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

Casa Wolfram 20 Minutes From Downtown - Chicago
10 16 reviews
Chicago
07/17 – 07/26
HK$2275/nighttotal: HK$20475 (9 )

Casa Wolfram 20 Minutes From Downtown

1 2
apartment , Chicago
This two-bedroom Chicago apartment is situated in Logan Square, offering convenient access to the Blue Line 'L' train and numerous amenities.
The 5-guest property features a fully equipped kitchen (fridge, freezer, microwave, dishwasher), air conditioning, free on-street parking, and a fitness centre; nearby attractions include award-winning restaurants and bars.
Charming Single-family Home For 6! Free Parking! - Chicago
9.9 141 reviews
Chicago
07/24 – 07/26
HK$4028/nighttotal: HK$8056 (2 )

Charming Single-family Home For 6! Free Parking!

1 5
apartment , Chicago
This four-bedroom Chicago apartment, ideal for families, is conveniently located near the Bloomingdale Trail, offering easy access to Humboldt Park, Logan Square, and Wicker Park.
The property boasts a fully equipped kitchen, private garden with slackline, free on-site parking for two cars, Smart TVs in each bedroom, and accommodates up to six guests.
A Quiet Stay While You Are Away Oak Park - Chicago
9.9 194 reviews
Chicago
10/06 – 10/15
HK$1810/nighttotal: HK$16290 (9 )

A Quiet Stay While You Are Away Oak Park

1 2
apartment , Oak Park
This two-bedroom flat is located in Oak Park's Frank Lloyd Wright district, a short distance from Concordia and Dominican Universities and a designated historic area known for its collection of homes designed by the famous architect. It has received excellent ratings for location, cleanliness, and user satisfaction.
The property has a private sun porch with a park view and can accommodate up to five guests. Amenities include a fully equipped kitchen with a fridge, freezer, microwave, dishwasher, and complimentary coffee and tea, a garden, parking, and a UVC light disinfected bathroom with clean towels, toothbrush, and toothpaste.
The Oak Park Loft, Including Garage - Chicago
10 10 reviews
Chicago
06/23 – 06/27
HK$2479/nighttotal: HK$9916 (4 )

The Oak Park Loft, Including Garage

2 1
apartment , Oak Park
This Oak Park flat, a newly renovated 1880s loft designed by Errol Kirsch, enjoys a central location, offering easy access to Chicago's 'L' train and is within 48km of both Midway and O'Hare airports, and close to Frank Lloyd Wright and Ernest Hemingway sites.
The 83 square metre (893 square feet) two-bedroom, one-bathroom property sleeps four, includes a garage, garden, and modern amenities such as air conditioning and internet access, alongside an exquisitely designed bathroom.

Best Chicago holiday rentals with parking

Bee's Knees - Ritzy, 1924 Chicago Bungalow - Chicago
10 20 reviews
Chicago
08/14 – 08/16
HK$10567/nighttotal: HK$21134 (2 )

Bee's Knees - Ritzy, 1924 Chicago Bungalow

4 10
apartment , Chicago
This four-bedroom Chicago house, located in Humboldt Park, is 0.8 km from Humboldt Park and 4.7 km from the United Centre.
The 4-bedroom property sleeps 10 guests, boasts a fully equipped kitchen, private patio, free Wi-Fi, and is close to public transport links, making it ideal for families or groups visiting Chicago.
Stunning 3 Bedrooms 2 Bathrooms Getaway Chicago! - Chicago
10 1 review
Chicago
06/23 – 06/24
HK$5322/nightfor 1 night

Stunning 3 Bedrooms 2 Bathrooms Getaway Chicago!

3 2
apartment , Chicago
This Chicago flat is situated in a residential district, approximately 8.5 kilometres from Wrigley Field and 10.3 kilometres from Lincoln Park Zoo.
This 242 square metre residence accommodates up to 15 guests, featuring three bedrooms, two bathrooms, air conditioning, a balcony, a garden, and a fully equipped kitchen with a dishwasher and microwave, alongside free WiFi.
Modern 3 Br Apt - 5 Mins To Downtown Sleeps 10 - Chicago
Chicago
07/20 – 07/21
HK$3307/nightfor 1 night

Modern 3 Br Apt - 5 Mins To Downtown Sleeps 10

1 2
apartment , Chicago
This Pilsen apartment, situated in Chicago's Lower West Side, is a short distance from 18th Street's restaurants and bars, and a few kilometres from the city centre.
This three-bedroom dwelling, spanning 88 square metres, offers three queen beds, two sofa beds, and a queen air mattress, sleeping up to ten guests, and features classic arcade games and four Smart TVs.
Jacuzzi, Movie Theater, Game Room, Gym, Arcade, Backyard, King Ste, Portage Park - Chicago
Chicago
07/30 – 08/02
HK$17799/nighttotal: HK$53397 (3 )

Jacuzzi, Movie Theater, Game Room, Gym, Arcade, Backyard, King Ste, Portage Park

5 13
apartment , Chicago
This spacious five-bedroom, three-bathroom luxury flat is situated in Chicago's Portage Park district, offering a residential setting approximately 13 to 14 kilometres from downtown attractions such as Millennium Park and Skydeck Chicago.
This expansive 204 square metre residence accommodates up to sixteen guests and features an entertainment basement with a home cinema, games, and a gym, alongside a private garden with a hot tub and outdoor games.

