Chicago, IL holiday rentalscozycozy

Holiday Rentals in Chicago, IL

13982 available vacation rental offers

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13982 Holiday rentals and Airbnb in Chicago, IL

Wrigleyroost <5 Min To Cubs/train/lake! - Chicago, IL
10 114 reviews
Chicago, IL
2 3
161 €/nighttotal: 1610 € (10 )

Wrigleyroost <5 Min To Cubs/train/lake!

apartment - Chicago
This three-bedroom apartment in Chicago's Wrigleyville neighbourhood is situated close to Wrigley Field and Lake Michigan's cycle paths, offering easy access to public transport.
The family-friendly flat, sleeping up to six (with an air mattress), boasts a fully equipped kitchen, a private deck, and access to a shared backyard with a fire pit; a travel cot is also provided.
Luxe Stay + Balcony | Top Food, Shops, Music, Bars - Chicago, IL
10 41 reviews
Chicago, IL
4 3
721 €/nighttotal: 5047 € (7 )

Luxe Stay + Balcony | Top Food, Shops, Music, Bars

apartment - Chicago
This three-bedroom Chicago apartment, situated in Andersonville, offers easy access to Lake Michigan and is within a 5-10 minute transit ride of popular attractions including Wrigleyville, the Loop, and Chinatown.
The 1908 Prairie School-style property boasts a fully equipped kitchen with high-end appliances, a private balcony, hotel-quality linens, and amenities such as beach gear and a Bluetooth sound system, comfortably sleeping six guests.
3br Uchicago Medical Midway Museums Large Comfy %S - Chicago, IL
10 3 reviews
Chicago, IL
2 3
184 €/nighttotal: 1288 € (7 )

3br Uchicago Medical Midway Museums Large Comfy %S

apartment - Chicago
This three-bedroom flat is situated in the West Woodlawn area of Hyde Park, Chicago, close to the University of Chicago Medical Centre, Midway Airport, and museums such as the DuSable Museum of African American History and the Museum of Science and Industry.
Offering queen-size beds, a fully equipped kitchen, high-speed internet (400 Mbps), and parking, this first-floor apartment sleeps six and includes the unique option of a paint-removal workshop.
Prime Downtown 2br With Resort Amenities - Chicago, IL
9.8 366 reviews
Chicago, IL
5 2
981 €/nighttotal: 2943 € (3 )

Prime Downtown 2br With Resort Amenities

apartment - Chicago
This apartment is situated in Chicago's Financial District, a short walk from Millennium Park and the Chicago River, placing you in the heart of the city's bustling energy. The apartment enjoys excellent ratings for user experience, location, and cleanliness, ensuring a comfortable and enjoyable stay.
The apartment spans 115 square metres and features a stylish interior with high-end finishes. You'll have access to a range of amenities including a swimming pool, fitness centre, and a garden, making it easy to relax and enjoy your time in the city.
Charming Andersonville Garden 1 Bdrm W/parking. - Chicago, IL
9.8 292 reviews
Chicago, IL
2 1
156 €/nighttotal: 312 € (2 )

Charming Andersonville Garden 1 Bdrm W/parking.

apartment - Chicago
This one-bedroom Chicago apartment is located in the Edgewater/Andersonville neighbourhood, offering easy access to Lake Michigan and its attractions.
The 65-square-metre flat features a fully equipped kitchen, a comfortable living area with a smart TV, and accommodates up to three guests, with on-site laundry facilities and assigned parking.
Mccormick Place Luxurious And Spacious 3br In Downtown Chicago With Optional Parking Sleeps 10 Guests - Chicago, IL
9.6 113 reviews
Chicago, IL
2 3
299 €/nighttotal: 897 € (3 )

Mccormick Place Luxurious And Spacious 3br In Downtown Chicago With Optional Parking Sleeps 10 Guests

apartment - Chicago
This three-bedroom flat is situated in Downtown Chicago, just a short distance from renowned attractions like the Field Museum and the Art Institute of Chicago. The accommodation has received excellent reviews for its location, cleanliness, and overall experience.
The property comfortably sleeps eight guests and features a fully equipped kitchen with a dishwasher and oven. Guests can enjoy a range of amenities, including a fitness centre, a terrace, and on-site parking.
3br/2ba Dual-level W/ King Bed, Tvs & Washer/dryer - Chicago, IL
9.9 67 reviews
Chicago, IL
4 3
443 €/nighttotal: 3101 € (7 )

