Vacation Rentals in Chicago, IL

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

Uncover Top-Tier Family Holiday Rentals in Chicago, IL, United States

Give the entire crew plenty of space to relax and unwind after a busy day of sightseeing at family holiday rentals in Chicago, IL, United States.

4br City Retreat, Great For Business & Family - Chicago, IL
9.7 12 reviews

4br City Retreat, Great For Business & Family

apartment, Chicago
This corporate suite is centrally located in Chicago, providing convenient access to the city's central business district and cultural attractions, approximately 2 kilometres from Millennium Park.
This spacious 4-bedroom, 3-bathroom flat accommodates up to 10 guests, offering a fully equipped kitchen, air conditioning, internet, and on-site fitness centre, making it ideal for families and corporate stays.
Gold Coast Home|rooftop |Pooltable |Parking |Views - Chicago, IL
9.8 67 reviews

Gold Coast Home|rooftop |Pooltable |Parking |Views

apartment, Chicago
This Gold Coast residence, a spacious four-bedroom house, is situated in Chicago's prestigious Gold Coast neighbourhood, within 1.6km of the Magnificent Mile and Oak Street Beach, and a short drive from Millennium Park and Navy Pier.
The 372-square-metre property boasts four bedrooms, four-and-a-half bathrooms, sleeping up to twelve guests, plus a rooftop terrace, indoor games area, mini-gym, and private parking; a fully equipped kitchen and modern living area complete this Chicago dwelling.
Zoo Holiday Retreat - Chicago, IL
9.9 14 reviews

Zoo Holiday Retreat

apartment, Brookfield
This Brookfield apartment is situated near Brookfield Zoo and under 1.6km from the Burlington Northern Santa Fe railway station, offering easy access to Chicago city centre.
The four-bedroom, two-bathroom property sleeps eight, boasting a fully equipped kitchen, air conditioning, parking, and internet access; its proximity to local restaurants and the zoo makes it ideal for family stays.
Bliss In Brookfield- 5br, 3ba, Fenced Yard - Chicago, IL
9.7 60 reviews

Bliss In Brookfield- 5br, 3ba, Fenced Yard

apartment, Brookfield
This Brookfield, Illinois property, a five-minute walk from the Metra train station, is situated 21 kilometres from Midway Airport and 24 kilometres from O'Hare International Airport.
This five-bedroom, three-bathroom house sleeps eleven guests, boasts three living areas, a fully-equipped kitchen including a dishwasher, and a fully-fenced backyard; children's amenities are provided in the finished basement.

Best Chicago, IL holiday rentals with parking

Bright 2br Luxury Corner Suite With Optional Parking Sleeps 6 Guests Near Mccormick Place And Soldier Field - Chicago, IL
9.0 224 reviews

Bright 2br Luxury Corner Suite With Optional Parking Sleeps 6 Guests Near Mccormick Place And Soldier Field

apartment, Chicago
This modern apartment is located in Chicago's McCormick Place district, just a short distance from the Field Museum of Natural History and the Art Institute of Chicago. The property has received excellent ratings for location, cleanliness, and overall user experience.
The apartment has two bedrooms and two bathrooms, comfortably accommodating up to six guests. It comes with a fully equipped kitchen, a fitness centre, a terrace, and on-site parking, making it perfect for families or groups of friends exploring the city.
Huge Pet Friendly East Albany Park Apartment - Chicago, IL
9.8 217 reviews

Huge Pet Friendly East Albany Park Apartment

apartment, Chicago
This apartment is situated near the border of Albany Park and Ravenswood Manor, just a short walk from Kedzie and Lawrence Avenues, offering access to a diverse range of restaurants and bars. The property has received excellent ratings for location, cleanliness and user experience.
The two-bedroom flat can accommodate up to four guests and includes a renovated kitchen, bathroom, and in-unit laundry. Guests can enjoy a private back porch deck, a shared garden, and free street parking.
Double Play Wrigley - Prime Location Across From Wrigley Field & Transit - 2br Apts - Chicago, IL
9.2 635 reviews

Double Play Wrigley - Prime Location Across From Wrigley Field & Transit - 2br Apts

apartment, Chicago
This two-bedroom apartment is located in the Lakeview neighbourhood, just a 3.7km walk from Lincoln Park Zoo and a short distance from Wrigley Field, a famous baseball stadium known for its lively atmosphere. The apartment has received very good ratings for cleanliness and user experience, and an excellent rating for its location.
The apartment has one bathroom and includes a terrace, garden, and parking. It is equipped with a kitchen including a fridge, freezer, microwave oven, and dishwasher, as well as air conditioning and free Wi-Fi.
Lincoln Park Cozy 3bd Home Near Zoo | Lake | Shops - Chicago, IL
9.8 162 reviews

Lincoln Park Cozy 3bd Home Near Zoo | Lake | Shops

apartment, Chicago
This Chicago apartment rental is superbly located in Lincoln Park, less than 1.6km from DePaul University and within 1.6km of Lincoln Park Zoo, the lakefront, Second City, and Park West.
The three-bedroom property, sleeping eight guests, boasts an open-plan living, dining, and kitchen area with a high ceiling and original brickwork, plus two full bathrooms, a half-bathroom, a well-equipped kitchen, in-unit laundry (shared), and a garden; free on-street parking is available (permit required overnight for $15).

