The 29 Best Holiday Rentals in Illinois

Ranked 1 out of 607 in the Illinois region, as well as being 1 of 173 for holiday rentals in Chicago.

• “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

Ranked 2 out of 607 in the Illinois region, as well as being 1 of 1 for holiday rentals in Elizabeth.

• “An experience to be recommended and repeated...”
• “Wonderful!”
• “place was nice the food was good and the host was very nice”
• See more reviews of Derinda House

Ranked 3 out of 607 in the Illinois region, as well as being 2 of 173 for holiday rentals in Chicago.

• “Great option for multiple guests very close to Wrigley Field.”
• “Great location.”
• “Very attentive hosts.”
• See more reviews of Wrigley Oasis! Steps from the Field! - 3BD 1BA

Ranked 4 out of 607 in the Illinois region, as well as being 3 of 173 for holiday rentals in Chicago.

• “Harika”
• “Perfect townhome in the lakeshore community area of Chicago. Convenient to everything!”
• “My family stayed for the week of Christmas. The apartment was filled with items that were very useful to make our stay e”
• See more reviews of Chicago Charm

Ranked 5 out of 607 in the Illinois region, as well as being 4 of 173 for holiday rentals in Chicago.

• “Very quiet and comfortable. Loved the decor! Comfortable beds.”
• “It was perfect for our family.”
• “Excellent space for a family with a dog, great location!”
• See more reviews of The Avondale Guesthouse

Ranked 6 out of 607 in the Illinois region, as well as being 5 of 173 for holiday rentals in Chicago.

• “The host's behavior was extremely disappointing.”
• “Superb accommodation.”
• “Most comfortable Chicago stay!”
• See more reviews of 2F Chicago's Little Italy near West Loop & Downtown

Ranked 7 out of 607 in the Illinois region, as well as being 6 of 173 for holiday rentals in Chicago.

• “A quiet, clean, comfortable stay!”
• “Heart of Bronzeville”
• “Amazing experience. Would like to introduce to anyone that would want to visit Chicago.”
• See more reviews of Forrestville Ave Large Suite

Ranked 8 out of 607 in the Illinois region, as well as being 2 of 36 for holiday rentals in Peoria.

• “Convenient.”
• “I like it has fridge, oven, coffee maker and toaster.”
• “Excellent”
• See more reviews of Mon Chateau

Ranked 9 out of 607 in the Illinois region, as well as being 7 of 173 for 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

Ranked 10 out of 607 in the Illinois region, as well as being 8 of 173 for holiday rentals in Chicago.

• “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

Ranked 11 out of 607 in the Illinois region, as well as being 9 of 173 for holiday rentals in Chicago.

• “Staff is brilliant”
• “Location and view are top notch.”
• “Would visit again”
• See more reviews of Sentral Michigan Avenue

Ranked 12 out of 607 in the Illinois region, as well as being 10 of 173 for holiday rentals in Chicago.

• “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

Ranked 13 out of 607 in the Illinois region, as well as being 11 of 173 for holiday rentals in Chicago.

• “Pretty apartment”
• “Almost a perfect place!”
• “Clean & nice inside. Maybe check Google street view if concerned about the area.”
• See more reviews of Perfect place to enjoy the city or just relax

Ranked 14 out of 607 in the Illinois region, as well as being 12 of 173 for holiday rentals in Chicago.

• “first time on a Kass property and will look for more”
• “Great location and amazing apartment!”
• “Great views, plenty of room, felt safe”
• See more reviews of Kasa South Loop Chicago

Ranked 15 out of 607 in the Illinois region, as well as being 13 of 173 for holiday rentals in Chicago.

• “My stay for the first time in Chicago was beyond amazing”
• “Perfect”
• “Greta value for the money and super convenient location.”
• See more reviews of Sonder The Opal

Ranked 16 out of 607 in the Illinois region, as well as being 1 of 2 for holiday rentals in Richmond.

• “Awesome high quality getaway in a quaint town. Bonus charging station for EV owners!”
• “Location couldn't have been better, walk to excellent...”
• “Perfect location for a fall weekend getaway!”
• See more reviews of Richmond No. 267

Ranked 17 out of 607 in the Illinois region, as well as being 14 of 173 for holiday rentals in Chicago.

• “It was amazing stay very good in comincate very nice location”
• “Perfect”
• “Great experience! Free Parking permits are amazing. Keyless entry is amazing too.”
• See more reviews of 2 Bed Apt w/ Office, Free Parking, Near Wrigley

Ranked 18 out of 607 in the Illinois region, as well as being 15 of 173 for 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

Ranked 19 out of 607 in the Illinois region, as well as being 16 of 173 for holiday rentals in Chicago.

• “We absolutely loved the location.”
• “Peaceful apartment great for couples”
• “Perfect little place. Safe and by everything”
• See more reviews of ✪ Cozy 1 Bedroom close to Downtown Chicago ✪

Ranked 20 out of 607 in the Illinois region, as well as being 17 of 173 for holiday rentals in Chicago.

• “The host was very helpful and communicative and the space was well kept and accommodating.”
• “Comfortable place to enjoy touring the city from.”
• “Spacious, safe location”
• See more reviews of The Blue Golden Luxury Modern 3- Bedroom Apartment in Chicago

Ranked 21 out of 607 in the Illinois region, as well as being 18 of 173 for holiday rentals in Chicago.

• “Nice stay”
• “The apartment was very clean and comfortable.”
• “Great Apt to stay”
• See more reviews of Adorable 2 bedroom with free street parking

Ranked 22 out of 607 in the Illinois region, as well as being 19 of 173 for holiday rentals in Chicago.

• “Short break in Chicago.”
• “Clean, comfortable, good value.”
• “Good price in comparison with the hotels in the city center,...”
• See more reviews of 1549 North Maplewood Avenue

Ranked 23 out of 607 in the Illinois region, as well as being 1 of 5 for holiday rentals in West Dundee.

• “The space was excellent for our stay.”
• “Relaxing and very cute place in a charming town.”
• “The photos caught our eyes before we booked, and seeing it with our own eyes didn’t disappoint!”
• See more reviews of Hip Urban Loft-Small Town Charm-124 LOFTS #2

Ranked 24 out of 607 in the Illinois region, as well as being 20 of 173 for holiday rentals in Chicago.

• “My stay was awesome.”
• “A delightful stay in a calm area of Chicago, with everything you need for a short stay.”
• “awesome”
• See more reviews of Sonder South Wabash

Ranked 25 out of 607 in the Illinois region, as well as being 21 of 173 for 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!

Ranked 26 out of 607 in the Illinois region, as well as being 1 of 9 for holiday rentals in Galena.

• “Even though this place had the perfect amount of Galena charm, it didn’t matter how dated the home was, I do expect for”
• “The three of us just went for a day getaway and overnight...”
• “Short”
• See more reviews of Galena Penthouse overlooking Main Street with FREE off street parking

Ranked 28 out of 607 in the Illinois region, as well as being 23 of 173 for holiday rentals in Chicago.

• “Great place in a nice area. Awesome amenities and comfy.”
• “The space of the place the cleanineas of the place how it...”
• “I paid half the price for double the amenaties.”
• See more reviews of Winter Wonderland Retreat and Your Chicago Chill Getaway

Ranked 29 out of 607 in the Illinois region, as well as being 24 of 173 for 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

Ranked 30 out of 607 in the Illinois region, as well as being 25 of 173 for holiday rentals in Chicago.

• “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