Holiday rentals in Skokie

Find and book unique accommodation on Airbnb

Quick stats about holiday rentals in Skokie

  • Total holiday rentals

    Explore 130 holiday rentals in Skokie

  • Nightly prices starting at

    Skokie holiday rentals start at €34 per night before taxes and fees

  • Verified guest reviews

    Over 5,960 verified reviews to help you choose

  • Family-friendly holiday rentals

    80 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wifi availability

    130 of Skokie holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Skokie rentals

  • 4.8 Average rating

    Skokie stays are highly rated by guests – averaging 4.8 out of 5!

Top-rated holiday rentals in Skokie

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

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Top guest favourite
A modern kitchen and living area are showcased within an open-concept space. The kitchen features stainless steel appliances and a large island with seating for three. The cozy living area includes comfortable seating and a low wooden coffee table, complemented by warm wooden flooring.
Flat in West Rogers Park
4.99 out of 5 average rating, 109 reviews

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

Why stay anywhere when you can experience luxury during your travels. This brand new 1-BR apartment was designed with a touch of elegance and offers amenities to make your experience not just satisfying, but memorable. At your finger tips is a full kitchen; luxury bathroom with enormous walk-in shower; separate bedroom w/ queen bed (extra day bed in living room to sleep 3 total); garage parking; garden access; cozy workspace; 2-Smart TVs; bicycle; ample storage for longer stays; WIFI; and more.

Top guest favourite
Home in Northbrook
4.98 out of 5 average rating, 131 reviews

*King bed *Outdoor Living *Sought-After Area

Welcome to our sophisticated ranch style home, nestled in the serene, central Chicago neighborhood of Northbrook. This carefully curated home offers a peaceful retreat in a walkable neighborhood with nearby shopping and dining. With its elegant decor, comfortable furnishings, and modern amenities, the home provides a haven of relaxation. Whether you're enjoying a cup of coffee on the private patio or exploring the area, this home provides the perfect backdrop for a memorable vacation experience.

Top guest favourite
The living area features a spacious sectional sofa and a coffee table at its center. A TV is positioned against a light-colored wall, while a dining space can be seen in the background with a small table and chairs. Natural light is welcomed through multiple windows.
Flat in Evanston
4.96 out of 5 average rating, 318 reviews

Stylish & Comfy Gem near Downtown~Balcony~Parking

My 2nd floor, 2 BD/1BA home sits in a quiet cul-de-sac, about 1 mi 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. -Electric Fireplace -Fully Equipped Kitchen -Queen Sized Bedrooms

Guest favourite
A single-story brick house is presented with a spacious front yard, featuring trimmed greenery and a walkway of stone steps leading to the front door. A driveway, visible to the right, accommodates a garage door with a dark finish.
Home in Skokie
4.95 out of 5 average rating, 121 reviews

Cozy 2 bedroom house/w garage in Skokie

Charming 2B/1.5B house in Skokie IL. This Airbnb boasts plenty of amenities including WIFI, Roku TV's, fully furnished, a beautiful backyard, workout gym and sauna in the basement and a kitchen with top of the line appliances. The house sits on a quiet residential street just 2 minutes away from the nearest interstate taking you to beautiful Downtown Chicago in about 25min . Downtown Skokie is a few minutes away, plenty of shopping options 5min to Village Crossing and 15min to Old Orchard Mall.

Top guest favourite
A modern kitchen and dining area are presented, featuring a sleek island with bar stools and a dining table with six chairs. Natural light is provided by large windows, and contemporary fixtures enhance the space's functionality and design.
Flat in Evanston
4.92 out of 5 average rating, 201 reviews

New 3bd/1.5 bth Apt w/private prkg

A perfect hideaway! This quiet, secluded unit is nestled in lush greenery within walkng dist (1.5M) to NWU. Enjoy our renowned restaurants and theaters, plus easy access to downtown Chgo’s many attractions via the Metra; Sleeps up to 7 guests, with 2 queen beds, 2 single beds, and an 8-foot couch in Liv rm; Ultra-modern kitchen equipped with everything; Dedicated parking space in rear of the bldng; free high-speed Wi-Fi is included. Host lives nearby and responds promptly to any inquiries

Top guest favourite
The open living area features a spacious sectional sofa facing a modern stone fireplace. A wall-mounted smart TV is visible above the fireplace, while a kitchen island with bar seating is positioned nearby. Natural light enters through windows, enhancing the neutral decor.
Home in Skokie
5 out of 5 average rating, 50 reviews

Casa 22 Luxury & Modern 3BD 2BA Home in Skokie

Welcome to Casa 22! Our spacious 3-bed, 2-bath home in Skokie is perfectly designed for groups, families, or business travelers. With room for up to 6 guests, this home combines contemporary décor with thoughtful amenities for a comfortable stay. Located in a prime neighborhood near shopping, dining, and transit, you’re minutes from O'hare Airport and Downtown Chicago. Whether you’re here for work or play, this home offers a serene stay with easy access to everything the city has to offer!

