The 30 best holiday rentals in Chicago
based on 5,764 holiday rental reviews on Booking.com
Guests' Choice
1F Cozy Home in Little Italy near Downtown West Loop United Center
#1 of 137 Holiday rentals in Chicago
Last review posted: 12 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
Chicago Charm
#2 of 137 Holiday rentals in Chicago
Last review posted: 36 days ago
“Excellent Chicago Choice”
“Harika”
“Perfect townhome in the lakeshore community area of Chicago. Convenient to everything!”
See more reviews of Chicago Charm
Wrigley Oasis! Steps from the Field! - 3BD 1BA
#3 of 137 Holiday rentals in Chicago
Last review posted: 8 days ago
“Loved it! Will definitely stay again!”
“This was the perfect place to relax after a long day exploring Chicago.”
“Great option for multiple guests very close to Wrigley Field.”
See more reviews of Wrigley Oasis! Steps from the Field! - 3BD 1BA
2F Chicago's Little Italy near West Loop & Downtown
#4 of 137 Holiday rentals in Chicago
Last review posted: 2 days ago
“We’ll be back! Excellent.”
“Great place - would come again!”
“Fantastic place to stay. 100% satisfied”
See more reviews of 2F Chicago's Little Italy near West Loop & Downtown
The Avondale Guesthouse
#5 of 137 Holiday rentals in Chicago
Last review posted: 3 days ago
“Very cozy place and a nice neighborhood.”
“The space was perfect for our group.”
“property managers were very nice and willing to accomodate our soecial request to enter property earlier than check in t”
See more reviews of The Avondale Guesthouse
Forrestville Ave Large Suite
#6 of 137 Holiday rentals in Chicago
Last review posted: 13 days ago
“Lovely and peaceful location”
“The host was very nice, the rooms were cleanly and the area...”
“Great Stay!”
See more reviews of Forrestville Ave Large Suite
Northside FAMLYNEST Lincoln Sq 4BR 2BA 2P Rare find
#7 of 137 Holiday rentals in Chicago
Last review posted: 8 days ago
“An all-around great experience from the host, to the house, to the neighborhood.”
“very good experience”
“Amazing Stay”
See more reviews of Northside FAMLYNEST Lincoln Sq 4BR 2BA 2P Rare find
The Penthouse at Grand Plaza
#8 of 137 Holiday rentals in Chicago
Last review posted: 19 days ago
“Very nice appartment with a incredible view of Chicago and...”
“They required a manually printed sheet to check in which was...”
“The view is amazing and the fireplace”
See more reviews of The Penthouse at Grand Plaza
Trendy West Town Flat - 2 bed / 1.5 bath w parking
#9 of 137 Holiday rentals in Chicago
Last review posted: 236 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
Sentral Michigan Avenue
#10 of 137 Holiday rentals in Chicago
Last review posted: 2 days ago
“Amenities are amazing, location is perfect, nice looking...”
“The furniture was lower quality”
“Unfriendly employees”
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2 Bed Apt w/ Office, Free Parking, Near Wrigley
#11 of 137 Holiday rentals in Chicago
Last review posted: 3 days ago
“Comfortable and modern apartment, great location”
“10 star apartment”
“Great and nice apartment in Chicago”
See more reviews of 2 Bed Apt w/ Office, Free Parking, Near Wrigley
Kasa South Loop Chicago
#12 of 137 Holiday rentals in Chicago
Last review posted: 3 days ago
“Location was great - easy walk from Blue Line train from...”
“Convenient and relaxing. A Great place to see Chicago, recharge your batteries, do some laundry.”
“A wonderful experience with a few hiccups.”
See more reviews of Kasa South Loop Chicago
Perfect place to enjoy the city or just relax
#13 of 137 Holiday rentals in Chicago
Last review posted: 4 days ago
“Very nice, would book again!”
“Comfortable and safe”
“Everything was great, I have no problems with the property”
See more reviews of Perfect place to enjoy the city or just relax
Sonder The Opal
#14 of 137 Holiday rentals in Chicago
Last review posted: 5 days ago
“Mixed feelings stay”
“Great location with nice amenities”
“It was good. Could have been better.”
See more reviews of Sonder The Opal
The Blue Golden Luxury Modern 3- Bedroom Apartment in Chicago
#15 of 137 Holiday rentals in Chicago
Last review posted: 19 days ago
“Beautiful, quiet apartment with easy access to Downtown.”
“Great location, went to a Cubs game.”
“The host was very helpful and communicative and the space was well kept and accommodating.”