3br/2ba Dual-level W/ King Bed, Tvs & Washer/dryer

apartment - Chicago
This spacious Jefferson Park duplex apartment, situated in a convenient middle neighbourhood approximately 24km from O'Hare International Airport, Chicago Premium Outlets, and Allstate Arena, offers easy access to public transport via the Jefferson Park Transit Centre.
The three-bedroom, two-bathroom property sleeps six guests and boasts two living areas, a fully equipped kitchen with dishwasher, a private backyard, high-speed Wi-Fi, and a wet bar; laundry facilities are shared.
Entire Below Level Studio W/ Private Sauna - Chicago, IL
10 87 reviews
Chicago, IL
2 1
361 €/nighttotal: 1083 € (3 )

Entire Below Level Studio W/ Private Sauna

studio - Chicago
This West Town studio apartment is ideally located near Logan Square, Bucktown, and Wicker Park, offering easy access to the Blue Line (a 1.9km walk) for quick travel to the city centre and O'Hare International Airport.
The self-contained apartment, sleeping up to three guests, boasts a private sauna and jacuzzi, a full kitchen, Chromecast, and secure parking, all within easy reach of the 606 trail and Divvy bike stations.
2 Bedroom In Wrigleyville With 2 Garage Spots - Chicago, IL
9.8 64 reviews
Chicago, IL
5 2
415 €/nighttotal: 1245 € (3 )

2 Bedroom In Wrigleyville With 2 Garage Spots

apartment - Chicago
This Wrigleyville/Lakeview flat is minutes from Wrigley Field and a short public transport journey from Lake Michigan.
The two-bedroom, one-bathroom apartment sleeps six, features a newly renovated kitchen and bathroom, in-unit laundry, and is conveniently located near the Brown Line for easy access to the rest of Chicago.
Cozy 2br Near Uchicago, Msi & Obama Center - Chicago, IL
10 4 reviews
Chicago, IL
3 2
227 €/nighttotal: 681 € (3 )

Cozy 2br Near Uchicago, Msi & Obama Center

apartment - Chicago
This 2-bedroom garden flat is located in Chicago's historic Woodlawn district, offering convenient access to the University of Chicago (1.6 kilometres away), UChicago Medicine, the Museum of Science and Industry, and the Obama Presidential Center.
This property accommodates up to four guests and features air conditioning, private parking, a garden, and a kitchen equipped with a fridge, freezer, and microwave, with a grocery store just a 4-minute walk away.
Humbolt Park 2 Bed 2 Bath With 2 Car Garage! - Chicago, IL
10 3 reviews
Chicago, IL
2 2
98 €/nighttotal: 6860 € (70 )

Humbolt Park 2 Bed 2 Bath With 2 Car Garage!

apartment - Chicago
This brand new, spacious flat in Chicago's West Loop offers convenient access to the city centre, being a 16-minute drive from the Chicago Loop and 18 minutes from Millennium Park, with Humbolt Park Health just 7 minutes away by car.
This two-bedroom, two-bathroom apartment accommodates up to four guests and features modern amenities including a fully equipped kitchen with a dishwasher, air conditioning, private garage access, and a workstation.
Toca Bella ~ 7mins To Downtown - Chicago, IL
10 32 reviews
Chicago, IL
2 1
149 €/nighttotal: 1043 € (7 )

Toca Bella ~ 7mins To Downtown

apartment - Chicago
This Bronzeville apartment offers a lakeside location in Chicago, a seven-minute (approximately 4.5 km) drive from downtown attractions including McCormick Place.
The 70 square metre flat comprises one bedroom, one bathroom, and accommodates four guests, featuring a modern kitchen, high-speed internet, and smart TVs.

