The 30 Best Vacation Rentals in Chicago
based on 5,909 vacation rental reviews on Booking.com
Guests' Choice
1F Cozy Home in Little Italy near Downtown West Loop United Center
#1 of 175 vacation rentals in Chicago
Last review posted 46 days ago
“Great property and well worth the value, so much room and...”
“I love this place! Great location, friendly hosts, lovely decor, and a dedicated parking spot. 10/10”
“The best reasonable mansion near Chicago downton”
See more reviews of 1F Cozy Home in Little Italy near Downtown West Loop United Center
Wrigley Oasis! Steps from the Field! - 3BD 1BA
#2 of 175 vacation rentals in Chicago
Last review posted 16 days ago
“Great option for multiple guests very close to Wrigley Field.”
“Great location.”
“Very attentive hosts.”
See more reviews of Wrigley Oasis! Steps from the Field! - 3BD 1BA
Chicago Charm
#3 of 175 vacation rentals in Chicago
Last review posted 6 days ago
“Harika”
“Perfect townhome in the lakeshore community area of Chicago. Convenient to everything!”
“My family stayed for the week of Christmas. The apartment was filled with items that were very useful to make our stay e”
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2F Chicago's Little Italy near West Loop & Downtown
#4 of 175 vacation rentals in Chicago
Last review posted 2 days ago
“I highly recommend this place for a tourist visit to Chicago”
“The host's behavior was extremely disappointing.”
“Superb accommodation.”
See more reviews of 2F Chicago's Little Italy near West Loop & Downtown
The Avondale Guesthouse
#5 of 175 vacation rentals in Chicago
Last review posted 6 days ago
“Very quiet and comfortable. Loved the decor! Comfortable beds.”
“It was perfect for our family.”
“Excellent space for a family with a dog, great location!”
See more reviews of The Avondale Guesthouse
Forrestville Ave Large Suite
#6 of 175 vacation rentals in Chicago
Last review posted 13 days ago
“A quiet, clean, comfortable stay!”
“Heart of Bronzeville”
“Amazing experience. Would like to introduce to anyone that would want to visit Chicago.”
See more reviews of Forrestville Ave Large Suite
The Penthouse at Grand Plaza
#7 of 175 vacation rentals in Chicago
Last review posted 44 days ago
“The view is amazing and the fireplace”
“Excellent place to stay when visiting Chicago.”
“A high scale apartment in the best location with best views”
See more reviews of The Penthouse at Grand Plaza
Northside FAMLYNEST Lincoln Sq 4BR 2BA 2P Rare find
#8 of 175 vacation rentals in Chicago
Last review posted 24 days ago
“Again it was a delight! I would recommend this property to anyone looking for a nice comfortable reasonable place to sta”
“Ivan kept great communication with us during our whole stay and always made sure we had everything we needed. Wonderful!”
“This unit was clean and in a safe quiet neighborhood. Although we had our own vehicle, the metro was very close. Good ch”
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Perfect place to enjoy the city or just relax
#9 of 175 vacation rentals in Chicago
Last review posted 19 days ago
“Pretty apartment”
“Almost a perfect place!”
“Clean & nice inside. Maybe check Google street view if concerned about the area.”
See more reviews of Perfect place to enjoy the city or just relax
Sentral Michigan Avenue
#10 of 175 vacation rentals in Chicago
Last review posted yesterday
“I love this hotel, it was in a great area, perfect views, and nice amenities.”
“My stay was pleasant, I will be returning.”
“A superb Apartment right in the heart of Downtown”
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Trendy West Town Flat - 2 bed / 1.5 bath w parking
#11 of 175 vacation rentals in Chicago
Last review posted 189 days ago
“Had a short, but lovely, stay in the apartment.”
“Home away from home”
“As nice as advertised!”
See more reviews of Trendy West Town Flat - 2 bed / 1.5 bath w parking
Kasa South Loop Chicago
#12 of 175 vacation rentals in Chicago
Last review posted 2 days ago
“Loved Chicago”
“first time on a Kass property and will look for more”
“Great location and amazing apartment!”
See more reviews of Kasa South Loop Chicago
2 Bed Apt w/ Office, Free Parking, Near Wrigley
#13 of 175 vacation rentals in Chicago
Last review posted 8 days ago
“Great and nice apartment in Chicago”
“It was amazing stay very good in comincate very nice location”
“Perfect”
See more reviews of 2 Bed Apt w/ Office, Free Parking, Near Wrigley
Sonder The Opal
#14 of 175 vacation rentals in Chicago
Last review posted 3 days ago
“Great location.”
“Great concept with the short term rentals, location was...”
“My stay for the first time in Chicago was beyond amazing”
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Luxéry Stay Chicago - Across from McCormick Place & Wintrust Arena
#15 of 175 vacation rentals in Chicago
Last review posted 12 days ago
“Not recommended”
“Good base to explore Chicago”
“A really good option for business trip”
See more reviews of Luxéry Stay Chicago - Across from McCormick Place & Wintrust Arena
✪ Cozy 1 Bedroom close to Downtown Chicago ✪
#16 of 175 vacation rentals in Chicago
Last review posted 4 days ago
“Really nice & cozy appartement, top Location and a...”
