Vacation rentals in Chicago, IL

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Chicago, IL vacation rentals
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Best Vacation rentals and Airbnb offers in Chicago, IL

Best family friendly Chicago, IL vacation rentals

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

Spacious 5 Br / King Size Beds + Private Parking! - Chicago, IL
9.6 18 reviews
Chicago, IL
02/07 – 06/07
3016 ﺩ.ﺇ/nighttotal: 12064 ﺩ.ﺇ (4 )

Spacious 5 Br / King Size Beds + Private Parking!

5 10
apartment , Chicago
This five-bedroom, three-bathroom apartment in Chicago's East Garfield Park neighbourhood is situated 0.8 km from the Green Line CTA station, offering easy access to the city centre and attractions such as the Garfield Park Conservatory (1.4 km away).
The 149 square metre property sleeps twelve guests and boasts a fully equipped kitchen, including a dishwasher; a garden and spa; and parking, plus excellent guest reviews.
Group Lux In Old Town/gold Coast (+Private Roof) - Chicago, IL
9.8 144 reviews
Chicago, IL
27/06 – 30/06
2346 ﺩ.ﺇ/nighttotal: 7038 ﺩ.ﺇ (3 )

Group Lux In Old Town/gold Coast (+Private Roof)

1 5
apartment , Chicago
This Old Town duplex apartment, a short walk (0.8-1.6km) from the Red Line CTA and Wells Street's restaurants, offers easy access to Chicago's attractions.
The 279 square metre property boasts multiple bedrooms sleeping several guests, two kitchens, three bathrooms, a rooftop deck, private courtyard, and parking, ideal for families or groups exploring the city.
Awesome Location Gold Coast 1br Apt - Chicago, IL
9.5 43 reviews
Chicago, IL
09/07 – 13/07
1284 ﺩ.ﺇ/nighttotal: 5136 ﺩ.ﺇ (4 )

Awesome Location Gold Coast 1br Apt

1 2
apartment , Chicago
This Gold Coast flat offers exceptional access to Chicago's attractions, being within a short walk (less than 1.6km) of Oak Street Beach and the Magnificent Mile, and close to the Clark/Division Red Line station.
The one-bedroom, one-bathroom apartment sleeps four, includes a fully equipped kitchen with fridge, freezer, microwave, and dishwasher, plus air conditioning and internet access; nearby activities include exploring the Loop, River North, and Navy Pier.
Family 7bd Home With Game Rm, Hot Tub, And Sauna - Chicago, IL
9.7 131 reviews
Chicago, IL
30/07 – 02/08
10895 ﺩ.ﺇ/nighttotal: 32685 ﺩ.ﺇ (3 )

Family 7bd Home With Game Rm, Hot Tub, And Sauna

1 13
apartment , Chicago
This Chicago single-family home, location unspecified but implying proximity to Chicago's attractions, offers a spacious seven-bedroom, four-and-a-half-bathroom dwelling perfect for large groups.
The property boasts a fully equipped kitchen, basement recreation area with pool table, private garden with patio furniture and grill, accommodating up to 16 guests and providing ample space for relaxation and entertainment.

Best Chicago, IL vacation rentals with parking

Fulton Market / Noble Square Free Parking, Laundry, 2.5 Miles To Mag Mile! - Chicago, IL
9.6 12 reviews
Chicago, IL
01/08 – 31/08
1217 ﺩ.ﺇ/nighttotal: 36510 ﺩ.ﺇ (30 )

Fulton Market / Noble Square Free Parking, Laundry, 2.5 Miles To Mag Mile!

