Holiday Rentals in Chicago, IL

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Chicago, IL holiday rentals
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Best Holiday rentals and Airbnb offers 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

Skylit Boho Retreat In Wicker Park - Chicago, IL
9.4 245 reviews

Skylit Boho Retreat In Wicker Park

apartment, Chicago
This two-bedroom flat in Chicago's Wicker Park Bucktown district places guests within easy reach of the city's main attractions, offering a convenient base for exploration.
The accommodation sleeps up to five guests and includes a full kitchen, air conditioning, a shared patio, and is located approximately 5.6 kilometres from Millennium Park, with a 420-friendly environment and a pack and play available on request.
Comfortable 3br Getaway W/ Bonus Attic Lounge To Relax - Chicago, IL
9.2 11 reviews

Comfortable 3br Getaway W/ Bonus Attic Lounge To Relax

apartment, Calumet Park
This three-bedroom Chicago apartment, located in the Calumet Park neighbourhood in the city's south suburbs near the Indiana border, offers easy access to attractions such as the Museum of Science and Industry and is a short distance from downtown Chicago.
The property features a spacious layout including a loft area, sleeps six guests, and includes a kitchenette, free Wi-Fi, a smart TV, and on-site parking.
2br/2ba Condo W/ Balcony & Garage - Near Hospitals - Chicago, IL
10 2 reviews

2br/2ba Condo W/ Balcony & Garage - Near Hospitals

apartment, Chicago
This 2-bedroom, 2-bathroom condo is located between Chicago's South Loop and Bronzeville districts, offering easy access to the city centre and the lakefront, with McCormick Place just a short walk away and Insight Hospital in the immediate vicinity.
This 119-square-metre flat, suitable for up to four guests, features a primary suite with a king-size bed and en-suite bathroom, a second bedroom with a queen-size bed and workspace, a fully equipped kitchen, in-unit laundry, and a private balcony, all within a secure, controlled-access building.
Luxury Soho Styled Two-level Townhouse - Old Town - Chicago, IL
9.9 159 reviews

Luxury Soho Styled Two-level Townhouse - Old Town

apartment, Chicago
This luxurious Old Town duplex townhouse, a five-minute walk from the beach and adjacent to Second City and Lincoln Park, offers a prime Chicago location.
The 268 square metre property boasts a spacious open-plan layout, sleeping up to twelve guests, and includes three bedrooms, three bathrooms, a chef's kitchen with Gaggenau appliances, and convenient parking options.

Best Chicago, IL holiday rentals with parking

Visit United Center & Explore The City Of Chicago - Chicago, IL
9.6 285 reviews

Visit United Center & Explore The City Of Chicago

apartment, Chicago
This Chicago apartment, ideally located near the United Centre, is a short 0.8 km walk from the Green Line and offers easy access to the West Loop, The Loop, and other major attractions such as McCormick Place (3.2 km).
The two-bedroom, one-bathroom flat sleeps four guests and includes a kitchen with fridge, freezer, microwave, and stove, plus air conditioning, a garden, parking, and a back deck and front porch.
Tiny Cozy Guesthouse In Quiet Family Neighborhood - Chicago, IL
9.9 29 reviews

Tiny Cozy Guesthouse In Quiet Family Neighborhood

cabin, Dunning
This Chicago cabin rental, conveniently located in [Insert Specific Chicago Neighbourhood/Area – e.g., Lincoln Park, a 5km radius from the Magnificent Mile], offers a family-friendly escape.
Sleeping up to four guests in two bedrooms and one bathroom, the lodge provides a fully equipped kitchen (fridge, microwave), air conditioning, parking, internet access, and accepts pets.
Lakeview Loft-vintage Chicago, Modern Amenities - Chicago, IL
9.9 595 reviews

Lakeview Loft-vintage Chicago, Modern Amenities

apartment, Chicago
This Lakeview flat is ideally situated in Chicago's Lakeview neighbourhood, less than 0.8km from the Brown and Red Line 'L' trains, under 1.6km from Wrigley Field, and 2.4km from the lakefront.
The freshly remodelled one-bedroom loft, sleeping four guests, boasts a king-size bed, 65" TV, private patio, fully equipped kitchen (fridge, microwave), and self check-in; nearby activities include exploring Wrigleyville and enjoying Chicago's lakefront.
Downtown Chicago Stay With Free In & Out Parking 6 - Chicago, IL
No reviews

Downtown Chicago Stay With Free In & Out Parking 6

apartment, Chicago
This 2-bedroom flat in central Chicago offers prime downtown access, situated 500 metres from Millennium Park and 800 metres from the Chicago Riverwalk, with the Art Institute of Chicago also within easy walking distance.
This 67 square metre apartment accommodates up to six guests with two queen beds, a sofa bed, and an inflatable mattress, featuring a fully equipped kitchen, air conditioning, parking, and access to a gym, with streaming services provided for entertainment.

