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

Bright Family-friendly Lincoln Square 2-bed 1-bath - Chicago, IL
9.9 420 reviews
Chicago, IL
01/09 – 04/09
162 â‚¬/nighttotal: 486 â‚¬ (3 )

Bright Family-friendly Lincoln Square 2-bed 1-bath

1 2
apartment , Chicago
This two-bedroom flat is situated on a quiet street in Lincoln Square, a charming neighbourhood on Chicago's north side, just a short walk from the Rockwell brown line station and local shops. The property has consistently received excellent ratings for its cleanliness, location, and overall guest experience.
The flat comfortably sleeps five guests, with a queen-size bed in each bedroom and a fold-out sofa in the living room. Guests can enjoy a private porch, a well-equipped kitchen with a dishwasher, a washer and dryer, and free street parking.
Spacious & Charming Th Skokie Dt | Sleeps 8 W/crib - Chicago, IL
9.4 13 reviews
Chicago, IL
28/07 – 06/08
379 â‚¬/nighttotal: 3411 â‚¬ (9 )

Spacious & Charming Th Skokie Dt | Sleeps 8 W/crib

1 8
apartment , Skokie
This three-storey townhouse is situated in Skokie, Illinois, near downtown Skokie, Emily Oaks Nature Centre, and a playground, offering convenient access to local amenities.
The 3-bedroom, 2.5-bathroom property sleeps up to 8 guests and features a fully equipped kitchen, in-unit laundry, a finished basement with a pool table, multiple Smart TVs, and designated parking, plus free on-street parking.
Chic City Escape | 2br Retreat W/ Parking. - Chicago, IL
10 181 reviews
Chicago, IL
25/11 – 29/11
197 â‚¬/nighttotal: 788 â‚¬ (4 )

Chic City Escape | 2br Retreat W/ Parking.

1 2
apartment , Chicago
This Wicker Park flat is a one-minute walk from Milwaukee Avenue and a 1.6km drive from Lake Michigan, offering easy access to the Damen Blue Line.
The two-bedroom, one-bathroom apartment sleeps four, features free on-site parking, eleven-foot ceilings, exposed brick, and a fully equipped kitchen including a dishwasher; nearby activities include exploring Milwaukee Avenue and the lakefront.
Awesome Location Gold Coast 1br Apt - Chicago, IL
9.5 43 reviews
Chicago, IL
09/07 – 13/07
302 â‚¬/nighttotal: 1208 â‚¬ (4 )

Awesome Location Gold Coast 1br Apt

1 2
apartment , Chicago
This Gold Coast flat offers exceptional access to Chicago's attractions, being within a short walk (less than 1.6km) of Oak Street Beach and the Magnificent Mile, and close to the Clark/Division Red Line station.
The one-bedroom, one-bathroom apartment sleeps four, includes a fully equipped kitchen with fridge, freezer, microwave, and dishwasher, plus air conditioning and internet access; nearby activities include exploring the Loop, River North, and Navy Pier.

Best Chicago, IL holiday rentals with parking

Lux Chicago Sfh 6 Br House W/ Garage + Yard - Chicago, IL
10 4 reviews
Chicago, IL
28/08 – 02/09
1060 â‚¬/nighttotal: 5300 â‚¬ (5 )

Lux Chicago Sfh 6 Br House W/ Garage + Yard

1 13
apartment , Chicago
This six-bedroom flat offers a prime location in Chicago's Andersonville district, providing convenient walking access to local shops, restaurants, and nightlife.
This spacious residence accommodates up to fourteen guests and features a chef's kitchen with Thermidor appliances, a professionally landscaped garden with a grill, and a rare two-car garage.
Jacuzzi, Movie Theater, Game Room, Gym, Arcade, Backyard, King Ste, Portage Park - Chicago, IL
Chicago, IL
31/07 – 03/08
1884 â‚¬/nighttotal: 5652 â‚¬ (3 )

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

5 11
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.
Premium 2br Michigan Suite With Skyline Views Near Mccormick Place & Lakefront - Chicago, IL
10 1 review
Chicago, IL
28/06 – 05/07
278 â‚¬/nighttotal: 1946 â‚¬ (7 )

Premium 2br Michigan Suite With Skyline Views Near Mccormick Place & Lakefront

2 5
apartment , Chicago
This Near South Side Chicago flat is conveniently located less than 1.6km from State Street and McCormick Place, and within 3.2km of Soldier Field and Lake Michigan.
The 88 square metre property offers two bedrooms, two bathrooms, sleeps eight guests, and includes a fully equipped kitchen, terrace, garden, fitness centre, and parking.
Vibrant 3br Pilsen Stayfree Parkingnear Downtown - Chicago, IL
10 35 reviews
Chicago, IL
20/07 – 24/07
406 â‚¬/nighttotal: 1624 â‚¬ (4 )

Vibrant 3br Pilsen Stayfree Parkingnear Downtown

3 4
apartment , Chicago
This flat is in Chicago's Lower West Side, a short walk from 18th Street and approximately 5 kilometres from Downtown Chicago's Grant Park and Millennium Park.
This 79 square metre residence offers three bedrooms accommodating up to five guests, featuring a full kitchen, air conditioning, complimentary garage parking for one vehicle, and is equipped with 24/7 security cameras.

