuring dedicated entertainment zones including an arcade game room and a theatre room, alongside a well-equipped kitchen and a home gym. With keyless entry and free street parking, this pet-friendly residence provides a comfortable base for exploring the city, complete with air conditioning and an on-site washer and dryer for your convenience.
Lakeview Loft-vintage Chicago, Modern Amenities - Chicago
9.9 595 reviews

Lakeview Loft-vintage Chicago, Modern Amenities

apartment, Chicago
This Lakeview flat is ideally situated in Chicago's Lakeview neighbourhood, less than 0.8km from the Brown and Red Line 'L' trains, under 1.6km from Wrigley Field, and 2.4km from the lakefront.
The freshly remodelled one-bedroom loft, sleeping four guests, boasts a king-size bed, 65" TV, private patio, fully equipped kitchen (fridge, microwave), and self check-in; nearby activities include exploring Wrigleyville and enjoying Chicago's lakefront.
2br  Newly Furnished Modern Apt  Near O'hare - Chicago
No reviews

2br Newly Furnished Modern Apt Near O'hare

apartment, Chicago
This Cook County flat offers convenient access to O'Hare International Airport (ORD), approximately 16 kilometres away, and the Donald E. Stephens Convention Centre, also around 16 kilometres distant, with Presence Resurrection Medical Centre a mere 800 metres from your doorstep.
This three-bedroom, one-bathroom property accommodates up to five guests, features a fully equipped kitchen with a coffee maker, a comfortable living area with a 55-inch 4K Smart TV, a dedicated workspace, and in-building coin-operated laundry facilities, with free street parking available.
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