Frequently asked questions about holiday rentals in Chicago, IL

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

    You've got to see the iconic Willis Tower, formerly known as the Sears Tower, for incredible views of the city. A trip to Millennium Park is a must, with the Cloud Gate sculpture, affectionately known as 'The Bean', and the Crown Fountain. And don't forget to take a stroll along Navy Pier, enjoying the Ferris wheel and the bustling atmosphere.
  • 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 atmosphere, consider staying in the trendy Wicker Park or Bucktown neighbourhoods. If you prefer a quieter experience with easy access to the city centre, the Lincoln Park area is a good choice. For a more budget-friendly option, check out the Logan Square neighbourhood.
  • 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 wide variety of animals. The Shedd Aquarium is a must-visit for families, with interactive exhibits and fascinating marine life. The Field Museum, with its dinosaur exhibits and cultural displays, is also a popular choice for families.
  • 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?

    To secure the best deals and availability, it's best to book your vacation rental in Chicago at least 3-4 months in advance, particularly during peak season, which runs from May to September. If you're flexible with your travel dates, you might find better deals outside of peak season.
  • 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 lively events scene. The Chicago Blues Festival in June is a highlight for music lovers. The Taste of Chicago in July offers a culinary journey through the city's diverse food scene. The Lollapalooza music festival in August attracts crowds with its eclectic lineup of artists.
  • 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 free walking tour to explore the city's history and architecture. Visit the Art Institute of Chicago on Tuesdays, when admission is free after 5 pm. Enjoy a picnic in Millennium Park, taking in the views and the atmosphere.
  • What are the best restaurants with local dishes in Chicago, IL?

    For classic Chicago-style deep-dish pizza, try Lou Malnati's or Pizzeria Bebu. For a taste of the city's Polish heritage, visit the iconic Old Town Restaurant. If you're looking for a unique dining experience, try the Chicago-style hot dog at Portillo's.
  • What are the best walking or cycling routes in Chicago, IL?

    The Lakefront Trail offers stunning views of Lake Michigan and is perfect for both walking and cycling. The 606 Bloomingdale Trail, a former railway line transformed into a park, is a popular cycling route. For a scenic walk, explore the Lincoln Park Zoo and its surrounding area.
  • Are there pet-friendly attractions in Chicago, IL?

    Many parks and attractions in Chicago are pet-friendly. The Lincoln Park Zoo welcomes well-behaved dogs on a leash. Navy Pier also allows dogs in designated areas. Check the specific attraction's website for their pet policy.
  • 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 kitchen facilities, allowing you to prepare your own meals and save on dining costs. Many rentals also feature unique local charm and character.
  • What are the top sports attractions and facilities in Chicago, IL?

    Chicago is a sports city! Catch a game at Wrigley Field, home to the Chicago Cubs baseball team. The United Center is home to the Chicago Bulls basketball team and the Chicago Blackhawks hockey team. Soldier Field is the home of the Chicago Bears football team.

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Discover Holiday Rentals with a Balcony in Chicago, IL, United States

Browse holiday rentals with balconies in Chicago, IL, United States and enjoy sweeping city views from your own space.

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.
Beautiful 32' Rv Located In South Chicago Suburb - Chicago, IL
10 1 review

Beautiful 32' Rv Located In South Chicago Suburb

apartment, Alsip
This unique 32-foot recreational vehicle in Alsip, a south Chicago suburb, is situated approximately 22.5 to 25.7 kilometres from Chicago attractions including Guaranteed Rate Field, the Museum of Science and Industry, the Field Museum, and Willis Tower, with Midway International Airport being just 10.9 kilometres away.
This 400 square metre accommodation offers one bedroom and one bathroom, comfortably sleeping up to seven guests with amenities such as a kitchen, air conditioning, a terrace/balcony, and parking, alongside complimentary WiFi.
Walk To Wrigley Field/monthly Discounts Available - Chicago, IL
9.8 204 reviews

Walk To Wrigley Field/monthly Discounts Available

apartment, Chicago
This apartment is located in Lakeview, a lively neighbourhood just a short walk from Wrigley Field and across the street from the Metro, with easy access to the city's attractions. It has been highly rated by previous guests for its comfortable accommodation and excellent location.
The apartment has three bedrooms and one bathroom, comfortably accommodating up to six guests. The kitchen is equipped with a fridge, microwave oven, and dishwasher, and the property also offers a terrace/balcony, garden, parking, and air conditioning.
Top Rated W/free Street Parking+ 2 King Beds 1 Single +In Unit-laundry +1.5 Bath - Chicago, IL
10 5 reviews

