Holiday Homes in Chicago

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Featured Holiday Homes in Chicago

Fridge, microwave, oven, stovetop
Lincoln Park Living - Suite 2!
10.0 out of 10, Exceptional, (2)
"Location can't be beat. 15 min drive to Lincoln Park Zoo though (which was our destination) -not 3 min We were so happy with the location and it had all that we needed stocked. Finding free parking was relativrly easy which is a great plus. But if you are looking for a quiet place, this is not for you. You have to sacrifice peace & quiet for the location"
Lincoln Park Living - Suite 2!
TV
Luxury Downtown Penthouse with Private Rooftop!
10.0 out of 10, Exceptional, (4)
"Good host"
Luxury Downtown Penthouse with Private Rooftop!
Private kitchen
Your Next Vacation Home
10.0 out of 10, Exceptional, (9)
"This home was very Beautiful and More Spacious than expected with a Beautiful back yard that we sadly didn’t get to enjoy because of the rain. The house location was great with A lot of stores and restaurants nearby. Next time we have a Family gathering I definitely will be rebooking"
The price is NZ$497
includes taxes & fees
28 May - 29 May
Your Next Vacation Home
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Property grounds
Breathtaking Downtown Penthouse B - Sleeps 11
10.0 out of 10, Exceptional, (2)
"We booked this property for a stay while I took 2 of my sons to the Twins game at Guaranteed Rate Field. Overall it was a great place to stay, it was close to the Field Museum and Lincoln Park Zoo that we went to, and was easy to get to and from the baseball park as well. I do hope they get the tv on the rooftop patio working though, we didn’t really use that space since the tv wasn’t working while we were there. That was the only real downfall of the trip!"
Breathtaking Downtown Penthouse B - Sleeps 11
Property grounds
✽ Charming Cottage ✽ close to College/Town/Station
10.0 out of 10, Exceptional, (30)
"Great place for staying for visiting Wheaton. Very clean."
The price is NZ$477
includes taxes & fees
20 May - 21 May
✽ Charming Cottage ✽ close to College/Town/Station
Fridge, microwave, oven, stovetop
Game room/King Bed /Wi-Fi/Deck + Fire Pit
10.0 out of 10, Exceptional, (13)
"Relaxing, quiet and clean neighborhood. Love the retro decor. Kitchen is well equipped for those that might want to cook. A few branches were down in backyard, furniture wasn't set out yet such as outdoor dining table and chairs or gazebo, but overall property was in good condition. Thank you for a relaxing place to stay."
The price is NZ$696
includes taxes & fees
21 May - 22 May
Game room/King Bed /Wi-Fi/Deck + Fire Pit
Smart TV, table football, stereo
Freshly Remodeled Cozy Home
10.0 out of 10, Exceptional, (15)
"Place was clean and decor was nice and owner responed very nice to any questions."
Freshly Remodeled Cozy Home
Fridge, microwave, oven, stovetop
Updated Forest Park 3 BR Bungalow
10.0 out of 10, Exceptional, (82)
"This vrbo exceeded expectations from the photos. The vrbo was extemely clean, well maintained, and our dog enjoyed the yard. We also felt very safe walking at night and really enjoyed the proximity to Oak Park attractions, and the green line el stop is a 5 minute walk away. We intend to stay again when visiting the Chicago suburbs!"
Updated Forest Park 3 BR Bungalow
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
10.0 out of 10, Exceptional, (149)
"We had a little spring break getaway, and this was a perfect home base. Host was responsive and helpful, and the house had everything we needed to have a home away from home. Highly recommend this location, lots of space and a central location."
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Exterior
Cozy, King bed with heated bathroom!
9.8 out of 10, Exceptional, (8)
"Great"
Cozy, King bed with heated bathroom!
Exterior
Breathtaking home close to Schaumburg, Chicago
9.8 out of 10, Exceptional, (37)
"It was a perfect location and plenty of space for family of 8 plus visiting friends. Mike was a great host and we got to enjoy some firewood he had set up for us to have a fire. Highly recommend! The description says 4 bathrooms and there are 3 bathrooms…the only discrepancy."
Breathtaking home close to Schaumburg, Chicago
Exterior
Charming Oak Park Home w/ Private Fire Pit!
9.8 out of 10, Exceptional, (8)
