
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.
LocationValueSleep quality

Spacious Studio w/Balcony in Bucktown/Wicker Park
My place is in the heart of one of Chicago's Hottest and Hippest neighborhoods(Wicker Park/Bucktown) with everything you need or want within a short walk - Transportation(Blue Line Train) which is a direct shot to and from O'hare airport, Dining, Nightlife, High End boutique shopping. 15 minutes to the Magnificent Mile, Millennium Park, Wrigley Field. Perfect for couples, solo adventurers, and business travelers with Internet and Cable TV included. Sleeps 2 adults comfortably w/sleeper sofa.
ValueFamilyQuiet

Sunny Jumbo Studio
Bright and sunny Oak Park jumbo garden studio, steps from cute downtown, train to Chicago, and amazing local tourist destinations- like the Hemingway Home and the Wright Studio. This welcoming studio was completely rehabbed and updated. We put a lot of care into designing a relaxing apartment with all the amenities. The main room features a king-sized bed, office nook, and fully stocked entertainment area, with games, books, and a TV. The spacious kitchen and luxurious bathroom are brand new!
FamilyValueLaundry

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.
FamilyValueRiver

Comfortable and Cozy Apartment
Enjoy this simple and cozy apartment! Located just a few blocks from stores like Walgreens, Aldi, Target, Laundromat and various restaurants. Its conveniently located just a 10 minute walk from the orange line cta train station. Disfrutá de la sencillez de este alojamiento tranquilo y céntrico. Ubicada a dos minutos de tiendas como target, Walgreens, Aldi, Lavandería y restaurantes . Estamos a 10 minutos del aeropuerto midway y 15 minutos del centro de Chicago.
FamilyValueParking

Blue Brick Apartment in Bridgeport - Park for Free
• Free street parking • Trains to Downtown!! • Fully stocked kitchen • Walk to dining & bars! • Free parking pad in rear • Noise monitoring equipment • Walk score 93! Bike Score 92! • 600 sq ft apartment | 1st floor | Patio • Safe, working class neighborhood! • Commute to Downtown: 15min (drive) • 28min (transit/train) | 22min(bike) • Building video surveillance alarm system • Washer | Dryer | Dishwasher are included • Rideshare (Uber/Lyft) | Bikeshares(Divvy)
LocationValueQuiet

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.
FamilyValueCleanliness

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.
LocationFamilyAccuracy

LIVN West Loop Chicago Queen 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.
ValueLocationIndoor spaces

1BR Bright Bucktown Loft - Great Location!
Welcome to your ideal Chicago getaway! Located in vibrant Bucktown, this top-floor, modern rehab combines contemporary style with classic Chicago charm. Sitting right off beautiful Holstein Park, you are just a short walk from two Blue Line stops—getting you to the Loop in under 30 minutes! Plus, you'll be within a 15-minute stroll of Logan Square’s top restaurants, nightlife, and shops along Milwaukee Avenue.
ValueFamilyDecor

Ina's Beachwood Inn In the Heart of Wicker Park
Located on the second floor of Ina Mae Tavern & Packaged Goods, one of Chicago's best new restaurants, the Beachwood Inn has a private balcony overlooking the entire restaurant's bustling action so guests will never miss out on the happenings - from live music to brunch and dinner. The space is perfect for travelers who want to immerse themselves in a true local experience.
ValueFamilyAmenities

iKlektik House Chicago/Cardinal
A Space perfect for Two Adults with Custom Craftsmanship, amazing artwork and CLOSE TO THE UNITED CENTER!!! Fully furnished one bedroom in Ukrainian Village/West Town. Close to Division St, Wicker Park, and Bucktown. The space is amazing...just read the reviews! There is FREE street parking. Not suitable for children. WE DO NOT RENT ON "CL" DO NOT WIRE $ IT'S A SCAM
ValueFamilyAccuracy
Popular amenities for West Side apartment rentals
Weekly apartment rentals

A Quiet Stay While You Are Away Oak Park
LocationValueSleep quality

Bucktown Brick Cottage Apartment
ValueFamilyParks

Fulton House #1 (2bd/ 1ba)
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The Bell House: Apartment #1
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【Central】- Eclectic Fun 1BR APT in Wicker Park
ValueFamilyAmenities

Breathtaking & Chic Oasis Loc in Desirable Old Twn
FamilyValueWi-Fi

Explore Lincoln Park from a Polished Apartment
FamilyLocationAmenities

Stylish 2-Bedroom Wicker Park Apartment
ValueFamilyCheck-in
Private apartment rentals

Condo Near Downtown Chicago
LocationFamilyBathroom

Zen City Escape | Patio + Free Parking
FamilyLocationAccess

Stay Above Chicago's Post-Punk Museum - 4BR Loft
LocationBathroomGetting around

Modern Luxe Retreat in Pilsen’s Colorful Center
ValueFamilyComfort

Chicago Getaway: Family-Friendly 2BD 2BA Apartment
LocationDecorGetting around

Chicago stay Near Midway Airport • CTA • Downtown
LocationHospitalityCleanliness

Loft-Inspired Pilsen Retreat | 10 min to Downtown
FamilyValueGetting around

Beautiful Modern 1 bed/2bath West Town apartment
LocationCleanlinessAccuracy
Apartment rentals with a hot tub

Spacious and Ideally located in the Lakeview area
LocationFamilyHospitality

Top Floor Views + Central Comfort
FamilyLocationLaundry

Luxury 3BD Penthouse – Private Patio+Skyline Views
LocationFamilyCheckout

Skyline Oasis: City & Lake Views
FamilyLocationComfort

Luxury South Loop Apt
LocationIndoor spacesView

Level One Bedroom Suite | Fulton Market
LocationValueView

DuSable International House Near The Obama Library
LocationValueWalkability

Checkerboard Studio, Private Outdoor Hot Tub, Yard
LocationValueAccuracy
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- Wrigley Field
- Soldier Field
- Lincoln Park
- United Center
- Grant Park
- Navy Pier
- Millennium Park
- Indiana Dunes State Park
- Naval Station Great Lakes
- 875 North Michigan Avenue
- Six Flags Great America
- The Field Museum
- Shedd Aquarium
- University of Chicago
- Humboldt Park
- Guaranteed Rate Field
- Lincoln Park Zoo
- Loyola University Chicago
- Union Park
- Frank Lloyd Wright Home and Studio
- Donald E Stephens Convention Center
- Wilmot Mountain Ski Resort
- Beachwalk Vacation Rentals
- Garfield Park Conservatory
- Things to do West Side
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