Frequently asked questions about holiday rentals in Chicago, IL

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

    You definitely shouldn't miss the iconic Willis Tower, formerly known as the Sears Tower, for panoramic views of the city. A visit to Millennium Park is a must, with the Cloud Gate sculpture, known as 'The Bean', and Crown Fountain. And no trip to Chicago is complete without experiencing the vibrant nightlife and diverse cuisine in the city's many neighbourhoods.
  • What are the best Airbnb and vacation rentals in Chicago, IL?

    2bd/2ba Mag Mile Masterpiece (+Rooftop), Kasa | Walk To Lincoln Park Zoo | Chicago and Charming Chicago-style - Vintage - Tv Nfl Pass are the most popular Airbnb and vacation rentals in Chicago, IL among travelers.

  • 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, bustling experience, consider staying in the trendy Wicker Park or Bucktown neighbourhoods. If you prefer a more relaxed atmosphere, Lincoln Park or Lakeview offer a mix of residential streets and green spaces. And if you're looking for a historic setting, the Gold Coast or River North are great options.
  • 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 with a variety of animals and exhibits. The Shedd Aquarium is a great place to learn about marine life, and the Field Museum offers fascinating exhibits on dinosaurs and other natural history subjects. For a fun day out, consider visiting the Museum of Science and Industry or the Art Institute of Chicago.
  • What are the best vacation 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?

    The best time to book a vacation rental is during the shoulder seasons, in spring (April-May) or autumn (September-October), when the weather is pleasant, and the crowds are smaller. However, if you prefer a festive atmosphere, you can book during the summer, when the city hosts various festivals and events.
  • 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 festival scene. The Taste of Chicago in July is a great food festival, and the Chicago Blues Festival in June is a must for music lovers. The Lollapalooza music festival in August attracts thousands of music fans, and the Chicago Air and Water Show in August is a spectacular event.
  • 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?

    Take a stroll along the scenic Lakefront Trail, offering stunning views of Lake Michigan. Explore the free exhibits at the Art Institute of Chicago or the Field Museum. Enjoy a picnic lunch in Millennium Park, surrounded by beautiful architecture and public art. And don't forget to check out the free concerts and events happening in various parks and public spaces throughout the city.
  • What are the best restaurants with local dishes in Chicago, IL?

    For a taste of Chicago's iconic deep-dish pizza, head to Lou Malnati's or Pizzeria Bebu. For a classic Chicago hot dog, try Portillo's or The Wiener's Circle. And if you're looking for a more upscale dining experience, Alinea or Next offer innovative and inventive cuisine.
  • What are the best walking or cycling routes in Chicago, IL?

    The Lakefront Trail offers a scenic 18.5-mile path along the shores of Lake Michigan, perfect for walking, running, or cycling. For a more urban experience, explore the Magnificent Mile, a stretch of Michigan Avenue lined with luxury shops and skyscrapers. And for a unique perspective on the city, consider a bike tour through the various neighbourhoods.
  • Are there pet-friendly attractions in Chicago, IL?

    Yes, many attractions in Chicago are pet-friendly. The Lincoln Park Zoo welcomes well-behaved dogs on leash, and the Millennium Park offers designated dog-friendly areas. Many restaurants also 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 provide more space and privacy than a hotel room, often with a kitchen and laundry facilities. They can also be more affordable, especially for families or groups. And many offer unique locations and charming character, allowing you to experience the city like a local.

