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

Movie Room, Garden Oasis In Central Manor - Chicago
9.2 98 reviews

Movie Room, Garden Oasis In Central Manor

apartment, Chicago
This Bridgeport, Chicago apartment is conveniently located a short walk from local bars and restaurants, approximately 2.4km from the city centre, 1.6km from the beaches, and 0.8km from Chinatown.
Sleeping up to 12 guests, this three-bedroom, two-bathroom dwelling boasts a fully equipped kitchen, a recreation room with projector and air hockey, a large deck and patio, and access to a fitness centre and parking; a seven-seater SUV is available for hire.
Luxury Penthouse Collection Ph1 - Fulton Market - Chicago
10 2 reviews

Luxury Penthouse Collection Ph1 - Fulton Market

apartment, Chicago
This modern flat, offering two bedrooms and two bathrooms, is located in Chicago's Fulton Market district, a prime area for nightlife and dining, with convenient access to the city's attractions.
Guests can enjoy spectacular city views from the common rooftop, private parking, and access to the building's fitness centre, with a capacity for up to eight people.
2-car Parking, Pingpong, Arcade, 3 Floors! - Chicago
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.
Luxe Vintage Loft, 10min To Downtown, Retro Movie Theatre - 15% Discount Applied - Chicago
8.8 13 reviews

Luxe Vintage Loft, 10min To Downtown, Retro Movie Theatre - 15% Discount Applied

apartment, Chicago
This spacious Chicago apartment, ideal for families or groups, is situated in New City, offering easy access to Lake Michigan, Grant Park, and major museums such as the Art Institute of Chicago and the Field Museum (distances unspecified).
Sleeping 8-12 guests, the three-bedroom, three-bathroom property boasts a fully equipped kitchen, themed rooms (including a retro cinema and galaxy kids' room), smart TVs, high-speed Wi-Fi, and family-friendly amenities like cribs and high chairs, alongside a garden, spa and parking.

Best Chicago holiday rentals with parking

Welcome To The Wrightwood - Chic & Newly Renovated - Chicago
10 68 reviews

Welcome To The Wrightwood - Chic & Newly Renovated

apartment, Chicago
This Logan Square house, steps from Logan Square's restaurants and bars, offers a prime Chicago location.
The three-story property features two kitchens, four bedrooms sleeping ten, three bathrooms, and a two-car garage; amenities include air conditioning, Wi-Fi, and a garden.
Luxury Designer Apartment 802| Gold Coast/old Town - Chicago
9.9 27 reviews

Luxury Designer Apartment 802| Gold Coast/old Town

apartment, Chicago
This newly refurbished loft flat is located in Chicago's Gold Coast and Old Town districts, a few steps from Michigan Avenue, Lake Michigan, and Wells Street.
This accommodation for up to 8 guests offers 2 bedrooms, 2 bathrooms, a full gym, a rooftop sundeck, and one complimentary parking space, with a chef's kitchen and city views.
Modern Stylish 1br, Free Parking, Prime Location - Chicago
9.3 77 reviews

Modern Stylish 1br, Free Parking, Prime Location

apartment, Chicago
This Chicago apartment is situated a few blocks from the Loop, within easy reach of attractions such as Chinatown (3.2km), McCormick Place (4.8km), and Guaranteed Rate Field (4.8km), offering convenient access to the city's major landmarks.
The one-bedroom flat sleeps three guests, boasting a fully equipped kitchen, in-unit laundry, fast Wi-Fi, and amenities including toiletries and fresh linens; a queen bed and sofa bed provide flexible sleeping arrangements.
River North 3br/2ba: Huge, Parking, Center Chicago - Chicago
10 197 reviews

River North 3br/2ba: Huge, Parking, Center Chicago

apartment, Chicago
This apartment is situated in Chicago's River North district, just a short walk from Oak Street and Ohio Street beaches, offering easy access to the city's vibrant lakefront. The property boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
This spacious three-bedroom apartment can comfortably accommodate up to 10 guests, with a total floor area of 167 square metres. Guests can enjoy a range of amenities, including a fully equipped kitchen, a private balcony, free parking, and access to a spa, garden, and internet.

