Holiday Rentals in Chicago, IL

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Chicago, IL holiday rentals
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13982 Holiday rentals and Airbnb in Chicago, IL

Best family friendly Chicago, IL holiday rentals

Among the 13982 accommodations in Chicago, IL, here are the 4 best family friendly rentals

Modern Studio Near Mccormick Close To Downtown - Chicago, IL
No reviews

Modern Studio Near Mccormick Close To Downtown

apartment, Chicago
This studio flat is situated just outside Chicago's central business district, offering a 5-minute drive to McCormick Place and a 10-15 minute drive to The Loop, with close proximity to the Museum Campus and the lakefront.
This family-friendly apartment accommodates up to four guests and features a fully equipped kitchen, air conditioning, Wi-Fi, a fitness centre, a rooftop lounge with grills, and secure parking for one vehicle.
The Twin Lions: Bespoke Travel Lodge W/ Speakeasy* - Chicago, IL
9.0 21 reviews

The Twin Lions: Bespoke Travel Lodge W/ Speakeasy*

apartment, Chicago
This apartment is located in Chicago, just 3.4 kilometres from Lincoln Park Zoo and 4.3 kilometres from United Center, offering easy access to attractions and a vibrant neighbourhood. It has received excellent ratings for location, cleanliness, and overall user experience.
This three-bedroom flat, spanning 139 square metres, comfortably accommodates up to 11 guests. It features a private speakeasy and garden, a bespoke travel lodge design, an outdoor fireplace, a spacious interior, a private entrance and patio, continental breakfast and BBQ facilities, and pet-friendly accommodations.
Duplex 3 Bed 2 Bat Apt Steps From Lincoln Square - Chicago, IL
8.7 8 reviews

Duplex 3 Bed 2 Bat Apt Steps From Lincoln Square

apartment, Chicago
This three-bedroom Chicago duplex apartment is situated in Lincoln Square, approximately 3.7km from Lincoln Park Zoo, 3.7km from Wrigley Field, and 6.9km from Loyola University Chicago.
The 119 square metre property features two living rooms, two bathrooms, sleeps ten guests, and includes free parking, a terrace, a garden, and a fully equipped kitchen.
2 Bdrm Quiet Berwyn Apt W/ Free Garage - Chicago, IL
9.8 75 reviews

2 Bdrm Quiet Berwyn Apt W/ Free Garage

apartment, Berwyn
This Berwyn apartment, situated 22.5 kilometres from downtown Chicago, offers easy access to attractions such as Navy Pier, Millennium Park, and the Willis Tower.
The two-bedroom, one-bathroom flat sleeps six guests and features a fully equipped kitchen, in-building laundry facilities, guaranteed garage parking, and a shared patio; the entire second floor provides complete privacy.

Best Chicago, IL holiday rentals with parking

Stunning 2 Floor Apt With Rooftop - View Of Loop! - Chicago, IL
9.4 358 reviews

Stunning 2 Floor Apt With Rooftop - View Of Loop!

apartment, Chicago
This Noble Square/West Town duplex apartment is ideally situated within walking distance of many Chicago attractions.
This spacious 149-square-metre (1600 sq ft) three-bedroom, two-and-a-half-bathroom property boasts a rooftop deck with city skyline views, a private backyard, and accommodates up to twelve guests, featuring a fully equipped kitchen, in-unit laundry, and on-site management.
Lower Level Luxury - Chicago, IL
9.6 11 reviews

Lower Level Luxury

apartment, Chicago
This Chicago flat is located in a prime district, offering convenient access to major landmarks and attractions.
This family-friendly 255 square meter apartment features one bedroom, one bathroom, air conditioning, WiFi, and a kitchenette, accommodating up to seven guests with private check-in and check-out.
Peaceful & Airy Modern-chic Condo In Trendy Pilsen - Chicago, IL
9.8 483 reviews

Peaceful & Airy Modern-chic Condo In Trendy Pilsen

apartment, Chicago
This newly renovated two-bedroom, two-bathroom apartment in Chicago's Pilsen neighbourhood is located a mere 0.32 kilometres from the CTA line, offering easy access to the city centre.
The 2-queen bed, 1-twin sleeper sofa flat sleeps four, features a fully equipped kitchen including a dishwasher and in-unit laundry facilities, plus a smart TV with streaming services and free street parking with permits provided.
De-lima Quaters: Ideal For All Groups - Chicago, IL
9.5 55 reviews

De-lima Quaters: Ideal For All Groups

apartment, Bellwood
This Bellwood flat offers convenient access to central Chicago and O'Hare International Airport, located 13 kilometres away in a quiet district.
This two-bedroom residence accommodates up to six guests and features a fully equipped kitchen, air conditioning, free parking, on-site laundry, a private backyard with a tented patio, and fast Wi-Fi.

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.