Top guest favourite
The exterior view of the property is framed by lush greenery, including small trees and ornamental plants. A stone pathway leads to the entrance, which features a light-colored door. The building's soft hues complement the natural surroundings under a clear blue sky.
Guest house in Evanston
5 out of 5 average rating, 103 reviews

Mr. Hughes’ Attic, an 80s-themed coach house

Welcome to Mr. Hughes' Attic, a private coach house that pays homage to John Hughes (who filmed many of his movies nearby!) Located in NW Evanston, your stay includes a queen bed, full kitchen, laundry, full bath, dedicated workspace, private balcony, free parking, streaming TV, and more. We're a short walk to Central St shops, restaurants and the Metra train, a five-minute drive to Northwestern, and less than 30 minutes to Chicago. Not wheelchair or ADA accessible. License# STR004.

Top guest favourite
A light-filled living room features a comfortable beige sofa with an accent pillow and a light throw. Adjacent windows allow natural light to stream in, highlighting the wooden flooring and decorative area rug. A small side table holds a lamp, contributing to the calm atmosphere.
Flat in Evanston
4.97 out of 5 average rating, 547 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.

Top guest favourite
An open floor plan living area features a spacious couch paired with a dark coffee table. A soft area rug complements the hardwood flooring. The dining area is visible, showcasing a table for six. Large windows provide natural light to the inviting space.
Townhouse in Evanston
5 out of 5 average rating, 123 reviews

The NICEST place in Evanston for Families 1500Main

Fully Furnished 2-story, 2 bedroom attached Duplex with a King bed in the Primary bedroom and a pair of Twin beds in the 2nd bedroom. Couch on main floor is also a sofa bed that sleeps two if needed. Main floor is wide open floor plan. This space has been set up specifically for short-term rentals of 1-2 weeks or months and has previously been used by Guests looking for homes in the Evanston area or having construction done. We cater to Families visiting Northwestern University.

Guest favourite
A comfortable living room features a blue sectional sofa adorned with soft throws, paired with a wooden coffee table. Natural light enters through large windows, highlighting a stylish armchair and an entertainment unit beneath a mounted TV.
Flat in Evanston
4.9 out of 5 average rating, 144 reviews

Guest Favorite Escape Next to the Beach

1st-floor unit with one flight of stairs. Older building with radiant heat managed by the building. Experience the best of Evanston in our cozy 1BR/1BA apartment near Lake Michigan. Enjoy a fully equipped kitchen, a comfortable bedroom with a queen bed, and a clean bathroom. Explore nearby beaches, stroll along the lakefront, and discover vibrant downtown shops and restaurants. Easy public transit to downtown Chicago. Book now for a memorable Evanston getaway!

Top guest favourite
The spacious bathroom features a freestanding tub and a glass-enclosed shower. A large mirror with a decorative frame is mounted on one wall. The floor is covered with a patterned rug, complementing the warm wall color and wood flooring.
Flat in Evanston
4.97 out of 5 average rating, 221 reviews

Stunning, Sunny Flat with Beautiful Backyard

Home away from home in a wonderful and walkable Evanston neighborhood, convenient to downtown, Lake Michigan, Northwestern and more. Treat yourself and your family to this wonderful two-bedroom, masterfully remodeled flat, with all the conveniences and comfort. Off street private parking. Recent updates: New king size bed, 65-inch HD TV, washer & dryer, and more. We follow EPA/CDC protocol and prepare for your stay with intensive cleaning and disinfecting.

Top guest favourite
An open-concept living area features large windows that invite natural light and provide a view of the cityscape. A comfortable blue sofa is adorned with patterned pillows, while a light wood coffee table sits in front of it. A dining space with black chairs complements the modern kitchen.
Apartment in Evanston
4.96 out of 5 average rating, 139 reviews

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

Urban-Luxe experience at the Bliss of Evanston Condo. Elegant finishes and a sweeping Sky Terrace view of downtown Evanston. Resort-like amenities with fitness center, outdoor pool, free parking in indoor GAR, biz ctr, and much more. 2 bedrooms, 2 full baths, 2 roll-out beds welcome you to a comfortable stay near Northwestern University, Loyola, and Kellogg and minutes from Chicago Downtown.

Popular amenities for Skokie holiday rentals

When is the best time to visit Skokie?

