Vacation Rentals in Chicago, IL

13982 available vacation rental offers

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Chicago, IL vacation rentals
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13982 Vacation rentals and Airbnb in Chicago, IL

Best family friendly Chicago, IL vacation rentals

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

Casanova Modern City Living - Chicago, IL
9.8 80 reviews

Casanova Modern City Living

apartment, Chicago
This spacious four-bedroom house, ideal for families, is located in Chicago's North Kenwood/Bronzeville neighbourhood, a short walk from Lake Michigan and a 6.4km drive from the Loop.
Offering a three-floor layout with a private garden, patio, parking, and all modern conveniences including a fully equipped kitchen and air conditioning, this Chicago residence comfortably sleeps eight guests and provides easy access to the city's attractions.
Skylights, King Bed, 2 Bedrooms - Chicago, IL
9.8 298 reviews

Skylights, King Bed, 2 Bedrooms

apartment, Chicago
This two-bedroom apartment is situated in Irving Park East, just a short distance from the CTA Blue Line and buses, making it easy to explore all that Chicago has to offer. The apartment has received excellent ratings for location, cleanliness and user experience.
The apartment comfortably accommodates up to six guests and comes equipped with a full kitchen, laundry facilities, and a 42-inch flat-screen TV with Roku. Guests can enjoy the convenience of free on-street parking and key code entry for flexible arrival times.
Fulton Market Townhome, 4 Levels & 4 Bedrooms - Chicago, IL
10 286 reviews

Fulton Market Townhome, 4 Levels & 4 Bedrooms

house, Chicago
This spacious four-bedroom townhouse is situated in Chicago's West Loop/Fulton Market district, offering easy access to Restaurant Row and major attractions such as Navy Pier and the Loop, all within a convenient distance.
The 91-metre-squared, four-storey property comfortably sleeps up to 15 guests, boasting a fully equipped kitchen, private parking, two outdoor spaces including a rooftop terrace, and high-speed internet access; nearby activities include exploring the culinary delights of Fulton Market and utilising excellent public transport links to O'Hare Airport.
Spacious 3br Corner Stay With Optional Parking And Gym Access Near Mccormick Place, Grant Park And Soldier Field - Chicago, IL
9.5 2 reviews

Spacious 3br Corner Stay With Optional Parking And Gym Access Near Mccormick Place, Grant Park And Soldier Field

apartment, Chicago
This spacious Chicago apartment is conveniently located near the Museum Campus, approximately 2.4 kilometres from the Field Museum and within 3.2 kilometres of the Art Institute of Chicago and the Chicago Symphony Orchestra.
The 102-square-metre property features a three-bedroom, two-bathroom layout sleeping up to ten guests, and includes amenities such as a fully equipped kitchen, fitness centre access, and complimentary Wi-Fi.

Best Chicago, IL holiday rentals with parking

Spacious Beautiful Condo - Chicago, IL
9.7 130 reviews

Spacious Beautiful Condo

apartment, Chicago
This Chicago apartment's precise location within the city is unspecified, preventing a detailed description of its proximity to specific landmarks or districts.
This three-bedroom, two-bathroom condo sleeps seven, boasting a spacious open-plan layout, a fully equipped kitchen with a Keurig coffee maker, a 55-inch Samsung TV, and a master bathroom jacuzzi; parking is also available.
Luxury 5bd Home: Sauna, Hot Tub, Rooftop, Game Rm - Chicago, IL
9.5 97 reviews

Luxury 5bd Home: Sauna, Hot Tub, Rooftop, Game Rm

apartment, Chicago
This Chicago residence, conveniently located within the city limits and offering free street parking, provides easy access to various attractions.
Boasting a spacious 418 square metre layout, this five-bedroom, five-bathroom house sleeps sixteen guests and features a rooftop terrace, home gym, games room, and a Clive Christian kitchen with Sub-Zero and Wolf appliances.
Modern Apt W Private Entrance Washer Dryer Free Parking - Chicago, IL
9.3 6 reviews

Modern Apt W Private Entrance Washer Dryer Free Parking

apartment, Chicago
This Chicago basement flat is located approximately 5.6km from Loyola University Chicago, 10.3km from Wrigley Field, and 17.7km from downtown attractions including the United Centre and the Museum of Contemporary Art.
The 46 square metre self-contained apartment features one bedroom, one bathroom, sleeps up to 11 guests, and includes free Wi-Fi, air conditioning, parking, and all linen.
Cozy Ukrainian Village Two Bedroom Apartment - Chicago, IL
9.7 270 reviews

Cozy Ukrainian Village Two Bedroom Apartment

apartment, Chicago
This two-bedroom apartment is situated in Chicago's Ukrainian Village, a short bus ride (via the #66 Chicago Avenue bus) from the city centre and within walking distance of numerous local cafes and shops.
The 2-bathroom flat, sleeping up to four guests, offers a fridge, freezer, dishwasher, air conditioning, on-street parking (permits provided), and a shared laundry in the basement; it's a 1910 building reflecting Chicago's architectural heritage.

