The 30 best holiday rentals in Chicago

#3 of 138 Holiday rentals in Chicago

• “Perfect! Convenient”
• “Loved it! Will definitely stay again!”
• “This was the perfect place to relax after a long day exploring Chicago.”
• See more reviews of Wrigley Oasis! Steps from the Field! - 3BD 1BA
• • Lakeview

#6 of 138 Holiday rentals in Chicago

• “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
• • Bronzeville

#8 of 138 Holiday rentals in Chicago

• “We had a wonderful stay.”
• “Very nice appartment with a incredible view of Chicago and...”
• “They required a manually printed sheet to check in which was...”
• See more reviews of The Penthouse at Grand Plaza
• • River North

#10 of 138 Holiday rentals in Chicago

• “Great gym and facilities (rooftop terrace, free coffee in...”
• “Amenities are amazing, location is perfect, nice looking...”
• “The furniture was lower quality”
• See more reviews of Sentral Michigan Avenue
• • Chicago Loop

#11 of 138 Holiday rentals in Chicago

• “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
• • Chicago Loop

#12 of 138 Holiday rentals in Chicago

• “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
• • Lakeview

#14 of 138 Holiday rentals in Chicago

• “Mixed feelings stay”
• “Great location with nice amenities”
• “It was good. Could have been better.”
• See more reviews of Sonder The Opal
• • River North

#16 of 138 Holiday rentals in Chicago

• “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 ✪
• • Wicker Park

#17 of 138 Holiday rentals in Chicago

• “Easy to find and very relaxing after long days at a trade show. It was clean and mostly quiet.”
• “Great location!”
• “The unit was clean, well-decorated, convenient, and perfectly peaceful.”
• See more reviews of Luxéry Stay Chicago - Across from McCormick Place & Wintrust Arena
• • South Loop

#19 of 138 Holiday rentals in Chicago

• “Great place to stay, easy parking.”
• “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”
• See more reviews of 1549 North Maplewood Avenue
• • Wicker Park

#20 of 138 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

#21 of 138 Holiday rentals in Chicago

• “Very nice to deal with.”
• “We loved Chicago.”
• “Very pleased with the location and professionalism”
• See more reviews of Lincoln Park Aparment with Backyard!
• • Lincoln Park

#23 of 138 Holiday rentals in Chicago

• “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
• • South Loop

#24 of 138 Holiday rentals in Chicago

• “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
• • Lakeview

#27 of 138 Holiday rentals in Chicago

• “Needs to improve their light blocking, but otherwise a perfect accommodation.”
• “Fast, pain free check in process! Clean and super cute rooms!”
• “Noisy if you have the wrong neighbours 😳”
• See more reviews of Sonder Market Hall
• • West Loop

#29 of 138 Holiday rentals in Chicago

• “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
• • Lakeview

#30 of 138 Holiday rentals in Chicago

• “Clean house and close to Downtown”
• “Everything was pretty good.”
• “Amazing spot will stay again 10/10”
• See more reviews of Ethan 3 rooms
• • Bridgeport