2 2
apartment , Chicago
This West Town apartment is ideally located less than 1.6km from Wicker Park and 4.8km from the Magnificent Mile, offering easy access to the Blue Line 'L' train.
This 84 square metre flat sleeps six guests, features two bedrooms, one bathroom, in-unit laundry, free street parking, and a fully equipped kitchen; nearby attractions include numerous restaurants and shops.
Norwood Park/edison Park! Workstation & In-unit Laundry! 2nd Floor Apt - Chicago, IL
Chicago, IL
22/06 – 22/07
1523 ﺩ.ﺇ/nighttotal: 45690 ﺩ.ﺇ (30 )

Norwood Park/edison Park! Workstation & In-unit Laundry! 2nd Floor Apt

2 1
apartment , Chicago
This two-bedroom flat is situated in the Norwood Park/Edison Park neighbourhood of Chicago, a quiet area located 12 kilometres from Loyola University Chicago and 15 kilometres from Wrigley Field.
The 85 square metre property can accommodate up to four guests and features a fully equipped kitchen, a patio, a garden, and outdoor play equipment, ideal for families with children.
Private Historical Mansion,luxury Home In Chicagos Gold Coast, Event-capable. - Chicago, IL
10 33 reviews
Chicago, IL
07/08 – 09/08
18879 ﺩ.ﺇ/nighttotal: 37758 ﺩ.ﺇ (2 )

Private Historical Mansion,luxury Home In Chicagos Gold Coast, Event-capable.

5 12
apartment , Chicago
This luxurious five-bedroom house is located on Chicago's Gold Coast, just a block from the beach and within walking distance of Oak Street and Michigan Avenue's best shopping. The property has received excellent user ratings and offers a comfortable stay for up to 14 guests.
The 650 square metre house has been recently renovated and features a fully equipped kitchen, a rooftop terrace with city views, and a spa. Guests can enjoy a range of amenities, including a jacuzzi, a garden, parking, and a personal assistant.
Modern 2br/2ba Corner Suite Near Mccormick Place - Chicago, IL
9.6 160 reviews
Chicago, IL
28/07 – 03/08
2527 ﺩ.ﺇ/nighttotal: 15162 ﺩ.ﺇ (6 )

Modern 2br/2ba Corner Suite Near Mccormick Place

1 5
apartment , Chicago
This two-bedroom Chicago apartment, situated in the South Loop district, is a short walk from McCormick Place and offers easy access to Michigan Avenue and public transport.
The 2-bathroom suite sleeps six guests comfortably, featuring a fully equipped kitchen, in-unit laundry, a fitness centre, and optional parking for £23 per day near Soldier Field and the Museum Campus.

Frequently Asked Questions about vacation rentals in Chicago, IL

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

    You absolutely have to see the iconic Willis Tower, formerly known as the Sears Tower. It's the tallest building in Chicago and offers incredible views of the city. You can't miss a stroll along the Magnificent Mile, with its luxury shops and restaurants. And no trip to Chicago is complete without a visit to Millennium Park, home to the Cloud Gate sculpture, affectionately known as 'The Bean', and the Crown Fountain.
  • 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 and central location, consider staying in the River North neighbourhood. It's packed with restaurants, bars, and art galleries, and you're within easy walking distance of the Magnificent Mile and Millennium Park. If you prefer a quieter, more residential vibe, Lincoln Park is a great option. It's known for its beautiful park, the Lincoln Park Zoo, and a charming mix of shops and restaurants.
  • 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 option, it's free to enter and has a wide variety of animals. The Shedd Aquarium is another great choice, with its impressive collection of marine life. For a dose of history and fun, the Field Museum is always a hit with kids, especially the Sue the T-Rex exhibit.
  • 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?

    If you want to experience the city's lively festivals and warm weather, book your vacation rental during the summer months, from June to August. But keep in mind that prices will be higher during this peak season. For a more budget-friendly option, consider visiting during the shoulder seasons, in spring or autumn, when the weather is still pleasant and the 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?

    Chicago is a city that loves its festivals! In the summer, you can't miss the Taste of Chicago, a massive food festival with delicious local cuisine. For music lovers, Lollapalooza is a huge music festival held in Grant Park in August. And for a unique cultural experience, head to the Chicago Blues Festival in June.
  • 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?