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Avg. temp-4°C-2°C4°C10°C16°C21°C24°C23°C19°C12°C5°C-1°C

Frequently Asked Questions

  • What are the best places to stay in Skokie?

    Skokie has vacation rentals near Downtown, around parks, and in residential neighborhoods, giving easy access to shopping and locally rooted restaurants. Look for options with amenities suited to your group, and consider stays close to public transit for added convenience.

  • What are the best things to do in Skokie with kids?

    Kids enjoy interactive exhibits at the Illinois Holocaust Museum, nature exploration at Emily Oaks Nature Center, and creative play in local parks or splash pads. Community events and craft programs add options for family outings year round.

  • What are some of the best things to do in Skokie?

    Explore the exhibits at the Illinois Holocaust Museum, walk through landscape trails at Emily Oaks Nature Center, and discover public art installations in Skokie Northshore Sculpture Park. Downtown Skokie has eateries, shops, and community events.

  • How is the weather in Skokie?

    Skokie has cold winters around 19–32°F (−7–0°C) and warm summers near 66–85°F (19–29°C), with moderate rainfall throughout the year. Spring and autumn bring milder temperatures, so pack layered clothing to adjust with the seasons.

  • When is the best time to visit Skokie?

    Late spring and early autumn are often recommended for comfortable temperatures, blooming parks, and seasonal community events. Summer appeals to visitors with outdoor festivals, farmer’s markets, and longer daylight hours.

  • What are the best places to visit in Skokie?

    Explore the Illinois Holocaust Museum and Education Center, stroll through Emily Oaks Nature Center, and discover artistic exhibits at the Skokie Northshore Sculpture Park. Downtown Skokie has shops, eateries, and locally organized events.

  • What are some hiking trails in Skokie?

    Emily Oaks Nature Center has short trails ideal for leisurely walks and wildlife spotting. The Skokie Northshore Sculpture Park features paved paths surrounded by art installations and greenery.

  • What are some family activities we can do in Skokie?

    Families explore hands-on exhibits at the Illinois Holocaust Museum’s youth area, take nature walks at Emily Oaks Nature Center, and visit playgrounds or splash pads in local parks. Community centers often feature inclusive programs and seasonal activities.

  • What are some of the best day trip ideas from Skokie?

    Explore botanical gardens and vibrant neighborhoods in the surrounding area, or visit Chicago for world-renowned museums, architecture, and lakefront walks. Nature lovers often head to nearby forest preserves and scenic parks.

  • Are there any pet friendly accommodations available in Skokie?

    Skokie has pet friendly vacation rentals, especially in residential neighborhoods and near parks. Many stays welcome dogs, making it convenient to visit nearby walking trails or green spaces.

  • What are some local tips for visiting Skokie?

    Explore Skokie’s mix of cultural centers, parks, and dining spots reflecting the town’s diversity. Dress in layers, as temperatures vary throughout the year, and try connecting with locals for recommendations on distinct food or hidden park spots.

  • What is Skokie known for?

    Skokie is known for its diverse community, cultural institutions, and locally rooted culinary scene. The Illinois Holocaust Museum highlights education and remembrance, while green spaces invite nature exploration.

  • What are the best hidden gems to explore in Skokie?

    Emily Oaks Nature Center is frequently suggested for quiet walks and pond views, while local bakeries and multicultural markets showcase distinct flavors and traditions. Community gardens and neighborhood parks around Skokie provide relaxed spaces off the main routes.

  • What are the best foods to try in Skokie?

    Skokie has vibrant flavors, often featuring locally rooted Jewish delicatessens, Eastern European bakeries, and Middle Eastern restaurants. Try dishes like falafel, fresh bagels, and savory pierogies; multicultural markets also highlight diverse snacks and sweets.

  • What should I bring for a trip to Skokie?

    Pack comfortable walking shoes, layers for shifting temperatures, and a rain jacket or umbrella, especially in spring or autumn. A reusable water bottle and sunscreen are helpful for time spent in parks or outdoor spaces.

  • What is the nightlife in Skokie like?

    Skokie has casual nightlife, with locally rooted bars, relaxed lounges, and family-friendly venues for evening gatherings. For more lively options, many visitors explore nearby urban areas known for music, comedy, and diverse bites.

  • What are the most popular events or festivals in Skokie?

    Skokie Festival of Cultures is often recommended in late spring, with food, music, and performances reflecting the town’s diversity. Summer brings farmer’s markets and community fairs, while holiday parades brighten the winter season.

  • Are there family friendly vacation rentals in Skokie?

    Skokie has family friendly vacation rentals, particularly in residential neighborhoods and near local parks. Many options feature spacious layouts and easy access to playgrounds or nature centers.