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Holiday Homes in Chicago Grayland Station

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Chicago Grayland Station holiday homes

A modern living room with a sofa, armchair, coffee table, and a decorative vase on a console table.

1. 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
A modern kitchen with dark cabinetry, a white countertop, and a wooden floor.

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

Old Irving Neighborhood | 20 Min Uber to Mag Mile
Irving Park
9.4 out of 10, Exceptional, (6 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
A water park with a green slide, a water jet feature, and a pool area.

3. 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, (47 reviews)
"Superb host and excellent accommodations. Can't get better than this experience. "
United States
Michael S.
Historic 1920s Private Bungalow Near Logan Square, pool and beach
A modern kitchen with white cabinets, a central island, stainless steel appliances, and pendant lighting.

4. Stunning 6 BR Home * Chicago * Centrally Located

Stunning 6 BR Home * Chicago * Centrally Located
Albany Park
9.4 out of 10, Exceptional, (27 reviews)
"Great place to stay when visiting Chicago."
United States
G T.
Stunning 6 BR Home * Chicago * Centrally Located
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

5. 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)
"We had a great time and accommodations were great as well."
United States
Jackie S.
5 Star Epicurean Experience with Hip, Modern, Gazebo with BBQ Grill & Sleeps 16
A modern hotel room with a bed, a sofa, a coffee table, a TV, and artwork on the wall.

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

Sleeps 26 • Modern Multi-Unit • Gym • Workspaces
Irving Park
The price is NZ$2,614
includes taxes & fees
5 Oct - 6 Oct
Sleeps 26 • Modern Multi-Unit • Gym • Workspaces
A modern kitchen with blue cabinets, a wooden island, stainless steel appliances, and a dining area with a table and chairs.

7. 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, (12 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
A modern kitchen with white cabinets, a granite countertop, and a stainless steel range hood.

8. 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, (13 reviews)
"Perfect spot and location!"
United States
Andrew V.
Stunning 4-Bed 4-Bath Home - Prime Location OHare & Downtown <25-min, Free PRKNG
A modern living room with a curved dark blue sofa, a glass coffee table, and a beige armchair. There is a ceiling fan, large windows, and a plant on the windowsill.

9. 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
A backyard patio with a fire feature, a wooden table with snacks, and a seating area with patterned cushions.

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
A modern kitchen with white cabinets, a marble countertop, and a central island with bar stools.

11. 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!
A spacious kitchen with a large island, stainless steel appliances, and a modern pendant light.

12. 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, (8 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
A spacious kitchen with a large island, pendant lighting, and a dining area with a view to the outside.

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

Modern Logan Square Luxury: 5 bedroom - sleeps 16!
Avondale
9.8 out of 10, Exceptional, (54 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!
A spacious living room with a large chandelier, multiple seating options, and a chessboard on the floor.

14. 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!
A modern living room with a flat-screen TV, a sofa, a coffee table, and a large window.

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

Irving Park/Avondale Updated Vintage Top Unit in 2-Flat
Irving Park
9.4 out of 10, Exceptional, (3 reviews)
"I stayed here with my adult sons and it was fantastic. Very clean, within walking distance to good restaurants and coffee as well as train and bus lines. We loved it!"
United Kingdom
Carla E.
Irving Park/Avondale Updated Vintage Top Unit in 2-Flat
A modern living room with a hanging chair, a glass coffee table, a TV, and a potted plant.

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
A modern kitchen with a large island, stainless steel appliances, and pendant lighting.

17. Game Room, Deck & Yard: Chicago Home

Game Room, Deck & Yard: Chicago Home
Albany Park
9.8 out of 10, Exceptional, (6 reviews)
"I had a great stay and the home was amazing everything was a 10/10"
United States
Mariah N.
Game Room, Deck & Yard: Chicago Home
A compact kitchen with dark cabinets, a microwave, a stove, and a dining area with a table and chairs.

18. 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!
A modern kitchen with white cabinets, a stainless steel stove, and a microwave.

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

Beautiful Home - Great for Groups, Parking & Food
Irving Park
Beautiful Home - Great for Groups, Parking & Food
A hallway with hardwood flooring, white walls, and a door on the right.

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

Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

10/10 Excellent
"Staff was great and we had a great stay"
Jennifer 1-night trip
Posted 2 hours ago
Hampton Inn & Suites Chicago Medical District UIC

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