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

Duplex 3 Bed 2 Bat Apt Steps From Lincoln Square - Chicago, IL
8.7 8 reviews
Chicago, IL
12/07 – 14/07
SG$609/nighttotal: SG$1218 (2 )

Duplex 3 Bed 2 Bat Apt Steps From Lincoln Square

3 5
apartment , Chicago
This three-bedroom Chicago duplex apartment is situated in Lincoln Square, approximately 3.7km from Lincoln Park Zoo, 3.7km from Wrigley Field, and 6.9km from Loyola University Chicago.
The 119 square metre property features two living rooms, two bathrooms, sleeps ten guests, and includes free parking, a terrace, a garden, and a fully equipped kitchen.
Explore Lincoln Park From A Polished Apartment - Chicago, IL
10 312 reviews
Chicago, IL
23/12 – 28/12
SG$371/nighttotal: SG$1855 (5 )

Explore Lincoln Park From A Polished Apartment

1 2
apartment , Chicago
This Lincoln Park studio apartment is ideally situated near Armitage and Halsted Avenues, offering easy access to the Red and Brown Line 'L' train stations for exploring Chicago's city centre.
The self-catering apartment, sleeping up to four guests, boasts a fully equipped kitchen (fridge, freezer, microwave, dishwasher), free parking, and convenient keypad entry; nearby attractions include Lincoln Park itself.
Group-friendly 5br Suite Sleeps 12 With Billiards, Optional Parking And Gym Access Near Mccormick Place And Soldier Field - Chicago, IL
9.0 1 review
Chicago, IL
01/07 – 06/07
SG$938/nighttotal: SG$4690 (5 )

Group-friendly 5br Suite Sleeps 12 With Billiards, Optional Parking And Gym Access Near Mccormick Place And Soldier Field

5 11
apartment , Chicago
This luxurious Chicago apartment, near the Museum Campus, is 2.4km from the Field Museum and within 3.2km of both the Art Institute of Chicago and the Chicago Symphony Orchestra.
The 253 square metre five-bedroom, three-bathroom suite sleeps up to twelve guests and boasts a fully equipped kitchen, fitness centre access, patio, and on-site parking; Midway International Airport is 15km away.
Giant 5br W/ Pool Table, 15 Min To Cubs & Mag Mile - Chicago, IL
10 6 reviews
Chicago, IL
28/08 – 30/08
SG$2269/nighttotal: SG$4538 (2 )

Giant 5br W/ Pool Table, 15 Min To Cubs & Mag Mile

1 10
apartment , Chicago
This substantial five-bedroom residence in Chicago's Irving Park district offers convenient access to major attractions, situated a 15-25 minute Uber journey from landmarks such as Wrigley Field, the city centre, The Bean sculpture, Soldier Field, the United Center, and the Riverwalk.
This early 1900s Craftsman Foursquare property accommodates up to 14 guests with its five bedrooms featuring hotel-quality bedding, three bathrooms, a fully equipped kitchen with a large peninsula, and a dedicated games room complete with a pool table and a 75-inch smart television, all supported by high-speed Wi-Fi.

Best Chicago, IL holiday rentals with parking

New Luxuriously Detailed 4 Bedroom/2ba Home Minutes Away From Attractions&ohare - Chicago, IL
Chicago, IL
27/06 – 04/07
SG$837/nighttotal: SG$5859 (7 )

New Luxuriously Detailed 4 Bedroom/2ba Home Minutes Away From Attractions&ohare

4 8
apartment , Bensenville
This spacious Bensenville apartment, near Rosemont Theatre and Drury Lane Theatre, offers convenient access to cultural attractions and is within a short driving distance – approximately 16km – of the Bloomingdale Park District Museum and Frank Lloyd Wright Historic District.
The four-bedroom property, sleeping up to 12 guests, boasts a king-size master bed, multiple double beds, a jetted Jacuzzi bath, four Smart TVs (including a 65-inch 144hz model), in-unit laundry facilities, and a garden terrace; nearby recreational activities include fishing, swimming, and access to Edge Ice Arena and Addison Ice Arena.
Huge 1700 Sqft 3bd West Loop Penthouse W/ Balcony - Chicago, IL
9.2 345 reviews
Chicago, IL
20/10 – 23/10
SG$405/nighttotal: SG$1215 (3 )

