Best Vacation rentals and Airbnb offers in Chicago, IL
9.5 169 reviews
Chicago, IL
10/07 – 14/07
1815 ﺩ.ﺇ/nighttotal: 7260 ﺩ.ﺇ (4 )
Pilsen Haven Near Downtown & Tranit
1 4
apartment , Chicago
This three-bedroom, three-bathroom Chicago apartment, perfect for groups of up to eight, boasts a prime location offering easy access to the city's attractions; precise proximity to specific landmarks isn't specified but the description suggests a neighbourhood with a unique urban feel. The self-catering flat features a modern kitchen, spacious open-plan living area with a fold-out sofa bed, dedicated workspace, and high ceilings; private entrance, parking, and excellent guest reviews complete this comfortable Chicago dwelling.
9.3 212 reviews
Chicago, IL
03/08 – 11/08
641 ﺩ.ﺇ/nighttotal: 5128 ﺩ.ﺇ (8 )
Vibrant Studio Close To Andersonville And Train
1 2
apartment , Chicago
This Chicago studio flat offers excellent location near numerous shops, cafes, and restaurants, with its precise location unspecified but within walking distance of various dining and entertainment options. Sleeping up to four guests, this self-catering apartment boasts a well-equipped kitchenette including a dishwasher, microwave, and Kuerig coffee maker, a queen bed and queen-size sofa bed, on-site laundry, and essential toiletries; smart TV and Wi-Fi are also provided.
10 1 review
Chicago, IL
27/06 – 04/07
653 ﺩ.ﺇ/nighttotal: 4571 ﺩ.ﺇ (7 )
Cozy Urban Retreat Near Midway Perfect For Travelers!
1 2
apartment , Chicago
This Chicago Lawn flat, situated in Gage Park, is approximately 48 kilometres from Chicago city centre and Midway International Airport. The one-bedroom apartment, sleeping up to four guests, features a kitchen-diner, air conditioning, internet access, and is ideally located for exploring the Museum of Science and Industry, Field Museum, and McCormick Place.
9.3 8 reviews
Chicago, IL
27/06 – 04/07
579 ﺩ.ﺇ/nighttotal: 4053 ﺩ.ﺇ (7 )
New Private Apt- Pilsen Downtown
1 2
apartment , Chicago
This East Pilsen flat offers convenient access to Chicago's city centre, Soldier Field, Grant Park, and the United Centre, with public transport links including Metra, the 'L' train, and Greyhound readily available. The newly remodelled one-bedroom apartment sleeps four guests, featuring a fully equipped kitchen, keypad entry, and a blend of vintage and modern design elements including sealed rust print floors and quartz countertops, perfect for exploring Chicago's attractions.
10 340 reviews
Chicago, IL
20/08 – 25/08
1162 ﺩ.ﺇ/nighttotal: 5810 ﺩ.ﺇ (5 )
A Stylish, Sundrenched Chicago Ravenswood Flat
1 4
apartment , Chicago
The Orange Cat Flat is a three-bedroom apartment situated in Chicago's Ravenswood neighbourhood, above Bad Johnny's tavern and conveniently located for exploring the city's diverse offerings. This two-floor dwelling sleeps six guests and boasts a fully equipped kitchen (fridge, freezer, microwave, dishwasher), air conditioning, a garden, parking, and unique features such as designer wallpaper and locally crafted ceramics.
9.8 24 reviews
Chicago, IL
21/07 – 23/07
782 ﺩ.ﺇ/nighttotal: 1564 ﺩ.ﺇ (2 )
Springfield Serenity
2 5
apartment , Chicago
Springfield Serenity, a two-bedroom flat in Chicago, is situated in a district offering a peaceful retreat, with convenient access to local attractions. This accommodation for up to five guests features a meditation corner, an entertainment room with Pac-Man, self-check-in, and complimentary street parking, all within a stylish interior of green-blue and gold tones.
