Are there family-friendly vacation rentals in Skokie?

Skokie has more than 70 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

Are there vacation rentals with a dedicated workspace in Skokie?

Yes! Work meets play with ease at over 90 vacation rentals in Skokie featuring dedicated workspaces. Stay connected and productive in your home away from home.

Do apartment rentals in Skokie have free parking?

Absolutely! We offer over 20 apartment rentals with free parking in Skokie. Enjoy a tailored experience with all the comforts you desire.

Are there pet-friendly vacation rentals in Skokie?

Four-legged friends are welcome in Skokie. Choose from more than 40 vacation rentals for guests traveling with pets.

Do apartment rentals in Skokie have a kitchen?

Absolutely! We offer over 30 apartment rentals with a kitchen in Skokie. Enjoy a tailored experience with all the comforts you desire.

Do apartment rentals in Skokie have air conditioning?

Absolutely! We offer over 30 apartment rentals with air conditioning in Skokie. Enjoy a tailored experience with all the comforts you desire.

What are the most popular amenities for House Rentals in Skokie?

Enhance your stay in our House Rentals with the most popular amenities: over 60 homes with a kitchen, over 70 homes with wifi, over 70 homes with air conditioning, over 50 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

Do apartment rentals in Skokie have wifi?

Absolutely! We offer over 30 apartment rentals with wifi in Skokie. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Skokie

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Skokie

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

Guest suite in West Town

4.96 out of 5 average rating, 331 reviews

Secret Garden | Noble Square | Wicker Park

While our place truly is a tucked away secret sanctuary, we are also in a sweet spot of ULTRA CONVENIENCE. Wicker Park/Noble Square/West Town has many great bars & restaurants & is an amazing location for exploring the city. WALK to the action on Division St. or Chicago Ave, Chicago's upcoming gallery district. A 1/2 block to the 56 bus takes you to the Loop in 10 min, or to the heart of Wicker Park in 5. A 10 min walk to the BLUE LINE serving O'Hare & Downtown. And Divvy bikes 1/2 block away.

Guest favorite

Rental unit in Edgewater

4.89 out of 5 average rating, 92 reviews

Adorable Private Edgewater Suite

Cozy exposed brick, garden unit on a quiet street, perfect for relaxing after a night out in the city! Comfy, queen-sized bed, full kitchenette and gated private side entrance so its the perfect spot for your trip to Chicago! We are right by the exciting nightlife of Andersonville and a 10 minute walk to the beach/start of the Lakefront trail. Public Transit is close and easily accessible, the redline "L" can get you downtown in a half-hour train ride. Close to Loyola University, Go Ramblers!

Superhost

Home in Highland Park

5 out of 5 average rating, 28 reviews

Sanctuary on the Ravine

Take it easy at this unique and tranquil get away, walking distance to Ravinia and Beaches 3 Blocks.This historic, beautifully decorated and well maintained home has a lovely, peaceful & serene setting. Multiple indoor and outdoor seating arrangements. Fully stocked kitchen that opens to family room looking out onto several multilevel brick patios and a quiet, private ravine. The extra large living room has a down feathered sectional couch that seats up to 10 people. No parties or gatherings

Guest favorite

Rental unit in West Lake View

4.93 out of 5 average rating, 143 reviews

Sun drenched 2 bedroom 1 bath with Kitchen & W/D

Welcome to beautiful Roscoe Village! Come relax and enjoy a gorgeous loft-like condo that has a huge sun-drenched living room and opens up right to the kitchen. Enjoy cooking on your own in the spacious kitchen and rest easily at night in a spacious king bed in the main bedroom. We love and welcome pets - so no need to leave your fur baby at home. Uber to Wicker Park and Logan Square. You’ll have your own private entrance with a lock box to get into the condo. We look forward to hosting you!

