Holiday Rentals in Chicago, IL

13982 available vacation rental offers

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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

Cozy Nest In Chicago's Vibrant Lincoln Square - Chicago, IL
9.9 276 reviews

Cozy Nest In Chicago's Vibrant Lincoln Square

apartment, Chicago
This three-bedroom duplex is situated near the Brown Line train station, providing easy access to the city's vibrant attractions and diverse neighbourhoods. The property enjoys excellent ratings for its location, cleanliness, and user experience.
The spacious apartment is perfect for families or groups of up to five guests, with a dedicated dining room, game room, and a pack 'n play for younger children. Guests can enjoy a fully equipped kitchen, a dedicated workspace, entertainment options including a Roku-equipped TV, board games, and an air hockey and foosball table, as well as a private outdoor table and grill for warmer months.
The Clubhouse Wrigleyville - Chicago, IL
9.9 402 reviews

The Clubhouse Wrigleyville

apartment, Chicago
This spacious two-bedroom Chicago apartment is situated in Wrigleyville, 0.16 km from Wrigley Field and 0.16 km from the nightlife, yet surprisingly quiet.
The 111.5 sq m property, sleeping up to 12 guests, boasts a fully equipped kitchen, a garden, parking, and excellent user reviews; it's also conveniently located 0.16 km from the Red Line and within walking distance of Lake Michigan beaches.
Cushy Pad Fully Remodeled 10 Min From Ohare. - Chicago, IL
9.6 106 reviews

Cushy Pad Fully Remodeled 10 Min From Ohare.

apartment, Chicago
This Chicago ranch-style house, near the border of Park Ridge and Rosemont, is a block from the Blue Line and Kennedy Expressway, offering easy access to O'Hare International Airport and Chicago's city centre.
The self-catering property sleeps two guests in one bedroom and one bathroom, boasting a fully equipped kitchen, private backyard access, on-site laundry facilities, and is conveniently located near a Starbucks and various amenities.
The Palmer Street House - Logan Square - Chicago, IL
9.2 62 reviews

The Palmer Street House - Logan Square

apartment, Chicago
This Logan Square duplex, a 15-minute drive (approx. 24km) from Chicago's city centre and near the 606 trail, offers easy access to public transport.
The spacious 150m² three-bedroom, two-bathroom property sleeps up to seven guests and includes a private patio, fully equipped kitchen, in-unit laundry, and family-friendly amenities such as a cot and high chair.

Best Chicago, IL holiday rentals with parking

Adorable Single Family Home In Logan Square - Chicago, IL
10 85 reviews

Adorable Single Family Home In Logan Square

apartment, Chicago
This Chicago flat is located in the Logan Square district, offering proximity to Lake Michigan and Millennium Park, with Michigan Avenue and Navy Pier within 1.6 kilometres for shopping.
This spacious 223 square metre residence accommodates up to six guests and features three bedrooms, two bathrooms, a garden, spa, and a two-car garage, with opportunities for watersports and hiking nearby.
Spacious Renovated Brownstone - Chicago, IL
9.6 16 reviews

Spacious Renovated Brownstone

apartment, Chicago
This Rogers Park flat, a block from Clark Street's shops and restaurants, is less than 1.5km from Loyola Red Line station, Lake Michigan, and Little India.
This two-bedroom, one-bathroom apartment sleeps six, boasting a sunroom, in-unit laundry, a well-equipped kitchen with gas stove and dishwasher, and a gas fireplace; free street parking is available during the day.
Spacious 2br Near Univ Of Chicago Home Away From Home - Chicago, IL
No reviews

Spacious 2br Near Univ Of Chicago Home Away From Home

apartment, Chicago
This Hyde Park flat is ideally situated for those visiting the University of Chicago, with 63rd Street Beach just 2.1 kilometres away and the Museum of Science and Industry – Chicago 2.4 kilometres distant.
This apartment offers parking, free WiFi, air conditioning, and a private terrace, alongside a fully equipped kitchen and a flat-screen TV for up to 11 guests, with a 11:00 AM check-out.
The Avondale Garden Unit - Chicago, IL
9.8 438 reviews

The Avondale Garden Unit

apartment, Chicago
This garden flat is located in the Irving Park neighbourhood, just 5km from Wrigley Field and 11km from downtown Chicago. It benefits from excellent user, location and cleanliness ratings, making it a great choice for travellers.
The property is a 93 square metre, two-bedroom flat with a guest capacity of four. It offers a private entrance, free parking, a well-equipped kitchen, comfortable bedding, a laundry facility, and a garden.

