Search Vacation Homes in Skokie

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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Skokie vacation homes

Fridge, microwave, oven, stovetop
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS

Vacation Home in Skokie

Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
10.0 out of 10, Exceptional, (34)
"Great place to congregate with family and a pet. Lots of room to gather."
United States
Leone W.
The price is AED 1,219
AED 2,577 total
includes taxes & fees
5 Jan - 6 January 2026
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Outdoor dining
Culinary DREAM - Tranquil Home - Pizza Oven/BBQ/Smoker

Vacation Home in Skokie

Culinary DREAM - Tranquil Home - Pizza Oven/BBQ/Smoker
9.4 out of 10, Exceptional, (6)
"Super clean and great neighborhood still close to downtown. A fun 20 min uber drive away! "
United States
Kurt P.
The price is AED 1,833
AED 3,092 total
includes taxes & fees
11 Dec - 12 Dec
Culinary DREAM - Tranquil Home - Pizza Oven/BBQ/Smoker
Smart TV
Getaway Near ORD With Great Local Amenities

Vacation Home in Des Plaines

Getaway Near ORD With Great Local Amenities
9.0 out of 10, Wonderful, (4)
"Very nice and clean place to stay at. Great communication from property manager. I would absolutely stay here again!"
United States
Stephanie G.
The price is AED 256
AED 1,022 total
includes taxes & fees
11 Dec - 12 Dec
Getaway Near ORD With Great Local Amenities
Private kitchen
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking

Vacation Home in La Grange Highlands

Guesthouse Gem 2BR, Smart TVs, W/D, & Parking
10.0 out of 10, Exceptional, (2)
"Good communication from beginning to the end. Will definitely stay at this property again on my next Chicago vacation."
United States
Arnie B.
The price is AED 355
AED 985 total
includes taxes & fees
11 Dec - 12 Dec
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking
Fridge, microwave, oven, stovetop
Modern Apt in Trendy Neighborhood w/ Free Parking

Vacation Home in Avondale

Modern Apt in Trendy Neighborhood w/ Free Parking
2.0 star property
The price is AED 328
AED 679 total
includes taxes & fees
14 Dec - 15 Dec
Modern Apt in Trendy Neighborhood w/ Free Parking
Outdoor dining
Perfect modern 3-bedroom house Near Chicago • Fireplace & Yard

Vacation Home in Schaumburg

Perfect modern 3-bedroom house Near Chicago • Fireplace & Yard
The price is AED 505
AED 619 total
includes taxes & fees
11 Dec - 12 Dec
Perfect modern 3-bedroom house Near Chicago • Fireplace & Yard
Smart TV
Enamored in Elmhurst

Vacation Home in Elmhurst

Enamored in Elmhurst
2.0 star property
10.0 out of 10, Exceptional, (13)
"Great stay"
United States
Aaron B.
The price is AED 780
AED 1,811 total
includes taxes & fees
11 Dec - 12 Dec
Enamored in Elmhurst
Exterior detail
Master qtr close to nature & easy urban facilities

Vacation Home in Riverwoods

Master qtr close to nature & easy urban facilities
9.8 out of 10, Exceptional, (73)
"It was a great respite."
United States
VIncent L.
The price is AED 327
AED 678 total
includes taxes & fees
15 Dec - 16 Dec
Master qtr close to nature & easy urban facilities
Terrace/patio
Modern Victorian Vibes ❤️ | Character & Charm

Vacation Home in Oak Park

Modern Victorian Vibes ❤️ | Character & Charm
10.0 out of 10, Exceptional, (26)
"Great location and walkable to restaurants. "
United States
Laura B.
The price is AED 578
AED 1,789 total
includes taxes & fees
11 Dec - 12 Dec
Modern Victorian Vibes ❤️ | Character & Charm
Microwave, oven, stovetop, dishwasher
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Vacation Home in Maywood

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
8.0 out of 10, Very Good, (19)
"Very nice place "
United States
Elliot H.
The price is AED 545
AED 890 total
includes taxes & fees
11 Dec - 12 Dec
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Property grounds
Walk to Wrigley Field! Townhouse w/ Pool Table

Vacation Home in Lakeview

Walk to Wrigley Field! Townhouse w/ Pool Table
2.0 star property
The price is AED 511
AED 2,317 total
includes taxes & fees
11 Dec - 12 Dec
Walk to Wrigley Field! Townhouse w/ Pool Table
Exterior detail
Vintage Urban Retreat

