The 30 best holiday rentals in Chicago

#2 of 183 Holiday rentals in Chicago

• “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
• • Lakeview

#6 of 183 Holiday rentals in Chicago

• “Great Stay!”
• “A quiet, clean, comfortable stay!”
• “Heart of Bronzeville”
• See more reviews of Forrestville Ave Large Suite
• • Bronzeville

#7 of 183 Holiday rentals in Chicago

• “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
• • River North

#9 of 183 Holiday rentals in Chicago

• “The accommodation suited our needs.”
• “Friendly staff, clean space and great location”
• “Great time with my family. We used the spa before bed and in the morning.”
• See more reviews of Sentral Michigan Avenue
• • Chicago Loop

#12 of 183 Holiday rentals in Chicago

• “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
• • Chicago Loop

#13 of 183 Holiday rentals in Chicago

• “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
• • Lakeview

#14 of 183 Holiday rentals in Chicago

• “A very worthwhile accommodation for a great break”
• “Worst experience ever, will never stay there again.”
• “Good place good location.”
• See more reviews of Sonder The Opal
• • River North

#15 of 183 Holiday rentals in Chicago

• “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 ✪
• • Wicker Park

#16 of 183 Holiday rentals in Chicago

• “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
• • South Loop

#19 of 183 Holiday rentals in Chicago

• “'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
• • Wicker Park

#20 of 183 Holiday rentals in Chicago

• “Modern clean comfortable apartment”
• “It was peaceful and quiet. Very close to soldier field. Will definitely stay there again.”
• “My stay was awesome.”
• See more reviews of Sonder South Wabash
• • South Loop

#21 of 183 Holiday rentals in Chicago

• “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!
• • Lincoln Park

#22 of 183 Holiday rentals in Chicago

• “This property is at a great location.”
• “Location, roof top pool and patio.”
• “Modern comfort in the middle of the Windy City”
• Fully Furnished Apt Near Millenium Park- 29 has been reviewed 8 times. Some users didn't leave a comment, while other reviews are written in Español or English (US).
• • Chicago Loop

#24 of 183 Holiday rentals in Chicago

• “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
• • Chicago Loop

#28 of 183 Holiday rentals in Chicago

• “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
• • Lincoln Park

#29 of 183 Holiday rentals in Chicago

• “Amazing”
• “N/a”
• “Good time but probably not going to do it again bc they require the customer to scan their face.”
• See more reviews of Sonder Market Hall
• • West Loop

#30 of 183 Holiday rentals in Chicago

• “Clean and in a convenient location, but right against the light rail and very noisy”
• “Great Location!”
• “From the photos online, I was thinking we were getting the upstairs, rather than the basement apartment. But glad it was”
• See more reviews of The Double Play, Wrigley Flats - Cubs! - Located Right next to Wrigley and Transit
• • Lakeview