Popular destinations

Best Chicago, IL holiday rentals with a balcony

Bridgeport Place -Free Parking, Mccormick-sox Park - Chicago, IL
9.8 8 reviews

Bridgeport Place -Free Parking, Mccormick-sox Park

apartment, Chicago
This Chicago flat is located in Bridgeport, a short distance from downtown Chicago, Chinatown, Guaranteed Rate Field (Sox Park), and McCormick Place.
The one-bedroom apartment, sleeping up to four guests with a sofa bed, boasts a private patio with a Weber gas barbecue, self check-in, and is near a river walk with kayaking opportunities.
Charming Newly Updated  3-bed Chicago Apartment. Extended Stay Discount - Chicago, IL
10 1 review

Charming Newly Updated 3-bed Chicago Apartment. Extended Stay Discount

apartment, Chicago
This three-bedroom apartment in Greater Grand Crossing, Chicago, is situated approximately 16 kilometres from the city centre, offering convenient access to public transport links such as the Metra and CTA, and proximity to several hospitals and universities.
The 79-square-metre property, sleeping up to six guests, features a fully equipped kitchen, a terrace, garden, and in-unit laundry facilities; a personal chef service is available upon request.
Last-minute Chicago Home With Rooftop Views +Private Hot Tub -Garage-sleeps 12 - Chicago, IL
10 3 reviews

Last-minute Chicago Home With Rooftop Views +Private Hot Tub -Garage-sleeps 12

apartment, Chicago
This West Town apartment, situated in Chicago, is conveniently located within a 5-8km radius of attractions such as Fulton Market, the United Centre, Grant Park, Michigan Avenue, and Lake Michigan.
Sleeping up to 12 guests, this three-bedroom, three-bathroom dwelling boasts a king suite with fireplace and steam shower, a queen suite with private roof deck access, a fully equipped kitchen with balcony, a private garage, and a stunning roof deck with Willis Tower views.
Feelin Nauti Near Wrigley - Chicago, IL
No reviews

Feelin Nauti Near Wrigley

apartment, Chicago
This one-bedroom flat is situated in Chicago's Lakeview district, within a 10-minute walk of Wrigley Field, Southport Corridor shops, and Boystown nightlife, with the Addison Brown Line 'L' train station just 550 metres away.
Guests can enjoy exclusive use of the entire first floor of a duplex, accommodating two people with one bathroom, air conditioning, a kitchen equipped with a fridge, microwave, and dishwasher, and a complimentary parking space, plus a free membership to The Metropolitan for stays under 14 days.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday rentals with air conditioning

Family Friendly, Lovely 6 Bd Retreat W/ Game Room, Back Deck & Bar - Chicago, IL
9.8 15 reviews

Family Friendly, Lovely 6 Bd Retreat W/ Game Room, Back Deck & Bar

apartment, Chicago
This six-bedroom home is situated in Jefferson Park, a quiet neighbourhood in Chicago, just 10 kilometres from Navy Pier and Michigan Avenue, and within easy reach of the airport and downtown. The property has received excellent reviews from previous guests.
The apartment offers 297 square metres of space, comfortably accommodating up to 16 guests. It features a fully equipped kitchen, a games room, a spa, a garden, a terrace, parking, and a Super Mario-themed bunk room for kids.
Chic 3br/2ba Oasis In The Heart Of Wicker Park - Chicago, IL
9.6 62 reviews

Chic 3br/2ba Oasis In The Heart Of Wicker Park

apartment, Chicago
This Wicker Park apartment in Chicago offers excellent access to public transport, being a short walk from the CTA train and the 606 trail.
The three-bedroom property, sleeping up to eight guests, boasts a full kitchen, in-building laundry, on-site parking (suitable for smaller cars), a private garden with fire pit and grill, and a projector; numerous bars and restaurants are within 0.16 km.
Cool And Modern Chicago Apartment Near Transit - Chicago, IL
9.9 273 reviews

Cool And Modern Chicago Apartment Near Transit

apartment, Chicago
This apartment is located in a walk-up building in Chicago, just a short distance from the Magnificent Mile and Millennium Park, with easy access to public transport. The property has received excellent ratings from previous guests for its cleanliness, location, and overall experience.
The apartment is well-equipped for a comfortable stay, with three bedrooms and a spacious living area, accommodating up to five guests. The kitchen includes modern appliances, a dining area, and a laundry room, while the living area features a 50-inch TV with Roku, Wi-Fi, and a reserved parking spot.
Luxury Designer Penthouse | Gold Coast/old Town - Chicago, IL
9.6 59 reviews

Luxury Designer Penthouse | Gold Coast/old Town

apartment, Chicago
This luxurious Chicago penthouse apartment is situated in the Gold Coast and Old Town neighbourhoods, a short walk from Michigan Avenue and Lake Michigan.
The two-bedroom, two-bathroom dwelling boasts a chef's kitchen, a 65-inch smart TV, free parking, and access to a rooftop sundeck, fitness centre, and lounge; sleeping up to eight guests and offering stunning city views.
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