Vacation Home in Oak Park

Vintage Urban Retreat
10.0 out of 10, Exceptional, (13)
"This location was very convenient, and in close proximity to both downtown Oak Park, and the greater Chicago area."
United States
Thomas P.
The price is AED 607
AED 1,826 total
includes taxes & fees
11 Dec - 12 Dec
Vintage Urban Retreat
4 bedrooms, iron/ironing board, travel crib, WiFi
Theater • Game Room • Gym • Firepit • 4BR Home

Vacation Home in Belmont Cragin

Theater • Game Room • Gym • Firepit • 4BR Home
2.0 star property
The price is AED 342
AED 2,006 total
includes taxes & fees
5 Jan - 6 January 2026
Theater • Game Room • Gym • Firepit • 4BR Home
Private kitchen
Spacious Deck & Balcony, Game Area, Garage

Vacation Home in Glen Ellyn

Spacious Deck & Balcony, Game Area, Garage
9.6 out of 10, Exceptional, (18)
"Great place to stay. "
United States
Jason T.
The price is AED 659
AED 1,898 total
includes taxes & fees
11 Dec - 12 Dec
Spacious Deck & Balcony, Game Area, Garage
Exterior
Townhome with Game Zone, Big Beds, & Smart TVs

Vacation Home in Westmont

Townhome with Game Zone, Big Beds, & Smart TVs
The price is AED 571
AED 1,629 total
includes taxes & fees
11 Dec - 12 Dec
Townhome with Game Zone, Big Beds, & Smart TVs
Fridge, microwave, oven, stovetop
Cozy Home by O'Hare + EV Plug

Vacation Home in Des Plaines

Cozy Home by O'Hare + EV Plug
9.0 out of 10, Wonderful, (4)
"Charming property in a quiet neighborhood. Host were exceptionally accommodating and replied promptly with questions. Would happily stay in this home again."
United States
Michael H.
The price is AED 595
AED 1,249 total
includes taxes & fees
15 Dec - 16 Dec
Cozy Home by O'Hare + EV Plug
Fridge, microwave, oven, stovetop
Wonderful in Wood Dale, right by O’Hare airport!

Vacation Home in Wood Dale

Wonderful in Wood Dale, right by O’Hare airport!
10.0 out of 10, Exceptional, (17)
"Great property and great host!"
United States
Darin H.
The price is AED 658
AED 1,444 total
includes taxes & fees
11 Dec - 12 Dec
Wonderful in Wood Dale, right by O’Hare airport!
Private kitchen
LUXE 3 BR, 2 BA + Hot Tub

Vacation Home in Elmhurst

LUXE 3 BR, 2 BA + Hot Tub
8.8 out of 10, Excellent, (38)
"A really nice house, clean and well kept. Neighborhood is older but nice and quiet. Close to highway and lots of restaurants. The owner was very responsive and great to work with. I plan on using this VRBO again in future. Backyard was fenced in and I might bring my pets next time. "
United States
Scott C.
The price is AED 545
AED 1,212 total
includes taxes & fees
15 Dec - 16 Dec
LUXE 3 BR, 2 BA + Hot Tub
Paper towels, dining tables
PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast WiFi

Vacation Home in streamwood

PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast WiFi
10.0 out of 10, Exceptional, (2)
"Was nice would recommend staying with you folks"
United States
Richard W.
The price is AED 713
AED 1,549 total
includes taxes & fees
16 Dec - 17 Dec
PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast WiFi
Smart TV, video games, foosball, table tennis
Your Chicago Hub~ 4 minute Walk to Train~ Pets OK

Vacation Home in Brookfield

Your Chicago Hub~ 4 minute Walk to Train~ Pets OK
10.0 out of 10, Exceptional, (3)
"This house is a 5 star VRBO!The amenities are amazing! Coffee barsGames for kidsComfortable spacesNice kitchenGreat beddingOur host was very responsive and flexible. "
United States
Barbara R.
The price is AED 760
AED 2,039 total
includes taxes & fees
17 Dec - 18 Dec
Your Chicago Hub~ 4 minute Walk to Train~ Pets OK
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 Skokie Hotel Reviews

River Hotel

River Hotel

10/10 Excellent
"Great location, comfortable room, and nice staff."
Claudia 1-night trip
Posted 2 hours ago
River Hotel