See more reviews of The Blue Golden Luxury Modern 3- Bedroom Apartment in Chicago
Luxéry Stay Chicago - Across from McCormick Place & Wintrust Arena
#16 of 137 Holiday rentals in Chicago
Last review posted: 10 days ago
“Great location!”
“The unit was clean, well-decorated, convenient, and perfectly peaceful.”
“Not recommended”
See more reviews of Luxéry Stay Chicago - Across from McCormick Place & Wintrust Arena
✪ Cozy 1 Bedroom close to Downtown Chicago ✪
#17 of 137 Holiday rentals in Chicago
Last review posted: 14 days ago
“Little comfy”
“Really nice & cozy appartement, top Location and a...”
“We absolutely loved the location.”
See more reviews of ✪ Cozy 1 Bedroom close to Downtown Chicago ✪
Adorable 2 bedroom with free street parking
#18 of 137 Holiday rentals in Chicago
Last review posted: 6 days ago
ENVITAE 3BR Luxury Corner Loft with Navy Pier Views
#19 of 137 Holiday rentals in Chicago
Last review posted: 58 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
1549 North Maplewood Avenue
#20 of 137 Holiday rentals in Chicago
Last review posted: 15 days ago
“Perfect Humbolt Park Getaway”
“Nothing much to say abt the stay except that what you need is available ; if you don’t mind the experience or feeling of”
“The building is not new, but a very clean and well-kept...”
See more reviews of 1549 North Maplewood Avenue
Lincoln Park Aparment with Backyard!
#21 of 137 Holiday rentals in Chicago
Last review posted: 4 days ago
“Very nice to deal with.”
“We loved Chicago.”
“Very pleased with the location and professionalism”
See more reviews of Lincoln Park Aparment with Backyard!
Spacious 5-BR Apt next to transit Free Parking
#22 of 137 Holiday rentals in Chicago
Last review posted: 7 days ago
“Amazing experience! Will definitely rent from again!”
“Very communicative and site in quiet neighborhood”
“This was probably the best stay I had!”
See more reviews of Spacious 5-BR Apt next to transit Free Parking
Sonder South Wabash
#23 of 137 Holiday rentals in Chicago
Last review posted: 4 days ago
“Modern small studio apartment.”
“It is a very nice and well equipped flat perfect for a family (not to share with work colleagues)”
“Good but could be better”
See more reviews of Sonder South Wabash
Cozy Studio near Wrigley field and Boystown
#24 of 137 Holiday rentals in Chicago
Last review posted: 29 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
#25 of 137 Holiday rentals in Chicago
Last review posted: 4 days ago
“Please ensure that the door code works for the next stay and check your amenities to make sure things are working proper”
“Great apartment!”
“Ideal location for Chicago marathon 20 minutes to downtown.”
See more reviews of Cozy 1 bedroom, 1 min from Irving Park Blue line, free parking
The Twin Lions: Bespoke Travel Lodge w/ Speakeasy*
#26 of 137 Holiday rentals in Chicago
Last review posted: 37 days ago
“Good choice!”
“We had a really fun weekend here!”
“Very well furnished and had absolutely everything you need...”
The Twin Lions: Bespoke Travel Lodge w/ Speakeasy* has been reviewed 7 times. Some users didn't leave a comment, while other reviews are written in English (US) or 繁體中文 .
Sonder Market Hall
#27 of 137 Holiday rentals in Chicago
Last review posted: 14 days ago
“Fast, pain free check in process! Clean and super cute rooms!”
“Noisy if you have the wrong neighbours 😳”
“I would use Sonder again here or in other locations.”
See more reviews of Sonder Market Hall
The Double Play, Wrigley Flats - Cubs! - Located Right next to Wrigley and Transit
#28 of 137 Holiday rentals in Chicago
Last review posted: 2 days ago
“Very convenient, clean, and comfortable”
“It was horrible.”
“Loved it very easy instructions and was well explained...”
See more reviews of The Double Play, Wrigley Flats - Cubs! - Located Right next to Wrigley and Transit
Superior
#29 of 137 Holiday rentals in Chicago
Last review posted: 8 days ago
“Great amenities, Great location, great host. Perfect”
“A good experience.”
“Home away from home”
See more reviews of Superior
Ethan 3 rooms
#30 of 137 Holiday rentals in Chicago
Last review posted: 11 days ago
“Clean house and close to Downtown”
“Everything was pretty good.”
“Amazing spot will stay again 10/10”
See more reviews of Ethan 3 rooms
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