Holiday Rentals in Chicago, IL

13982 available vacation rental offers

-
7
2
1
  • airbnb
  • booking
  • bookabach
  • expedia
  • tripadvisor
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelscom
  • hotelopia
Chicago, IL holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

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

4br Wrigley  Walk To Wrigley  Sleeps 8  Garage - Chicago, IL
10 59 reviews

4br Wrigley Walk To Wrigley Sleeps 8 Garage

apartment, Chicago
This newly built four-bedroom, three-bathroom flat is located in Chicago's Wrigleyville district, 100 metres from the Red Line Addison Station and directly opposite Wrigley Field.
This family-friendly accommodation for up to eight guests offers a full kitchen, living room, air conditioning, garden, and complimentary garage parking, with an in-unit washer/dryer and immediate access to numerous cafes, restaurants, and shops.
Mccormick Place 2br Oasis With Patio, Gym Near Museum Campus & Soldier Field - Chicago, IL
9.0 2 reviews

Mccormick Place 2br Oasis With Patio, Gym Near Museum Campus & Soldier Field

apartment, Chicago
This Near South Side Chicago flat is conveniently located a short walk from State Street and McCormick Place, and within 3.2km of Soldier Field and Lake Michigan.
The 79 square metre apartment sleeps six guests and boasts three bedrooms, two bathrooms, a fully equipped kitchen including a dishwasher, in-unit laundry, free Wi-Fi, and access to a fitness centre and parking.
Clean & Sunny, 2bd, Private Deck, 15min To Wrigley! - Chicago, IL
10 22 reviews

Clean & Sunny, 2bd, Private Deck, 15min To Wrigley!

apartment, Chicago
This Irving Park, Chicago flat is a short walk from Addison and Irving Park buses, a 15-minute walk (approx. 1.2km) from the train, and a 15-minute bus ride or free shuttle to Wrigley Field.
The 84-square-metre (904 sq ft) two-bedroom apartment sleeps six, boasting a fully equipped kitchen, in-unit laundry, a private porch, access to a shared garden, and is close to Horner Park and numerous restaurants and bars.
Huge 5br Heart Of Fulton Market | Duplex Of Dreams - Chicago, IL
9.4 18 reviews

Huge 5br Heart Of Fulton Market | Duplex Of Dreams

apartment, Chicago
This five-bedroom duplex flat is located in Chicago's Fulton Market district, 2.6 kilometres from the United Center, 3.2 kilometres from Downtown/The Loop, and 4 kilometres from Millennium Park.
This family-friendly residence accommodates up to 12 guests, offering two outdoor patios, a foosball table, a children's play area, and a single off-street parking space, alongside a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher.

Best Chicago, IL holiday rentals with parking

Stylish River North Suites: Luxury Living Near Chicagos Best Shopping&nightlife - Chicago, IL
9.8 11 reviews

Stylish River North Suites: Luxury Living Near Chicagos Best Shopping&nightlife

apartment, Chicago
This Level River North apartment, a two-bedroom suite offering 93 square metres of space, is situated in the River North district, minutes from the Magnificent Mile and the Loop.
The flat boasts two bathrooms, sleeps six guests, includes a fully equipped kitchen, balcony, and access to a swimming pool, sauna, and parking, with nearby water activities such as motor boating on the Chicago River readily available.
Rustic Retreat Near Hosp - Chicago, IL
9.3 49 reviews

Rustic Retreat Near Hosp

apartment, Berwyn
This Berwyn apartment is ideally situated a short walk from restaurants and the BNSF Metra station, offering easy access to Oak Park and Chicago city centre by car or train.
The one-bedroom flat sleeps four guests and features a fully equipped kitchen, 50" Smart TV, free street parking, and shared laundry facilities within the building; keyless entry is provided.
Elegant & Bright Pilsen Stay With Colorful Decor - Chicago, IL
9.6 39 reviews

Elegant & Bright Pilsen Stay With Colorful Decor

apartment, Chicago
This two-bedroom flat is situated in Chicago's Pilsen district, a few hundred metres from the Damen Pink Line, providing convenient access to local murals and cultural attractions.
This well-appointed flat for four guests features a fully equipped kitchen, air conditioning, dedicated parking, and an in-unit washer/dryer, with a walk-in shower and a half bathroom.
Sleeps7 • 2br • Coffee Station • Backyard W/ Grill - Chicago, IL
No reviews

Sleeps7 • 2br • Coffee Station • Backyard W/ Grill

apartment, Chicago
This Chicago detached house is located approximately 12 kilometres from the United Centre and 12.2 kilometres from Lincoln Park Zoo, offering straightforward access to several key city attractions.
This detached house provides accommodation for up to 7 guests across 2 bedrooms, featuring a fully equipped kitchen with an oven and microwave, complimentary WiFi, and a backyard with a grill, all within a 1000 square metre floor area.

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, take a boat trip on the Chicago River, and wander around Millennium Park, where you'll find the famous Cloud Gate sculpture, nicknamed 'The Bean'.
  • 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, try Wicker Park or Bucktown. If you prefer a more relaxed vibe, Lincoln Park or Lakeview are great choices. You'll find plenty of options in each of these neighbourhoods.
  • 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 Shedd Aquarium is a must-see, especially for kids. Lincoln Park Zoo is free and has a variety of animals, and the Museum of Science and Industry is always a hit with 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?

    Summer is the peak season, so booking in advance is essential. You can often find good deals in the shoulder seasons, like spring or autumn, when the weather is still pleasant but crowds are smaller.
  • 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?

    The Chicago Blues Festival in June is a great time to experience the city's musical heritage. The Taste of Chicago in July offers a chance to sample local cuisine, and Lollapalooza in August is a huge music festival.
  • 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 Lakefront Trail, visit the free museums on the Museum Campus, or explore the diverse neighbourhoods like Chinatown or Little Italy. These are all great ways to experience the city without breaking the bank.
  • What are the best restaurants with local dishes in Chicago, IL?

