A clear lake with a wooden dock, snow-covered mountains, and evergreen trees in the background.

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Homewood vacation homes

A living room with a brown sofa, a coffee table, and a patterned rug. There is a staircase leading to another room.

1. Spacious 3br home near Chicago, fenced yard for pets

Spacious 3br home near Chicago, fenced yard for pets
Richton Park
9.0 out of 10, Wonderful, (30 reviews)
"Very spacious accommodations in a very nice neighborhood. Convenient to food and shopping. Great value for the cost. "
United States
Greg S.
The price is AED 783
AED 1,722 total
includes taxes & fees
20 Oct - 21 Oct
Spacious 3br home near Chicago, fenced yard for pets
A modern kitchen with grey cabinets, a dishwasher, and a ceiling fan.

2. 3-bedroom house in lovely Matteson with cool AC breeze

3-bedroom house in lovely Matteson with cool AC breeze
Matteson
10.0 out of 10, Exceptional, (1 review)
"clean, comfortable, hosts very responsive to communications, neighborhood felt safe, perfect location for our stay to attend sectionals NTRP tennis tournament at HF Racquet and Fitness Club"
United States
Susan H.
The price is AED 1,223
AED 2,385 total
includes taxes & fees
14 Oct - 15 Oct
3-bedroom house in lovely Matteson with cool AC breeze
A bedroom with a bed, a nightstand, a wall-mounted lamp, and a plant.

3. Romantic Escape - Adult Playhouse with Exotic Dungeon

Romantic Escape - Adult Playhouse with Exotic Dungeon
South Holland
8.8 out of 10, Excellent, (13 reviews)
"enjoyed my stay cant wait to book again "
United States
Anonymous traveler
The price is AED 1,432
AED 1,745 total
includes taxes & fees
19 Oct - 20 Oct
Romantic Escape - Adult Playhouse with Exotic Dungeon
A bedroom with a stone wall, a TV mounted on it, a bed with a white comforter, and a view of the outdoors through a window.

4. Beautifully furnished one bedroom loft located in Chicago's South side suburb

Beautifully furnished one bedroom loft located in Chicago's South side suburb
Hazel Green
10.0 out of 10, Exceptional, (1 review)
"Super great location, we had a concert at Tinley Park, then explored Chicago with a river cruise and Second City Everything was perfect and so eat to just chill, come and go as we pleased In a nice neighborhood and interior was furnished beautifully. Definitely worth the price !!"
United States
Nick L.
The price is AED 900
AED 1,261 total
includes taxes & fees
14 Oct - 15 Oct
Beautifully furnished one bedroom loft located in Chicago's South side suburb
A modern kitchen with wooden cabinets, stainless steel appliances, and a white countertop island.

5. Modern 3BR w/Deck · Minutes from I-65. Fenced Yard

Modern 3BR w/Deck · Minutes from I-65. Fenced Yard
Merrilville
8.8 out of 10, Excellent, (3 reviews)
"Great location, excellent pet friendly home. Communication with the host was great."
United States
Lynda L.
The price is AED 680
AED 1,687 total
includes taxes & fees
14 Oct - 15 Oct
Modern 3BR w/Deck · Minutes from I-65. Fenced Yard
A wooden deck with a railing, a staircase, and a window with a wreath.

6. Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
Robertsdale
9.8 out of 10, Exceptional, (35 reviews)
"I had a fun stay "
United States
Jusu K.
The price is AED 526
AED 761 total
includes taxes & fees
18 Oct - 19 Oct
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
A modern kitchen with dark wood cabinets, stainless steel appliances, a granite countertop, and a small island with stools.

7. Lockport Haven/3 King Beds/Wi-fi/Near Downtown!

Lockport Haven/3 King Beds/Wi-fi/Near Downtown!
Lockport
10.0 out of 10, Exceptional, (15 reviews)
"Perfect spot for our group of 6! More than enough dishes/silverware etc. the house was clean and comfortable. Would definitely stay again if in the area."
United States
Kathy L.
The price is AED 826
AED 1,906 total
includes taxes & fees
8 Nov - 9 Nov
Lockport Haven/3 King Beds/Wi-fi/Near Downtown!
A hotel room with two beds, each with green bedding and multiple pillows, a bedside table with a lamp, and a framed plant on the wall.

8. The Grand Gathering Place -Making Forever Memories Near Chicago & Hard Rock

The Grand Gathering Place -Making Forever Memories Near Chicago & Hard Rock
Merrillville
10.0 out of 10, Exceptional, (2 reviews)
"Good location clean full amenities lots of space and convenience."
United States
david d.
The price is AED 1,901
AED 3,820 total
includes taxes & fees
20 Oct - 21 Oct
The Grand Gathering Place -Making Forever Memories Near Chicago & Hard Rock
A living room with a brick fireplace, a television mounted above it, and a dining area with a table and chairs.

9. Couples Getaway - Guesthouse/ In-Law Suite with Jacuzzi/Sauna/Pool

Couples Getaway - Guesthouse/ In-Law Suite with Jacuzzi/Sauna/Pool
Merrillville
9.8 out of 10, Exceptional, (8 reviews)
"The house was cozy and very clean. The hot tub was amazing! Check-in instructions were clear and easy to follow. The host was very helpful and responsive to messages. We would definitely stay again. Thank you!"
United States
Anonymous traveler
The price is AED 1,102
AED 1,740 total
includes taxes & fees
14 Oct - 15 Oct
Couples Getaway - Guesthouse/ In-Law Suite with Jacuzzi/Sauna/Pool
A modern living room with a grey sofa, a black coffee table, and a large window with a view of a house and greenery.

10. Entire home in Lockport, Illinois

Entire home in Lockport, Illinois
Lockport
8.8 out of 10, Excellent, (5 reviews)
"The house is very clean. The host was very kind and responsive. "
United States
Susan B.
The price is AED 718
AED 1,563 total
includes taxes & fees
15 Oct - 16 Oct
Entire home in Lockport, Illinois
A large, two-story house with a covered patio and a well-maintained lawn.

11. Spacious 5-Bedroom Golf Course Home for Getaways

Spacious 5-Bedroom Golf Course Home for Getaways
Merrillville
10.0 out of 10, Exceptional, (7 reviews)
"It was a fantastic experience from arrival to departure. We've played the course every year and our group comes from all over Chicago. It was great to stay the night and enjoy the property versus driving back at the end of our round. The hospitality was great and the accommodations were first class."
United States
Jon R.
The price is AED 3,306
AED 4,180 total
includes taxes & fees
14 Oct - 15 Oct
Spacious 5-Bedroom Golf Course Home for Getaways
A living room with a large flat-screen TV, a brown sofa, a glass coffee table, and orange curtains.

12. Coastal Home | Patio & Firepit | Backyard Games

Coastal Home | Patio & Firepit | Backyard Games
Merrillville
The price is AED 1,337
AED 1,711 total
includes taxes & fees
27 Oct - 28 Oct
Coastal Home | Patio & Firepit | Backyard Games
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 Homewood Hotel Reviews

Courtyard by Marriott Chicago Midway Airport

Courtyard by Marriott Chicago Midway Airport

10/10 Excellent
"Jennifer at the front desk was amazing. So helpful and accommodating to us when our room wasn't ready. Being welcomed so warmly to our stay just set a great tone for our entire time in Chicago. Thank you Jennifer!"
Marina 2-night trip
Posted 1 hour ago
Courtyard by Marriott Chicago Midway Airport

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