“We absolutely loved the location.”
“Peaceful apartment great for couples”
See more reviews of ✪ Cozy 1 Bedroom close to Downtown Chicago ✪
The Blue Golden Luxury Modern 3- Bedroom Apartment in Chicago
#17 of 175 vacation rentals in Chicago
Last review posted 33 days ago
“The host was very helpful and communicative and the space was well kept and accommodating.”
“Comfortable place to enjoy touring the city from.”
“Spacious, safe location”
See more reviews of The Blue Golden Luxury Modern 3- Bedroom Apartment in Chicago
Adorable 2 bedroom with free street parking
#18 of 175 vacation rentals in Chicago
Last review posted 2 days ago
“Lovely apartment for family ,”
“Thank you for hosting my stay!”
“Nice stay”
See more reviews of Adorable 2 bedroom with free street parking
1549 North Maplewood Avenue
#19 of 175 vacation rentals in Chicago
Last review posted yesterday
“'L' Of A Time In Chicago”
“Great location with plenty of amenities for a long or short stay.”
“Short break in Chicago.”
See more reviews of 1549 North Maplewood Avenue
Sonder South Wabash
#20 of 175 vacation rentals in Chicago
Last review posted 3 days ago
“My stay was awesome.”
“A delightful stay in a calm area of Chicago, with everything you need for a short stay.”
“awesome”
See more reviews of Sonder South Wabash
Lincoln Park Aparment with Backyard!
#21 of 175 vacation rentals in Chicago
Last review posted 186 days ago
“We loved Chicago.”
“Very pleased with the location and professionalism”
“A great place to stay and free street parking. Would definitely stay here again!”
See more reviews of Lincoln Park Aparment with Backyard!
Winter Wonderland Retreat and Your Chicago Chill Getaway
#22 of 175 vacation rentals in Chicago
Last review posted 202 days ago
“Great place in a nice area. Awesome amenities and comfy.”
“The space of the place the cleanineas of the place how it...”
“I paid half the price for double the amenaties.”
See more reviews of Winter Wonderland Retreat and Your Chicago Chill Getaway
ENVITAE 3BR Luxury Corner Loft with Navy Pier Views
#23 of 175 vacation rentals in Chicago
Last review posted 11 days ago
“Location, upper floor, view”
“Service from host is excellent.”
“Stunning views, beautiful apartment”
See more reviews of ENVITAE 3BR Luxury Corner Loft with Navy Pier Views
Spacious 5-BR Apt next to transit Free Parking
#24 of 175 vacation rentals in Chicago
Last review posted 5 days ago
“Amazing experience! Will definitely rent from again!”
“Very communicative and site in quiet neighborhood”
“This was probably the best stay I had!”
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Cozy Studio near Wrigley field and Boystown
#25 of 175 vacation rentals in Chicago
Last review posted 4 days ago
“Very disappointing; I would never stay at this place again.”
“Great location, great studio”
“Good value”
See more reviews of Cozy Studio near Wrigley field and Boystown
Cozy 1 bedroom, 1 min from Irving Park Blue line, free parking
#26 of 175 vacation rentals in Chicago
Last review posted 34 days ago
“Ideal location for Chicago marathon 20 minutes to downtown.”
“It was perfect for our weekend getaway.”
“There were some minor challenges but overall worked out for my purpose.”
See more reviews of Cozy 1 bedroom, 1 min from Irving Park Blue line, free parking
The Double Play, Wrigley Flats - Cubs! - Located Right next to Wrigley and Transit
#27 of 175 vacation rentals in Chicago
Last review posted 3 days ago
“From the photos online, I was thinking we were getting the upstairs, rather than the basement apartment. But glad it was”
“Overall, a positive experience.”
“Location.”
See more reviews of The Double Play, Wrigley Flats - Cubs! - Located Right next to Wrigley and Transit
Sonder Market Hall
#28 of 175 vacation rentals in Chicago
Last review posted 4 days ago
“I liked how there was a dishwasher and washing machine.”
“Solid property with everything needed for a visit to the West Loop.”
“Great property at a great price in a solid location.”
See more reviews of Sonder Market Hall
Lincoln Park 3 BR Penthouse
#29 of 175 vacation rentals in Chicago
Last review posted 23 days ago
“Great location and cool space”
“The host was great. Comped our parking due to terribly cold weather! Easy in/out!”
“BAIT AND SWITCH. I WAS NOT GIVEN THE "PENTHOUSE" UNIT I BOOKED AND PAID FOR IN ADVANCE.”
See more reviews of Lincoln Park 3 BR Penthouse
Fully Furnished Apt Near Millenium Park- 29
#30 of 175 vacation rentals in Chicago
Last review posted 13 days ago
“This property is at a great location.”
“Location, roof top pool and patio.”
“Modern comfort in the middle of the Windy City”
See more reviews of Fully Furnished Apt Near Millenium Park- 29
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