Vacation rentals in West Side

Chicago Modern Condo 2BR2BA, Balcony, Free Park

Experience upscale city living with @TheDreamRentals in this stylish 2-bedroom, 2-bath Airbnb located in Chicago’s vibrant Tri-Taylor neighborhood. This modern retreat features sleek interiors, spacious bedrooms with queen beds, a fully equipped gourmet kitchen, and designer finishes throughout. Enjoy high ceilings, large windows, and smart amenities just minutes from downtown, the United Center, and the Illinois Medical District. Perfect for professionals, couples, or small groups seeking comf

Sunny full floor (Sleeps 4+ guests)

A whole floor to yourself — the floor is entirely/ exclusively yours! Full floor finished basement w/ light from glass sliding doors, 1.5 private bedrooms, and 2 desks. Spic & span - steamed cleaned after every guest! New memory foam regular queen size bed w/ 2 more queen size airbeds (per request). 7 mins by car to downtown or 2 blocks to train station/ bus stop that both go into downtown. Street level parking available. Masks are optional, not required. Chicago Registration #: R21000069179

Betty BnB

Free admission to The World's Smallest Betty White Museum! Oh, and a comfortable king-sized bed in a newly updated studio apartment. Centrally located in Oak Park, close to cafes and transit. Quiet, friendly neighborhood with ample street parking and a pub across the street. This is a basement unit with a kitchenette (NO STOVE/OVEN), cozy TV room, desk nook, and full bathroom. The bed is king-sized and has a firm mattress. The floors slope and there's no thermostat, but it's cute + welcoming

City Chickens Studio

Yes, chickens are allowed in Chicago, but don’t worry, we’re Ladies Only—No Roosters! Our little farm is a memorable spot to spend your visit to the city. The friendly ladies will welcome you, but they won’t tell you that the train from O’Hare to downtown is just down the block or that there are plenty of coffee shops, restaurants, and friendly Midwesterners all over the place happy to help you find your way around. If you’re looking for a unique and perfectly-sized spot, this is it.

G1. Next to Downtown! Best location

Bedroom for rent in the desirable neighborhood of Lakeview. Location is its most important fact. It is right in front of one of the biggest supermarkets(Whole Foods). There are multiple stores just one block away such as target, xsport fitness, banks. Different restaurants and more. Walkable to brown line train to go downtown as well as bus stops to go all possible directions. Beautiful apartment, bedroom with closet. All you can think of at a great price. host lives in the same apt

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

Private Bed and Bathroom in a Great Location

Located in Ukranian Village, the new "hot" neighborhood, it's close to many great eateries and pubs. A beautiful yard filled with flowers and plants and a large deck in back with a canopy to sit outside and unwind at the end of the day. Inside is very comfy. A combination of vintage and modern. The guest room has a queen size mattress and curtains heavy enough to block out the street lights. Its one short block from Chicago Avenue and the #66 bus that goes down town.

Chic retreat near the best of Lakeview & Wrigley

Stylish, centrally-located getaway perfect for a visit to the Windy City! This charming space was freshly renovated in early 2022 with ample space (nearly 1500 sq ft), a Peloton exercise bike, and kitchenette. Located in the trendy Southport Corridor blocks from the best of Chicago's north side; shopping, fine dining, bars, Wrigley Field, close to Brown line train public transit with Whole Foods at the end of the block!

Great location. Free parking.

Great location in Chicago's Wicker Park/Bucktown community. Fully furnished living room, bedroom with queen bed and bathroom. Internet, central heating/ac, small refrigerator, microwave, cable TV, dvd/Blu-ray, coffee maker. Small safe. Private free parking. One block from blue line (Division). From O’Hare via train – 35 min. 10 min to the city via blue line.

Cozy Little Village Studio

Kick back and unwind in this Cozy Chicago flat. This newly renovated unit is conveniently located in the “little village” community and offers a convenient stay with everything you need to enjoy Chicago. Come stay in a historic red brick building within an authentic Chicago community.

The Blue Room

A spacious single-family home; minutes away from Midway Airport (train station), within walking distance from gorgeous and dog-friendly parks, and walking distance of plentiful of supermarkets and convenience stores. Downtown Chicago is just about 40 minutes away from a train ride.

Antique Filled Home

Our warm and inviting home is located in historic Oak Park, home of Frank Lloyd Wright and Ernest Hemingway. The green line will whisk you to the center of Chicago in 25 minutes and it is less than three blocks from our front door.