Holiday rentals in West Side

4.86 out of 5 average rating, 117 reviews

Flat in Forest Park

City-Accessible Basement Retreat

Discover a perfect mix of small-town charm and city life in this cozy basement unit. Situated just a 7-minute walk from the train station, downtown Chicago is easily accessible for work/leisure. The neighborhood is a treasure trove of local restaurants, bars, and stores, ensuring you're never far from what you need. A convenient gas station/store is right behind your home for quick needs. Ideal for a simple, connected lifestyle with the city’s pulse at your doorstep. Your urban retreat awaits!

Top guest favourite

5 out of 5 average rating, 11 reviews

Designer Garden Unit in Bridgeport

Welcome to Bridgeport! You're a short walk from the best coffee shops, vintage stores, cocktail bars, art galleries, parks, restaurants, and Rate Field, the home of the White Sox! The neighborhood has so much to offer! Just minutes from Chinatown, McCormick Place, and 10 minutes to downtown Chicago! Be sure to check out my guidebook for recs! I look forward to hosting you! -Free street parking -easy Uber/Lyft 24/7 -easy access to public transit -15-25 mins from Midway -30-45 mins from O'Hare

4.83 out of 5 average rating, 42 reviews

Dwntown Mins Away/Relax & Stay! Bus/Train Friendly

Take it easy in this peaceful and cozy sleeper, central to everything Chicago has to offer and only minutes from downtown. Take advantage of all of the amenities while your here and enjoy the city night life with all of the great entertainment and restaurants Chicago has to offer. Newley rehabbed with high end appliances and fixtures that you, your significant other or family can enjoy. This relaxing vibe is one that will make it feel like a home away from home with all that it has to offer.

4.97 out of 5 average rating, 309 reviews

Flat in Cicero

COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy

Located on a tranquil city side street, this property is walking distance to numerous restaurants and stores. Enjoy easy access to public transportation, including Metra train, CTA Pink Line, and a direct CTA bus to Midway Airport. Downtown Chicago is a mere 20-minute drive away, with the United Center and Soldier Field just 15 minutes away. Ideal for a quick getaway, an overnight stay before your flight, or an extended work assignment. Unwind on the patio, complete with a fire pit and grill.

5 out of 5 average rating, 20 reviews

Bright and full of life!

Charming apartment steps away from iconic Route 66 (Ogden Avenue) and public transportation. Cozy retreat boasts a fully stocked kitchen, comfy beds, and a designated workspace with a printer - perfect for remote workers or travelers who need to stay productive. The apartment is filled with natural light and surrounded by lush greenery, including a beautiful veg garden in the summer and plenty of plants throughout. Sunny, bright space, and relaxing. Pet owners, furry friends are welcome here!

Superhost

Guest suite in Chicago

5 out of 5 average rating, 5 reviews

ENC-Chi Arts Suite Near United Center & Downtown

Enjoy a cozy stay in our garden level artist apartment below our private home as we embrace life as empty nesters. Centered in the East Garfield Park community. We’re just a 12-minute commute to downtown Chicago and 7 minutes to the West Loop, IL medical district, and United Center and three blocks from the popular Garfield Park Conservatory. Plus, conveniently located half a mile from essential amenities like grocer, fast-food, Chase bank, and Walgreens. Experience comfort and value with us!

4.95 out of 5 average rating, 62 reviews

Home in Chicago

Private Logan Square Garden Apt

Welcome to our cozy West Logan Square/West Humboldt Park/Hermosa garden apartment! Perfect for tradeshow/business travelers, solo travelers, &couples. Enjoy a comfy queen-size bed, workspace, fast Wi-Fi, and huge Smart TV w Roku. Plenty of power outlets to keep your devices charged. Get ready in bathroom w/ ample counter space & large mirror. Cook in the well-equipped kitchen with full-sized appliances, spices/oil, microwave & coffee/tea bar. Note: Hosts occupy first floor of the home.

