The 26 Best Holiday Rentals in Illinois

Ranked 1 out of 915 in the Illinois region, as well as being 1 of 264 for holiday rentals in Chicago.

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• “The flat is prestine clean and really cosy.”
• “A fabulous home located walking distance from the amazing food in little Italy.”
• See more reviews of 1F Cozy Home in Little Italy near Downtown West Loop United Center

Ranked 2 out of 915 in the Illinois region, as well as being 2 of 264 for holiday rentals in Chicago.

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• “The place was exactly like the photos the beds were...”
• “Wish every vacation rental was up to the standards of this property.”
• See more reviews of Chicago Charm

Ranked 3 out of 915 in the Illinois region, as well as being 3 of 264 for holiday rentals in Chicago.

• “4 real bedrooms and 2 full bathrooms”
• “Cozy family home in a great location”
• “Clean, efficient, excellent host.”
• See more reviews of Northside FAMLYNEST Lincoln Sq 4BR 2BA 2P Rare find

Ranked 4 out of 915 in the Illinois region, as well as being 4 of 264 for holiday rentals in Chicago.

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• “Beautiful property, well maintained and stocked in a great neighbourhood.”
• See more reviews of 2F Chicago's Little Italy near West Loop & Downtown

Ranked 5 out of 915 in the Illinois region, as well as being 1 of 2 for holiday rentals in Richmond.

• “Loved it!”
• “Second stay. Will be back. Love this place. Nice weekend getaway.”
• “We were very impressed! We will be back!”
• See more reviews of Richmond No. 267

Ranked 6 out of 915 in the Illinois region, as well as being 5 of 264 for holiday rentals in Chicago.

• “A really nice and clean property in a great location!”
• “I enjoyed my stay and I wish I could stay longer but they are always fully booked.”
• “Excellent apartment.”
• See more reviews of Pulaski Point Properties

Ranked 7 out of 915 in the Illinois region, as well as being 1 of 10 for holiday rentals in West Dundee.

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• “Great!”
• “Beautiful and large room.”
• See more reviews of Hip Urban Loft-Small Town Charm-124 LOFTS #2

Ranked 8 out of 915 in the Illinois region, as well as being 6 of 264 for holiday rentals in Chicago.

• “Will book again.”
• “Wonderful short and sweet”
• “We enjoyed the ambiance and it’s just far enough from the ballpark to avoid the crowds and close enough to get there in”
• See more reviews of Wrigley Oasis! Steps from the Field! - 3BD 1BA

Ranked 9 out of 915 in the Illinois region, as well as being 7 of 264 for holiday rentals in Chicago.

• “What an excellent place to stay!!”
• “The house is very well equipped and has everything you need...”
• “Comfortable stay in Irving Park. Stay here if you can!”
• See more reviews of Irving Park updated vintage top unit 2-flat

Ranked 10 out of 915 in the Illinois region, as well as being 8 of 264 for holiday rentals in Chicago.

• “Can't recommend”
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• “Lovely apartment in a great location.”
• See more reviews of The Penthouse at Grand Plaza

Ranked 11 out of 915 in the Illinois region, as well as being 9 of 264 for holiday rentals in Chicago.

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• See more reviews of The Avondale Guesthouse

Ranked 12 out of 915 in the Illinois region, as well as being 1 of 1 for holiday rentals in Elizabeth.

• “You will love this place.”
• “Loved it!”
• “Lovely & comfortable with an amazing breakfast.”
• See more reviews of Derinda House

Ranked 13 out of 915 in the Illinois region, as well as being 10 of 264 for holiday rentals in Chicago.

• “Great for families travelling to Chicago”
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• “A LOT of space!”
• See more reviews of Forrestville Ave Large Suite

Ranked 14 out of 915 in the Illinois region, as well as being 2 of 10 for holiday rentals in West Dundee.

• “Excellent, will continue to stay here when I come into town.”
• “The room was beautiful and will stay again”
• “perfect location and comfortable and safe.”
• See more reviews of Hip Urban Loft - Small Town Charm -124 LOFTS #3

Ranked 15 out of 915 in the Illinois region, as well as being 11 of 264 for holiday rentals in Chicago.

• “Great stay”
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• “It was like being at home”
• See more reviews of Trendy West Town Flat - 2 bed / 1.5 bath w parking

Ranked 16 out of 915 in the Illinois region, as well as being 12 of 264 for holiday rentals in Chicago.

• “Friendly host and nice and cute place, but I wish the furniture was newer, at least not noisy.”
• “It’s a nice cozy home”
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• See more reviews of Superior

Ranked 17 out of 915 in the Illinois region, as well as being 2 of 38 for holiday rentals in Springfield.

• “Beautiful place!”
• “一切都非常完美，房东非常热情体贴，是这几年住过最好的民宿，来春田市选这家一定没错，所有主要景点步行可达。”
• “Stay was great. Could use a curtain on the main level Master bedroom door window to deck.”
• See more reviews of The Audrey - Springfield

Ranked 18 out of 915 in the Illinois region, as well as being 13 of 264 for holiday rentals in Chicago.

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• “Lovely for families and quiet folks. Not a hotel but a new concept.”
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• See more reviews of Sentral Michigan Avenue

Ranked 19 out of 915 in the Illinois region, as well as being 3 of 38 for holiday rentals in Springfield.

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• “Pleasant”
• “An amazing opportunity to experience Springfield in Luxury and style”
• See more reviews of The Bressmer

Ranked 21 out of 915 in the Illinois region, as well as being 15 of 264 for holiday rentals in Chicago.

• “Location”
• “Nice and close to Wrigley Field”
• “Not pleased”
• See more reviews of 2 Bed Apt w/ Office, Free Parking, Near Wrigley

Ranked 23 out of 915 in the Illinois region, as well as being 17 of 264 for holiday rentals in Chicago.

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• “Beautiful vacation stay apartment!”
• “Great location , real crappy communication. Miserable stay because it was almost 80° in the apartment the entire time.”
• See more reviews of Luxéry Stay Chicago - Themed Units! Close to Downtown, McCormick Place & Wintrust Arena

Ranked 24 out of 915 in the Illinois region, as well as being 1 of 11 for holiday rentals in Galena.

• “Very comfortable.”
• “Wonderful! Will be a repeat place to stay.”
• “The view was great during a winter storm, really pretty.”
• See more reviews of Summer Specials! Cozy King Beds, Pool Access, Galena Territory Amenities, Fireplace, Great Location in Galena Territory on Lake Galena

Ranked 25 out of 915 in the Illinois region, as well as being 18 of 264 for holiday rentals in Chicago.

• “Great accommodation in a great location!”
• “Great location and spacious apartment.”
• “Reid was a fantastic host.”
• See more reviews of Bucktown Private Condo

Ranked 26 out of 915 in the Illinois region, as well as being 3 of 38 for holiday rentals in Peoria.

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• “I honestly liked everything about the apartment, it felt...”
• See more reviews of ConTemporary Stay in Central Peoria

Ranked 29 out of 915 in the Illinois region, as well as being 21 of 264 for holiday rentals in Chicago.

• “Nice clean apartment, conveniently located”
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• See more reviews of Sonder by Marriott Bonvoy The Opal Apartments River North

Ranked 30 out of 915 in the Illinois region, as well as being 22 of 264 for holiday rentals in Chicago.

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• “I would recommend this property. It was the best sleep I’ve ever had away from home.”
• “Train noise seemed louder then any other place I stayed in...”
• See more reviews of Fulbrix Bright Designer Apartments with West Loop Views