Holiday Rentals in Chicago, IL

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Chicago, IL holiday rentals
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10119 Holiday rentals and Airbnb in Chicago, IL

Best family friendly Chicago, IL holiday rentals

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

The Hotel & Athletic Club At Midtown - Chicago, IL
9.0 1120 reviews
Chicago, IL
29/06 – 24/07
368 €/nighttotal: 9200 € (25 )

The Hotel & Athletic Club At Midtown

1 2
resort , Chicago
The Hotel & Athletic Club at Midtown is conveniently located in Chicago's Midtown neighbourhood, just a short distance from popular attractions like Wrigley Field, Lincoln Park Zoo, and United Center. The hotel consistently receives high ratings for its cleanliness, location, and overall experience, making it a popular choice for travellers.
The hotel offers a range of comfortable and modern rooms, each equipped with amenities such as air conditioning, flat-screen TVs, and private bathrooms. Guests have access to a wide array of facilities including indoor and outdoor swimming pools, a spa, a fitness centre, tennis courts, and a variety of fitness classes, making it a great choice for those seeking a wellness-focused getaway.
Bright, Spacious 2br Apt In Heart Of Logan Square! - Chicago, IL
9.9 111 reviews
Chicago, IL
29/06 – 04/07
251 €/nighttotal: 1255 € (5 )

Bright, Spacious 2br Apt In Heart Of Logan Square!

1 4
apartment , Chicago
This Logan Square apartment, a newly renovated basement flat in a historic building, is situated a 0.8 km walk from Logan Square and the Logan Square Blue Line 'L' station, offering easy access to O'Hare International Airport and Chicago's city centre.
The two-bedroom, one-bathroom dwelling boasts a full kitchen with granite worktops and stainless steel appliances, in-unit laundry, a private patio, and sleeps four guests, with access to a shared garden and is perfect for exploring the area's restaurants and bars.
Bootlegger House Sleeps 10-20 Free Tv & Parking - Chicago, IL
10 4 reviews
Chicago, IL
11/09 – 13/09
1261 €/nighttotal: 2522 € (2 )

Bootlegger House Sleeps 10-20 Free Tv & Parking

6 11
apartment , Chicago
This Chicago apartment, ideal for large groups, is situated in a peaceful neighbourhood near Lincoln Park, 2.7km from Lincoln Park Zoo and 5.5km from the 360 Chicago Observation Deck, offering easy access to Fullerton Beach and Wrigley Field.
The 325 square metre property boasts six bedrooms, two bathrooms, sleeps 10-20 guests, and includes a garden, tennis court, parking, and a balcony; nearby activities include fishing.
Lincoln Park 3 Br Penthouse - Chicago, IL
9.1 140 reviews
Chicago, IL
25/06 – 26/06
243 €/nightfor 1 night

Lincoln Park 3 Br Penthouse

3 1
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.

Best Chicago, IL holiday rentals with parking

Spacious 3br 420-friendly Mccormick & Uic Campus 2001 S State St - 3c - Chicago, IL
Chicago, IL
16/07 – 17/07
607 €/nightfor 1 night

Spacious 3br 420-friendly Mccormick & Uic Campus 2001 S State St - 3c

3 5
apartment , Chicago
This three-bedroom flat in Chicago's Near West Side is situated within 3.2 kilometres of Grant Park, the Art Institute of Chicago, and the Willis Tower, and is conveniently close to the McCormick Place and UIC campuses.
This accommodation offers a hot tub, air conditioning, complimentary WiFi, and a fully equipped kitchen, sleeping up to 13 guests with a 11:00 AM check-out time.
Kasa | Elevate Your Stay, Premium 1bd | Chicago - Chicago, IL
9.6 341 reviews
Chicago, IL
20/08 – 23/08
327 €/nighttotal: 981 € (3 )

Kasa | Elevate Your Stay, Premium 1bd | Chicago

1 2
apartment , Chicago
This Chicago apartment rental is ideally situated in the downtown area, a stone's throw from Oak Street Beach and a short walk (approximately 0.8 km) from Michigan Avenue and Millennium Park.
The one-bedroom, one-bathroom flat offers self-check-in, sleeps three guests, includes a fully equipped kitchen with dishwasher and in-unit laundry, plus high-speed Wi-Fi, a Smart TV, and access to a fitness centre and garden; pets are welcome (with restrictions).
Lincoln Park Light Filled Loft - Chicago, IL
9.9 320 reviews
Chicago, IL
11/09 – 16/09
298 €/nighttotal: 1490 € (5 )

