Top Vacation Homes in Cook County in 2026

Cook County Vacation Homes
Illinois
United States of America
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Top Cities in Cook County

A wooden boardwalk over a river, surrounded by trees and greenery.

Tinley Park

A frozen river with snow-covered banks and trees in the background during sunset.

Matteson

Our top choices for Cook County vacation homes

A modern interior with large windows, a wooden floor, and a conference table with chairs.

A modern office space with a large meeting table, comfortable seating, and large windows offering a view of the city.

A modern living room with a large window, a grey sofa, a round coffee table, and two abstract paintings on the wall.

1. 4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line

Near North Side

9.4 out of 10, Exceptional, (29 reviews)

9.4/10

Exceptional

(29 reviews)

"This was a great property. It was easy to access, easy transportation near by, Whole Foods is right around the corner and the neighborhood is very pleasant. Will definitely stay here again."

Josh

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line

A dining area with a glass-top table, beige upholstered chairs, a patterned rug, and a chandelier.

A living room with a glass coffee table, a potted plant, a flat-screen TV, a dining table with chairs, and a clock on the wall.

A modern kitchen with dark wooden cabinets, a white stove, a microwave, and a sink.

A living room with a glass coffee table, a gray sofa, and a patterned rug.

2. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub

Elmhurst

8.6 out of 10, Excellent, (64 reviews)

8.6/10

Excellent

(64 reviews)

"We had a wonderful stay"

Anonymous traveler

The price is AED 661

AED 661

AED 1,360 total

includes taxes & fees

12 Oct - 13 Oct

LUXE 3 BR, 2 BA + Hot Tub

A television on a wooden cabinet displaying a streaming service interface with various app icons and a search bar.

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a central island with stools.

A bedroom with a bed, a chair, a ceiling fan, a window with curtains, and a wall with a dreamcatcher and a framed picture.

A room with two striped armchairs, a small wooden table, and a lamp. A window with blinds and curtains is visible.

3. Charming Home in Portage Park

Charming Home in Portage Park

Portage Park

8.2 out of 10, Very good, (11 reviews)

8.2/10

Very good

(11 reviews)

"Plenty of lovely little restaurants and places near by! I think the best part is having a 3 minute *walk* to a full on grocery store. Great little VRBO, no complaints!"

Dwayne M.

Charming Home in Portage Park

A staircase with wooden steps leading to a kitchen area.

A living room with a grey sofa, a wooden shelf unit, and a black door.

A dining table set with white plates, bowls, and glasses, surrounded by upholstered chairs.

A modern kitchen with white cabinets, a granite countertop, a stainless steel stove, and a microwave.

4. Cozy 3-bedroom house in family-oriented Melrose Park.

Cozy 3-bedroom house in family-oriented Melrose Park.

Melrose Park

9.6 out of 10, Exceptional, (51 reviews)

9.6/10

Exceptional

(51 reviews)

"Great time overall"

Lucus

Cozy 3-bedroom house in family-oriented Melrose Park.

A living room with a beige sofa, a coffee table, a patterned rug, and a wall art piece.

A modern bathroom with a white sink, toilet, and glass shower enclosure.

A modern kitchen with white cabinets, a microwave, a stove, and a dishwasher.

A bedroom with a bed, bedside tables, a desk, and a patterned rug.

5. Modern 2-Bedroom House with Free Parking and Convenient Location,

Modern 2-Bedroom House with Free Parking and Convenient Location,

Skokie

5.4 out of 10, (6 reviews)

5.4/10

(6 reviews)

"Conveniently located to good retail and restaurants!Mir was a great host and provided excellent communication. Would definitely stay again."

Damario J.

Modern 2-Bedroom House with Free Parking and Convenient Location,

A living room with a dark blue sofa, a dining table with chairs, and a large window with curtains.

A staircase leading to a white balcony with a railing, surrounded by blooming pink trees.

A kitchen with wooden cabinets, a central island, and a large window.

A kitchen with wooden cabinets, a large island, a sink, and a stove.

6. Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

Near North Side

9.4 out of 10, Exceptional, (127 reviews)

9.4/10

Exceptional

(127 reviews)

"Was perfect size for the group we had staying. Was easy to walk to anywhere we needed to go."

Rheann H.

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

A modern kitchen with blue cabinets, stainless steel appliances, and a wooden floor.

A hallway with a patterned rug, a black bench, and a framed artwork on the wall.

A stone house with a white door, a small porch, and a mailbox.

A backyard with a wooden fence, a grassy lawn, and a patio area with a chair and table.