Popular destinations

Best Chicago, IL holiday rentals with a balcony

Luxury Meets Comfort: River North Rentals With Chic Style & Prime Chicago Access - Chicago, IL
8.0 1 review

Luxury Meets Comfort: River North Rentals With Chic Style & Prime Chicago Access

apartment, Chicago
This Level River North apartment, a 70 square metre (753 square foot) one-bedroom flat, is situated in the River North district, minutes from the Magnificent Mile and a short distance across the river from the Loop.
The self-catering property sleeps four guests and boasts a fully equipped kitchen, including a dishwasher, plus a terrace, swimming pool, sauna, and parking; nearby riverside parks offer green space.
Experience Downtown Chicago At Millennium - Luxury Apartments In The Loop - Chicago, IL
8.5 100 reviews

Experience Downtown Chicago At Millennium - Luxury Apartments In The Loop

apartment, Chicago
This apartment is located in downtown Chicago, within half a mile of the city centre, close to attractions like the CIBC Theatre, Willis Tower, and DePaul University. The apartment has received excellent ratings for location, cleanliness, and overall experience.
The apartment is suitable for up to five guests and has a fully equipped kitchen. It also offers a range of amenities including a private terrace, a swimming pool, a jacuzzi, and free Wi-Fi.
Skyline View Duo For Groups: Unmatched Luxury Stay - Chicago, IL
No reviews

Skyline View Duo For Groups: Unmatched Luxury Stay

apartment, Chicago
This six-bedroom, six-bathroom penthouse apartment in Chicago's River West district is just 800 metres from Logan Square and 1.3 kilometres from Fulton Market, offering spacious city living with excellent transport links.
Accommodating up to 14 guests, this residence boasts a chef's kitchen, Smart TVs, Sonos sound systems, and access to building amenities including a gym, yoga studio, outdoor swimming pool, and hot tub, with a Pack 'n Play available on request.
2br Retreat In Downtown + City Skyline Views - Chicago, IL
No reviews

2br Retreat In Downtown + City Skyline Views

apartment, Chicago
This Gold Coast flat is situated in Chicago, a mere 10-minute walk from Lincoln Park and steps from Michigan Avenue.
This spacious 242 square metre apartment accommodates up to five guests and boasts two bedrooms, two bathrooms, a private balcony with skyline views, and access to a rooftop pool deck, gaming centre, and health club.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday rentals with air conditioning

Fun Logan Square Stay  Games  Pets  Sleeps 5 - Chicago, IL
9.6 14 reviews

Fun Logan Square Stay Games Pets Sleeps 5

apartment, Chicago
This private top-floor flat is situated in Chicago's Avondale/Logan Square district, offering convenient access to local bars and eateries, with the city centre approximately 8 kilometres away.
This one-bedroom accommodation, suitable for up to four guests, features a kitchenette with a mini-fridge and microwave, in-unit laundry facilities, high-speed Wi-Fi, and retro gaming options, all within a classic Chicago building.
15 Min To Lake Michigan, Parking, Washer/dryer - Chicago, IL
9.8 77 reviews

15 Min To Lake Michigan, Parking, Washer/dryer

apartment, Chicago
This stylish, modern two-bedroom basement flat is situated on Chicago's North Side, a short distance from Lincolnwood, Evanston, and Skokie.
Offering a private entrance, designated parking, in-unit laundry, high-speed internet, and family-friendly amenities including a pack 'n play and high chair, this Chicago apartment comfortably sleeps four guests and boasts a fully equipped kitchen with granite countertops.
Stone Mansion Sleeps 10-20 Free Parking Near Lake, Red Line And Wrigley - Chicago, IL
9.8 343 reviews

Stone Mansion Sleeps 10-20 Free Parking Near Lake, Red Line And Wrigley

apartment, Chicago
This charming apartment is situated near the Red Line train in Chicago, placing you within easy reach of bars, cafes, shops, restaurants, and the Lakefront. The apartment consistently receives excellent ratings for its user experience, location, and cleanliness.
This spacious home offers four bedrooms, two bathrooms, and a large living room, spanning a generous 214 square metres. Guests can enjoy modern amenities such as Wi-Fi, laundry facilities, and HDTVs, as well as a charming backyard area perfect for relaxing.
Cheerful 3 Story Townhouse Old Town/lp - Chicago, IL
9.7 245 reviews

Cheerful 3 Story Townhouse Old Town/lp

house, Chicago
This three-storey townhouse is ideally located in Lincoln Park, Chicago, within easy reach (less than 1.6 km) of Lincoln Park Zoo, Lake Michigan, the Magnificent Mile, and Old Town's restaurants and shops.
Offering two bedrooms with queen-size beds and a cot, plus a sofa bed, sleeping up to six guests, this property features a private patio, in-unit laundry, free off-street parking, and central air conditioning and heating.
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