Top Rated W/free Street Parking+ 2 King Beds 1 Single +In Unit-laundry +1.5 Bath

apartment, Dunning
This newly renovated Scandinavian-inspired flat is located in Dunning, Chicago, offering convenient access to cultural sites like the Chicago History Museum and Chicago Theatre, as well as landmarks such as the Merchandise Mart and Cloud Gate.
This first-floor residence provides accommodation for up to five guests, featuring three bedrooms, private in-unit laundry, fast WiFi, smart TVs, and a large eat-in kitchen, with exclusive access through a private garage entrance.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday rentals with air conditioning

New Home W/view & Party Deck - 2nd Floor - Chicago, IL
9.8 65 reviews

New Home W/view & Party Deck - 2nd Floor

apartment, Chicago
This charming holiday home is situated in Chicago's Lakeview neighbourhood, just 0.8 kilometres from Wrigley Field and 1.0 kilometre from the Vic Theatre, offering easy access to both entertainment and local attractions. The apartment has received excellent user ratings, ensuring a pleasant stay for all guests.
This comfortable apartment spans 149 square metres and comfortably accommodates up to 8 guests in its three bedrooms and two bathrooms. The apartment features a fully equipped kitchen, a private patio, a garden, and a range of entertainment options, including a foosball table, ensuring a fun and relaxing stay for all.
Stylish 3br Gem In Prime Location - Chicago, IL
10 2 reviews

Stylish 3br Gem In Prime Location

house, Chicago
This Chicago dwelling is located 1.4 kilometres from Guaranteed Rate Field and 2.4 kilometres from Grant Park, with Midway International Airport 8.1 kilometres away.
This 167 square metre property offers 3 bedrooms and 2 bathrooms, accommodating up to 12 guests with amenities including a fully equipped kitchen, free WiFi, air conditioning, and an on-site fitness centre.
50th Floor Mag Mile Views, Balcony, Pool, Gym - Chicago, IL
9.8 135 reviews

50th Floor Mag Mile Views, Balcony, Pool, Gym

apartment, Chicago
This apartment is situated in downtown Chicago, just a short walk from the city's main attractions, offering stunning views from its 50th-floor location. The property has received excellent reviews for its cleanliness, location, and overall experience.
The flat is ideal for two guests and features a modern interior with floor-to-ceiling windows showcasing panoramic city views. Guests can enjoy access to a fitness centre, swimming pool, and other amenities, making this a great choice for a comfortable and convenient stay in the Windy City.
Newly Updated 1bd/1b In Old Irving Chicago! - Chicago, IL
9.7 159 reviews

Newly Updated 1bd/1b In Old Irving Chicago!

apartment, Chicago
This Chicago apartment, ideally located in a safe and quiet neighbourhood, offers easy access to public transport and is within walking distance of numerous restaurants and bars.
The one-bedroom flat sleeps four guests, features a fully equipped kitchen, two smart TVs, a dedicated workspace, in-building laundry facilities, and free parking – a rare find in Chicago – alongside 400 MB Wi-Fi.

Book Your Next Luxury Holiday Rental in Chicago, IL, United States

Treat yourself to smart-home features, high-end interiors, and curated artwork at luxury holiday rentals in Chicago, IL, United States.

Go Out Or Stay In... This Property Has Everything You Need For A Perfect Visit - Just Steps From Humboldt Park By Allset Turnover - Chicago, IL
9.4 152 reviews

Go Out Or Stay In... This Property Has Everything You Need For A Perfect Visit - Just Steps From Humboldt Park By Allset Turnover

apartment, Chicago

Browse Downtown Holiday Rentals in Chicago, IL, United States

Spend less time navigating public transport and more time exploring attractions from central holiday rentals in Chicago, IL, United States.

The Stadium Overlook (Fitness Center  Sauna) - Chicago, IL
9.9 59 reviews

The Stadium Overlook (Fitness Center Sauna)

apartment, Chicago
Livn West Loop Chicago Classic Studio Apartment - Chicago, IL
9.7 91 reviews

Livn West Loop Chicago Classic Studio Apartment

apartment, Chicago
Modern And Bright 2br On Michigan Ave With Optional Parking And Gym Access Near Soldier Field & Grant Park - Chicago, IL
9.5 2 reviews

Modern And Bright 2br On Michigan Ave With Optional Parking And Gym Access Near Soldier Field & Grant Park

apartment, Chicago
The Metropolitan Retreat (Fitness Center  Sauna) - Chicago, IL
9.9 115 reviews

The Metropolitan Retreat (Fitness Center Sauna)

apartment, Chicago
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