Huge 1700 Sqft 3bd West Loop Penthouse W/ Balcony

3 3
apartment , Chicago
This penthouse apartment is located in the West Loop, a trendy neighbourhood just 1.6 kilometres from Chicago's renowned restaurants and nightlife, with a lively atmosphere and a rich history. It has received excellent ratings from previous guests for its location, cleanliness, and overall experience.
The apartment has three bedrooms and two bathrooms, comfortably accommodating up to nine guests. Amenities include a fully equipped kitchen, a private balcony with a pellet grill, a Jacuzzi tub, and a selection of streaming services on a large TV, ensuring a relaxing and enjoyable stay.
Perfect Place To Enjoy The City Or Just Relax - Chicago, IL
8.3 166 reviews
Chicago, IL
28/08 – 31/08
SG$284/nighttotal: SG$852 (3 )

Perfect Place To Enjoy The City Or Just Relax

1 2
apartment , Chicago
This one-bedroom flat is situated in Chicago, just a short distance from the United Center and Union Station, making it ideal for exploring the city's sporting and transport hubs. The apartment has received consistently high ratings for cleanliness, location and overall experience.
The 93 square metre flat comfortably accommodates up to seven guests. Amenities include a fully equipped kitchen with a dishwasher and coffee machine, air conditioning, free Wi-Fi and towels and bed linen.
The Roscoe Village Guesthouse - Chicago, IL
9.5 7 reviews
Chicago, IL
07/09 – 10/09
SG$336/nighttotal: SG$1008 (3 )

The Roscoe Village Guesthouse

3 6
apartment , Chicago
This Roscoe Village flat is situated 2.3km from Wrigley Field and within an 8km radius of Loyola University Chicago, Water Tower Place, 360 Chicago, and the Museum of Contemporary Art Chicago.
The one-bedroom, one-bathroom apartment sleeps eleven guests, features a fully equipped kitchen, free Wi-Fi, air conditioning, and a flat-screen TV; local shops and restaurants are nearby.

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

Mag Mile Mega Entire Floor 4bd 4ba +Rooftop&gym - Chicago, IL
9.7 646 reviews
Chicago, IL
03/09 – 09/09
SG$1932/nighttotal: SG$11592 (6 )

Mag Mile Mega Entire Floor 4bd 4ba +Rooftop&gym

4 2
apartment , Chicago
This Gold Coast/Streeterville flat is ideally located between Michigan Avenue and Lake Michigan, a short walk from Oak Street Beach and the Magnificent Mile.
The 279 square metre (approximately 2997 square feet) luxury residence boasts two bedrooms, two bathrooms (one with a jetted bath), a fully equipped chef's kitchen, and access to a rooftop deck with city views; additional amenities include a fitness centre, spa, and parking.
Beautiful, Cozy, Stylish Bucktown, Wicker Park House, Perfect Chicago Location. - Chicago, IL
Chicago, IL
27/06 – 31/07
SG$1091/nighttotal: SG$37094 (34 )

Beautiful, Cozy, Stylish Bucktown, Wicker Park House, Perfect Chicago Location.

3 1
apartment , Chicago
This West Town family-friendly house, ideal for Chicago city breaks, is located less than 1.6km from The Salt Shed and Humboldt Park, and under 4.8km from both the United Centre and Michigan Avenue.
Sleeping up to 10 guests, this three-bedroom property boasts a fully equipped kitchen, balcony, garden, spa, concierge service, parking, and free Wi-Fi; nearby attractions include Damen and Division train stations.
Blueground River North Pool Wd Nr Mile Chi-1202 - Chicago, IL
Chicago, IL
27/06 – 31/07
SG$532/nighttotal: SG$18088 (34 )