Frequently asked questions about holiday rentals in Chicago, IL

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

    You absolutely must see the iconic Willis Tower (formerly Sears Tower) for breathtaking city views. A trip to Millennium Park is essential, with the Cloud Gate sculpture (affectionately known as 'The Bean') and Crown Fountain being must-sees. No visit to Chicago is complete without a stroll along Navy Pier, enjoying the Ferris wheel and the vibrant atmosphere.
  • What are the best Airbnb and vacation 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, with plenty of shops, restaurants, and nightlife. If you prefer a more relaxed atmosphere, Lincoln Park is a great choice, with beautiful parks, museums, and a thriving local scene.
  • 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 option, with a wide variety of animals. The Shedd Aquarium is a must-visit for marine life enthusiasts, and the Field Museum offers engaging exhibits on dinosaurs and other natural history topics. For a fun day out, head to Navy Pier, where you can enjoy rides, games, and a carousel.
  • 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?

    To avoid peak crowds and high prices, booking your vacation rental in the shoulder seasons, like spring (April-May) or autumn (September-October), is a good idea. You'll still experience pleasant weather and fewer crowds. However, if you want to enjoy the city's festivals and events, summer (June-August) is a popular time, but be prepared for higher prices and larger crowds.
  • 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 Chicago Blues Festival in June is a must-see for music lovers. The Taste of Chicago in July offers a culinary journey through the city's diverse food scene. For a unique experience, check out the Chicago Air and Water Show in August.
  • 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 walk or cycle along the Lakefront Trail for stunning views of Lake Michigan. Explore the free museums, like the Art Institute of Chicago or the Museum of Contemporary Art. Enjoy a picnic in Millennium Park or Grant Park, soaking up the city's energy.
  • What are the best restaurants with local dishes in Chicago, IL?

    For a classic Chicago hot dog, head to Portillo's. If you're looking for deep dish pizza, Lou Malnati's is a local favourite. For a taste of the city's Polish heritage, try the pierogies at the famous Old Town Sausage and Deli.
  • What are the best walking or cycling routes in Chicago, IL?

    The Lakefront Trail offers a scenic route along Lake Michigan, stretching for 18.5 km. For a more urban experience, explore the 606 Bloomingdale Trail, a former railway line transformed into a greenway. You can also cycle along the Chicago Riverwalk, enjoying the city's architecture.
  • Are there pet-friendly attractions in Chicago, IL?

    Many parks in Chicago are dog-friendly, including Millennium Park and Grant Park. You can also find dog-friendly restaurants and cafes throughout the city. The Lincoln Park Zoo is also pet-friendly, allowing well-behaved dogs on leashes.
  • What are the benefits of choosing a vacation rental in Chicago, IL?

    Vacation rentals offer more space and privacy compared to hotels. You can enjoy a home-like environment with amenities like a kitchen, allowing you to prepare your own meals. They often come with unique features and character, giving you a more authentic local experience.
  • What are the top sports attractions and facilities in Chicago, IL?

    Chicago is a major sports city, home to the Chicago Cubs (baseball), Chicago White Sox (baseball), Chicago Bulls (basketball), Chicago Blackhawks (ice hockey), and Chicago Bears (American football). You can catch a game at Wrigley Field, Guaranteed Rate Field, United Center, or Soldier Field.