    A walk or bike ride along the Lakefront Trail offers stunning views of Lake Michigan and the city skyline, and it's completely free. The Lincoln Park Zoo is another great free attraction, with a wide variety of animals to see. You can also find free concerts and events in Millennium Park throughout the year.
  • What are the best restaurants with local dishes in Chicago, IL?

    For a taste of Chicago's famous deep-dish pizza, head to Lou Malnati's Pizzeria. If you're craving a classic Chicago hot dog, try Portillo's Hot Dogs. And for a truly unique dining experience, try Al's Beef, known for its delicious Italian beef sandwiches.
  • What are the best walking or cycling routes in Chicago, IL?

    The Lakefront Trail is a must-do for any visitor, offering stunning views of Lake Michigan and the city skyline. It's a great option for both walking and cycling. For a more urban experience, try the 606 Bloomingdale Trail, a former railway line transformed into a raised park with beautiful views of the city.
  • Are there pet-friendly attractions in Chicago, IL?

    Many parks and attractions in Chicago are pet-friendly, including Millennium Park, Lincoln Park, and the Lakefront Trail. You can even take your furry friend for a ride on the Chicago Riverwalk, which has designated pet-friendly areas.
  • What are the benefits of choosing a vacation rental in Chicago, IL?

    Vacation rentals offer more space and privacy than a hotel room, often with amenities like a kitchen and laundry facilities. They can also be a more budget-friendly option, especially for families or groups. And you'll often find them in more convenient locations, closer to the attractions you want to see.
  • What are the top sports attractions and facilities in Chicago, IL?

    Chicago is a city that loves its sports! Catch a game at Wrigley Field, home to the Chicago Cubs baseball team, or visit Guaranteed Rate Field, where the Chicago White Sox play. For basketball fans, the United Center is home to both the Chicago Bulls and the Chicago Blackhawks hockey team.

Destinations nearby

Best Chicago, IL vacation rentals with a balcony

Entire Apt In Heart Of Chicago - Chicago, IL
9.8 8 reviews
Chicago, IL
13/08 – 14/08
1958 ﺩ.ﺇ/nightfor 1 night

Entire Apt In Heart Of Chicago

2 1
apartment , Chicago
This Chicago apartment, situated in Wrigleyville, is an 8-minute walk from Wrigley Field and within 3.5km of Lincoln Park Zoo and Fullerton Beach.
The one-bedroom, one-bathroom flat sleeps six guests and features a fully equipped kitchen, free Wi-Fi, a balcony, and a flat-screen TV; nearby attractions include Wrigley Field and Lincoln Park Zoo.
Landing | Incredible 1bd, Gym, Yoga Studio - Chicago, IL
Chicago, IL
01/09 – 31/10
580 ﺩ.ﺇ/nighttotal: 34800 ﺩ.ﺇ (60 )

Landing | Incredible 1bd, Gym, Yoga Studio

1 2
studio , Chicago
This Near West Side studio apartment is located a short distance from Chicago's Art Institute and the Chicago Theatre, and is also close to the United Centre.
This 72 square metre one-bedroom flat offers air conditioning, Wi-Fi, a terrace, and accommodates two guests.
Elegant 3-bed, 3-bath Home In Chicago <25-minutes To Ohare & Downtown + Parking - Chicago, IL
9.8 8 reviews
Chicago, IL
21/07 – 23/07
2436 ﺩ.ﺇ/nighttotal: 4872 ﺩ.ﺇ (2 )

Elegant 3-bed, 3-bath Home In Chicago <25-minutes To Ohare & Downtown + Parking

3 7
apartment , Chicago
This Irving Park family home, situated 4.7km from Wrigley Field and 5km from Portage Park, offers easy access to Chicago's Brown Line and Lake Michigan (approx. 9.7km).
The 279 square metre property sleeps up to 10 guests in three bedrooms and three bathrooms, boasting a fully equipped kitchen, terrace, garden, parking, and free Wi-Fi.
Welcome To Our Charming 2bd 2ba Pilsen Apartment - Chicago, IL
7.5 2 reviews
Chicago, IL
03/07 – 06/07
1193 ﺩ.ﺇ/nighttotal: 3579 ﺩ.ﺇ (3 )

