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

Wicker-logan Modernhouse W/garage 2 Blocks Fromcta - Chicago
9.9 50 reviews
Chicago
06/29 – 07/03
HK$2796/nighttotal: HK$11184 (4 )

Wicker-logan Modernhouse W/garage 2 Blocks Fromcta

1 4
apartment , Chicago
This modern two-bedroom, two-bathroom house is ideally located on the border of Logan Square and Wicker Park, Chicago, a two-minute walk from the Western Blue Line 'L' train station, offering easy access to the city centre.
The property boasts free garage parking, lightning-fast fibre optic WiFi, a fully equipped kitchen, and can comfortably accommodate four guests; optional cleaning services are available for stays exceeding one week.
Livn Millennium Park Downtown Chicago Superior 1br - Chicago
10 2 reviews
Chicago
07/01 – 07/18
HK$3776/nighttotal: HK$64192 (17 )

Livn Millennium Park Downtown Chicago Superior 1br

1 2
apartment , Chicago
This newly renovated one-bedroom flat is located in downtown Chicago's Loop district, a mere 200 metres from Millennium Park and Michigan Avenue, placing it steps from the city's premier shopping and dining.
This family-friendly apartment offers a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, and in-unit laundry, with a guest capacity of two, providing convenient access to the Theater District and public transport.
3br/2ba + Pull Out Sofa Bed + No Stairs + Backyard - Chicago
10 44 reviews
Chicago
07/03 – 07/12
HK$2962/nighttotal: HK$26658 (9 )

3br/2ba + Pull Out Sofa Bed + No Stairs + Backyard

1 7
apartment , Worth
This family-friendly house in Worth sleeps eight guests across three bedrooms and two bathrooms, boasting a fully equipped kitchen with dishwasher and a garden with parking.
The property offers air conditioning, internet access, and is pet-friendly, with further details on its precise location in Worth and nearby attractions to be confirmed.
Affordable Month To Month In The Heart Of Chicago. 30 Day Minimum Bookings. - Chicago
9.6 226 reviews
Chicago
08/20 – 09/19
HK$1583/nighttotal: HK$47490 (30 )

Affordable Month To Month In The Heart Of Chicago. 30 Day Minimum Bookings.

2 2
apartment , Chicago
This two-bedroom apartment is situated in the River North neighbourhood of Chicago, just under a kilometre from Michigan Avenue and the Loop, close to Millennium Park and the Chicago Riverwalk, offering easy access to the city's main attractions. The apartment has received excellent user ratings for its location, cleanliness, and overall experience.
The apartment is spacious, covering 111 square metres and comfortably accommodating up to six guests. It features a fully equipped kitchen, two bathrooms, air conditioning, parking, and a 65-inch TV with cable and HBO, as well as being pet-friendly.

Best Chicago holiday rentals with parking

2 Full Bed Smoking - Chicago
Chicago
07/03 – 07/05
HK$1349/nighttotal: HK$2698 (2 )

2 Full Bed Smoking

1 2
apartment , Chicago
This motel is situated near the University of Chicago Hospitals Heliport, 4.6 kilometres from the Museum of Science and Industry and 7.7 kilometres from Guaranteed Rate Field.
This apartment offers air-conditioned rooms with two double beds, accommodating up to four guests, and includes on-site parking and a 24-hour front desk.
Luxe Duplex - Private Gym -Huge Backyard -Arcade- King Beds - Garage-ev Charger - Chicago
9.4 22 reviews
Chicago
07/03 – 07/12
HK$5437/nighttotal: HK$48933 (9 )

Luxe Duplex - Private Gym -Huge Backyard -Arcade- King Beds - Garage-ev Charger

3 7
apartment , Chicago
This spacious apartment in Portage Park, Chicago, is just a short drive from the city centre, Rosemont and O'Hare Airport, making it an ideal base for exploring the city. The apartment has received excellent guest reviews and is perfect for families or groups of friends.
The apartment is 242 square metres in size and can accommodate up to seven guests. It has a fully equipped kitchen, a private gym, a garden, a terrace, and a spa, offering everything you need for a comfortable and enjoyable stay.
Lincoln Park 3 Br Penthouse - Chicago
9.1 140 reviews
Chicago
06/25 – 06/26
HK$2194/nightfor 1 night

Lincoln Park 3 Br Penthouse

3 2
apartment , Chicago
This Lincoln Park penthouse apartment in Chicago is situated 2.4km from Fullerton Beach, 2.5km from North Avenue Beach, and 2.1km from Wrigley Field.
This three-bedroom dwelling boasts 165 square metres of space, sleeping up to 11 guests and offering amenities including a terrace, garden, tennis court, parking, and free Wi-Fi.
Cozy Chic Retreat Near Downtown - Sleeps 7 - Chicago
Chicago
06/28 – 07/12
HK$1374/nighttotal: HK$19236 (14 )

Cozy Chic Retreat Near Downtown - Sleeps 7

2 3
apartment , Chicago
This Chicago flat in the Lawndale district is situated a short drive from Michigan Avenue and State Street shopping, and within reasonable proximity to the Field Museum of Natural History and McCormick Place.
This 70 square metre dwelling offers two bedrooms and one bathroom, accommodating up to seven guests with a sofa bed and air mattress, and features over 10,000 arcade games for in-unit entertainment.

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.