7. Your Home Away From Home in Sauk Village

Your Home Away From Home in Sauk Village

Sauk Village

7.4 out of 10, Good, (10 reviews)

7.4/10

Good

(10 reviews)

"It was a great place to stay while visiting my family for the weekend. They j"

Johanna G.

Your Home Away From Home in Sauk Village

A modern balcony with a city view, a cushioned chair, a small table with a plant, and a potted plant on the floor.

A bedroom with a large bed, a window, and three framed documents on the wall.

A modern building with a glass facade, surrounded by a courtyard with benches and greenery.

8. ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments

Near North Side

9.4 out of 10, Exceptional, (33 reviews)

9.4/10

Exceptional

(33 reviews)

"Super clean great location short drive to everything we wanted to see!"

eric p.

The price is AED 1,113

AED 1,113

AED 2,479 total

includes taxes & fees

14 Oct - 15 Oct

ENVITAE Hotel, 4BR Luxury Modern Apartments

A beach with palm trees, a white fence, and a city skyline in the background.

A spacious conference room with a long table, leather chairs, and a sofa.

A hotel room with two beds, a chandelier, large windows with curtains, and a television.

A multi-story building with a stone facade, large windows, and a black metal fence.

9. Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces

Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces

Downtown Chicago

10.0 out of 10, Exceptional, (24 reviews)

10/10

Exceptional

(24 reviews)

"good place"

Irving Raul Q.

Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces

A modern kitchen with stainless steel appliances, a microwave, and a wooden floor.

A modern living room with a sofa, a round coffee table, a plant, and a view of the city through large windows.

10. Modern 3BR Apartment Near North Ave Shops

Modern 3BR Apartment Near North Ave Shops

Near North Side

9.8 out of 10, Exceptional, (7 reviews)

9.8/10

Exceptional

(7 reviews)

Modern 3BR Apartment Near North Ave Shops

A spacious kitchen with wooden cabinets, a central island with bar stools, and pendant lighting.

A circular fire pit table surrounded by two white cushioned chairs, with a brick building and a wooden staircase in the background.

A room with a sliding glass door leading to a balcony with a wooden railing and potted plants.

A spacious kitchen with a large island, wooden cabinets, and pendant lighting.

11. Luxurious Four-Level Home with Personal Touches Everywhere

Luxurious Four-Level Home with Personal Touches Everywhere

Lakeview

10.0 out of 10, Exceptional, (63 reviews)

10/10

Exceptional

(63 reviews)

"Our family of 12 were in town for a wedding and had a wonderful stay at this beautiful home. Everything was as described and Jeremy was so helpful! Will definitely stay again!"

Robert C.

Luxurious Four-Level Home with Personal Touches Everywhere

A modern kitchen with wooden cabinets, granite countertops, stainless steel appliances, and pendant lighting.

A living room with a grey sofa, two ottomans, a coffee table, a ceiling fan, and a large window with curtains.

A single-story house with a front door, sliding glass windows, and a patio area with a table and chairs.

A spacious kitchen with wooden cabinets, a dining area with a table and chairs, and a large window overlooking a backyard.

12. Single Family home in Schaumburg, IL 3 bed/ 2 full baths/ fully fenced backyard

Single Family home in Schaumburg, IL 3 bed/ 2 full baths/ fully fenced backyard

Schaumburg

9.8 out of 10, Exceptional, (50 reviews)

9.8/10

Exceptional

(50 reviews)

"Everything was great, very convenient for the show we were attending. 2nd time staying here, hope to stay next time as well."

Jeff M.

Single Family home in Schaumburg, IL 3 bed/ 2 full baths/ fully fenced backyard

A dining table with a bottle of wine, two glasses, a vase with white flowers, and a cheese board with fruits.

A white arched cabinet with glass doors, containing kitchen appliances like a blender, toaster, and kettle.

A modern living room with a white sofa, a round coffee table, a fireplace, and a flat-screen TV mounted on the wall.

A room with a black bean bag chair, a small table with a plant, and a tic-tac-toe game on a clear glass table.

13. Sleeps 18 • 8BR • Game Room • Gym • Theater

Sleeps 18 • 8BR • Game Room • Gym • Theater

Portage Park

10.0 out of 10, Exceptional, (9 reviews)

10/10

Exceptional

(9 reviews)

"The house is beautiful with plenty of space, the park is right across the street, was able to host a birthday party with lots to keep the kids entertained and have space to eat and mingle, the rooms were comfortable and surprisingly large for how small the house looks from the outside. The host responded promptly and was accommodating. Would book and recommend to others!"

Ashley Y.