Best family friendly Chicago, IL holiday rentals

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

Stylish & Spacious Wicker Park Airbnb! - Chicago, IL
9.9 162 reviews
Chicago, IL
3 3
307 €/nighttotal: 1228 € (4 )

Stylish & Spacious Wicker Park Airbnb!

apartment - Chicago
This three-bedroom Chicago apartment is situated on a quiet street in the Wicker Park neighbourhood, within easy walking distance of the area's restaurants, boutiques, and art galleries.
The first-floor flat offers a spacious layout sleeping up to five guests, boasting a fully equipped kitchen, family-friendly amenities (including a Pack 'N Play and high chairs), free on-street parking, and Roku TV with Wi-Fi.
Two-story Stunner In Iconic Old Town Chicago By Allset Turnover - Chicago, IL
9.6 146 reviews
Chicago, IL
5 3
699 €/nighttotal: 2097 € (3 )

Two-story Stunner In Iconic Old Town Chicago By Allset Turnover

apartment - Chicago
This Old Town Chicago condo is located blocks from the North and Wells intersection, offering easy access to the Second City comedy club and other attractions in the area.
The three-bedroom, three-bathroom property sleeps eight guests and features a fully equipped chef's kitchen, a living room, a dedicated workspace, and a terrace/balcony plus garden; street parking is available or can be pre-booked via apps such as SpotHero or ParkWhiz.
Little Italy 4br Retreat With Optional Parking - Chicago, IL
Chicago, IL
8 4
990 €/nighttotal: 1980 € (2 )

Little Italy 4br Retreat With Optional Parking

apartment - Chicago
This four-bedroom flat is located in Chicago's Little Italy district, 13.97 kilometres from Midway International Airport.
This spacious accommodation offers a fully equipped kitchen, air conditioning, free WiFi, a private balcony and terrace, and on-site paid parking, comfortably accommodating up to 23 guests.
Woodlawn Oasis...10 Minutes To Dining & Downtown - Chicago, IL
9.6 160 reviews
Chicago, IL
5 3
601 €/nighttotal: 1803 € (3 )

Woodlawn Oasis...10 Minutes To Dining & Downtown

apartment - Chicago
This spacious three-bedroom house is ideally located near the University of Chicago and a beach, approximately 8-24 km from Hyde Park, downtown Chicago, and Soldier Field.
The property boasts a basement entertainment area with a pool table and table tennis, a large private garden with BBQ facilities, and sleeps up to 12 guests, offering a fully equipped kitchen and numerous modern amenities.

Best Chicago, IL holiday rentals with parking

Quiet 1 Bedroom 1 Free Parking High Speed Wi-fi - Chicago, IL
8.5 4 reviews
Chicago, IL
2 1
471 €/nighttotal: 2355 € (5 )

Quiet 1 Bedroom 1 Free Parking High Speed Wi-fi

apartment - Chicago
This Chicago flat is located 1.76 kilometres from Fullerton Beach and Wrigley Field, and 2.74 kilometres from Lincoln Park Zoo.
This 46 square metre abode offers a fully equipped kitchen with a dishwasher and oven, air conditioning, complimentary on-site parking, free high-speed Wi-Fi, and casino access for up to three guests.
W2 - ️ New And Clean! Big Apartment With Parking - Chicago, IL
9.9 591 reviews
Chicago, IL
1 2
377 €/nighttotal: 3393 € (9 )

W2 - ️ New And Clean! Big Apartment With Parking

apartment - Chicago
This apartment is located in Chicago, just a short walk from Montrose Beach and a few miles from Wrigley Field, Loyola University Chicago, and Lincoln Park Zoo, offering easy access to some of the city's most popular attractions. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
The apartment has three bedrooms and three living areas, making it perfect for large groups. It comes with a fully equipped kitchen, free Wi-Fi, air conditioning, parking, and towels and bed linen are provided.
Sunny Jumbo Studio In The Heart Of Oak Park - Chicago, IL
9.7 722 reviews
Chicago, IL
1 1
199 €/nightfor 1 night

