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 10119 accommodations in Chicago, IL, here are the 4 best family friendly rentals

Renovated 6 Bedroom 5 Bathroom Home 10 Minutes From Downtown Chicago - Chicago, IL
9.2 22 reviews
Chicago, IL
30/06 – 05/07
SG$1160/nighttotal: SG$5800 (5 )

Renovated 6 Bedroom 5 Bathroom Home 10 Minutes From Downtown Chicago

6 10
apartment , Chicago
This six-bedroom Chicago residence is located in Bronzeville, a short distance from Lake Michigan and downtown.
The 334 square metre property boasts a spacious layout, accommodating up to 15 guests with six bedrooms, five bathrooms, a private garden, and secure parking; nearby attractions include Bronzeville's restaurants and shops.
5 Mins To Downtown Chi Sleeps 10 - Parking + Games - Chicago, IL
10 3 reviews
Chicago, IL
11/08 – 12/08
SG$758/nightfor 1 night

5 Mins To Downtown Chi Sleeps 10 - Parking + Games

1 2
apartment , Chicago
This Pilsen apartment, situated in Chicago's Lower West Side, is a short walk from 18th Street's restaurants and galleries and minutes from Chicago's city centre.
The 90-square-metre, three-bedroom flat sleeps 8-10 guests, offering three queen beds, two sofa beds, a queen air mattress, a well-equipped kitchen, four Smart TVs, arcade games, board games, high-speed Wi-Fi, and free street parking with one off-street space.
Spacious And Luxurious 3br Near Mccormick Place And Soldier Field With Optional Parking - Sleeps 10 - Chicago, IL
9.3 4 reviews
Chicago, IL
19/08 – 23/08
SG$629/nighttotal: SG$2516 (4 )

Spacious And Luxurious 3br Near Mccormick Place And Soldier Field With Optional Parking - Sleeps 10

3 10
apartment , Chicago
This spacious Chicago apartment, near McCormick Place convention centre, is conveniently located 2.4km from the Field Museum, 2.9km from the Art Institute of Chicago, and 3km from the Chicago Symphony Orchestra.
The 111 square metre property sleeps up to 10 guests, boasting three bedrooms, two bathrooms, a fully equipped kitchen with dishwasher, free Wi-Fi, on-site parking including an electric vehicle charging point, and a garden.
Luxe Duplex-king Beds-gym-huge Backyard-game Room - Chicago, IL
9.7 76 reviews
Chicago, IL
14/07 – 18/07
SG$610/nighttotal: SG$2440 (4 )

Luxe Duplex-king Beds-gym-huge Backyard-game Room

1 6
apartment , Chicago
This three-bedroom apartment is situated on the Northwest side of Chicago, just a short distance from the city centre and Rosemont, offering easy access to a range of attractions and entertainment options. The apartment has received excellent ratings for location, cleanliness, and user experience, making it a great choice for travellers seeking a comfortable and well-maintained home away from home.
The apartment is spacious and modern, comfortably accommodating up to seven guests, and features a fully equipped kitchen, a private gym, and a large fenced-in garden with a BBQ grill and fire pit. Guests can enjoy a range of amenities, including high-speed internet, smart TVs, a washer and dryer, and a private patio with a gas fire table, perfect for relaxing after a day of exploring Chicago.

Best Chicago, IL holiday rentals with parking

Bucktown Private Condo - Chicago, IL
9.3 40 reviews
Chicago, IL
17/09 – 19/09
SG$631/nighttotal: SG$1262 (2 )

Bucktown Private Condo

2 2
apartment , Chicago
This Bucktown condo, situated in Chicago's trendy Bucktown neighbourhood, is approximately 5km from Wrigley Field, 3.5km from Lincoln Park Zoo, and 4.5km from the United Centre.
The 106-square-metre property features two bedrooms, one bathroom, sleeps seven guests, and includes a fully equipped kitchen, terrace, garden, parking, and free Wi-Fi.
Ukrainian Village Garden Retreat - Chicago, IL
10 329 reviews
Chicago, IL
23/07 – 27/07
SG$346/nighttotal: SG$1384 (4 )

Ukrainian Village Garden Retreat

1 2
apartment , Chicago
This Chicago apartment rental is situated in Ukrainian Village, a short distance from Wicker Park.
The one-bedroom flat offers a queen-sized bed, in-unit laundry, free garage parking, high-speed internet (100+ Gbps), and a private garden; it comfortably sleeps two guests.
King Bed, Game Room & Fire Pit | Lcp Collection - Chicago, IL
8.4 5 reviews
Chicago, IL
02/08 – 03/08
SG$1152/nightfor 1 night

King Bed, Game Room & Fire Pit | Lcp Collection

3 2
apartment , Westchester
This Westchester, Illinois apartment is conveniently located near Brookfield Zoo (approx. 24km), Oak Brook Center (approx. 16km), and the Forest Preserves (approx. 16km), offering easy access to downtown Chicago (approx. 40km).
This three-bedroom, 142 square metre property sleeps six, boasting a fully equipped kitchen, in-unit laundry, a private garden with fire pit, and a games room featuring Pac-Man, Mortal Kombat, foosball, and air hockey.
Chic 3bed 2bath Home With Free Parking Close To United Center - Chicago, IL
9.8 18 reviews
Chicago, IL
08/10 – 09/10
SG$768/nightfor 1 night

Chic 3bed 2bath Home With Free Parking Close To United Center

3 1
apartment , Oak Park
This family-friendly Oak Park house, situated within 5km of both the Frank Lloyd Wright Historic District and Concordia University Chicago, offers convenient access to local attractions and public transport.
The 139 square metre property boasts three bedrooms, two bathrooms, sleeps six guests, and includes a fully equipped kitchen, private garden, parking, and free Wi-Fi.

