Vacation rentals in Skokie

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Top-rated vacation rentals in Skokie

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Guest favorite

Apartment in Evanston

4.95 out of 5 average rating, 115 reviews

Vintage sunlit 2.5 BR apt. Perfect for families!

Welcome to the sunny, spacious, 2nd floor full apartment of our 1920's home! While we live downstairs, the whole upstairs space is yours. Living room, dining room, kitchen w/ DW, full bath, 2 BR, charming sitting room w/ electric FP. Perfect for up to 5 guests. The vintage kitchen is well supplied including Keurig. LR has sofa-bed, love seat, games & 50" ROKU smart TV to connect to streaming services. Kid stuff inc. pk & play Easy 20 min walk for trains to city, 5 min drive to lake. Wifi

Sep 17 – 24

R3,092 ZAR per night

Guest favorite

Guesthouse in Evanston

4.98 out of 5 average rating, 202 reviews

Cottage in a Garden

Enjoy the serenity of our secret garden from your private guest house. Enjoy privacy on the covered sun porch. Watch butterflies float by in the pollinator garden. Listen to evening quiet on the patio overlooking the garden. Spin some records from the eclectic collection. Stroll the leafy neighborhood. Stop for a beer at award-winning Temperance Brewery. 5 minute walk to Divvy bike station gives you access to all of Chicago and CTA/Metra train. Short ride to lakefront, Northwestern, downtown.

Mar 15 – 22

R2,895 ZAR per night

Guest favorite

Guest suite in Chicago

4.98 out of 5 average rating, 111 reviews

Gorgeous Studio 15 Minutes From Ohare!

Private, cozy and spacious studio apartment. This wonderful apartment is clean and ready to be your home away from home in Chicago! Full kitchen and bath! Spacious Backyard! Free Parking! On a beautiful treelined street in the Dunning neighborhood. Great for couples & business travelers! Close to great restaurants and parks, Rosemont Convention Center (10 minutes), O’ Hare Aiport (15 minutes), Downtown (35-45minutes). *Travel times are non rush hour and can increase depending on time/events*

Sep 13 – 20

R1,713 ZAR per night

Guest favorite

Apartment in Evanston

4.97 out of 5 average rating, 406 reviews

Charming, Sunny Apartment with Backyard Garden

House of the Blue Doors Enjoy staying with us in this spacious 1st floor flat. Furnished by the resident designer in tasteful neutrals, original curated artwork, one of a kind furniture and accent pieces. Sip morning coffee or a glass of wine in the sunlit kitchen or front porch, fire up the backyard grill for a barbecue. Soak in the award winning Chicago ceramic artist designed and made floor in the bathroom. Close to Northwestern, Chicago, Lake Michigan, everything Evanston offers.

Feb 12 – 19

R2,901 ZAR per night

Guest favorite

Guest suite in Evanston

4.97 out of 5 average rating, 213 reviews

A guest suite centrally located, but so quiet...

IF... you want to race into the city to see a play, go for a jog along the lake, have a quick coffee with a friend or enjoy a fine restaurant to celebrate a special occasion, it's all here in the lovely lakeside town of EVANSTON, IL. You can enjoy it all while living in my guest suite w/private kitchen, private bath, private entry, shared laundry area and......., if you need it, garage parking, too! Enjoy my garden on warm summer days; in winter, you will love the heated floor!

Feb 28 – Mar 7

R2,868 ZAR per night

Guest favorite

Apartment in Evanston

4.95 out of 5 average rating, 210 reviews

Crisp and Clean 2BD Getaway Near Downtown Evanston

My top floor, 2 bedroom home sits in a quiet cul-de-sac, about a mile from downtown Evanston; a 15 min walk to the Dempster Purple line station, which brings you right into Chicago. Northwestern and Loyola are nearby for a visit too! The area has wonderful lakeside parks and beaches, so no matter the time of year, you'll appreciate the natural beauty! Grocery stores, coffee shops, and restaurants are within walking distance as well.

Dec 2 – 9

R2,732 ZAR per night

Guest favorite

Guest suite in Evanston

4.83 out of 5 average rating, 326 reviews

Huge, cozy one bedroom semi-basement apartment

1000 SF Close both to Chicago area and the lake and the suburbs. It has a side separate entrance from the main house. One bedroom with one queen bed. A pull out couch too. A fully equipped kitchen. One full bathroom with a shower , no tub. A cozy living room with TV. This propery has surveillance cameras . Strict rules will be applied to violation of maximum capacity of 4 people. The place is not rented for parties !

Jul 16 – 23

R1,769 ZAR per night

Guest favorite

Apartment in Skokie

4.91 out of 5 average rating, 530 reviews

Cozy Garden Unit in Quiet Neighborhood

A cozy garden unit in the heart of skokie, off of a quiet residential street with plenty of street parking. Just a mile away from the Skokie-Dempster Yellow line train that leads to downtown Chicago, and within a mile from Old Orchard Mall and plenty of great eateries such as: Chick-fil-A, Portillo's, Culver's, Oberwies, Kaufman's Bagel, and more. 15 minutes away from Evanston and the Beautiful Lake Michigan shoreline!