Sunny Jumbo Studio In The Heart Of Oak Park

studio - Oak Park
This charming studio apartment is situated in Oak Park, just a short walk from the train station, the Hemingway Home, and Frank Lloyd Wright Studio, making it ideal for exploring the area's cultural attractions. It boasts excellent ratings for location, cleanliness, and user experience.
The spacious studio apartment can comfortably accommodate up to three guests and features a king-sized bed, a day bed, a well-equipped kitchen, and a modern bathroom with a walk-in shower. Guests can enjoy a sunny terrace, a private garden, and free parking, making this a comfortable and convenient base for exploring Oak Park.
Small And Cozy 2br Apartment Pilsen Nocleaning Fee - Chicago, IL
9.6 134 reviews
Chicago, IL
2 2
116 €/nighttotal: 580 € (5 )

Small And Cozy 2br Apartment Pilsen Nocleaning Fee

apartment - Chicago
This Chicago flat is situated in the Pilsen neighbourhood, offering easy access to the area's cultural attractions, though precise distances aren't specified.
The recently renovated two-bedroom apartment sleeps four comfortably, featuring a king-size and a queen-size bed, plus additional sleeping arrangements; amenities include a fridge, microwave, air conditioning, private patio access, parking, and a shared garden.

Frequently asked questions about holiday rentals in Chicago, IL

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

    You can't go wrong with a visit to Millennium Park, where you'll find the iconic Cloud Gate sculpture, affectionately known as 'The Bean'. A trip to Navy Pier is a must, with its Ferris wheel, shops, and restaurants. And no trip to Chicago is complete without a deep-dish pizza experience.
  • 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 and central location, consider staying in the River North neighbourhood. It's close to the Magnificent Mile, the Chicago River, and many restaurants and bars. If you prefer a more residential and quiet vibe, Lincoln Park is a great option, with its beautiful park and proximity to the zoo.
  • 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, popular with families, and the Shedd Aquarium is a great option for marine life enthusiasts. The Field Museum is also a favourite, with its dinosaur exhibits and other natural history displays.
  • 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?

    Booking your vacation rental in advance is always a good idea, especially during peak season, which runs from May to September. If you're looking for a more affordable option, consider visiting during the shoulder seasons, April-May and September-October, when the weather is still pleasant.
  • 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 events scene. The Taste of Chicago, a massive food festival, takes place in July. The Chicago Blues Festival in June is a popular event, and the Lollapalooza music festival in August attracts crowds from all over.
  • 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?

    Chicago has many free and affordable activities. A stroll along the Lakefront Trail offers stunning views. You can enjoy free concerts at Millennium Park's Pritzker Pavilion. And exploring the many diverse neighbourhoods is a great way to experience the city's character.
  • What are the best restaurants with local dishes in Chicago, IL?

    Chicago is a foodie's paradise. For a classic deep-dish pizza experience, Lou Malnati's is a must-try. For authentic Italian, try Tufano's Vernon Park Tap. And for a taste of Chicago's Polish heritage, visit Smak Tak.
  • 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 transformed into a park, is a great option for a more urban cycling experience.
  • Are there pet-friendly attractions in Chicago, IL?

    Chicago is a pet-friendly city. The Lincoln Park Zoo welcomes well-behaved dogs on leash. Many parks, such as Millennium Park, have designated areas for dogs. And many restaurants 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 offer more space and privacy compared to hotels. They often come with amenities like kitchens, which allow you to prepare your own meals and save money. And they can be a great option for families or groups travelling together.

Popular destinations

Best Chicago, IL holiday rentals with a balcony

Flexhome Ukrainian Village • 2br • Walkable + Private Balcony · Sleeps 6 - Chicago, IL
8.1 32 reviews
Chicago, IL
2 2
186 €/nighttotal: 930 € (5 )

Flexhome Ukrainian Village • 2br • Walkable + Private Balcony · Sleeps 6

apartment - Chicago
Flexhome Ukrainian Village 2BR D2 is situated in Chicago's Ukrainian Village neighbourhood, 2.1km from the United Centre and 4.5km from Water Tower Place.
This two-bedroom apartment, offering 55 square metres of space, sleeps nine guests and includes a fully equipped kitchen with dishwasher, in-unit laundry, air conditioning, a balcony, and free Wi-Fi.
Flexhome Ukrainian Village  2br  Walkable + Private Balcony · Sleeps 6 - Chicago, IL
8.8 14 reviews
Chicago, IL
5 2
500 €/nighttotal: 1500 € (3 )

