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Holiday Homes in Chicago Grayland Station

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Our top choices for Chicago Grayland Station holiday homes

1. Gorgeous 5 BDR/ 4BA in Logan Square w/Parking!

Gorgeous 5 BDR/ 4BA in Logan Square w/Parking!
Avondale
9.2 out of 10, Wonderful, (50 reviews)
"Maria was a pleasure to work with . Her home was in a great location and close to downtown."
United States
Debra G.
Gorgeous 5 BDR/ 4BA in Logan Square w/Parking!

2. Historic 1920s Private Bungalow Near Logan Square, pool and beach

Historic 1920s Private Bungalow Near Logan Square, pool and beach
Hermosa
10.0 out of 10, Exceptional, (49 reviews)
"Fantastic part of town and a great hostess. Would recommend to anyone with a family."
United States
Martha M.
Historic 1920s Private Bungalow Near Logan Square, pool and beach

3. Stunning 6 BR Home * Chicago * Centrally Located

Stunning 6 BR Home * Chicago * Centrally Located
Albany Park
9.4 out of 10, Exceptional, (29 reviews)
"Great place to stay when visiting Chicago."
United States
G T.
Stunning 6 BR Home * Chicago * Centrally Located

4. 5 Star Epicurean Experience with Hip, Modern, Gazebo with BBQ Grill & Sleeps 16

5 Star Epicurean Experience with Hip, Modern, Gazebo with BBQ Grill & Sleeps 16
Portage Park
10.0 out of 10, Exceptional, (9 reviews)
"The property was a perfect size for our group. It was exactly as advertised. It has everything you need for a weekend gathering with friends or family. The neighborhood was quite and safe. Will definitely recommend and will use again for future bookings."
United States
edz b.
5 Star Epicurean Experience with Hip, Modern, Gazebo with BBQ Grill & Sleeps 16

5. Old Irving Neighborhood | 20 Min Uber to Mag Mile

Old Irving Neighborhood | 20 Min Uber to Mag Mile
Irving Park
9.6 out of 10, Exceptional, (7 reviews)
"This home was great! Walking distance to some local breweries, restaurants, and just a short ride to downtown and the beaches. Plenty of beds for a large family/group and 2 big flat screen tv’s. The back yard was perfect for relaxing and enjoying the beautiful weather. Collette made the Check-in / check out process so easy and she was extremely accommodating. Thanks again for a great stay!"
United States
David
Old Irving Neighborhood | 20 Min Uber to Mag Mile

6. Irving Park/Avondale Updated Vintage Top Unit in 2-Flat

Irving Park/Avondale Updated Vintage Top Unit in 2-Flat
Irving Park
9.6 out of 10, Exceptional, (4 reviews)
"It was very clean and quiet!"
United States
Zachary H.
Irving Park/Avondale Updated Vintage Top Unit in 2-Flat

7. Modern 6 BR 3 Baths 11 beds Sleeps 17 Birthday

Modern 6 BR 3 Baths 11 beds Sleeps 17 Birthday
Albany Park
10.0 out of 10, Exceptional, (3 reviews)
"We enjoyed our stay! The home is beautiful and the backyard is a great spot for a large group to hang out."
United States
Blake S.
Modern 6 BR 3 Baths 11 beds Sleeps 17 Birthday

8. Updated Chicago Bungalow on a Beautiful and Calm Neighborhood Greenway Boulevard

Updated Chicago Bungalow on a Beautiful and Calm Neighborhood Greenway Boulevard
Belmont Cragin
9.4 out of 10, Exceptional, (13 reviews)
"Very clean, spacious, and host was very kind n helpful. "
United States
Daisha C.
Updated Chicago Bungalow on a Beautiful and Calm Neighborhood Greenway Boulevard

9. Stunning 4-Bed 4-Bath Home - Prime Location OHare & Downtown <25-min, Free PRKNG

Stunning 4-Bed 4-Bath Home - Prime Location OHare & Downtown <25-min, Free PRKNG
Irving Park
9.6 out of 10, Exceptional, (14 reviews)
"Perfect spot and location!"
United States
Andrew V.
Stunning 4-Bed 4-Bath Home - Prime Location OHare & Downtown <25-min, Free PRKNG

