Holiday rentals in North Chicago

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Top-rated holiday rentals in North Chicago

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

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Guest favourite
A cozy living area features two gray sofas with light cushions arranged around a TV stand. A 55" Smart TV is positioned against a neutral wall, which is complemented by a cityscape photograph. Wood flooring adds warmth to the space, enhanced by natural light from the windows.
Bungalow in North Chicago
4.91 out of 5 average rating, 118 reviews

Cozy gated home | Minutes away from Navy bases.

This home is the most convenient and closest home for families visiting for the Navy’s bootcamp graduations. Relax with the whole family at this peaceful gated bungalow. Located within walking distance (1 Mile) to Recruit training command (RTC) and Naval Station Training Command (NSTC) 1.7 miles. This home is perfect for visiting to see your graduating Sailors or if you are visiting Six Flags Great America, Gurnee Mills outlet mall. There are plenty of brewers, restaurants, beaches and parks.

Guest favourite
A bright bedroom features a four-poster bed with a sheer canopy, dressed in crisp white linens and a soft blue throw. A cozy blue armchair sits beside a small table, offering a comfortable seating area. A scenic landscape artwork adorns the wall, complementing the inviting space.
Flat in Uptown
4.77 out of 5 average rating, 47 reviews

13 mins DT | 4 mins Lake | Elegant Style Loft

Welcome to Uptown Chicago, proudly hosted by TIBO Ventures. Standout Features: • 𝗙𝘂𝗹𝗹𝘆 𝘀𝘁𝗼𝗰𝗸𝗲𝗱 𝗸𝗶𝘁𝗰𝗵𝗲𝗻 with modern appliances • 𝗦𝗺𝗮𝗿𝘁 𝗧𝗩 𝗮𝗻𝗱 𝗱𝗲𝗱𝗶𝗰𝗮𝘁𝗲𝗱 𝘄𝗼𝗿𝗸𝘀𝘁𝗮𝘁𝗶𝗼𝗻 — perfect for professionals or remote workers • In-unit washer/dryer and dishwasher for convenience • Rooftop area with breathtaking city views • Fitness center access to stay active during your stay • Steps from Montrose Beach, Aragon Ballroom, and Riviera Theatre • Parking available

Guest favourite
A spacious living area features a blue couch facing a large television mounted on the wall. A decorative rug complements a wooden dining table set for four, accented with plates and glassware. Natural light filters through large windows, enhancing the inviting layout.
Home in North Chicago
4.88 out of 5 average rating, 105 reviews

Spacious 2-br, 1 bath home w/AC near Naval Base

Welcome to our Airbnb, perfectly situated for your convenience. Located near the navy base, Six Flags Great America, and an hour drive to the bustling city of Chicago, our accommodations offer the ideal gateway to a multitude of attractions and activities. And when it’s time to rest, our comfortable accommodations awaits you. Whether you’re here for business or pleasure. At our Airbnb, we prioritize your comfort and convenience. Book now and let us be your gateway to an extraordinary stay.

Guest favourite
A well-defined stone pathway leads to the entrance of the prairie-style home, bordered by lush green grass and neatly trimmed hedges. Hanging flower baskets add vibrant touches above the cozy seating area, surrounded by the serene backdrop of towering oak trees.
Guest suite in Riverwoods
4.95 out of 5 average rating, 449 reviews

Master qtr close to nature & easy urban facilities

This amazing prairie style home sits on 2 acre land surrounded by lush lawn and majestic oak trees - a nature lover's dream with unparalleled serenity. Vacation-like setting blends country-like quiet with nearby conveniences including shopping, trains, restaurants, highways, Ravinia (18 MINs drive). 5 MINs to I 294. 20 MINS to O'HARE; 5 Mins to Discover, Baxter; 10 MINs to Walgreens Deerfield campus, TRINITY INT'L UNIVERSITY; 15 MINS to Lake Forest Academy. 25 MINs to Great Lakes Navy Base.

Top guest favourite
The living area features a velvet sofa adorned with colorful pillows, complemented by a matching armchair. A glass coffee table is centered on a patterned area rug, with a bookshelf displaying decorative items and books in the background.
Guest house in Lake Forest
4.94 out of 5 average rating, 139 reviews

The Green Door - safe and calm with walkability

This charming guesthouse in Lake Forest is only steps away from beautiful Market Square — the historic retail center of the community. Inside it features loads of light, in-unit washer and dryer, a well-equipped kitchen and a professionally designed stylish and calming interior. Outside, it has a vintage (ie. older) porch/breezeway with classic outdoor games. Walk to two grocery stores, bars/restaurants and our historic train station that connects to Chicago and various corporate shuttles.

Guest favourite
A comfortable living area is designed with a gray sofa and a black coffee table, complemented by a dining table. A work desk is positioned near large windows, allowing natural light. A ceiling fan is visible, and a flat-screen TV is mounted on the wall.
Flat in Libertyville
4.88 out of 5 average rating, 34 reviews

305

Kick back and relax in this calm, stylish space. This peaceful, quiet apartment is walking distance to beautiful downtown Libertyville. The building is very nicely maintained with an elevator. Located 7 miles from Great Lakes Naval Base and 35 miles from downtown Chicago. The unit is very clean with all brand new furnishings and appliances including HD tv's in both the living room and bedroom. Free ample parking. On-site laundry one floor down. Fast wifi with a dedicated work space.