Welcome To Our Charming 2bd 2ba Pilsen Apartment

1 4
apartment , Chicago
This 2-bedroom, 2-bathroom flat in Chicago's Pilsen district is situated 3.2 kilometres from the United Center and 5.8 kilometres from Union Station.
This 93 square metre dwelling offers air conditioning, a private balcony, a fully equipped kitchen with a dishwasher and oven, on-site casino, and accommodates up to six guests.

Best Chicago, IL vacation rentals with air conditioning

Lovely Chicago Apt | Hip Location W/ Top Food - Chicago, IL
9.7 564 reviews
Chicago, IL
17/08 – 22/08
638 ﺩ.ﺇ/nighttotal: 3190 ﺩ.ﺇ (5 )

Lovely Chicago Apt | Hip Location W/ Top Food

1 3
apartment , Chicago
This one-bedroom flat is situated in Chicago's Andersonville neighbourhood, just a short walk from Uptown's Asia on Argyle and a few minutes from Foster Beach and the Lakefront Trail. The apartment has received excellent ratings for location, cleanliness and overall experience.
The flat has one bedroom and one bathroom, suitable for up to four guests. It comes equipped with a kitchen including a fridge, microwave oven and dishwasher, as well as air conditioning, parking and internet access.
Luxurious Cozy Boho 10 Min To Downtown Sleeps 5 - Chicago, IL
9.8 75 reviews
Chicago, IL
01/07 – 06/07
619 ﺩ.ﺇ/nighttotal: 3095 ﺩ.ﺇ (5 )

Luxurious Cozy Boho 10 Min To Downtown Sleeps 5

1 3
apartment , Chicago
This Chicago apartment rental is located in Little Village, a 10-minute drive (approx. 4.8km) from the city centre, 4.8km from Little Italy and Chinatown, and a 15-minute drive (approx. 11.2km) from Millennium Park and Soldier Field.
The one-bedroom flat sleeps five guests comfortably, offering a full kitchen, washer/dryer, in-unit entertainment (two smart TVs, Pac-Man arcade game, board games), a mini-patio with grill, and enhanced security features including keyless entry.
Walk To Wrigley/ Boystown -Chicago 3br/2ba Duplex-paid Parking Available! - Chicago, IL
9.0 132 reviews
Chicago, IL
14/11 – 05/12
1102 ﺩ.ﺇ/nighttotal: 23142 ﺩ.ﺇ (21 )

Walk To Wrigley/ Boystown -Chicago 3br/2ba Duplex-paid Parking Available!

3 3
apartment , Chicago
This Lakeview, Chicago flat is a short walk from Wrigley Field and offers easy access to Boystown, Southport Corridor, and public transport.
The three-bedroom, two-bathroom duplex sleeps eight, features keyless entry, Wi-Fi, a smart TV, and a garden, plus nearby access to Lake Michigan, Millennium Park (accessible via public transport), and various water sports.
Andersonville Garden Living - Chicago, IL
9.6 142 reviews
Chicago, IL
26/08 – 29/08
669 ﺩ.ﺇ/nighttotal: 2007 ﺩ.ﺇ (3 )

Andersonville Garden Living

1 2
apartment , Chicago
This Chicago garden flat, conveniently located off Clark Street near Coffee Studio and Little Bad Wolf, offers easy access to shops and restaurants.
The one-bedroom apartment sleeps three, boasting a brand-new kitchen and bathroom, two full-size beds (one in a private bedroom, one in a living room nook), two Ashley Furniture reclining leather couches, a smart TV with Netflix, private laundry access, and free street parking.
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