Popular destinations

Best Chicago, IL holiday rentals with a balcony

Spacious 8 Bdr + 2 Kitchens + Garage! Sleeps 16! - Chicago, IL
9.6 12 reviews

Spacious 8 Bdr + 2 Kitchens + Garage! Sleeps 16!

house, Chicago
This eight-bedroom Avondale townhome, situated approximately 24 kilometres from O'Hare International Airport and two blocks from a major highway, offers easy access to Chicago's restaurants and attractions.
Sleeping sixteen guests comfortably, this spacious property boasts two fully equipped kitchens, two garage spaces, extensive amenities including fresh linens and streaming TV, and self check-in via keypad.
Luxury Penthouse Loft W/terrace  504 | River North - Chicago, IL
9.8 6 reviews

Luxury Penthouse Loft W/terrace 504 | River North

apartment, Chicago
This pet-friendly flat offers a prime downtown Chicago location, a 7-minute walk from Michigan Avenue and close to the Grand and Chicago Metro stations for convenient travel.
Spanning 111 square meters, this accommodation accommodates up to six guests with two bedrooms and two bathrooms, featuring air conditioning, a fireplace, a dedicated workspace, and laundry facilities, with nearby cycling and fishing opportunities.
43rd-floor Luxury Escape + Lake Views - Chicago, IL
No reviews

43rd-floor Luxury Escape + Lake Views

apartment, Chicago
This 2-bedroom flat is situated in Chicago's South Loop, a 5-minute walk from Grant Park and a 7-minute walk from the Art Institute of Chicago, offering convenient access to the Museum Campus and a notable culinary scene.
Guests can enjoy panoramic lake views from the 43rd floor, access to extensive building amenities including multiple swimming pools, a fitness centre, and a hot tub, as well as a fully equipped kitchen and Smart TVs for their stay.
Central Chicago Suite2 Access To Patio! - Chicago, IL
8.8 8 reviews

Central Chicago Suite2 Access To Patio!

apartment, Chicago
This Goose Island apartment, situated in the West Town district of Chicago, offers easy access to Michigan Avenue and Navy Pier, and is within a reasonable driving distance (approximately 8-10 km) of the Field Museum, Museum of Science and Industry, United Centre, and Wrigley Field.
This two-bedroom, 93 square metre flat sleeps up to nine guests, boasting a fully equipped kitchen, a terrace, and hotel-like amenities including Hulu Live TV and access to popular streaming services; a shared rooftop deck offers city views.

Best Chicago, IL holiday rentals with air conditioning

Cozy Chicago Stay | Private Entry + Free Parking - Chicago, IL
10 62 reviews

Cozy Chicago Stay | Private Entry + Free Parking

apartment, Chicago
This Bridgeport flat is situated approximately 3.2km from Chinatown, offering easy access to major Chicago attractions such as McCormick Place and Guaranteed Rate Field, all within a 10-18 minute drive.
The newly renovated one-bedroom apartment sleeps four, features a fully equipped kitchen, in-unit laundry, and high-speed Wi-Fi, providing a comfortable base for exploring the city.
Kasa Lake Shore Chicago | Two Bedroom King & Queen - Chicago, IL
9.7 15 reviews

Kasa Lake Shore Chicago | Two Bedroom King & Queen

apartment, Chicago
This Kasa Lake Shore Chicago residence is located a stone's throw from Lake Michigan, Navy Pier, and the Magnificent Mile, placing you within 500 metres of these key Chicago attractions.
This two-bedroom, two-bathroom flat comfortably accommodates up to six guests and features a fully equipped kitchen, in-unit laundry, high-speed Wi-Fi, air conditioning, and on-site amenities including a fitness centre and a communal lounge.
Feelin Nauti  1br + Parking Near Wrigley - Chicago, IL
10 65 reviews

Feelin Nauti 1br + Parking Near Wrigley

apartment, Chicago
This Chicago apartment, ideally situated in Wrigleyville, is a short 0.97 km walk from the Addison Brown Line 'L' train station and within easy reach of Wrigley Field, Lincoln Park Zoo, and the Southport Corridor.
The self-contained ground-floor flat offers one bedroom, one bathroom, and sleeps two guests, boasting a full kitchen with complimentary coffee, free parking, and complimentary access to The Metropolitan co-working space in the Willis Tower.
Edgewater Escape, Charming 2 Br, Rooftop Solar - Chicago, IL
9.8 388 reviews

Edgewater Escape, Charming 2 Br, Rooftop Solar

apartment, Chicago
This Edgewater garden flat offers convenient access to Chicago's Red Line, providing easy transport to the city centre and Evanston, and is also within proximity of Lake Michigan.
The two-bedroom, one-bathroom apartment sleeps four, features a private backyard, complimentary breakfast items, and laundry facilities (for stays of three nights or more), plus eco-friendly heating and cooling.