Lincoln Park Light Filled Loft

1 4
apartment , Chicago
This studio apartment is located in Lincoln Park, a lively neighbourhood in Chicago, just a short distance from the lakefront and the Lincoln Park Zoo. The apartment is highly rated for its cleanliness, location, and overall experience.
The studio is a converted storefront, offering a spacious and open plan living space with floor-to-ceiling windows, covering 74 square metres and comfortably accommodating four guests. The studio comes with a fully equipped kitchen, a private garden, and parking facilities, as well as a comfortable sofa bed.
1 Free Parking Sleeps 10 - Chicago, IL
8.5 4 reviews
Chicago, IL
30/06 – 05/07
479 €/nighttotal: 2395 € (5 )

1 Free Parking Sleeps 10

3 10
apartment , Chicago
This Chicago flat is located between 3.9 and 5.9 kilometres from the United Centre, Water Tower Chicago, Museum of Contemporary Art, and Lincoln Park Zoo.
This 139 square metre flat comfortably accommodates up to 10 guests, featuring complimentary on-site parking, free Wi-Fi, a fully equipped kitchen with a dishwasher and oven, a washing machine, a fireplace, and two bathrooms.

Frequently asked questions about holiday rentals in Chicago, IL

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

    You can't go wrong with a visit to Millennium Park, where you'll find the iconic Cloud Gate sculpture, affectionately known as 'The Bean'. A trip to Navy Pier is a must, with its Ferris wheel, shops, and restaurants. And no trip to Chicago is complete without a deep-dish pizza experience.
  • What are the best Airbnb and holiday rentals in Chicago, IL?

  • What kind of vacation rentals can you find in Chicago?

    There's a wide range of vacation rental choices in Chicago to choose from, from houses to downtown apartments and penthouses.
  • Which neighborhood in Chicago, IL should you consider for a vacation rental?

    For a vibrant and central location, consider staying in the River North neighbourhood. It's close to the Magnificent Mile, the Chicago River, and many restaurants and bars. If you prefer a more residential and quiet vibe, Lincoln Park is a great option, with its beautiful park and proximity to the zoo.
  • What are the most popular Airbnbs in Chicago, IL?

  • What's the best one-day itinerary for Chicago?

    Kick things off Ferris Bueller style at the Art Institute of Chicago for some culture before heading over to "The Bean" at Millennium Park, making sure you leave the park via the BP Bridge, which will give you stunning views of the city's skyline. On the corner of Michigan Avenue and Randolph street, make sure you check out the Chicago Cultural Center for the stunning interior alone (the largest Tiffany stained-glass dome in the world is so worth it!). Cross through Grant Park and visit the Buckingham Fountain before heading south to the amazing Museum Campus, home to the Field Museum, Shedd Aquarium, and Adler Planetarium. Head up the Skydeck at Willis Tower (one of the world's tallest buildings) and if you dare, step on the ledge. Head over to the Chicago Riverwalk to find something to eat before hitting one of the famous jazz and blues clubs.
  • What are the top family-friendly attractions in Chicago, IL?

    The Lincoln Park Zoo is a fantastic free attraction, popular with families, and the Shedd Aquarium is a great option for marine life enthusiasts. The Field Museum is also a favourite, with its dinosaur exhibits and other natural history displays.
  • What are the best holiday rentals with a pool in Chicago, IL?

  • Where should you book a vacation rental in Chicago?

    It really depends on what you want. If you're want to be in the heart of the action, or it's your first visit to the Windy City, then book an apartment or a studio in the Chicago Loop downtown. However, some of the most popular places to book are Lincoln Park and Hyde Park when it comes to vacation rentals.
  • When is the best time to book a vacation rental in Chicago, IL?

    Booking your vacation rental in advance is always a good idea, especially during peak season, which runs from May to September. If you're looking for a more affordable option, consider visiting during the shoulder seasons, April-May and September-October, when the weather is still pleasant.
  • What are the best rentals for families and kids in Chicago, IL?