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

Tranquil Library Near Brown Line 2 Bed 1 Bath Vintage Private Unit @ Solar Lodge - Chicago
10 15 reviews

Tranquil Library Near Brown Line 2 Bed 1 Bath Vintage Private Unit @ Solar Lodge

apartment, Chicago
This 2-bedroom flat in Chicago's Albany Park district offers convenient access, being a 720-metre walk to Kedzie and a 800-metre walk to Kimball subway stations, with Copernicus Center and Portage Park a 5-minute drive away.
This accommodation for four guests includes a microwave, oven, stovetop, air conditioning, Wi-Fi, a television, and bathroom amenities, with proximity to attractions such as Michigan Avenue, Navy Pier, Lake Michigan, Millennium Park, Wrigley Field, and United Center.
Spacious Downtown Penthouse Vintage, Gym & Balcony #3 - Chicago
8.7 3 reviews

Spacious Downtown Penthouse Vintage, Gym & Balcony #3

apartment, Chicago
This downtown Chicago flat offers a prime location, situated 0.96 kilometres from Grant Park and a 12-minute walk from the CIBC Theatre, with DePaul University just an 8-minute walk away.
This 67 square metre residence accommodates up to 10 guests, featuring a private balcony with city views, complimentary WiFi, air conditioning, a fitness centre, and a kitchen equipped with a fridge, microwave, and dishwasher.
Wrigley 2br, 1ba With Free Parking - Chicago
8.9 11 reviews

Wrigley 2br, 1ba With Free Parking

apartment, Chicago
This two-bedroom Chicago apartment is situated near Wrigleyville, a 13-minute walk from Wrigley Field, 5.3km from Lincoln Park Zoo, and within 8km of Loyola University and 360 Chicago Observation Deck.
The 116 square metre property offers a spacious layout sleeping up to 11 guests, boasting a fully equipped kitchen, private entrance, garden, parking, and an outdoor fireplace; all within easy reach of local attractions.
Large Space With Garage - Chicago
10 1 review

Large Space With Garage

apartment, Chicago
This two-bedroom apartment is located in West Pullman, a neighbourhood in Calumet Park, around 32 kilometres south of downtown Chicago and a short drive from Lake Michigan. The area is quiet and residential, offering a peaceful retreat from the hustle and bustle of the city.
This comfortable home sleeps up to four guests and has a well-equipped kitchen, a relaxing living room, and a private balcony. You can enjoy modern amenities like air conditioning, a jacuzzi, and free parking, making it an ideal base for exploring Chicago.

Best Chicago holiday rentals with air conditioning

Rockwell By The River - Chicago
10 124 reviews

Rockwell By The River

apartment, Chicago
This three-bedroom Logan Square flat, in Chicago, Illinois, offers convenient access to local restaurants and breweries, and is a short cycle from other Logan Square attractions.
Sleeping seven guests, this newly renovated property features a queen-size pull-out sofa, keyless entry, a shared workspace, and access to a garden with a barbecue and fire pit (on request).
Entire House, Close To O'hare Airport - Chicago
9.7 171 reviews

Entire House, Close To O'hare Airport

house, Des Plaines
This four-bedroom apartment is situated in Des Plaines, just a short drive (approximately 5 kilometres) from O'Hare Airport, Allstate Arena, Rosemont Convention Center, and Fashion Outlet of Chicago. The apartment has received excellent user, location, and cleanliness ratings, making it a highly recommended choice for travellers.
The apartment offers a spacious layout with two bathrooms, a finished basement with a family room, and a capacity of eight guests. It is equipped with modern amenities such as a 65-inch Roku TV, Keurig coffee machine, air fryer, toaster oven, dishwasher, high-speed internet, laundry facilities, and access to a nearby lake.
Artistic Loft Rooftop  | 13 Mins Dt | 4 Mins Lake - Chicago
10 59 reviews

Artistic Loft Rooftop | 13 Mins Dt | 4 Mins Lake

apartment, Chicago
This Uptown Chicago flat is situated near Montrose Beach, a 1.4km walk from the Argyle Red Line station and within easy reach of several car parks.
The one-bedroom apartment sleeps two, features a fully equipped kitchen with dishwasher, in-unit laundry, a rooftop terrace with city views, and is close to the Aragon Ballroom and Riviera Theatre.
Cozy Bungalow Getaway - Chicago
10 73 reviews

Cozy Bungalow Getaway

apartment, Chicago
This Chicago garden flat is located in a historic bungalow neighbourhood near Northeastern Illinois University and North Park University, offering easy access to LaBagh Woods and Gompers Park, and approximately 32 kilometres from O'Hare International Airport.
The self-catering apartment features a queen-size bed, a sectional sofa, a study area, in-unit laundry facilities, and a private patio with barbecue, accommodating two guests and providing convenient access to public transport links.
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