Mar 26 – Apr 2

R2,653 ZAR per night

Guest favorite

Guest suite in Chicago

4.94 out of 5 average rating, 177 reviews

Lincoln Square In-laws Suite: Private Entrance

Garden apartment room with private entrance and ensuite bathroom. All the amenities you'll need for either a work trip, city sightseeing, or just a comfy bed. Located in the vibrant Lincoln Square neighborhood. Only minutes away from the train. Fast wifi, and a large desk for working away from home. P.S. You will most likely find a few beers from a Chicago brewery in the fridge.

Sep 15 – 22

R1,975 ZAR per night

Guest favorite

Apartment in Skokie

4.97 out of 5 average rating, 120 reviews

Charming Apt.Fully Equipped Prk.Inc 12 min 2 Lake

Newly renovated, 2-bedroom apartment. New appliances. Relaxing atmosphere. Walking distance to shopping, restaurants, grocery, train station, etc. Nice and quiet neighborhood. Central air & heating, washer & dryer, iron & ironing board, shampoo, conditioner, body wash, hair dryer, coffee maker, toaster, large fridge. All kitchen utensils available for use.

Aug 21 – 28

R3,239 ZAR per night

Superhost

Apartment in Evanston

4.83 out of 5 average rating, 215 reviews

Adorable 1BR apartment near Northwestern

Cozy and comfortable one bedroom apartment with full kitchen and updated bath. Recently re-decorated with fresh carpet, paint and new queen bed. Located on the second floor of a single family 2-flat style home in a quiet, residential neighborhood. Ample, free street parking. One additional person can be accommodated with blow-up mattress.

Aug 28 – Sep 4

R2,851 ZAR per night

Guest favorite

Guest suite in Skokie

4.86 out of 5 average rating, 148 reviews

Adorable studio style unit - Self check in ⚡️

Cozy studio style unit close to downtown Chicago, ORD airport, Wrigley Field, Old Orchard Mall, Northwestern University and much more! The unit has its own kitchen, full bath, Kurig coffee maker available and bottled water in the fridge for your use - all jam packed in this cozy secure space!

Jul 14 – 21

R2,921 ZAR per night

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

Westfield Old Orchard18 locals recommend

Lincolnwood Town Center12 locals recommend

Illinois Holocaust Museum & Education Center6 locals recommend

Pita Inn10 locals recommend

AMC Village Crossing 189 locals recommend

Maggiano's Little Italy3 locals recommend

Other great vacation rentals in Skokie

Guest favorite

Guest suite in Chicago

5.0 out of 5 average rating, 293 reviews

Private Lincoln Square one bed+bath studio apt.

Sep 17 – 24

R2,696 ZAR per night

Superhost

Apartment in Park Ridge

4.78 out of 5 average rating, 320 reviews

Modern Garden apartment (WHOLE UNIT)

Mar 2 – 9

R2,798 ZAR per night

Guest favorite

Apartment in Wilmette

4.86 out of 5 average rating, 119 reviews

Downtown Wilmette Micro Studio

Jun 20 – 27

R2,500 ZAR per night

Guest favorite

Apartment in Chicago

4.94 out of 5 average rating, 191 reviews

Spacious, light-drenched studio-private entrance!

Jul 13 – 20

R2,248 ZAR per night

Guest favorite

Guest suite in Chicago

4.99 out of 5 average rating, 136 reviews

BnB on Grace Street - Modern 2-Bedroom Guest Suite

Oct 14 – 21

R2,363 ZAR per night

Guest favorite

Apartment in Chicago

4.86 out of 5 average rating, 184 reviews

Cozy & Comfy 1bd In Historic Portage Park Bungalow

Jan 9 – 16

R1,553 ZAR per night

Superhost

Apartment in Chicago

4.88 out of 5 average rating, 104 reviews

LAKESIDE PIED `A TERRE STEPS TO BEACH

Oct 25 – Nov 1

R2,284 ZAR per night

Guest favorite

Guest suite in Chicago

4.96 out of 5 average rating, 102 reviews

1BR Historic Rogers Park/West Ridge unit- Sleeps 4

Jan 4 – 11

R2,128 ZAR per night

Show all

Quick stats about vacation rentals in Skokie

Total rentals
130 properties
Wifi availability
120 properties include access to wifi
Rentals with dedicated workspaces
80 properties have a dedicated workspace
Pet-friendly rentals
40 properties allow pets
Family-friendly rentals
70 properties are a good fit for families
Total number of reviews
6.2K reviews

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 80 vacation rentals in Skokie featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Skokie have free parking?
Absolutely! We offer over 50 house 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.
How much does it cost to stay in condo rentals in Skokie?
Experience the best of Skokie with our condo rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
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 Condo Rentals in Skokie?
Enhance your stay in our Condo Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

Vacation rentals in Skokie

Top-rated vacation rentals in Skokie

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

Guest suite in Chicago

Apartment in Park Ridge

Apartment in Wilmette

Apartment in Chicago

Guest suite in Chicago

Apartment in Chicago

Apartment in Chicago

Guest suite in Chicago

Quick stats about vacation rentals in Skokie

Total rentals

Wifi availability

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Are there family-friendly vacation rentals in Skokie?

Are there vacation rentals with a dedicated workspace in Skokie?

Do house rentals in Skokie have free parking?

Are there pet-friendly vacation rentals in Skokie?

Do apartment rentals in Skokie have a kitchen?

How much does it cost to stay in condo rentals in Skokie?

Do apartment rentals in Skokie have air conditioning?

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

Destinations to explore