Guest favorite

Home in Wrigleyville

4.91 out of 5 average rating, 172 reviews

Soaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP

Say "WOW" in this top floor, IMMACULATE SPACIOUS with cozy FIREPLACE + ROOFTOP overlooking skyline! Open 2-story layout w/7 bed options, 3 bathrooms, private rooftop with skyline. Luxury flooring, soaring high ceilings, fully-stocked kitchen + huge island, keyless entry, 2 HD TVs, & outdoor grill. Perfect for SPECIAL OCCASIONS! Next to all Wrigley bars & restaurants. Train to Downtown <12 mins. Private parking for rent. As a "GUEST FAVORITE" we boast >1220 5-star reviews across listings!

Guest favorite

Guest suite in Naperville

4.95 out of 5 average rating, 375 reviews

Lake facing cozy little studio with private entry

This is a luxurious cozy little studio facing the lake, featuring a private entrance that is attached to a single family home. The studio is equipped with a top quality queen bed, an in-suite kitchenette including a mini fridge, microwave, and induction top, as well as a luxurious full bathroom. The studio is situated in the safest and friendliest neighborhoods in Naperville conveniently located close to cafes, restaurants, markets, a biking trail, and just minutes away from I88.

Superhost

Rental unit in Logan Square

4.9 out of 5 average rating, 10 reviews

2-level PH w/ 2 Luxe Suites Combined; Spa Access

The top floor sprawling ranch with duplex down offers sky & outdoors views, privacy, & cathedral ceilings, it is connected to your rear 2nd floor suite with 10ft ceilings. A burgeoning neighborhood next to the 606 Trail Amenities: -Uber-fast Wifi streaming, -Hot tub house - 80" + 75" hi-def tv's - 3 sectional couches for living - Designed for an aristocratic feel - The touristy 606 Trail access 100ft away, - YMCA across the street with indoor Olympic size & kiddie-pools!

Superhost

Home in Austin

4.9 out of 5 average rating, 58 reviews

A Comfortable Stay While You are Away in Oak Park

Welcome to this Oak Park home, conveniently minutes from the main expressway, train station, downtown Chicago, and the Medical Center. This entire Oak Park house is ideal for travelers seeking a tranquil and welcoming space to unwind in after a long day, medical professionals, visiting patients at the Medical Center, and families needing long-term housing. The residence is minutes from downtown Oak Park and the historical landmarks of Frank Lloyd Wright's home and studio.

Guest favorite

Home in Schaumburg

4.96 out of 5 average rating, 46 reviews

Paradise in Schaumburg Low Cleaning Fee, 3 BR, 4Bd

Welcome to this inviting 3-bedroom, 1.5-bathroom home in a very safe and quiet neighborhood. Enjoy the tranquility while being close to all shopping, restaurants, and entertainment options. The spacious interior includes a bright living area and a functional kitchen. Additionally, an indoor park nearby offers a great place for year-round recreation. This home combines comfort, convenience, and a prime location, perfect for families and individuals alike.

Guest favorite

Guesthouse in Evanston

4.84 out of 5 average rating, 32 reviews

Tiny house in West Village Arts District

This tiny house (750 sq ft) invites you to explore Evanston's West Village Arts District and shop creative businesses. Just down the block is the newly renovated Robert Crown Recreation Center, where you can check out library books and movies, play soccer, tennis, ice hockey and go ice skating year round. This Tiny House is located in our backyard, so please be respectful of noise and the amount of guests you book on the reservation!

Superhost

Guesthouse in Lake Forest

4.83 out of 5 average rating, 101 reviews

Adorable Carriage House East Lake Forest

Cozy, private carriage house on a quiet, tree-lined street ideally located just minutes from the beach, Lake Forest College, and quaint downtown Lake Forest with convenient metra stop with service to Chicago. Enjoy your stay in this fully-furnished home, complete with TV, coffee machine, and in unit laundry. We look forward to hosting you soon!