"Me and my family stayed there and it has to be my favorite place when visiting family there was more than enough room for local family members to come and visit, the beds were so comfortable and the place was stocked with everything we needed. Communication was perfect we had to stay an extra day and they let us book it with no problem. Would definitely book to stay at again."
Charming Oak Park Home w/ Private Fire Pit!
Fridge, microwave, oven, stovetop
Beautiful, Remodeled Penthouse Unit in Old Town!
9.6 out of 10, Exceptional, (7)
"This property is huge for a city apartment. Our family of 5 (two parents, three kids) had plenty of space. The newly updated kitchen is very pretty. It is a short walk to many restaurants and Lincoln Park Zoo. The property manager was very responsive to my questions. We would definitely stay here again."
Beautiful, Remodeled Penthouse Unit in Old Town!
Smart TV, stereo
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
9.6 out of 10, Exceptional, (8)
"The proximity to Great Lakes Recruitment Center, Sarge’s Meet & Greet, restaurants, etc. is perfect. We were in town for our son’s boot camp graduation and knew we wanted more room to hang out than a typical hotel room would offer. It was great to be able to relax, watch movies, just hang out with our sailor for the precious two days we had. This place has location, location, location if you’re coming in for boot camp graduation."
The price is NZ$384
includes taxes & fees
19 May - 20 May
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
Interior
Elegant Mayor's Manor in Central Chicago - 9 Beds
9.6 out of 10, Exceptional, (8)
"Place was as described and worked perfect for our stay."
Elegant Mayor's Manor in Central Chicago - 9 Beds
Outdoor dining
national historic home near downtown airports no parties no events
9.4 out of 10, Exceptional, (19)
"Had a great time used space for birthday event!!"
The price is NZ$564
includes taxes & fees
19 May - 20 May
national historic home near downtown airports no parties no events
Terrace/patio
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
9.4 out of 10, Exceptional, (70)
"The house and location was perfect for our group trip to Chicago. Ample rooms and beds for everyone, and host was extremely responsive throughout the process and our stay. Walking distance to a bunch of great restaurants and bars. Would definitely stay again!"
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
TV, fireplace, books, offices
Prime location Historic Chicago Townhouse
9.4 out of 10, Exceptional, (59)
"Gorgeous, large townhouse. We loved the location and the townhouse itself. The lock box was a little confusing because there are 2. In the age of door codes, I wasn’t expecting this. Another word of note: the staircase is old and the wood is worn on some places. If you have small children or someone who is unstable on their feet you might want to consider this."
Prime location Historic Chicago Townhouse
Private kitchen
LUXE 3 BR, 2 BA + Hot Tub
9.2 out of 10, Wonderful, (9)
"Nice house in a nice, quiet neighborhood. Plenty of room for the whole family. Liked being able to park our car in the attached garage. Using the hot tub in backyard was very enjoyable. Our host was very pleasant and quick to respond."
The price is NZ$444
includes taxes & fees
19 May - 20 May
LUXE 3 BR, 2 BA + Hot Tub
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
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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.

Other property types in Chicago

Interior
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (400)
"It was amazing to have a whole apartment for the price of a hotel room... less actually. Their system is simple and painless. I will book here again!"
The price is NZ$288
includes taxes & fees
27 May - 28 May
Sentral Michigan Avenue
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)
"Everything was great. From easy check in to easy check out. The room was very nice and cozy. Very clean. Amazing view of downtown from the bedroom and balcony. I will be staying here again! "
Kasa Magnificent Mile Chicago
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$372
includes taxes & fees
28 May - 29 May
Sonder South Wabash
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.

Chicago Holiday Homes information

Number of reviews
243
Accommodation
480 Holiday Homes
Lowest Price
NZ$282
Highest Price
NZ$696

Recent Reviews in Chicago
Expedia verified reviews