  • What are Chicago's special dishes you should try?

    You can't come to Chicago without trying some deep-dish pizza, a Chicago icon. However, there's plenty else to chow down on. Chicago had a large Italian community, so you can try some great Italian-American dishes. If you want something quick to go, grab a spicy Italian beef sandwich from a local street food joint.
  • What events or festivals should visitors check out in and around Chicago, IL?

    Chicago is known for its vibrant events scene. The Taste of Chicago, a massive food festival, takes place in July. The Chicago Blues Festival in June is a popular event, and the Lollapalooza music festival in August attracts crowds from all over.
  • What are the best rentals or Airbnbs with a jacuzzi in Chicago, IL?

  • What is sites are there to see in Chicago?

    There's plenty to keep you on your feet on your next trip to Chicago. If you're an art lover, make sure you pay a visit to the Art Institute of Chicago, which is home to more than 300,000 artworks! But if you want a view that's more than paintings, then get yourself to the top of 360 Chicago for panoramas over the city from this 1000-ft-high observation deck. Millennium Park with its futuristic-looking Cloud Gate (AKA the Bean), is great place to explore. And that's just to get you started!
  • What are the best budget-friendly activities in Chicago, IL?

    Chicago has many free and affordable activities. A stroll along the Lakefront Trail offers stunning views. You can enjoy free concerts at Millennium Park's Pritzker Pavilion. And exploring the many diverse neighbourhoods is a great way to experience the city's character.
  • What are the best restaurants with local dishes in Chicago, IL?

    Chicago is a foodie's paradise. For a classic deep-dish pizza experience, Lou Malnati's is a must-try. For authentic Italian, try Tufano's Vernon Park Tap. And for a taste of Chicago's Polish heritage, visit Smak Tak.
  • What are the best walking or cycling routes in Chicago, IL?

    The Lakefront Trail is a popular choice for both walking and cycling, offering stunning views of Lake Michigan. The 606, a former railway line transformed into a park, is a great option for a more urban cycling experience.
  • Are there pet-friendly attractions in Chicago, IL?

    Chicago is a pet-friendly city. The Lincoln Park Zoo welcomes well-behaved dogs on leash. Many parks, such as Millennium Park, have designated areas for dogs. And many restaurants have outdoor patios where you can enjoy a meal with your furry friend.
  • What are the benefits of choosing a vacation rental in Chicago, IL?

    Vacation rentals offer more space and privacy compared to hotels. They often come with amenities like kitchens, which allow you to prepare your own meals and save money. And they can be a great option for families or groups travelling together.

Destinations nearby

Best Chicago, IL holiday rentals with a balcony

Mod West Loop 2br W/ Gym, Pool, W/d, Nr. Fulton Market, By Blueground - Chicago, IL
Chicago, IL
01/08 – 31/10
263 €/nighttotal: 23933 € (91 )

Mod West Loop 2br W/ Gym, Pool, W/d, Nr. Fulton Market, By Blueground

2 2
apartment , Chicago
This two-bedroom flat is situated in the West Loop, a lively district in downtown Chicago, just a 1.6 km walk from Union Station. The area is known for its trendy restaurants, shops, and bars, making it a great base for exploring the city.
This comfortable home offers 92 square meters of space, suitable for up to four guests, and features a fully equipped kitchen, a private balcony, and a laundry room. The apartment also benefits from access to a rooftop BBQ area, a gym, a swimming pool, a lounge, and a doorman.
The Penthouse, Lux Stay Near Downtown, Uofc & Lake - Chicago, IL
9.2 38 reviews
Chicago, IL
25/11 – 29/11
269 €/nighttotal: 1076 € (4 )

The Penthouse, Lux Stay Near Downtown, Uofc & Lake

2 2
apartment , Chicago
This Chicago penthouse apartment, near the University of Chicago campus and approximately 8km from Downtown Chicago, offers easy access to Lake Michigan and Oakwood Beach (a 17-minute walk away).
The 135-square-metre (1453 sq ft) property boasts two bedrooms, two bathrooms, a fully equipped kitchen, and a terrace, accommodating up to seven guests and providing free Wi-Fi and toiletries.
Large Renovated Delightful 2nd Floor Suite In Forest Park - Chicago, IL
9.6 7 reviews
Chicago, IL
27/06 – 30/06
205 €/nighttotal: 615 € (3 )