    For deep-dish pizza, try Lou Malnati's or Pizzeria Bebu. For Chicago-style hot dogs, try Portillo's or Superdawg. These are all classic Chicago eateries.
  • 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, is now a great place for a scenic walk or bike ride through the city.
  • Are there pet-friendly attractions in Chicago, IL?

    Lincoln Park Zoo is very pet-friendly, allowing dogs on leashes in designated areas. Many restaurants and cafes also have outdoor seating that welcomes dogs.
  • What are the benefits of choosing a vacation rental in Chicago, IL?

    Vacation rentals often offer more space and privacy than hotels, and you can usually cook your own meals, saving money. They also tend to be located in more residential neighbourhoods, giving you a more authentic feel of the city.
  • What are the top sports attractions and facilities in Chicago, IL?

    Wrigley Field, home to the Chicago Cubs, is a must-visit for baseball fans. Soldier Field is home to the Chicago Bears, and the United Center hosts the Chicago Bulls and Blackhawks.

Popular destinations

Best Chicago, IL holiday rentals with a balcony

Garage Parking - Vintage Charm - And A Fabulous Location! Easily Enjoy The Best Of Chicago! - Chicago, IL
9.6 320 reviews

Garage Parking - Vintage Charm - And A Fabulous Location! Easily Enjoy The Best Of Chicago!

apartment, Chicago
This two-bedroom Chicago apartment is situated in a neighbourhood a 1.6km walk from Chicago's best bars and restaurants.
The property offers a fully equipped kitchen, including a fridge, microwave, and dishwasher, accommodates four guests, and includes a private garage parking space, plus access to a shared garden.
2-story Penthouse Views, Fireplace, Pool, Gym - Chicago, IL
10 217 reviews

2-story Penthouse Views, Fireplace, Pool, Gym

apartment, Chicago
This aparthotel is located in Chicago's River North District, just a short walk from North Michigan Avenue and offering stunning views of Lake Michigan. It consistently receives excellent reviews from guests, praising its luxurious amenities and prime location.
The spacious apartment features two bedrooms, three bathrooms, and a generous 215 square metres of living space, comfortably accommodating up to eight guests. This modern apartment offers a fully equipped kitchen, a fireplace, a private terrace, and access to a swimming pool, Jacuzzi, sauna, and spa, ensuring a comfortable and enjoyable stay.
Mccormick Place Secret Oasis With Optional Parking For Up To 8 Guests - Chicago, IL
No reviews

Mccormick Place Secret Oasis With Optional Parking For Up To 8 Guests

apartment, Chicago
Holiday rental. Your accommodation will be located in Chicago.
Services and facilities: a fitness center, a fridge and air conditioning. Take advantage of the terrace in this apartment in Chicago.
Mich Ave Downtown Penthouse - Rooftop+gym - Chicago, IL
No reviews

Mich Ave Downtown Penthouse - Rooftop+gym

apartment, Chicago
This Michigan Avenue penthouse flat is located in the Downtown Chicago district, directly on Grant Park, 0.5 kilometres from the Red Line 'L' train station and within walking distance of landmarks such as Cloud Gate ("The Bean") and Soldier Field.
The one-bedroom, one-bathroom apartment sleeps two guests and features in-unit laundry, Wi-Fi, a queen-size bed, and access to a shared rooftop deck and gym; pet-friendly with additional fees applying.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday rentals with air conditioning

3br Spacious Home Away From Home. Coziest Neighborhood In Chicago. - Chicago, IL
9.9 152 reviews

3br Spacious Home Away From Home. Coziest Neighborhood In Chicago.

apartment, Chicago
This three-bedroom flat is situated in a neighbourhood close to the lakefront, offering easy access to the lake and nearby parks. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The property spans 111 square metres and comfortably accommodates up to six guests. Amenities include a fully equipped kitchen, a private back porch, and a range of extras such as coffee, toiletries, and plenty of towels and crockery.
Rustic Studio Apartment In The Heart Of Lincoln Square - Chicago, IL
9.7 261 reviews

Rustic Studio Apartment In The Heart Of Lincoln Square

studio, Chicago
This Lincoln Square studio apartment is conveniently located near the Brown Line, offering easy access to Wrigleyville and Chicago's city centre.
The self-contained unit sleeps two, features a fully equipped kitchen including a dishwasher, a smart TV with Netflix, and free street parking is available nearby; guests are asked to remove their shoes indoors.
Wicker Park Historic, Art-filled, Urban Oasis #1 - Chicago, IL
9.7 317 reviews

Wicker Park Historic, Art-filled, Urban Oasis #1

apartment, Chicago
This Wicker Park flat is situated a short distance from downtown Chicago, approximately 0.8 km from public transport and within easy walking distance of local restaurants and shops.
Sleeping up to five guests, this recently refurbished two-bedroom, one-bathroom apartment boasts a fully equipped kitchen, private parking, and access to a shared garden; nearby attractions include a Divvy bike station.
Sleeps7 • 2br • Coffee Station • Backyard W/ Grill - Chicago, IL
No reviews

Sleeps7 • 2br • Coffee Station • Backyard W/ Grill

apartment, Chicago
This two-bedroom flat in Chicago is situated in a walkable neighbourhood, 800 metres from local dining and shopping on Clark Street, and within driving distance of Wrigleyville nightlife (6.4 kilometres) and various museums.
This family-friendly apartment accommodates up to seven guests and offers a fully equipped kitchen with a coffee station, a spacious living area with a 55-inch Smart TV, and access to a shared outdoor space with grills, plus street parking and on-site laundry facilities.