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.

Destinations nearby

Best Chicago, IL holiday rentals with a balcony

Downtown Penthouse 5bd Views | Parking, Gym+pool - Chicago, IL
Chicago, IL
28/08 – 02/09
SG$4459/nighttotal: SG$22295 (5 )

Downtown Penthouse 5bd Views | Parking, Gym+pool

5 13
apartment , Chicago
This five-bedroom Chicago apartment, ideal for large groups, is situated in the downtown area, a short walk from State Street, the Art Institute of Chicago, and within 1.6 km of Millennium Park and Lake Michigan.
The 316 square metre property boasts five bathrooms, a fully equipped kitchen, private balcony with city views, on-site amenities including a swimming pool, fitness centre, and parking, accommodating up to twelve guests.
Rest Easy In The East Village - Quiet Street Only Steps To Top Restaurants, Bars, And Public Transportation By Allset Turnover - Chicago, IL
10 3 reviews
Chicago, IL
11/10 – 23/10
SG$622/nighttotal: SG$7464 (12 )

Rest Easy In The East Village - Quiet Street Only Steps To Top Restaurants, Bars, And Public Transportation By Allset Turnover

1 2
apartment , Chicago
This West Town Chicago apartment is situated 1.6km from The Salt Shed music venue and within 4.8km of both the United Centre and Michigan Avenue.
The one-bedroom property sleeps two guests and features a fully equipped kitchen, balcony, in-home laundry, and a dedicated library; nearby attractions include Division and Damen train stations.
Private Balcony, 1 Garage Parking, Sleeps 8! - Chicago, IL
10 2 reviews
Chicago, IL
10/07 – 12/07
SG$1125/nighttotal: SG$2250 (2 )

Private Balcony, 1 Garage Parking, Sleeps 8!

2 5
apartment , Chicago
This West Loop apartment, a three-minute drive from Fulton Market and under 13km from both Millennium Park and Navy Pier, offers convenient access to Chicago's key attractions.
The 107 square metre property boasts a two-bedroom layout sleeping up to eight guests, featuring a king-size bed, double bed, bunk bed, a fully equipped kitchen with Keurig coffee maker, in-unit laundry, private balcony, and a heated garage parking space.
Grant Park 2br Condo With Balcony Skyline View & Gym In Chicago Downtown - Chicago, IL
10 1 review
Chicago, IL
01/08 – 31/08
SG$792/nighttotal: SG$23760 (30 )

Grant Park 2br Condo With Balcony Skyline View & Gym In Chicago Downtown

2 2
apartment , Chicago
This two-bedroom flat is located in downtown Chicago, a 10-minute walk from DePaul University and within 2 kilometres of the city centre, with Grant Park and the Art Institute of Chicago mere steps away.
This 112 square metre apartment accommodates up to 13 guests and offers a balcony with skyline views, on-site amenities including a shared lounge and billiards, free WiFi, and private parking.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday rentals with air conditioning

Welcome To Chicago - Chicago, IL
10 1 review
Chicago, IL
30/06 – 30/09
SG$101/nighttotal: SG$9292 (92 )

Welcome To Chicago

1 1
apartment , Chicago
This flat in Chicago offers excellent transport links, being 483 metres from the Blue Line for direct access to downtown and O'Hare International Airport, and also close to the I-290 expressway.
This one-bedroom flat accommodates two guests and includes a kitchen with a fridge, air conditioning, and pets are welcome, with a garden also available.
Comfy Stay - Chicago, IL
10 127 reviews
Chicago, IL
17/07 – 19/07
SG$368/nighttotal: SG$736 (2 )

Comfy Stay

1 4
apartment , Chicago
This Chicago guest house is situated in a residential area near the University of Chicago, approximately 1.6 kilometres west of Lake Shore Drive, offering easy access to the Museum of Science and Industry (about 1.6km away).
The spacious condo boasts over 93 square metres of living space, featuring a bright, open-plan layout, a fully equipped kitchen with fridge, freezer, microwave, and dishwasher, plus one bathroom, free on-street parking, and 24-hour host support.
Sunny Logan Square Artists' Home - Chicago, IL
9.8 448 reviews
Chicago, IL
22/12 – 26/12
SG$272/nighttotal: SG$1088 (4 )

Sunny Logan Square Artists' Home

1 3
apartment , Chicago
This Logan Square flat, a mile (1.6 km) from the Logan Square Blue Line station and a five-minute walk from the Metra, offers easy access to the 606 trail.
The spacious three-bedroom second-floor property sleeps six, features a well-equipped kitchen with extra gadgets, a modern bathroom, shared laundry, a garden, parking, and fast internet with streaming services; nearby amenities include a grocery store 1.5 blocks away.
Modern Suite W/420-friendly & Fast Wi‑fi - Chicago, IL
9.3 12 reviews
Chicago, IL
10/07 – 12/07
SG$512/nighttotal: SG$1024 (2 )

Modern Suite W/420-friendly & Fast Wi‑fi

3 5
apartment , Chicago
This apartment in Chicago's South Loop offers excellent access to McCormick Place, just a 1.1 kilometre walk away, and Soldier Field, a 5-minute Uber ride, with Museum Campus, Navy Pier, the Art Institute of Chicago, and the Magnificent Mile all within a short drive.
This modern flat accommodates up to six guests with two bathrooms, features a fully equipped kitchen, in-unit laundry, high-speed Wi-Fi, and a 4K Roku HDTV, and is pet-friendly, with secure parking available for £24 per day and the Cermak-McCormick Place Red Line station nearby for public transport.
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