10. BoHo House - A Chic, 1903 Chicago Workers Cottage

BoHo House - A Chic, 1903 Chicago Workers Cottage
Avondale
10.0 out of 10, Exceptional, (21 reviews)
"Host was very communicative, property was clean and as described, stay was comfortable and fun."
United States
Elizabeth B.
BoHo House - A Chic, 1903 Chicago Workers Cottage

11. Modern Logan Square Luxury: 5 bedroom - sleeps 16!

Modern Logan Square Luxury: 5 bedroom - sleeps 16!
Avondale
9.8 out of 10, Exceptional, (55 reviews)
"East access to everything we needed, was the perfect size for a large group to move around easily. Would recommend"
United States
Michael C.
Modern Logan Square Luxury: 5 bedroom - sleeps 16!

12. New! Beautiful 7BD Home - Sleeps 15 + 2 Car Garage

New! Beautiful 7BD Home - Sleeps 15 + 2 Car Garage
Albany Park
10.0 out of 10, Exceptional, (3 reviews)
"Loved this impeccably clean home, neighborhood! A Chicago gem. "
United States
Mary S.
New! Beautiful 7BD Home - Sleeps 15 + 2 Car Garage

13. Elegant 3-Bed, 3-Bath Home in Chicago <25-minutes to O’Hare & Downtown + Parking

Elegant 3-Bed, 3-Bath Home in Chicago <25-minutes to O’Hare & Downtown + Parking
Irving Park
9.8 out of 10, Exceptional, (9 reviews)
"Great location, house was comfortable and well equipped. Great experience!"
United States
Shannon D.
Elegant 3-Bed, 3-Bath Home in Chicago <25-minutes to O’Hare & Downtown + Parking

14. Sleeps 26 • Modern Multi-Unit • Gym • Workspaces

Sleeps 26 • Modern Multi-Unit • Gym • Workspaces
Irving Park
10.0 out of 10, Exceptional, (1 review)
"Nice and spacious thanks again for good commuincation"
United States
Sasha H.
The price is NZ$3,388
includes taxes & fees
4 Dec - 5 Dec
Sleeps 26 • Modern Multi-Unit • Gym • Workspaces

15. 3 Bdrm 2 Bath House Sleeps 8-10 in Chicago 2.5 miles to Wrigley w/ 2 car garage.

3 Bdrm 2 Bath House Sleeps 8-10 in Chicago 2.5 miles to Wrigley w/ 2 car garage.
Irving Park
10.0 out of 10, Exceptional, (10 reviews)
"Good location All needed amenities Safe"
United States
Wes N.
3 Bdrm 2 Bath House Sleeps 8-10 in Chicago 2.5 miles to Wrigley w/ 2 car garage.

16. Chic 3BR King Bed+Work-Friendly+ Firepit

Chic 3BR King Bed+Work-Friendly+ Firepit
Irving Park
8.8 out of 10, Excellent, (3 reviews)
"very nice property with a wonderful host!"
United States
daelian m.
Chic 3BR King Bed+Work-Friendly+ Firepit

17. 6 BDRM/ 6 BATH LUX Avondale Home, Sleeps 15, Rooftop Deck & 2 Car Garage!

6 BDRM/ 6 BATH LUX Avondale Home, Sleeps 15, Rooftop Deck & 2 Car Garage!
Avondale
10.0 out of 10, Exceptional, (4 reviews)
"Great place to stay in Chicago"
United States
Erik B.
6 BDRM/ 6 BATH LUX Avondale Home, Sleeps 15, Rooftop Deck & 2 Car Garage!

18. Beautiful Home - Great for Groups, Parking & Food

Beautiful Home - Great for Groups, Parking & Food
Irving Park
Beautiful Home - Great for Groups, Parking & Food

19. LOGAN SQUARE: Chic, Comfy 1st Floor 2 BDRM APT! Parking Incld!

LOGAN SQUARE: Chic, Comfy 1st Floor 2 BDRM APT! Parking Incld!
Avondale
10.0 out of 10, Exceptional, (38 reviews)
"Well appointed place and in a good location. Parking pass works great!"
United States
Shelby
LOGAN SQUARE: Chic, Comfy 1st Floor 2 BDRM APT! Parking Incld!

20. Chicago Life Apartment - 3 bedroom

Chicago Life Apartment - 3 bedroom
Portage Park
Chicago Life Apartment - 3 bedroom
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.
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Top Chicago Grayland Station Hotel Reviews

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