The 30 Best Vacation Rentals in Chicago
based on 6,213 vacation rental reviews on Booking.com
Guests' Choice
1F Cozy Home in Little Italy near Downtown West Loop United Center
#1 of 185 vacation rentals in Chicago
Last review posted 24 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 185 vacation rentals in Chicago
Last review posted 13 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 185 vacation rentals in Chicago
Last review posted 16 days ago
“This was the perfect place to relax after a long day exploring Chicago.”
“Great option for multiple guests very close to Wrigley Field.”
“Great location.”
See more reviews of Wrigley Oasis! Steps from the Field! - 3BD 1BA
2F Chicago's Little Italy near West Loop & Downtown
#4 of 185 vacation rentals in Chicago
Last review posted yesterday
“Great place - would come again!”
“Fantastic place to stay. 100% satisfied”
“Perfect short stay”
See more reviews of 2F Chicago's Little Italy near West Loop & Downtown
The Avondale Guesthouse
#5 of 185 vacation rentals in Chicago
Last review posted 13 days ago
“Wonderful stay”
“The size of the apartment was large.”
“Very quiet and comfortable. Loved the decor! Comfortable beds.”
See more reviews of The Avondale Guesthouse
Forrestville Ave Large Suite
#6 of 185 vacation rentals in Chicago
Last review posted 4 days ago
“The host was very nice, the rooms were cleanly and the area...”
“Great Stay!”
“A quiet, clean, comfortable stay!”
See more reviews of Forrestville Ave Large Suite
The Penthouse at Grand Plaza
#7 of 185 vacation rentals in Chicago
Last review posted yesterday
“They required a manually printed sheet to check in which was...”
“The view is amazing and the fireplace”
“Excellent place to stay when visiting Chicago.”
See more reviews of The Penthouse at Grand Plaza
Northside FAMLYNEST Lincoln Sq 4BR 2BA 2P Rare find
#8 of 185 vacation rentals in Chicago
Last review posted 48 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”
See more reviews of Northside FAMLYNEST Lincoln Sq 4BR 2BA 2P Rare find
Perfect place to enjoy the city or just relax
#9 of 185 vacation rentals in Chicago
Last review posted 16 days ago
“I will return , excellent experience”
“Pretty apartment”
“Almost a perfect place!”
See more reviews of Perfect place to enjoy the city or just relax
Sentral Michigan Avenue
#10 of 185 vacation rentals in Chicago
Last review posted yesterday
“Overpriced for lack of attention to detail; rooms not inspected properly prior to guests arriving”
“Fantastic stay overlooking Grant Park”
“Not good”
See more reviews of Sentral Michigan Avenue
Trendy West Town Flat - 2 bed / 1.5 bath w parking
#11 of 185 vacation rentals in Chicago
Last review posted 213 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 185 vacation rentals in Chicago
Last review posted yesterday
“Good location.”
“Loved Chicago”
“first time on a Kass property and will look for more”
See more reviews of Kasa South Loop Chicago
2 Bed Apt w/ Office, Free Parking, Near Wrigley
#13 of 185 vacation rentals in Chicago
Last review posted yesterday
“10 star apartment”
“Great and nice apartment in Chicago”
“It was amazing stay very good in comincate very nice location”
See more reviews of 2 Bed Apt w/ Office, Free Parking, Near Wrigley
Sonder The Opal
#14 of 185 vacation rentals in Chicago
Last review posted yesterday
“Great location with nice amenities”
“It was good. Could have been better.”
“wonderful property at a great location, ideal for exploring...”
See more reviews of Sonder The Opal
Luxéry Stay Chicago - Across from McCormick Place & Wintrust Arena
#15 of 185 vacation rentals in Chicago
Last review posted 3 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 ✪
#16 of 185 vacation rentals in Chicago
Last review posted 28 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 185 vacation rentals in Chicago
Last review posted yesterday
“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
Adorable 2 bedroom with free street parking
#18 of 185 vacation rentals in Chicago
Last review posted 4 days ago
“Cleanliness”
“Feels just like living in the city again 😌”
“Lovely apartment for family ,”
See more reviews of Adorable 2 bedroom with free street parking
1549 North Maplewood Avenue
#19 of 185 vacation rentals in Chicago
Last review posted 3 days ago
“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...”
“'L' Of A Time In Chicago”
See more reviews of 1549 North Maplewood Avenue
Lincoln Park Aparment with Backyard!
#20 of 185 vacation rentals in Chicago
Last review posted yesterday
“Very nice to deal with.”
“We loved Chicago.”
“Very pleased with the location and professionalism”
See more reviews of Lincoln Park Aparment with Backyard!
Sonder South Wabash
#21 of 185 vacation rentals in Chicago
Last review posted 6 days ago
“No outdoor space. Misleading photos”
“Modern clean comfortable apartment”
“It was peaceful and quiet. Very close to soldier field. Will definitely stay there again.”
See more reviews of Sonder South Wabash
Spacious 5-BR Apt next to transit Free Parking
#22 of 185 vacation rentals in Chicago
Last review posted 29 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
Fully Furnished Apt Near Millenium Park- 29
#23 of 185 vacation rentals in Chicago
Last review posted 16 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
ENVITAE 3BR Luxury Corner Loft with Navy Pier Views
#24 of 185 vacation rentals in Chicago
Last review posted 35 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
Cozy Studio near Wrigley field and Boystown
#25 of 185 vacation rentals in Chicago
Last review posted 6 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 185 vacation rentals in Chicago
Last review posted 58 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
Sonder Market Hall
#27 of 185 vacation rentals in Chicago
Last review posted 2 days ago
The Twin Lions: Bespoke Travel Lodge w/ Speakeasy*
#29 of 185 vacation rentals in Chicago
Last review posted 14 days ago
“Good choice!”
“We had a really fun weekend here!”
“Very well furnished and had absolutely everything you need...”
See more reviews of The Twin Lions: Bespoke Travel Lodge w/ Speakeasy*
Chic & Updated Studio Apt in East Lakeview - Barry S1
#30 of 185 vacation rentals in Chicago
Last review posted 37 days ago
“Over priced, out dated, horrible owners!”
“A wonderful Chicago Apartment experience!”
“Great location, awful check in procedure and no welcome leaflet/information, we’re more interested in making money f”
See more reviews of Chic & Updated Studio Apt in East Lakeview - Barry S1
Previous page
1
2
3
4
5
6
7
Next page
Start of dialog content
How does it work?
It starts with a booking
It starts with a booking
The only way to leave a review is to first make a booking. That's how we know our reviews come from real guests who have stayed at the property.
Followed by a trip
Followed by a trip
When guests stay at the property, they check out how quiet the room is, how friendly the staff is, and more.
And finally, a review
And finally, a review
After their trip, guests tell us about their stay. We check for naughty words and verify the authenticity of all guest reviews before adding them to our site.
If you booked through us and want to leave a review, please sign in first.
End of dialog content
1982650|1,1982650