Illinois Holiday Rentals

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Top Cities in Illinois

Top Holiday Rentals Destinations in Illinois

Interior
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (395)
"The facility is fantastic. Really enjoyed the gym and pool. Our premium apartment was not the best. Although the corner suite offered a fantastic view the apartment was dirty and run down. Trains are very loud. Not sure that I would stay here again. For the same price you can book something in the north or downtown. "
The price is NZ$293
per night
27 May - 28 May
Sentral Michigan Avenue
Interior
Sonder Market Hall
3.5 star property
8.2 out of 10, Very good, (77)
"Gorgeous rooms. Simple and quiet property. "
The price is NZ$209
per night
27 May - 28 May
Sonder Market Hall
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (222)
"Nice location and nice property. We enjoyed our visit there."
Kasa Magnificent Mile Chicago
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City view from property
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (295)
"Overall the stay was amazing. We will definitely be booking here again."
The price is NZ$378
per night
28 May - 29 May
Sonder South Wabash
Exterior
Sonder The Burnham
3.5 star property
8.8 out of 10, Excellent, (52)
"We loved the space, very clean, great amenities, looks like a perfect combo of a cozy apartment and a hotel room. The only problem is that it’s not very soundproof, and you can hear people using restrooms or showering in the neighboring rooms. But would definitely stay again!"
The price is NZ$383
per night
28 May - 29 May
Sonder The Burnham
Interior
Found Chicago powered by Sonder
3.5 star property
7.6 out of 10, Good, (126)
"I enjoyed the fact that everything was close. The hotel was cleaned but I never saw a personal member. The code to enter didn't work and people inside had to help fellow clients to enter."
The price is NZ$413
per night
6 Jun - 7 Jun
Found Chicago powered by Sonder
Front of property - evening/night
Level Chicago – Old Town
4.0 star property
8.8 out of 10, Excellent, (207)
"Nice"
The price is NZ$595
per night
15 May - 16 May
Level Chicago – Old Town
50-inch Smart TV with satellite channels
The Neighborhood Hotel-Little Italy
2.0 star property
9.8 out of 10, Exceptional, (28)
"Great location, Great Neighborhood, plenty of dining options within walking distance. You can park by the hotel to unload and load and there is limited time meter parking or late night early am free parking streetside... When you can find it. There is a parking garage at the corner of Taylor and Paulina that is only $9 if in after 3p and out before 8a... Which is a steal by Chicago parking costs. It's a short 3 block walk to the hotel... Well lit and sidewalks. The only nitpick I can even...
The Neighborhood Hotel-Little Italy
1 bedroom, premium bedding, pillow-top beds, desk
WoodSpring Suites Chicago Addison
2.5 star property
6.0 out of 10, (184)
"ITS A VERY NICE AND UPBEAT ESTABLISHMENT.......I ENJOYED THE STAY ONLY THING I DIDNT LIKE WAS THERE HOUSE KEEPING SCHEDULE BUT OTHER THAN THAT ITS A NICE QUIET LOCATION WITH NICE PEOPLE"
The price is NZ$127
per night
15 May - 16 May
WoodSpring Suites Chicago Addison
Exterior
Sonder Jewelers Row
3.5 star property
8.2 out of 10, Very good, (99)
"This is an overall very convenient, clean and well maintained apartment hotel. Transportation is convenient, there are restaurants and other amenities nearby, and the facilities within the hotel are also good. However, the only downside is that it is close to the station and there is construction nearby, so it is very noisy. However, if I had the chance to choose again, I would choose this hotel. I am satisfied."
The price is NZ$413
per night
28 May - 29 May
Sonder Jewelers Row
Exterior
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (65)
"Very clean and comfortable. Great location very close to an L stop. Walkable to shopping and the lake front and river walk"
Kasa River North Chicago
Family Apartment, 3 Bedrooms, Non Smoking, Balcony | Living area
Kasa South Loop Chicago
4.0 star property
9.4 out of 10, Exceptional, (161)
"Highly recommend! Amazing view of the city and the lake, clean and quiet yet close to everything. Thoughtfully furnished with nice surprises like power strips, white noise machine in bedroom, electric kettle etc. It was ideal and we’d stay there again. "
Kasa South Loop Chicago
Studio
Yugo Guest Suites
2.0 star property
9.4 out of 10, Exceptional, (22)
"Highly recommend! Nice, clean modern studio suite. Large smart TV, comfortable bed, nice sitting area with small couch. Frig, stovetop, microwave & washer/dryer. Great bakery/coffee shop on 1st floor & Einstein Bageks across the street. Included parking too. You just need to bring a blow dryer and if you are going to check in after 5 PM, you need to call the front desk and ask them to leave your key in the lock box, which we did and was super easy."
Yugo Guest Suites
City view from property
Sonder The Plymouth
3.5 star property
8.4 out of 10, Very good, (66)
"Great place to stay and visit Chicago on foot. The property was exactly what we hoped for. "
The price is NZ$514
per night
27 May - 28 May
Sonder The Plymouth
3 bedrooms, WiFi, bed sheets
Your Home Away From Home
2.0 out of 10, (1)
"No me agradó"
The price is NZ$287
per night
15 May - 16 May
Your Home Away From Home
Private kitchen
Luxury Home Away From Your Home
9.0 out of 10, Wonderful, (106)
"The host communicated well. The area was busy but felt safe. I felt it was expensive for the location. Very clean."
Luxury Home Away From Your Home
Exterior
Walking distance to restaurants, shops and Lake Michigan,
9.8 out of 10, Exceptional, (156)
"This is a fantastic location just outside of the city on a quiet street but close to everything. The Property Manager (Ross) is fantastic with communication and even after our flight was delayed three times, he met us at the door, gave us a thorough tour of where everything is located, and some great tips on where to eat. It's a $20 UBER to the heart of the city (Millenium Park) and the place is spotless! Highly recommend if you're looking for a place to hang your hat for a few days!"
Walking distance to restaurants, shops and Lake Michigan,
Property grounds
Wrigley/Southport Corridor Garden Oasis +parking!
9.8 out of 10, Exceptional, (36)
"Great access to Wrigley/ South Port & Lake view neighborhoods. Very Clean and laid out space that maximizes the space in this unit. Will be back soon!"
Wrigley/Southport Corridor Garden Oasis +parking!
Property grounds
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
9.0 out of 10, Wonderful, (8)
"Excellent"
The price is NZ$314
per night
19 May - 20 May
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
Fridge, microwave, oven, stovetop
LakeHouse
10.0 out of 10, Exceptional, (6)
"I loved this house. It was clean, spacious, the piano made it that much better. I will definitely be back again."
LakeHouse
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.