Destinations nearby

Best Chicago holiday rentals with a balcony

Spacious Chicago Group Home! Walk To Train And Eats - Chicago
10 1 review
Chicago
12/22 – 12/30
HK$4854/nighttotal: HK$38832 (8 )

Spacious Chicago Group Home! Walk To Train And Eats

3 2
apartment , Chicago
This Chicago flat, ideal for group stays, is located 2.7 kilometres from Wrigley Field and 5.3 kilometres from Loyola University Chicago, with convenient access to public transport and local dining.
This spacious property offers 186 square metres of living space, accommodating up to 11 guests with three bedrooms, two bathrooms, a fully equipped kitchen including a dishwasher and oven, air conditioning, complimentary Wi-Fi, and in-unit laundry facilities.
Peaceful Zen Flat 2br Oasis With Free Parking - Chicago
10 3 reviews
Chicago
06/30 – 07/03
HK$3588/nighttotal: HK$10764 (3 )

Peaceful Zen Flat 2br Oasis With Free Parking

2 4
apartment , Chicago
This two-bedroom flat in Chicago's Ukrainian Village, West Town, is situated approximately 6.4 kilometres from Millennium Park and Lake Michigan, and 4.8 kilometres from the United Centre.
This pet-friendly apartment offers free parking, in-unit laundry, a kitchen with a fridge, microwave, and dishwasher, air conditioning, and accommodates up to five guests.
The Grand Kimball Lodge, Logan Square, Sleeps 20 - Chicago
10 3 reviews
Chicago
07/01 – 07/06
HK$19224/nighttotal: HK$96120 (5 )

The Grand Kimball Lodge, Logan Square, Sleeps 20

5 11
apartment , Chicago
This Logan Square dwelling is centrally located in Chicago, offering easy access to attractions such as Michigan Avenue and Millennium Park, though precise distances aren't specified.
This spacious, two-storey loft apartment boasts 278 square metres of living space, featuring five bedrooms, four bathrooms, two kitchens, two living areas, three outdoor spaces and sleeps up to twenty guests; amenities include a sauna, foosball table and record player.
Westchester House | Sleeps 10 | Near Chicago & Parks | Close To Restaurants & Easy Local Transport Access | Long Private Driveway - Chicago
Chicago
10/10 – 10/12
HK$7768/nighttotal: HK$15536 (2 )

Westchester House | Sleeps 10 | Near Chicago & Parks | Close To Restaurants & Easy Local Transport Access | Long Private Driveway

4 2
apartment , Westchester
This spacious four-bedroom flat in Westchester, IL, offers a suburban retreat just 40 kilometres from downtown Chicago, with convenient access to the I-290/I-294 motorways and the CTA Blue Line, placing it a short drive from Brookfield Zoo and Oakbrook Centre.
This family-friendly residence accommodates up to eight guests and features a large garden with an oversized patio, ideal for outdoor entertaining, alongside high-speed Wi-Fi and Smart TVs for remote work or leisure.

Best Chicago holiday rentals with air conditioning

Flexhome West Town 2br Duplex Apt T2 - Chicago
9.3 7 reviews
Chicago
07/17 – 07/18
HK$7364/nightfor 1 night

Flexhome West Town 2br Duplex Apt T2

2 1
apartment , Chicago
This West Town duplex in Chicago is located 2.7 kilometres from the United Centre, and within 3.9 kilometres of Union Station and 360 Chicago.
This 60 square metre flat offers two bedrooms and two bathrooms, accommodating up to nine guests with a fully equipped kitchen including a dishwasher and microwave, air conditioning, and complimentary WiFi.
Modern 3br 420-ok Near Mccormick & Soldier Field 2001 S State St - 2d - Chicago
Chicago
06/25 – 06/26
HK$4563/nightfor 1 night

Modern 3br 420-ok Near Mccormick & Soldier Field 2001 S State St - 2d

3 2
apartment , Chicago
This three-bedroom flat in Chicago is situated approximately 2.4 kilometres from the Field Museum of Natural History and within 3.2 kilometres of the Art Institute of Chicago, Grant Park, and Willis Tower, offering convenient access to McCormick Place and Soldier Field.
This accommodation provides WiFi, air conditioning, and a fully equipped kitchen with a dishwasher for up to 13 guests, featuring three bedrooms and two bathrooms suitable for families or groups.
Cozy Downtown Mich Ave #7 | Gym+rooftop - Chicago
9.7 297 reviews
Chicago
07/29 – 08/03
HK$9824/nighttotal: HK$49120 (5 )

Cozy Downtown Mich Ave #7 | Gym+rooftop

2 1
apartment , Chicago
This penthouse apartment is situated on Michigan Avenue, just a short walk from Grant Park and Lake Michigan, offering easy access to Chicago's vibrant attractions. The apartment boasts excellent user, location, and cleanliness ratings, making it a popular choice for travellers.
The two-bedroom, two-bathroom apartment offers 84 square metres of living space, providing ample room for relaxation and comfort. The apartment comes equipped with a modern kitchen, a spacious living area, a terrace, a garden, and a fitness centre, ensuring a comfortable and enjoyable stay.
1br Serene And Cozy Chicago Apartment - Manor 2 - Chicago
8.2 4 reviews
Chicago
07/09 – 07/12
HK$2068/nighttotal: HK$6204 (3 )

1br Serene And Cozy Chicago Apartment - Manor 2

1 2
apartment , Chicago
This one-bedroom flat in Chicago's Manor 2 district is located 5 kilometres from Wrigley Field and 7.5 kilometres from Loyola University Chicago.
This 67-square-metre apartment accommodates up to three guests and features a kitchen with a fridge and microwave, air conditioning, and complimentary WiFi.
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