Large Renovated Delightful 2nd Floor Suite In Forest Park

3 5
apartment , Forest Park
This Forest Park apartment rental is conveniently located near Madison Street, offering easy access to Oak Park's town centre (a short walk away) and is approximately 24-32 km from both Chicago city centre and O'Hare International Airport.
The three-bedroom, one-bathroom flat sleeps six guests and boasts a fully equipped kitchen (fridge, microwave, dishwasher), in-unit laundry, Wi-Fi, and a terrace; nearby attractions include Madison Street's shops and restaurants.
Classic Oak Park Home, 11 Mi To Downtown Chicago! - Chicago, IL
9.2 95 reviews
Chicago, IL
17/09 – 21/09
453 €/nighttotal: 1812 € (4 )

Classic Oak Park Home, 11 Mi To Downtown Chicago!

4 4
house , Oak Park
This four-bedroom house is situated in Oak Park, just 17 kilometres from downtown Chicago and 16 kilometres from Union Station, offering a peaceful setting within easy reach of the city's attractions. The property has received very good user ratings and excellent location and cleanliness ratings.
The 165 square metre house comfortably accommodates up to eight guests. It features a fully equipped kitchen with a dishwasher and oven, air conditioning, free Wi-Fi, a washing machine, a garden, a spa, and parking.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday rentals with air conditioning

Garage Parking! Stay In, Walk To Great Local Spots, Grab The Cta, Or Hop On I-290 - The Perfect Location For All Your Adventures By Allset Turnover - Chicago, IL
9.5 170 reviews
Chicago, IL
09/10 – 14/10
1460 €/nighttotal: 7300 € (5 )

Garage Parking! Stay In, Walk To Great Local Spots, Grab The Cta, Or Hop On I-290 - The Perfect Location For All Your Adventures By Allset Turnover

4 8
apartment , Chicago
This four-bedroom apartment is located in the Tri-Taylor neighbourhood of Chicago, just a short walk from the Medical District and Interstate 290, offering easy access to the city's attractions and amenities. It has received excellent ratings for location, cleanliness, and overall user experience.
The apartment is ideal for families or groups of up to eight people, with plenty of space for everyone to relax and enjoy their stay. It comes with a fully equipped kitchen, air conditioning, parking, and Wi-Fi, ensuring a comfortable and convenient experience.
Serene 2-bdrm: Sunlit Retreat In Heart Of The City - Chicago, IL
9.4 151 reviews
Chicago, IL
13/07 – 15/07
144 €/nighttotal: 288 € (2 )

Serene 2-bdrm: Sunlit Retreat In Heart Of The City

1 2
apartment , Chicago
This Logan Square flat is a three-minute walk (approximately 0.5 km) from the train station, offering easy access to Chicago's city centre and O'Hare International Airport.
The two-bedroom, one-bathroom apartment sleeps up to four guests and features a well-equipped kitchen, private deck, and laundry facilities; numerous restaurants, cafes, and gyms are within easy walking distance.
Modern Condo  Safe Chicago Stay Near Ohare - Chicago, IL
10 1 review
Chicago, IL
01/08 – 03/08
428 €/nighttotal: 856 € (2 )

Modern Condo Safe Chicago Stay Near Ohare

2 1
apartment , Chicago
This Cook County flat offers convenient access to O'Hare International Airport and the Blue Line, placing you within 1.6 kilometres of Parkway Bank Park Entertainment District, Rosemont Theatre, and Rivers Casino.
This two-bedroom flat accommodates up to four guests, featuring a full kitchen with high-end appliances, complimentary Wi-Fi, air conditioning, and free private parking, with pets welcome subject to registration and potential fees.
Beautiful (No Chores  No Cleaning Fees) - Chicago, IL
9.9 132 reviews
Chicago, IL
31/07 – 02/08
592 €/nighttotal: 1184 € (2 )

Beautiful (No Chores No Cleaning Fees)

1 1
apartment , Chicago
This stylish two-bedroom Chicago apartment, near Humboldt Park, offers easy access to the park's amenities.
The 50-inch TV, Netflix, Prime Video, in-unit laundry, and private patio with grill, accommodate four guests comfortably in this well-equipped flat.
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