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Compare 398 Vacation Homes in Riverdale with updated reviews, rates, and availability.

Cozy, Beautiful Downtown Unit CHI in Prime River North Location near Mag Mile -
10.0 out of 10, Exceptional, (11)
"The listing did not disappoint for our group of frienda reunighring for a 2 night event. It's just as described & more! Great location, the patio is such a bonus, Dan the host was amazing at communicating before & after, and that patio 😍 Thak you- we hope to he back soon! soon!"
Cozy, Beautiful Downtown Unit CHI in Prime River North Location near Mag Mile -
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
9.8 out of 10, Exceptional, (77)
"Property was clean, manager was very easy to communicate with, lots of spacious beds / bathrooms, parking was easy and kitchen and living space included everything we needed. Location near Wells Street, North Avenue, Lakefront and Brown Line was perfect. Everything was easily walkable. This was a great house in the middle of a nice neighborhood for a large group."
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
Luxury SOHO Styled Two-Level Townhouse - Old Town
10.0 out of 10, Exceptional, (10)
"We had a great stay at this property. It is walking distance from everything you need in old town but also safe, quiet, and secure! Would highly recommend to other groups looking for a weekend in Old Town Chicago!"
Luxury SOHO Styled Two-Level Townhouse - Old Town
Cozy, Beautiful Downtown Unit CHI in Prime River North Location near Mag Mile -
9.0 out of 10, Wonderful, (7)
"Great place to stay for a work conference at Sheraton. For three people it was much cheaper than the hotel."
Cozy, Beautiful Downtown Unit CHI in Prime River North Location near Mag Mile -
Luxury Home Away From Your Home
9.0 out of 10, Wonderful, (114)
"Definitely gently used but was comfortable. Ms. Linnie, the host, is very responsive and accommodating. Was missing hair dryers and flat sheets on beds but did not negatively affect our visit."
Luxury Home Away From Your Home
Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park
8.2 out of 10, Very Good, (34)
"The yard is awesome, of course the hot tub at the top of the hill was the best, and we enjoyed the firepit as well. The house was a tidy little cottage at which we enjoyed our stay. It’s within a short walk to the National Park and downtown Miller Beach. The neighborhood is fine, pretty secluded, and still close to most attractions."
Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park
Beautiful, Remodeled Penthouse Unit in Old Town!
9.2 out of 10, Wonderful, (14)
"This family trip works perfectly for our 12 family members. The location was great in old town and close to beach and other good places. We only wanted a mirror outside the bathroom so we do not have to wait for someone getting out of the bathroom just fto use the mirror. Otherwise everything was good."
Beautiful, Remodeled Penthouse Unit in Old Town!
Oak Park, IL, entire house, short walk to train.
9.4 out of 10, Exceptional, (19)
"Great host communicates well if you need him. Helped with all my concerns. Check in was was easy and smooth. Property inside and out was also clean and in a nice neighborhood with access to ALOT. Thank you"
Oak Park, IL, entire house, short walk to train.
Cozy Home Sweet Homewood.
10.0 out of 10, Exceptional, (11)
"Great and quiet location. Comfortable very clean neat enough space for us . We greatly recommend hopefully we able to stay next year. Nice backyard "
Cozy Home Sweet Homewood.
Stunning Condo #2 - Downtown River North!!!
9.4 out of 10, Exceptional, (10)
"Looks just like the pictures, the house was very clean and decorated so cute! The host was very easy to get in touch with if needed. Amazing stay!! "
Stunning Condo #2 - Downtown River North!!!
Nestled just behind Marquette Park. 5 minute walk to beach.
10.0 out of 10, Exceptional, (9)
"Could not be more thankful for her prompt replies and accommodations."
Nestled just behind Marquette Park. 5 minute walk to beach.