Flexhome Ukrainian Village 2br Walkable + Private Balcony · Sleeps 6

apartment - Chicago
This West Town apartment in Chicago offers convenient access to numerous parks, restaurants, and bars, with major attractions within easy reach.
The 55-square-metre (592-square-foot) flat features two queen-size beds, a sofa, one bathroom, in-unit laundry, and sleeps up to five guests, boasting a dedicated workspace and a smart TV with AirPlay.
Chic 1-bedroom Apartment,15mims From Downtown - Chicago, IL
9.6 8 reviews
Chicago, IL
2 1
170 €/nighttotal: 680 € (4 )

Chic 1-bedroom Apartment,15mims From Downtown

apartment - Chicago
This one-bedroom flat is located in Chicago's Bronzeville district, offering proximity to Lake Michigan and Grant Park, with Willis Tower and Merchandise Mart also accessible within a few kilometres.
This accommodation provides a queen bed, a fully equipped bathroom, and essential amenities such as an iron and hair dryer, suitable for up to two guests for short or long stays.
Experience Chicago Living Near United Center - Chicago, IL
9.0 42 reviews
Chicago, IL
2 3
203 €/nighttotal: 1015 € (5 )

Experience Chicago Living Near United Center

apartment - Chicago
This two-bedroom flat is situated in the Austin neighbourhood, about 10 miles west of downtown Chicago, offering a more residential atmosphere than the bustling city centre. It has received excellent user ratings, making it a popular choice for travellers.
The flat is suitable for up to five guests, with two bedrooms and a bathroom, plus a sunroom and a living room with three large sofas. The kitchen features modern appliances, including a fridge, microwave, and dishwasher, and there is also air conditioning, internet, and a swimming pool.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday rentals with air conditioning

Livn Millennium Park Downtown Chicago 2br - Chicago, IL
8.9 29 reviews
Chicago, IL
4 1
900 €/nighttotal: 6300 € (7 )

Livn Millennium Park Downtown Chicago 2br

apartment - Chicago
This two-bedroom flat is located in downtown Chicago, a six-minute walk from Millennium Station and 550 metres from DePaul University, placing it 800 metres from the city centre and 2.2 kilometres from Ohio Street Beach.
This apartment offers 51 square metres of living space, accommodating up to five guests with a fully equipped kitchen including a fridge, microwave, and dishwasher, alongside free Wi-Fi and air conditioning.
Private Balcony, Parking, 5 Min To Uc - Chicago, IL
9.9 154 reviews
Chicago, IL
6 2
607 €/nighttotal: 2428 € (4 )

Private Balcony, Parking, 5 Min To Uc

apartment - Chicago
This spacious Chicago apartment, ideal for families, is centrally located, offering easy access to both the United Centre and McCormick Place, convenient for event attendees.
The 167 square metre property boasts two bedrooms, two bathrooms, sleeps six to eight guests, and features a chef's kitchen, private balcony with city views, in-unit laundry, and secure parking with EV charging.
Guest Favorite Getaway | Lakeview | Near Wrigley - Chicago, IL
9.7 174 reviews
Chicago, IL
2 1
296 €/nighttotal: 1184 € (4 )

Guest Favorite Getaway | Lakeview | Near Wrigley

apartment - Chicago
This Chicago apartment rental is situated in Wrigleyville, a 1.9km walk or a short drive from Wrigley Field and the Wrigleyville Christkindlmarket.
The one-bedroom, one-bathroom flat sleeps two guests, offering a fully furnished interior with a full kitchen, Wi-Fi, and access to a paid laundry room within the building.
2mi To Obama Center - Pet-friendly Near Uoc! - Chicago, IL
9.6 4 reviews
Chicago, IL
2 2
280 €/nighttotal: 1400 € (5 )

2mi To Obama Center - Pet-friendly Near Uoc!

apartment - Chicago
This Woodlawn, Chicago flat is situated near Lake Michigan and Grant Park, approximately 3.2km from the Museum of Science and Industry and 4.8km from the Obama Presidential Center.
The 74 square metre ground-floor apartment sleeps four, offering two bedrooms, one bathroom, a private fenced yard, parking, and amenities including a Smart TV, workspace, washer/dryer, and complimentary toiletries.
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