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

Charming One Bed With Office Near Chicago - Chicago, IL
No reviews

Charming One Bed With Office Near Chicago

apartment, Forest Park
This Forest Park flat is situated 5.9 kilometres from Brookfield Zoo and a 14-minute walk from Boulevard Fine Art, with Midway International Airport 13 kilometres away.
This spacious one-bedroom flat, covering 74 square metres and accommodating two guests, offers a fully equipped kitchen, air conditioning, a private balcony, and WiFi.
1 Free Parking, Sleeps 10 - Chicago, IL
9.0 4 reviews

1 Free Parking, Sleeps 10

apartment, Chicago
This West Town flat is a 7-minute Uber ride from downtown Chicago's Millennium Park and a 15-minute trip to Navy Pier.
This 139 square metre dwelling offers three bedrooms, two bathrooms, and can host up to 10 guests, featuring a pool table that doubles as a dining table and a private patio.
Chic Little Italy 4br Stay With Optional Parking - Chicago, IL
10 1 review

Chic Little Italy 4br Stay With Optional Parking

apartment, Chicago
This four-bedroom flat is located in Chicago's Little Italy, within 2 kilometres of Union Station, the United Centre, Willis Tower, and the Art Institute of Chicago.
This 130-square-metre residence offers a kitchen equipped with a fridge, microwave, and dishwasher, air conditioning, free WiFi, and a terrace or balcony, with optional parking and on-site washing facilities available.
West Loop 2br, Walk To Top Restaurants, Sleeps 5 - Chicago, IL
No reviews

West Loop 2br, Walk To Top Restaurants, Sleeps 5

apartment, Chicago
This West Loop flat is situated within a 5-minute walk of Fulton Market Kitchen and 3 minutes from Union Park, offering convenient access to public transport for exploring Little Italy and Randolph Street Market.
This top-floor duplex provides accommodation for five guests across two bedrooms, featuring a fully equipped kitchen, a private balcony, and access to building amenities including a fitness centre, game room, co-working space, and an outdoor sky terrace with grills and firepits.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday rentals with air conditioning

Serene 2-bdrm: Sunlit Retreat In Heart Of The City - Chicago, IL
9.4 163 reviews

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

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.
3 Bedroom Apartment In Irving Park Neighborhood - Chicago, IL
9.9 17 reviews

3 Bedroom Apartment In Irving Park Neighborhood

apartment, Chicago
This Irving Park flat, an 18-minute Blue Line journey (approx. 10km) from central Chicago, offers easy access to Wrigley Field via the Addison bus route and is a short drive from motorways.
Sleeping seven guests, this newly renovated three-bedroom property features a queen-size bed, a double bed, two full-size bunk beds, a sofa bed, and a shared laundry room with a backyard; modern conveniences include built-in USB ports and ample storage.
Wicker Park Historic, Art-filled, Urban Oasis #2 - Chicago, IL
9.6 238 reviews

Wicker Park Historic, Art-filled, Urban Oasis #2

apartment, Chicago
This Wicker Park flat, a 5-minute (approximately 3.2km) drive from Chicago's city centre, offers easy access to shops, restaurants, and public transport.
The two-bedroom apartment sleeps five guests comfortably, boasting a fully equipped kitchen, private garden access, and designated parking; a second, similar apartment is available for larger groups.
Gym, Garage Parking, Balcony, Sleeps 4 - Chicago, IL
9.9 38 reviews

Gym, Garage Parking, Balcony, Sleeps 4

apartment, Chicago
This 83.6 square meter flat is situated in Chicago's West Loop, offering direct access to the city centre, with a private balcony overlooking Madison Street.
This 2-bedroom, 2-bathroom condo accommodates up to 4 guests and includes hotel-grade bedding, a fully-equipped kitchen with a Keurig coffee maker, high-speed WiFi, an in-unit washer/dryer, and free access to a fitness centre and one garage parking space.
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