Blueground River North Pool Wd Nr Mile Chi-1202

1 1
apartment , Chicago
This one-bedroom flat in Chicago's River North district offers proximity to attractions, situated a 13-minute walk from 360 Chicago and 0.8 miles (approximately 1.29 kilometres) from Millennium Park.
This air-conditioned apartment, spanning 71 square metres and accommodating up to three guests, features a private balcony, a fully equipped kitchen with a dishwasher and oven, complimentary WiFi, and access to an indoor swimming pool and fitness centre.
Entire Apt In Heart Of Chicago - Chicago, IL
Chicago, IL
25/11 – 29/11
SG$362/nighttotal: SG$1448 (4 )

Entire Apt In Heart Of Chicago

2 2
apartment , Chicago
This Chicago flat is located in Lakeview, offering convenient access to the Chicago Theatre, Art Institute of Chicago, Michigan Avenue shopping, Navy Pier, the Field Museum of Natural History, and the Chicago Museum of Science and Industry.
This two-bedroom flat sleeps up to six guests, featuring a queen bed in each bedroom and a sofa bed in the living area, with amenities including air conditioning, WiFi, and a microwave oven, plus a bathtub for relaxation.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday rentals with air conditioning

Beautiful Garden Unit In Logan Square! - Chicago, IL
9.8 163 reviews
Chicago, IL
25/09 – 27/09
SG$224/nighttotal: SG$448 (2 )

Beautiful Garden Unit In Logan Square!

1 2
apartment , Chicago
This Logan Square flat is situated a block from Kosciuszko Park, 0.6 km from the Healy Metra Station and 1.6 km from the CTA Blue Line, offering easy access to the 606 Bloomingdale Trail.
The one-bedroom, one-bathroom apartment sleeps four, features a large walk-in closet, open-plan living/dining area, and a garden, and is close to restaurants, bars and a cinema.
Cozy 2br/2ba By River, Sleeps6, W/d, Parking, Desk - Chicago, IL
10 73 reviews
Chicago, IL
06/07 – 10/07
SG$286/nighttotal: SG$1144 (4 )

Cozy 2br/2ba By River, Sleeps6, W/d, Parking, Desk

1 6
apartment , Chicago
This two-bedroom, two-bathroom apartment in Chicago's River North neighbourhood is situated near the South Branch of the Chicago River and a short walk from the Orange Line 'L' train, offering easy access to the Loop (approximately 2.4 kilometres away by car).
The 6-guest dwelling boasts stunning Chicago skyline views, a full kitchen with dishwasher, in-unit washer/dryer, two workspaces, a pull-out queen sofa bed, and is close to a gastro-tavern and a park district boathouse.
Modern Condo  Safe Chicago Stay Near Ohare - Chicago, IL
10 1 review
Chicago, IL
26/07 – 27/07
SG$487/nightfor 1 night

Modern Condo Safe Chicago Stay Near Ohare

2 2
apartment , Chicago
This Cook County flat offers convenient access to O'Hare International Airport and the Blue Line, placing you within 1.6 kilometres of Parkway Bank Park Entertainment District, Rosemont Theatre, and Rivers Casino.
This two-bedroom flat accommodates up to four guests, featuring a full kitchen with high-end appliances, complimentary Wi-Fi, air conditioning, and free private parking, with pets welcome subject to registration and potential fees.
Lux Apts With Lake Views And Top Amenities - Chicago, IL
9.8 38 reviews
Chicago, IL
30/06 – 03/07
SG$1040/nighttotal: SG$3120 (3 )

Lux Apts With Lake Views And Top Amenities

2 4
apartment , Chicago
This Chicago apartment rental offers exclusive lake views and is centrally located near the Field Museum of Natural History, Grant Park, and DePaul University, approximately 16km from Midway International Airport.
The self-catering property features two bathrooms, a private terrace with a hot tub, a fully equipped kitchen, free Wi-Fi, air conditioning, and access to an indoor pool, jacuzzi, fitness centre, and parking including electric vehicle charging.
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