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

Chic Gold Coast Convertible W/ Lounge Near Oak Street By Blueground - Chicago, IL
10 1 review
Chicago, IL
01/09 – 31/10
176 â‚¬/nighttotal: 10560 â‚¬ (60 )

Chic Gold Coast Convertible W/ Lounge Near Oak Street By Blueground

1 2
apartment , Chicago
This Chicago city centre flat offers a prime location, less than 0.8 km from State Street and Michigan Avenue, with Lake Michigan and Water Tower Place within a 1.6 km radius.
The self-catering apartment features a fully equipped kitchen, in-unit laundry, a private balcony with city views, and access to an on-site fitness centre, arcade, and barbecue facilities.
Luxury Penthouse Loft W/terrace  504 | River North - Chicago, IL
10 4 reviews
Chicago, IL
03/07 – 05/07
1069 â‚¬/nighttotal: 2138 â‚¬ (2 )

Luxury Penthouse Loft W/terrace 504 | River North

2 5
apartment , Chicago
This pet-friendly flat offers a prime downtown Chicago location, a 7-minute walk from Michigan Avenue and close to the Grand and Chicago Metro stations for convenient travel.
Spanning 111 square meters, this accommodation accommodates up to six guests with two bedrooms and two bathrooms, featuring air conditioning, a fireplace, a dedicated workspace, and laundry facilities, with nearby cycling and fishing opportunities.
Cozy Studio Suite, Steps From River North & Shops - Chicago, IL
9.0 2 reviews
Chicago, IL
28/07 – 30/12
327 â‚¬/nighttotal: 50685 â‚¬ (155 )

Cozy Studio Suite, Steps From River North & Shops

1 4
studio , Chicago
This Chicago Near North Side apartment is conveniently located a 14-minute walk from Armitage Avenue and a 3-minute drive (approximately 1.6km) from Lake Michigan, offering easy access to Millennium Park and the Field Museum.
The 65-square-metre (700 sq ft) self-catering studio sleeps four, boasting a private terrace, fully equipped kitchen, in-unit laundry, and access to an on-site fitness centre.
Blueground | River North, Pool & Gym, Nr Mile - Chicago, IL
Chicago, IL
01/09 – 31/10
247 â‚¬/nighttotal: 14820 â‚¬ (60 )

Blueground | River North, Pool & Gym, Nr Mile

2 2
apartment , Chicago
This 2-bedroom flat offers a prime location in Chicago's Near North district, a short walk from Michigan Avenue and State Street shopping, and within easy reach of Millennium Park and Lake Michigan.
This 97 square metre residence accommodates up to four guests and features a fully equipped kitchen, in-apartment laundry, air conditioning, and building amenities including a swimming pool and parking, with pets welcome.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday rentals with air conditioning

Location! Location! 2bd 1bth Spacious Apartment! - Chicago, IL
8.4 14 reviews
Chicago, IL
03/07 – 05/07
325 â‚¬/nighttotal: 650 â‚¬ (2 )

Location! Location! 2bd 1bth Spacious Apartment!

2 3
apartment , Chicago
This Chicago flat offers convenient access to landmarks such as Guaranteed Rate Field (2.2 kilometres), the Field Museum of Natural History (4.3 kilometres), and Union Station (4.7 kilometres), situated in a well-connected district.
This 48-square-metre apartment accommodates up to 7 guests across 2 bedrooms and 1 bathroom, featuring a fully equipped kitchen with a fridge and microwave, complimentary on-site parking, and free high-speed WiFi.
3br With Private Entrance - Garden Unit - Chicago, IL
9.2 191 reviews
Chicago, IL
25/06 – 29/06
222 â‚¬/nighttotal: 888 â‚¬ (4 )

3br With Private Entrance - Garden Unit

1 3
apartment , Chicago
This three-bedroom Logan Square garden flat offers a private entrance on a quiet street, a short walk from Palmer Square Park and approximately 1.6km from the Logan Square Blue Line station for easy access to downtown Chicago.
The self-check-in property sleeps six, boasts a fully equipped kitchen including a Keurig coffee machine, and provides amenities such as fresh towels, linens, and streaming TV, ensuring a comfortable stay.
Spacious Whole Apt Near Shopping And City - Chicago, IL
9.5 279 reviews
Chicago, IL
16/07 – 17/07
293 â‚¬/nightfor 1 night

Spacious Whole Apt Near Shopping And City

1 5
apartment , Cicero
This Cicero apartment, conveniently located near Midway Airport and Interstate 55, offers easy access to Chicago, approximately 16 kilometres from the city centre.
Sleeping up to seven guests, this two-bedroom, one-bathroom flat features a king-size bed, two double beds, a sofa bed, a fully equipped kitchen with dishwasher, and ample street parking, plus a large dining table and living room with TV.
Clean & Best Location 2br+2ba | Mapletree Suites - Chicago, IL
9.9 128 reviews
Chicago, IL
28/06 – 01/07
247 â‚¬/nighttotal: 741 â‚¬ (3 )

Clean & Best Location 2br+2ba | Mapletree Suites

1 2
apartment , Chicago
This West Loop apartment, steps from Target, Skinner Park and the CTA, offers easy access to the United Centre, the Loop and the Medical District in Chicago.
The 100 sq m suite comprises two bedrooms, two bathrooms, and sleeps five guests, featuring keyless entry, in-unit laundry, a fully equipped kitchen, two private balconies, and on-site amenities including Cafe L'Appetito and luggage storage.
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