Holiday rentals in West Side

Cool spot in cool neighborhood

Welcome to your private and cozy Midwestern getaway! This near west side spacious and open-concept, lower level apartment includes a fully-equipped kitchen, renovated spa-like private bathroom (w/ sit-down marble shower, dimmer lights and hand-held shower head) and generously-sized bedroom w/ a semi-plush, full-size mattress. The unit is well insulated (PERFECT FOR THE WINTER MONTHS) as it maintains warmth from its thick, frosted windows that prevent cold. Medical student housing at it's best.

WESTERN AVE ARTISTS LOFTS- Park Free

FREE street PARKING. Walk to Wicker Park restaurants, bars & shopping. 10 MINUTE WALK to CTA Blue line TRAIN-Damen stop. Premium queen mattress ( small bedroom but a queen bed) & brand new sofa bed. Full kitchen & washer & dryer in apartment. Resident artists work on first floor of this historic former telephone repair and switching station. Very laid back vibe. EVERYONE is Welcome. All guests must be on the reservation for $total. Note $30 per night per guest charge AFTER 2 Guests ( 3&4)

Plants and Art | Near Trendy Restaurants & Bars

Light-Filled Apartment Near Chicago’s Best Restaurants & Bars • Friends & Couples • A/C • Coffee Station w/Local Beans • Fully-Equipped Kitchen Whether you’re in town to explore or unwind, you’ll love the proximity to restaurants, cafes, and live music venues - the perfect home base for your Chicago adventure. Extra Fees: *only available upon request and approval* Early Check In@ 2pm : $50 @10am:$100 Late Checkout@ 1pm: $50 @9pm:$100 Shipping: $25 + UPS fees Required for 7+ Days: $80 Cleanin

*Entire City Apartment 1 block to Train Park Free

Perfectly private - large & comfortable with full kitchen. FREE & EASY street parking One block to (Green Line) train stop to United Center - Concerts, Bulls & Blackhawk games. Two stops to trendy West Loop Randolph bars, restaurants and shops. 10 minute ride downtown Chicago. Kitchen has cooking utensils & coffee, cream, sugar, spices. Shampoo/conditioner/towels/linens are provided. Free wifi. PLEASE NOTE No visitors No smokers no exceptions and agree per message to confirm reservation

ENC-Chi Arts Stu Near United Ctr & 12 mins to Loop

Enjoy a cozy stay in our garden level artist studio 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!

Retro Modern Bungalow | fire pit | free parking

Experience the city in style at Retro Modern Bungalow, the perfect pad for up to 4 friends. Featuring two spacious bedrooms—each with a king bed and luxury linens—a propane fire pit and a fully fenced [pup-friendly] back yard. Enjoy central HVAC, speedy WiFi, and a dedicated workspace. A pack-n-play crib is available at no cost. Central location just south of Oak Park, 15 mins from Midway airport, and 20 mins from downtown. Park for free in our garage or catch the train a few blocks away.

The Green Bungalow: Charming 1-BR apt. with patio

Situated in a residential neighborhood just outside the city limits, this lovely 2nd floor apartment is blocks from the Blue Line train and highway. Our newly renovated vintage unit has a full kitchen, hardwood floors, plenty of natural light, a backyard patio and its own private entrance. Our bungalow is walking distance to cafes, restaurants, shopping, music and nightlife. Enjoy the charm of the suburbs while having easy access to all the attractions Chicago's downtown has to offer.

Newly Remodeled in West Town

Charming one bedroom in prime West Town neighborhood. Located on a quiet, tree-lined street just blocks from trendy restaurants, bars and boutiques. Michelin Star Kasama is just a block away. Brand new kitchen & bathroom remodel. Fully stocked kitchen. The decor is entirely inspired by being cozy and relaxing with neutral tones. Private front yard sitting area is exclusive for the apartment and provides wonderful people and dog watching with a park right across the street.

Bright & Cozy 1-Bedroom Apartment in Logan Square

Bright and charming top floor apartment in the trendy Logan Square neighborhood. Located on a quiet tree lined residential street with multiple restaurants, bars, and coffee shops within walking distance. The CTA blue line station is an easy 20min walk or 10min bus ride away. Or hop on a Divvy Bike; the rental station is located at the end of the block. The 606 Bloomingdale Trail is less than 2 blocks away and is your direct route to endless amenities and destinations.