Guest favorite

Rental unit in Irving Park

4.96 out of 5 average rating, 275 reviews

Spacious 1BR apartment in a central location

Private 1BR in Avondale neighborhood of Chicago. Right off the Expressway, it's 20 mins from O'Hare, 20 mins from Downtown (both by Blue Line) 20 mins from Wrigley Field (bus). Comfortable and spacious attic apartment in a residential area. Lots of street parking.

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Skokie vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Skokie's top sights

Mariano's171 locals recommend

Starbucks42 locals recommend

Walker Bros. Original Pancake House30 locals recommend

Whole Foods Market30 locals recommend

Backlot Coffee22 locals recommend

Uru-Swati21 locals recommend

Other great vacation rentals in Skokie

Superhost

Home in West Lawn

4.92 out of 5 average rating, 24 reviews

Family Friendly Duplex/9 min from MDW/Free Parking

Guest favorite

Rental unit in West Town

4.85 out of 5 average rating, 125 reviews

3 BR condo with great views, free WIFI and parking

Superhost

Home in Lake Zurich

4.77 out of 5 average rating, 35 reviews

Comfortable 4 bedroom home with indoor fireplace

Guest favorite

Home in Schaumburg

4.85 out of 5 average rating, 71 reviews

Spacious 5 Bedroom 1 Level Renovated Modern House

Guest favorite

Rental unit in Albany Park

4.94 out of 5 average rating, 34 reviews

Elegant 4Bedroom with Free Parking in Albany Park

Guest favorite

Rental unit in Jefferson Park

4.9 out of 5 average rating, 10 reviews

City Gem: Stylish 3BR for Urban Explorers

Superhost

Condo in East Rogers Park

4.79 out of 5 average rating, 28 reviews

Spacious condo with open floor plan and fireplace

Guest favorite

Home in Lombard

5 out of 5 average rating, 15 reviews

Spacious Home in Chicago Suburbs

Show all

Quick stats about vacation rentals in Skokie

Total rentals
130 properties
Total number of reviews
7K reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
90 properties have a dedicated workspace
Wifi availability
130 properties include access to wifi

Frequently Asked Questions

Are there family-friendly vacation rentals in Skokie?
Skokie has more than 70 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there vacation rentals with a dedicated workspace in Skokie?
Yes! Work meets play with ease at over 90 vacation rentals in Skokie featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do apartment rentals in Skokie have free parking?
Absolutely! We offer over 20 apartment rentals with free parking in Skokie. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Skokie?
Four-legged friends are welcome in Skokie. Choose from more than 40 vacation rentals for guests traveling with pets.
Do apartment rentals in Skokie have a kitchen?
Absolutely! We offer over 30 apartment rentals with a kitchen in Skokie. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Skokie have air conditioning?
Absolutely! We offer over 30 apartment rentals with air conditioning in Skokie. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Skokie?
Enhance your stay in our House Rentals with the most popular amenities: over 60 homes with a kitchen, over 70 homes with wifi, over 70 homes with air conditioning, over 50 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do apartment rentals in Skokie have wifi?
Absolutely! We offer over 30 apartment rentals with wifi in Skokie. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Skokie

Top-rated vacation rentals in Skokie

Guest suite in West Town

Rental unit in Edgewater

Home in Highland Park

Rental unit in West Lake View

Home in Wrigleyville

Guest suite in Naperville

Rental unit in Logan Square

Home in Austin

Home in Schaumburg

Guesthouse in Evanston

Guesthouse in Lake Forest

Rental unit in Irving Park

Vacation rentals for every style

Apartments

Houses

Hotels

Popular amenities for Skokie vacation rentals

Stay near Skokie's top sights

Other great vacation rentals in Skokie

Home in West Lawn

Rental unit in West Town

Home in Lake Zurich

Home in Schaumburg

Rental unit in Albany Park

Rental unit in Jefferson Park

Condo in East Rogers Park

Home in Lombard

Quick stats about vacation rentals in Skokie

Total rentals

Total number of reviews

Family-friendly rentals

Pet-friendly rentals

Rentals with dedicated workspaces

Wifi availability

Frequently Asked Questions

Destinations to explore