The price is AED 866

AED 866

AED 3,858 total

includes taxes & fees

22 Oct - 23 Oct

Sleeps 18 • 8BR • Game Room • Gym • Theater

A spacious living room with a sofa, coffee table, and a staircase.

A modern kitchen with white cabinetry, stainless steel appliances, and a central island.

A modern living room with a sofa, two armchairs, a coffee table, and a bookshelf.

A two-story residential building with a brick facade and a blue exterior.

14. Bronzeville Jazz Room. Beautiful, cozy, centered, relaxing, rustic.

Bronzeville Jazz Room. Beautiful, cozy, centered, relaxing, rustic.

Bronzeville

10.0 out of 10, Exceptional, (9 reviews)

10/10

Exceptional

(9 reviews)

"Beautiful place! We found it to be perfectly located, quiet, and well-appointed. Tosin was very responsive to our inquiries. Would definitely stay here again on a trip to Chicago."

Shelly F.

Bronzeville Jazz Room. Beautiful, cozy, centered, relaxing, rustic.

A porch with a white railing, a wooden staircase, and a sign reading "URBAN 1710 FARMHOUSE".

A living room with a ceiling fan, a fireplace, and a coffee table.

A wooden staircase with a black handrail leading to a room with white walls and a white door.

A round wooden dining table with a patterned tablecloth, surrounded by four wooden chairs.

15. Urban Farmhouse near O’Hare Airport

Urban Farmhouse near O’Hare Airport

Des Plaines

9.4 out of 10, Exceptional, (65 reviews)

9.4/10

Exceptional

(65 reviews)

"This place was just amazing. Would totally stay again!!! "

Jennifer W.

Urban Farmhouse near O’Hare Airport

A kitchen with granite countertops, a stainless steel dishwasher, and a window with a view.

A wooden staircase with a handrail, a small window with blinds, and a wall-mounted mirror.

A kitchen with a granite countertop, wooden cabinets, a dining area with chairs, and a hallway leading to another room.

A kitchen with granite countertops, wooden cabinets, a dining area with chairs, and a hanging pendant light.

16. Relaxing Oak Park Home

Relaxing Oak Park Home

Oak Park

9.8 out of 10, Exceptional, (96 reviews)

9.8/10

Exceptional

(96 reviews)

"This was our 4th or 5th time staying. It is on a great street in a very walkable neighborhood"

Joan M.

Relaxing Oak Park Home

A living room with two dark sofas, a coffee table with a magazine, a TV, and a chair.

A modern kitchen with white tiles, stainless steel appliances, wooden shelves with plants, and a window with blinds.

A modern bedroom with a bed, bedside tables, a desk with a computer, and a decorative globe.

A dining area with a wooden table, chairs, a bowl of fruit, and a potted plant.

17. Luxury Modern home minutes from Downtown Chicago

Luxury Modern home minutes from Downtown Chicago

Lower West Side

10.0 out of 10, Exceptional, (30 reviews)

10/10

Exceptional

(30 reviews)

"Great stay. Great house. Great host. Tori is the best."

Nicholas K.

Luxury Modern home minutes from Downtown Chicago

A modern kitchen with stainless steel appliances, white cabinetry, and a wooden floor.

A room with two black upholstered chairs with studded edges, a small wooden side table, and a red ladder with a figure.

A bunk bed room with a ceiling light, a window with blinds, and a wall with a leafy pattern.

18. Sweet Home Chicago- 3 BR, 2.5 BA + Game Room, Hot Tub, near O'Hare, Rosemont

Sweet Home Chicago- 3 BR, 2.5 BA + Game Room, Hot Tub, near O'Hare, Rosemont

Dunning

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"This home was very welcoming! We drove all the way from southeast Georgia to find a clean, quiet home decorated with really cool colors and artwork! We reallyyyy enjoyed Chicago!"

Mandy A.

Sweet Home Chicago- 3 BR, 2.5 BA + Game Room, Hot Tub, near O'Hare, Rosemont

A dining area with a table set for six, a living room with a sofa and a coffee table, and a hallway leading to another room.

A residential street with a house, a sidewalk, a bench, and a one-way street sign.

A living room with two sofas, a coffee table, and a ceiling fan.

A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, a microwave, a coffee maker, and a toaster.

19. Updated Forest Park 3 BR Bungalow

Updated Forest Park 3 BR Bungalow

Forest Park

10.0 out of 10, Exceptional, (146 reviews)

10/10

Exceptional

(146 reviews)

"We were very pleased with the property and location! The beds were comfortable and amenities made it very homey. Would recommend and would stay again."

Janet E.