Top guest favourite
The modern kitchen features stainless steel appliances, including a refrigerator and stove. Light-colored cabinets provide ample storage, while a window allows natural light to brighten the space. A small table with chairs is positioned against the wall, enhancing functionality.
Home in Waukegan
4.94 out of 5 average rating, 155 reviews

The Indigo Cottage

This is a newly remodeled single-family home! It is small but has everything you need to enjoy time with family and friends during your stay in the Chicagoland area! There are two bedrooms each with a queen bed, an updated bathroom, a dining room with seating for 6, a cozy living room with a Crate & Barrel pull-out queen sofa bed, and a nice, updated kitchen! There's a brand-new washing machine and dryer in the basement. There's a nice patio table outside too in the private yard. Welcome!

Top guest favourite
The living room is well-lit by sunlight streaming through three large windows, accentuating a comfortable brown sofa and a stylish armchair. A wooden coffee table and a small dining table with two chairs offer ample seating. Unique artwork and decorative items add character to the space.
Flat in Noble Square
4.97 out of 5 average rating, 581 reviews

Fully Furnished Apartment Wicker Park Free Parking

Hello and welcome to all seeking a comfortable and convenient place to stay in Chicago! Please enjoy your time away from home in our fully furnished apartment located in the trendy neighborhood of Wicker Park! Please view the list below of all the wonderful amenities we offer to every guest staying out apartment. Again if you have any questions or comments please do not hesitate to ask. I look forward to seeing you and having your apartment ready soon! Thank you! One night available

Superhost
The open-concept living area features a fully-equipped kitchen with gray cabinets and granite countertops. A cozy seating area includes a sofa and a patterned area rug, complemented by a coffee table and a decorative side table, creating a functional and comfortable space.
Flat in West Town
4.65 out of 5 average rating, 20 reviews

Cool spot in cool neighborhood

Close to Madison/Randolph Street night life, Little Italy, Greek Town, Fulton Market and the United Center. Also close by is Bucktown, Wicker Park and Ukranine Village where shopping and more dining awaits. The private entrance open to a foyer leading to a large open floor great room extending to the kitchen. Amenities galore 2 tvs, spa like shower and a touch of Chicago charm. Illinois Medical District, Museum campus not far away. Close to cool festivals ie. Riot, Pitchfork.

Top guest favourite
The living area features a spacious sectional sofa and a modern armchair positioned around a low coffee table. Large windows provide natural light and a view of the lush green outside. Wall art adds visual interest to the room, complemented by warm wooden flooring.
Home in Waukegan
4.94 out of 5 average rating, 106 reviews

The Victory Park Ranch - West

We are excited to welcome you to this comfortable and newly renovated modern house, in the perfect location if you're visiting Northern Illinois/Chicago. Come see why Waukegan is nicknamed "Green Town" and is home to some of the finest parks, ravines, and walking trails. With an incredible sandy beach, lakefront, galleries, breweries, restaurants, and more, it is definitely a place to check out! We are very close to Six Flags, Great Lakes Naval Base, and The Genesee Theatre too!

Top guest favourite
A serene living area features a large sliding glass door leading to a deck with unobstructed views of Round Lake. Natural wood accents adorn the wall, while a plush sofa and a small coffee table create a relaxing seating space.
Home in Round Lake Beach
4.99 out of 5 average rating, 181 reviews

Round Lake Getaway Retreat

Looking for a calming, peaceful lakeside getaway for you and your loved one? Come stay at our remodeled retreat with private waterfront access to Round Lake. Enjoy peace and reflection meditating on the spirited lake waters rolling into shore. Wake up to inspirational lake views with soul warming coffee, tea or cocoa. Savor deep or lazy conversation with your loved one, surrounded by dreamy décor and captivating nature. Come and relax, restore, and rejuvenate by the lake!

Guest favourite
A vibrant studio features an orange bedspread on a spacious bed, complemented by a colorful mural in the background. A sleek kitchen with a bright green refrigerator and bar seating is visible. Natural light is provided by a window, while modern lighting fixtures enhance the decor.
Loft in Libertyville
4.92 out of 5 average rating, 24 reviews

The Hummingbird | Center of Downtown Libertyville

Welcome to The Hummingbird, a charming 375 sq ft studio in Historic Downtown Libertyville. Eclectic and stylish with Smeg appliances and high end finishes. Steps from top restaurants, nightlife, shops, and the Metra station. In the heart of the action, sharing a lively courtyard with one of Libertyville’s most popular restaurants. Perfect for couples or solo travelers who love being where the buzz is. Perfect for Navy Graduation or trips back to your home town!

Popular amenities for North Chicago holiday rentals

When is the best time to visit North Chicago?

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Frequently Asked Questions

  • Do house rentals in North Chicago have air conditioning?

    Absolutely! We offer over 20 house rentals with air conditioning in North Chicago. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in North Chicago have a kitchen?

    Absolutely! We offer over 10 house rentals with a kitchen in North Chicago. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in North Chicago?

    North Chicago has more than 40 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there pet-friendly vacation rentals in North Chicago?

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

  • How much does it cost to stay in serviced apartment rentals in North Chicago?

    Experience the best of North Chicago with our serviced apartment rentals, starting at about $50,000 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 North Chicago have free parking?

    Absolutely! We offer over 10 apartment rentals with free parking in North Chicago. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in North Chicago?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a kitchen, over 20 homes with wifi, over 20 homes with air conditioning, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there vacation rentals with a dedicated workspace in North Chicago?

    Yes! Work meets play with ease at over 40 vacation rentals in North Chicago featuring dedicated workspaces. Stay connected and productive in your home away from home.

Quick stats about holiday rentals in North Chicago

  • Total holiday rentals

    Explore 60 holiday rentals in North Chicago

  • Nightly prices starting at

    North Chicago holiday rentals start at € 50 per night before taxes and fees

  • Verified guest reviews

    Over 1,910 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wifi availability

    60 of North Chicago holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across North Chicago rentals

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