5 BR / 3.5 BA Newly Built Home in Logan Square!
7.6 out of 10, Good, (7)
"We had a minor hiccup in the beginning and Sandy got it taken care of within an Hour. Overall great stay"
5 BR / 3.5 BA Newly Built Home in Logan Square!
Stunning Duplex Condo #1 - Downtown River North
9.8 out of 10, Exceptional, (9)
"Great location. Took train from O’Hare, Transferred and took brown line 2 short blocks to condo. Place was very nice. Rooms very big with modern bathrooms. Enjoyed all Chicago had to offer. Would stay here again. "
Stunning Duplex Condo #1 - Downtown River North
Cozy, Beautiful Downtown Unit CHI in Prime River North Location near Mag Mile -
9.6 out of 10, Exceptional, (9)
"This place has plenty of space, a wonderful kitchen and 2 bathrooms. Perfect for big families or friend groups. We loved visiting Chicago, and this place had free parking, and amazing access to public transportation. It also very close to a couple convenience stores, places to eat, and Trader Joe’s and Whole Foods. Next time we probably wound NOT rent a car because the public transportation is incredibly close and easy to navigate, we hardly used our car. We went to 2 concerts at Wrigley Field,...
The price is AED 588
AED 1,434 total
includes taxes & fees
10 Oct - 11 Oct
Cozy, Beautiful Downtown Unit CHI in Prime River North Location near Mag Mile -
Cozy Midway Home
2.0 star property
9.6 out of 10, Exceptional, (5)
"I enjoyed my stay. The home was very clean and nice. Nice quiet location. A few things I would suggest to the host is maybe have black out curtains in the bedroom because I hated being woken up at 6am with the bright sun in the room. The curtains were see through. Also maybe have blinds in the kitchen because I felt exposed with no curtains or blinds and anyone can see in the house. And last I would have washcloths for the guest because not everyone travels with towels and washcloths. Other than...
Cozy Midway Home
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace
9.2 out of 10, Wonderful, (49)
"A beautiful apartment in a perfect location. Walking distance to Wells street in old town. The apartment itself was very comfortable and had everything we needed. The host also was very helpful with everything "
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace
Immaculate Brand New Penthouse Chicago!
9.4 out of 10, Exceptional, (8)
"This was such a convenient and overall great stay. There is plenty of room for everyone to sleep comfortably and check in/out was super easy. Definitely recommend this for large groups or families. Would stay here again! "
Immaculate Brand New Penthouse Chicago!
Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails
8.8 out of 10, Excellent, (29)
"The house is well maintained, living space was good for two adults and two teens. The beach is a walkable distance. Food and groceries are not far away. The area lacks a small vacation town feel but the house is great for a cook at home get away. Good street biking and running trails in the beach area."
Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails
Spacious and Sleek 4BD/2.5BA - Logan Square!
9.4 out of 10, Exceptional, (12)
"This home was perfect for my extended family and I to stay during a long weekend in Chicago. It’s a short drive from everything downtown and has tons of great restaurants, bars, coffee shops and stores nearby. Parking was a breeze with the whole street being free and always available, a rarity in Chicago! The balcony was perfect and utilized it a bunch with the cool summer days. "
Spacious and Sleek 4BD/2.5BA - Logan Square!
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Other property types in Riverdale

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (543)
"Wonderful place "
The price is AED 559
AED 764 total
includes taxes & fees
30 Sep - 1 Oct
Sentral Michigan Avenue
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (370)
"Great place to stay in the South Loop area. Super nice. Super clean. Super quiet."
The price is AED 721
AED 846 total
includes taxes & fees
21 Oct - 22 Oct
Sonder South Wabash
Sonder Market Hall
3.5 star property
8.8 out of 10, Excellent, (161)
"We were really impressed with the location from the green/ pink line. Shopping was a casual 15-20 minutes walk. 2 pubs across the road. Nice safe environment about the location "
The price is AED 434
AED 510 total
includes taxes & fees
22 Oct - 23 Oct
Sonder Market Hall
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.