4.75 out of 5 average rating, 326 reviews

Bright & Spacious| Free Parking |Trendy Bridgeport

Step inside and be greeted by an open-concept space bathed in natural light. High ceilings, hardwood floors perfectly blend vintage charm with modern elegance. The living area invites you to unwind after a day of exploring our vibrant city. Relax on the sofa, watch your favorite shows on our large flat-screen TV, or indulge in book in the cozy seating nook. Whether you're a solo traveler, couple, or friend group looking for an unforgettable adventure, this is the ultimate urban retreat.

Top guest favourite

5 out of 5 average rating, 11 reviews

2B Midcentury Artist Loft w King Bed

Welcome to Casa D'Mi Amá, this vibrant mid-century loft style apartment is centrally located in Little Village, one of the most vibrant Mexican-American communities and thriving shopping district in Chicago. Our community is known for its colorful murals and hundreds of Latinx-owned businesses and restaurants. We are just 4 mile away from downtown & Midway airport, three miles away from Pilsen & UIC, with public transportation right outside your door making it easy to plan your visit.

4.87 out of 5 average rating, 263 reviews

Spectacular Pilsen Studio for 2!

This chic studio in the heart of Pilsen is the perfect space to kick back and relax during your visit to the Windy City! The vibrant neighborhood always has something to offer to any type of traveler, and it's a quick trip to see most of the iconic Chicago sights. Easily walk to historic Thalia Hall, or drive to the Loop in just 5 minutes! You'll love the thoughtful touches and modern decor in the apartment, as well as the bright and welcoming main space.

Top guest favourite

4.99 out of 5 average rating, 230 reviews

Modern Apt with style & comfort in Pilsen Chicago

Enjoy a nicely updated studio in a safe, family-owned building located in Pilsen/Heart of Chicago conveniently located near Downtown, Chinatown, & Hyde Park to name a few. Public transportation is walking distance or you can go on a short drive to museums, parks, cafes, restaurants, bars, venues, and hip neighborhoods. Chicago has a full line up of festivals happening this year so feel confident in choosing my lovely space to be part of your experience.

4.7 out of 5 average rating, 271 reviews

Sonder Onterie | King Studio Apartment

Welcome to Onterie, where modern style meets an unbeatable location in the heart of Chicago's Magnificent Mile. You'll have world-class shopping and award-winning dining at your fingertips. Each apartment includes a fully equipped kitchen, in-suite laundry, and a Roku to stream your favorite shows. Unwind in the outdoor courtyard, or find focus in our co-working space. Onterie offers the perfect blend of city and lakeside living.

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Popular amenities for West Side holiday rentals

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Free parking on premises

Air conditioning

Other great holiday rentals in West Side

4.69 out of 5 average rating, 163 reviews

Hemingway's Room

MiriamRating, 5 stars1 week ago

Walking distance to the train station, one line that can take you straight to the airport, kind hosts, comfortable bed, good communication. Decent place for a decent price.

4.72 out of 5 average rating, 39 reviews

Bees Knees - Room 3

MikaylahRating, 5 stars2 weeks ago

I really enjoyed my stay here . Genova place is very affordable, well kept for a shared space . I like that everything was organized . Toiletries such as body soap , hair conditioner was provided as well as towels and linens . Genova was able to accommodate me as well with some plans that didn’t quite work out with my airfare . I was very grateful and appreciative of that as well . Very good and timely with communication on whatever I needed . I’m sure a future stay here will be planned out . Maybe sooner than later . Great host . Until next time …

Superhost

4.86 out of 5 average rating, 22 reviews

Bohemian Retreat Room – Near Downtown & UC!

수빈Rating, 5 stars1 month ago

It's close to the CTA, so it's easy to move I like that the communication with the host is fast. I traveled alone and stayed for 6 days, and I'm generally satisfied.

4.78 out of 5 average rating, 79 reviews

Beautiful Private Room 5 min to the City

IngridRating, 5 stars2 weeks ago

Super close to UIC, located in a quiet and safe neighborhood. It’s also not far from downtown Chicago. The apartment has five rooms, with a toilet on the first floor and a full bathroom on the second floor. It can get a bit crowded on weekends, which might make the bathrooms busier, but in my experience, they’ve remained clean despite being shared. That said, cleanliness may vary depending on the tenants. Also, the walls are a bit thin, so noise from the first floor can sometimes be heard upstairs. However, people generally keep quiet after 11 p.m.