Updated Forest Park 3 BR Bungalow

A modern living room with a large flat-screen TV, a sofa, a coffee table, and a dining area with a table and chairs.

A bedroom with a bed, white walls, wooden flooring, and a ceiling with exposed beams.

A modern kitchen with white cabinets, stainless steel appliances, and wooden flooring.

A dining area with a wooden table, white chairs, a small potted plant, and a sofa with cushions.

20. Spacious 5-bedroom house with movie room, game room and more!

Spacious 5-bedroom house with movie room, game room and more!

Berwyn

6.8 out of 10, (14 reviews)

6.8/10

(14 reviews)

"The home was exactly as described! Clean, comfortable and perfect for our group!"

Angela E.

Spacious 5-bedroom house with movie room, game room and more!

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 Cook County Hotel Reviews

The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good

"Hotel was unique and enjoyed the location. Room was very basic but functional. Lobby was very welcoming."

Lindsey Marie 3-night trip

Posted 7 hours ago

The Chicago Hotel Collection Ambassador Gold Coast

Sports Illustrated Resorts Chicago

10/10 Excellent

"Since Our flight kept being delayed; we arrived very early next day. We notified the front desk when this was happening. Upon our arrival, we were greeted with a friendly front desk person. Our room was ready. The room was spacious. It was beautiful. Staff in the front desk were very friendly and helpful."

Jacqueline 2-night trip

Posted 7 hours ago

Sports Illustrated Resorts Chicago

River Hotel

10/10 Excellent

"Great hotel"

Jose 1-night trip

Posted 8 hours ago

River Hotel

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent

"Perfect location. Everything within walking distance. Bar was amazing"

Mohit 3-night trip

Posted 9 hours ago

InterContinental Chicago Magnificent Mile by IHG

Eurostars Magnificent Mile

10/10 Excellent

"Great location, clean rooms, super kind staff."

Enrique 3-night trip

Posted 14 hours ago

Eurostars Magnificent Mile

Hilton Chicago

10/10 Excellent

"I enjoyed the property's elegance and location, with all the sightseeing sites within walking distance of the hotel. I also enjoyed the Irish pub and restaurant in the main lobby."

Linda 3-night trip

Posted 14 hours ago

Hilton Chicago

Fairmont Chicago at Millennium Park

10/10 Excellent

"Great location. Rooms are very comfortable, clean, and luxurious. Had a great sister's weekend at this location!"

Mona 1-night trip

Posted 20 hours ago

Fairmont Chicago at Millennium Park

The Godfrey Hotel Chicago

10/10 Excellent

"The property was well maintained. The front desk staff was always friendly and helpful. The valet parking was definitely expensive and overall we had a great stay"

Cleo 3-night trip

Posted 2 days ago

The Godfrey Hotel Chicago

Club Quarters Hotel, Central Loop, Chicago

10/10 Excellent

"Clean, quiet, comfortable, convenient with great check-in service. Affordable. Great location. All you need."

Forrest 1-night trip

Posted 3 days ago

Club Quarters Hotel, Central Loop, Chicago

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Flights from Evergreen Park
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Vacation Homes in Cook County

Change your mind

Treat yourself

Be picky

Check prices for these dates

Top Cities in Cook County

Tinley Park

Matteson

Our top choices for Cook County vacation homes

1. 4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line

2. LUXE 3 BR, 2 BA + Hot Tub

3. Charming Home in Portage Park

4. Cozy 3-bedroom house in family-oriented Melrose Park.

5. Modern 2-Bedroom House with Free Parking and Convenient Location,

6. Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

7. Your Home Away From Home in Sauk Village

8. ENVITAE Hotel, 4BR Luxury Modern Apartments

9. Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces

10. Modern 3BR Apartment Near North Ave Shops

11. Luxurious Four-Level Home with Personal Touches Everywhere

12. Single Family home in Schaumburg, IL 3 bed/ 2 full baths/ fully fenced backyard

13. Sleeps 18 • 8BR • Game Room • Gym • Theater

14. Bronzeville Jazz Room. Beautiful, cozy, centered, relaxing, rustic.

15. Urban Farmhouse near O’Hare Airport

16. Relaxing Oak Park Home

17. Luxury Modern home minutes from Downtown Chicago

18. Sweet Home Chicago- 3 BR, 2.5 BA + Game Room, Hot Tub, near O'Hare, Rosemont

19. Updated Forest Park 3 BR Bungalow

20. Spacious 5-bedroom house with movie room, game room and more!

Find vacation rentals that suit your style

Top Cook County Hotel Reviews

The Chicago Hotel Collection Ambassador Gold Coast

Explore a world of travel with Expedia