9.5 2 reviews
Chicago, IL
24/07 – 27/07
2176 ﺩ.ﺇ/nighttotal: 6528 ﺩ.ﺇ (3 )
Modern And Bright 2br On Michigan Ave With Optional Parking And Gym Access Near Soldier Field & Grant Park
2 8
apartment , Chicago
This family-friendly Chicago apartment, situated approximately 2.4 kilometres from the Field Museum and within 3.2 kilometres of the Art Institute of Chicago and the Chicago Symphony Orchestra, offers convenient access to major cultural attractions. The 84-square-metre property features a spacious two-bedroom, two-bathroom layout sleeping up to eight guests, complete with a fully equipped kitchen, complimentary Wi-Fi, private parking, and a patio offering city views; a fitness centre is optionally available.
9.8 9 reviews
Chicago, IL
25/06 – 26/06
1107 ﺩ.ﺇ/nightfor 1 night
Ideal 1-bedroom Stay
1 2
apartment , Chicago
This Lakeview flat in Chicago offers a convenient location, close to cultural attractions such as the Art Institute of Chicago and the Chicago Theatre, though precise distances aren't specified. The one-bedroom apartment sleeps two guests and includes a fully equipped kitchen with a fridge and microwave, air conditioning, and Wi-Fi; nearby activities and venues like McCormick Place and Wintrust Arena are easily accessible.
9.5 249 reviews
Chicago, IL
22/07 – 23/07
2255 ﺩ.ﺇ/nightfor 1 night
Entire House W/ King Bed & Garage Parking For 2!
3 8
house , Forest Park
This charming house is located in Forest Park, just 1.6km from Madison Street, a bustling area with shops, restaurants, and bars, and a 3-block walk from the CTA Blue Line "L" station, providing easy access to downtown Chicago. The property has received excellent ratings for its location, cleanliness, and overall user experience. The house features three bedrooms and one bathroom. Amenities include a fully equipped kitchen, air conditioning, parking, a fenced backyard, a washer and dryer, and flexible check-in/check-out options.
9.7 185 reviews
Chicago, IL
13/07 – 15/07
538 ﺩ.ﺇ/nighttotal: 1076 ﺩ.ﺇ (2 )
Funky & Newly Remodeled 1 Bed In Hip Logan Square
1 2
apartment , Chicago
This Logan Square flat is conveniently located within walking distance of popular restaurants such as Sugarmoon and Lou Malnati's Pizzeria, and is also close to the 606 Trail. The one-bedroom basement apartment, sleeping up to four guests, offers a well-equipped galley kitchen, Netflix and Amazon Prime access, and keyless entry; free on-street parking is also readily available nearby.
9.7 38 reviews
Chicago, IL
11/07 – 15/07
630 ﺩ.ﺇ/nighttotal: 2520 ﺩ.ﺇ (4 )
Nola Bochic-cozy 2 Br, 1 Bath Apartment. Fl 2
1 3
apartment , Chicago
This Chicago apartment, ideally located within 8km of Chinatown, the United Centre, and Midway Airport, offers easy access to the I-290 and I-55 expressways. The two-bedroom, one-bathroom flat sleeps six guests and boasts a well-equipped kitchen with stainless steel appliances, a jacuzzi bath, 55-inch Roku TV, free Wi-Fi, and access to a shared patio with BBQ.
9.5 645 reviews
Chicago, IL
24/08 – 26/08
672 ﺩ.ﺇ/nighttotal: 1344 ﺩ.ﺇ (2 )
Cozy 2 Bedroom In Heart Of Lakeview
1 3
apartment , Chicago
This Lakeview apartment offers convenient access to Wrigley Field and other attractions such as Schuba's Tavern and the Music Box Theatre, all within easy walking distance. The two-bedroom flat sleeps four guests and includes a kitchen with fridge, microwave, and dishwasher, plus a private patio with grill (seasonal), parking permits (Zone 383), and 24/7 self check-in.
Best family friendly Chicago, IL vacation rentals
Among the 10119 accommodations in Chicago, IL, here are the 4 best family friendly rentals
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.
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.
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.
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
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.
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.
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.
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?
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.
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?
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?
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
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.
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.
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.
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
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.
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.
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.
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.