The 30 best holiday rentals in Chicago

#2 of 174 Holiday rentals in Chicago

• “Convenient location. Spacious and comfortable apartment. East access in and out. Overall a great place to stay. We would”
• “The place was great in all respects.”
• “Enjoyed the stay and recommend it to anyone.”
• See more reviews of Wrigley Oasis! Steps from the Field! - 3BD 1BA
• • Lakeview

#3 of 174 Holiday rentals in Chicago

• “I deserve a refund she treated us like 2 kids, wil nverr book here again”
• “The place was very nice and clean.”
• “We loved our stay in Orlando and this place is right you can see it in the photos, it suprised me how much space we had”
• See more reviews of Forrestville Ave Large Suite
• • Bronzeville

#4 of 174 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

#5 of 174 Holiday rentals in Chicago

• “Very nice room, great kitchen.”
• “Localization and the room”
• “Great location and good value for your money”
• See more reviews of Sentral Michigan Avenue
• • Chicago Loop

#12 of 174 Holiday rentals in Chicago

• “Perfect!”
• “Excellent stay, it checked most boxes and was a great value.”
• “Great stay and great location”
• See more reviews of Kasa South Loop Chicago
• • Chicago Loop

#14 of 174 Holiday rentals in Chicago

• “Conveniently located to the convention center”
• “Great location for access to McCormick Place.”
• “Great venue close to restaurants and convention center and arena! Would highly recommend!”
• See more reviews of Luxéry Stay Chicago - Across from McCormick Place & Wintrust Arena
• • South Loop

#15 of 174 Holiday rentals in Chicago

• “Perfect to visit family in Chicago and taking advantage of early Christmas shopping.”
• “We were in town for the Iowa Hawkeye game at Wrigley Field. The apartment had all the essentials to make it a great stay”
• “Super communication, perfect directions, great area.”
• See more reviews of 2 Bed Apt w/ Office, Free Parking, Near Wrigley
• • Lakeview

#18 of 174 Holiday rentals in Chicago

• “Great location very comfortable and amazing view!”
• “Wonderful location, close to all main attractions.”
• “Location location location”
• See more reviews of Sonder The Opal
• • River North

#19 of 174 Holiday rentals in Chicago

• “Great neighborhood!”
• “Wonderful 3 BR apartment/stocked kitchen/nicely equipped & 5 min walk to brown/purple metro rail.”
• “As pictured and great location! Felt very safe.”
• See more reviews of Lincoln Park Gem
• • Lincoln Park

#20 of 174 Holiday rentals in Chicago

• “Peaceful apartment great for couples”
• “Perfect little place. Safe and by everything”
• “Our overall stay was excellent.”
• See more reviews of ✪ Cozy 1 Bedroom close to Downtown Chicago ✪
• • Wicker Park

#22 of 174 Holiday rentals in Chicago

• “Clean, comfortable, good value.”
• “Good price in comparison with the hotels in the city center,...”
• “Very big place.”
• See more reviews of 1549 North Maplewood Avenue
• • Wicker Park

#23 of 174 Holiday rentals in Chicago

• “My stay was enjoyable.”
• “It just like another home.”
• “Even after these small complaints, it was still a wonderful stay and my family would stay again!”
• See more reviews of Sonder South Wabash
• • South Loop

#24 of 174 Holiday rentals in Chicago

• “Below Average Stay. Only reason I would stay is that it is close to wrigleyville. Everything else was below average.”
• “No heat or hot water I can’t shower”
• “Beautiful street, close to Wrigley, beautiful unit, safe area”
• See more reviews of The Double Play Wrigley Field Flats
• • Lakeview

#25 of 174 Holiday rentals in Chicago

• “A wounderful stay”
• “Clean, spacious, good location.”
• “Clean and convenient.”
• See more reviews of Lincoln Park 3 BR Penthouse
• • Lincoln Park

#29 of 174 Holiday rentals in Chicago

• “Breathtaking”
• “We were in Chicago to see the Frankenstein Ballet which was wonderful!”
• “We really enjoyed our stay here. The views of the Chicago skyline were fantastic! Great location.”
• See more reviews of 2BR Elegant Premium Suite With Balcony & Sweeping City Views
• • River North

#30 of 174 Holiday rentals in Chicago

• “A wonderful Chicago Apartment experience!”
• “Great location, awful check in procedure and no welcome leaflet/information, we’re more interested in making money f”
• “Smelled so good! I enjoyed it.”
• See more reviews of Remodeled Studio Apartment in East Lakeview - Barry S1
• • Lakeview