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

Duplex 3 Bed 2 Bath Apt Steps From Lincoln Square - Chicago
9.8 22 reviews
Chicago
10/07 – 10/14
HK$8147/nighttotal: HK$57029 (7 )

Duplex 3 Bed 2 Bath Apt Steps From Lincoln Square

3 3
apartment , Chicago
This three-bedroom flat in Chicago's North Center district is a four-minute drive from Wrigley Field and a three-minute drive from the Riviera Theatre, with the Western 'L' station located 800 metres away.
This 186 square metre apartment accommodates six guests and offers a well-equipped kitchen, air conditioning, Wi-Fi, a barbecue grill, and on-site covered parking.
Windy City Getaway - 3br 2ba Chicago Townhouse Home - Chicago
9.5 2 reviews
Chicago
07/22 – 07/27
HK$5614/nighttotal: HK$28070 (5 )

Windy City Getaway - 3br 2ba Chicago Townhouse Home

3 5
house , Chicago
This Chicago townhouse, situated approximately 8-13 kilometres from Wrigley Field, Lincoln Park Zoo, and the United Centre, offers convenient access to major attractions.
Sleeping up to 17 guests, this three-bedroom, three-bathroom property boasts a fully equipped kitchen, in-unit laundry, free Wi-Fi, private parking, a fireplace, and a terrace/balcony; nearby activities include exploring Lincoln Park Zoo and catching a Cubs game at Wrigley Field.
Windy City Getaway | 3br 2ba Chicago Townhouse By Redawning - Chicago
Chicago
07/16 – 07/19
HK$5869/nighttotal: HK$17607 (3 )

Windy City Getaway | 3br 2ba Chicago Townhouse By Redawning

3 6
apartment , Chicago
This Irving Park flat in Chicago offers convenient access to the Metra Line, placing you within a 30-minute drive of downtown attractions, including Millennium Park and the Art Institute of Chicago.
This stylish three-storey townhome accommodates up to nine guests, featuring three bedrooms, two bathrooms, a fully equipped kitchen with modern appliances, and both a balcony and patio, with complimentary parking for two vehicles in the garage.
East Village 4-level-house With 5 Baths & Covered Attached Garage - Chicago
9.5 146 reviews
Chicago
10/08 – 10/13
HK$32176/nighttotal: HK$160880 (5 )

East Village 4-level-house With 5 Baths & Covered Attached Garage

4 2
apartment , Chicago
This four-storey townhouse is located in Chicago's East Village, a short walk from the Milwaukee 'L' station and a 12-minute subway ride from the Loop, Michigan Avenue, and the Lakefront. It has consistently received excellent user ratings for location, cleanliness, and overall experience.
The property offers 223 square metres of living space, comprising four bedrooms and five bathrooms. Guests can enjoy a range of amenities, including a fully equipped kitchen, private terraces, a spa-like bathroom, a fireplace, games, and a Sonos sound system.

Best Chicago holiday rentals with air conditioning

Airy & Spacious Loft - 1br Perfect For Long-term Stays - Chicago
Chicago
07/10 – 08/31
HK$976/nighttotal: HK$50752 (52 )

Airy & Spacious Loft - 1br Perfect For Long-term Stays

1 1
apartment , Chicago
This one-bedroom flat is situated in Chicago's Lower West Side, offering proximity to cultural institutions such as the Field Museum of Natural History and the Art Institute of Chicago, and within 2 kilometres of shopping on Michigan Avenue and entertainment venues including McCormick Place.
This accommodation provides air conditioning and internet for up to two guests, and is located near the United Center, offering a tranquil atmosphere for relaxation after exploring the city.
Explore Chicago From An Urban Sanctuary With Free Parking - Chicago
9.8 766 reviews
Chicago
08/13 – 08/15
HK$1748/nighttotal: HK$3496 (2 )

Explore Chicago From An Urban Sanctuary With Free Parking

1 2
apartment , Chicago
This Chicago apartment, situated in a historic neighbourhood near South Old Irving and Kilbourn Parks, is approximately 1.6 km from Wrigley Field.
The vintage-chic loft features a SMEG fridge, Netflix, free parking, a shared deck, sleeps two guests, and offers easy access to public transport and North Milwaukee Avenue's bars.
The Parkside Pavilion (Fitness Center • Lounge) - Chicago
9.8 52 reviews
Chicago
08/05 – 08/19
HK$2495/nighttotal: HK$34930 (14 )

The Parkside Pavilion (Fitness Center • Lounge)

1 4
apartment , Chicago
This luxurious Chicago Loop apartment offers a prime location, close to Michigan Avenue and within easy reach of Lake Michigan.
The one-bedroom suite, sleeping up to five guests, boasts a fully equipped kitchen (fridge, freezer, microwave, dishwasher), air conditioning, and access to a swimming pool, fitness centre, and garden; nearby attractions include numerous theatres and excellent shopping and dining opportunities.
Decompress On A Sophisticated Chaise At A Glamorous Hideaway - Chicago
9.9 188 reviews
Chicago
07/22 – 07/26
HK$2862/nighttotal: HK$11448 (4 )

Decompress On A Sophisticated Chaise At A Glamorous Hideaway

1 2
apartment , Chicago
This Chicago apartment, registration number R22000086754, is unfortunately lacking a precise address, preventing a definitive statement on its proximity to specific landmarks such as Millennium Park or Navy Pier.
The one-bedroom, one-bathroom flat sleeps three guests and boasts a spa-style jetted tub, a fully equipped kitchen with dishwasher, air conditioning, parking, and a garden.
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