
Apartment holiday rentals in West Side
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Top-rated apartment rentals in West Side
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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.
4.99 out of 5 average rating, 118 reviews
West Town 1-Bedroom Full Remodel
Located in the heart of West Town, this 1-bedroom, 1-bath comes equipped with a queen sofa bed and comfortably sleeps 4, plus an in-unit washer/dryer for your convenience. Remodeled in 2023, this stunning unit with 9ft ceilings in a Victorian building is footsteps away from all the amazing bars and restaurants Chicago Ave has to offer. Known for its array of multicultural cuisines, this strip offers everything from Korean fine dining to New Mexican brunch, and is near Chicago’s best attractions!
4.98 out of 5 average rating, 123 reviews
Luxury Loft Collection 01 - Terrace - River North
BRAND NEW LOFT IN RIVER NORTH! Enjoy your new private luxury loft in Chicago's newest and most luxurious building in bustling River North-the city's center of main nightlife and restaurants. This ultra high-end apartment features a private elevator, private terrace, free secured parking, 24 hour doorman, 3 bedrooms/3 bathrooms, and is perfect for families traveling to Chicago, professionals visiting the city on work trips, and everything in between. The cityscape views are unbeatable!
4.9 out of 5 average rating, 126 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
4.97 out of 5 average rating, 636 reviews
Kasa | Views from your Private Balcony | Chicago
When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.
4.81 out of 5 average rating, 1053 reviews
Explore Lincoln Park from a Polished Apartment
A bright, cozy, large studio in the heart of Lincoln Park! You enter with a keypad code which we give you a few days prior to your stay. You are steps away from Armitage Ave. and Halsted St. for walkable grocery stores, shops, restaurants and cafes, plus Red and Brown line train stations that access Downtown and other parts of the city. Street parking is relatively easy around the apartment with free residential parking stickers or an onsite garage space for $25/night.
5.0 out of 5 average rating, 325 reviews
Renovated LittleVillage Retreat
Welcome to our newly renovated retreat in Little Village, Chicago! This stylish unit blends modern amenities with classic charm. Features include a cozy living area with a smart TV, a fully equipped kitchen with stainless steel appliances, a comfortable bedroom with a work desk, and a pristine bathroom with contemporary design. Enjoy in-unit laundry and a secure entry. Convenient street parking and close to local attractions and dining. Perfect for early birds and explorers
4.87 out of 5 average rating, 151 reviews
Bright Boho Haven free parking
Welcome to our bright, newly constructed 1-bedroom, 1-bath Airbnb in the heart of Oak Park. Enjoy a sunny, modern space with a beautiful bathroom, free parking, and all the essentials. Just steps from grocery stores, coffee shops, and the Oak Park Blue Line stop—reach downtown Chicago in under 30 minutes. Perfect for a cozy getaway or work trip, with fast Wi-Fi, smart TV, kitchenette (no oven!) and a peaceful, walkable neighborhood. We can’t wait to host you!
4.84 out of 5 average rating, 126 reviews
Quaint Comfort Studio Near Downtown/Queen Bed
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.
4.99 out of 5 average rating, 288 reviews
Pilsen Modern Chic Retreat
Welcome to your perfect getaway! This stunning 2-bedroom home is the epitome of modern chic; offering an unforgettable blend of style and comfort. Designed for up to 6 guests, the space is crafted with thoughtful architectural details and an eye for eclectic decor. Located in the heart of Pilsen, known for its vibrant art scene, trendy restaurants, & local culture, you'll be perfectly situated to explore everything Chicago has to offer.
4.95 out of 5 average rating, 135 reviews
LIVN West Loop Chicago Classic Studio Apartment
Experience modern city living at LIVN West Loop Chicago, a stylish loft-style apartment studio at 555 W Jackson Blvd in one of the city’s most connected neighborhoods. This newly renovated studio features a full kitchen, in-unit washer and dryer, and clean, modern interiors. Walk to Union Station and Willis Tower. You are minutes from top dining, offices, and transit, ideal for business trips, weekend stays, or longer visits.
4.86 out of 5 average rating, 110 reviews
Modern 3BR with Private Rooftop & Free Parking
A beautiful and modern 2450 sq feet apartment with a private rooftop deck, a rooftop firepit, an additional private patio and yard, brand new appliances, and bright spacious interior. Free private on-premise parking (1 garage spot and one driveway spot) in the heart of Chicago and a blocks walk to the L-transit system provides easy access to both downtown, the greater Chicago area, and both major airports.
4.92 out of 5 average rating, 188 reviewsPopular amenities for West Side apartment rentals
Weekly apartment rentals

Spacious & Modern Treetop Oasis King Bed + Parking
4.98 out of 5 average rating, 101 reviews
【Central】- Eclectic Fun 1BR APT in Wicker Park
4.95 out of 5 average rating, 168 reviewsBright, Modern Apartment in a Vintage Greystone
4.92 out of 5 average rating, 444 reviews
Cozy Spacious Condo Sleeps 6
4.87 out of 5 average rating, 318 reviews
Charming retreat w/ fireplace
4.82 out of 5 average rating, 141 reviews
Stylish 2BR stunner w/ unbeatable location
4.92 out of 5 average rating, 207 reviews
iKlektik House Chicago/BlueJay
4.92 out of 5 average rating, 274 reviews
City-Accessible Basement Retreat
4.87 out of 5 average rating, 221 reviewsPrivate apartment rentals

Spectacular Pilsen Studio for 2!
4.88 out of 5 average rating, 336 reviews
Fulton House #1 (2bd/ 1ba)
4.94 out of 5 average rating, 121 reviews
Newly remodeled 1BR! Only 5 MIN walk to BLUE LINE!
4.91 out of 5 average rating, 397 reviews
Comfortable and Cozy Apartment
4.94 out of 5 average rating, 155 reviews
Garden on Warren
4.91 out of 5 average rating, 186 reviews
Modern Corner 2BR in Streeterville | Roof Deck | L
4.77 out of 5 average rating, 217 reviewsExplore the City from an Elegant, Urban Retreat
4.85 out of 5 average rating, 455 reviews
Sounds Of The City
4.88 out of 5 average rating, 184 reviewsApartment rentals with a hot tub

Checkerboard Studio, Private Outdoor Hot Tub, Yard
4.86 out of 5 average rating, 540 reviews
West Loop 2BR with Skyline Views + Prime Location
4.81 out of 5 average rating, 108 reviews
Level One Bedroom Suite | Fulton Market
4.69 out of 5 average rating, 36 reviews
Comfy Near Downtown Chicago
4.87 out of 5 average rating, 46 reviews
Luxury 3BD Penthouse – Private Patio+Skyline Views
4.84 out of 5 average rating, 43 reviews
Stylish Unit in Wicker Park| Whirlpool Tub|Balcony
4.67 out of 5 average rating, 52 reviews
Spacious and Ideally located in the Lakeview area
5.0 out of 5 average rating, 7 reviews
The Velvet Manor | Luxe 3BR • Jacuzzi • Garage
5.0 out of 5 average rating, 7 reviewsDestinations to explore
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- Wrigley Field
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