Holiday rentals with beach access in West Side

The master bedroom features a spacious bed with a tufted headboard and soft, neutral bedding. Two nightstands with lamps are on either side, and a television is mounted on the wall. Natural light filters through the wooden blinds, enhancing the warm wooden floors.

4.94 out of 5 average rating, 231 reviews

OLD TOWN TRIUMPHANT 2BD/2BA (+Rooftop&Parking)

Welcome to this Old Town Masterpiece! Guests love this home because: - Steps away from top-notch restaurants/entertainment on bustling Wells St. - Close to every popular attraction that makes Chicago so great - Room for reg-size SUV in private driveway! - Luxurious interior design - Tranquil rooftop w/ grill - Fast WiFi - Pillow-top Bamboo mattress in each master en-suite - State of the art kitchen - Exceptional workspace - 5 minute walk from red line (CTA L) We look forward to hosting you!

A modern living area features a spacious orange sofa and a wooden coffee table positioned on a light rug. A large flat-screen television is mounted on the wall, with a stylish lamp and potted plant nearby. An open kitchen with white cabinetry and stainless-steel appliances is visible in the background.

4.99 out of 5 average rating, 111 reviews

Bright & Modern Apt | Steps to Lake, Train, Food

This is the ideal location for your trip to Chicago! Steps from the Red Line Train, Foster Beach, Lake Shore Drive, Lake Front Trail, amazing Restaurants & a quality grocery store. You'll enjoy a clean & spacious 2 bedrooms apartment w/ friendly neighbors, flawless check-in & reserved parking. This place is safe & provides a beautiful & stocked apartment to relax after a busy day in the city. Short walk to Andersonville & Asia on Argyle for wonderful food options. The Riv &Aragon for concerts

A vibrant living area showcases eclectic décor, featuring a colorful mural with artistic motifs on one wall. A round coffee table sits in the center, surrounded by cream-colored sofas adorned with green cushions. A wet bar with wooden stools is visible in the background.

4.92 out of 5 average rating, 147 reviews

Hidden Gem:Artsy Speakeasy in Historic Bronzeville

Enjoy this fun and unique 1-bed 1.5-bath speakeasy in the heart of Chicago's Bronzeville District. This artsy vibe features eclectic décor, hand-painted murals, Smart TVs, wet bar, wellness studio, remote workspace, free street parking, and ground-level-step-free access. This cozy space is perfect for fun couples, solo adventurers, business travelers, and game night aficionados. Easy access to Downtown (6 miles to Mag Mile, Navy Pier, Millennium Park), Beach (1 mile), Museums, & Sports arenas.

A red brick three-flat building is presented with large windows and intricate architectural details. Colorful pumpkins are arranged in the front garden, which features lush greenery and blooming flowers. A rainbow flag is displayed prominently by the entrance, adding a touch of vibrant color.

5 out of 5 average rating, 127 reviews

Andersonville 2 bed with modern kitchen + bath

Hi, we're Mike and Lora. Our beautiful Mission-style three-flat is located about 100 ft. from Clark St. in Andersonville, with great bars, restaurants, and shopping just outside our door. Half a mile east is the Red Line, which gets you right downtown, and just past that is beautiful Foster Beach. We live upstairs and are happy to offer recommendations. We love it here! The apartment was rehabbed in 2019 and features a large kitchen with tons of counter space, in-unit laundry, and queen beds.

4.86 out of 5 average rating, 166 reviews

The master bedroom features a spacious bed dressed in soft linens, with a light blanket draped across the foot. A large mirror reflects natural light, and sliding glass doors lead to a private outdoor seating area. Warm hues accompany scenic artwork on the walls.

Home in Chicago

LAVISH LINCOLN PARK Home w/ Patio +attached garage

Escape into this Lincoln Park Hidden Gem! Guests love this home because: - Surrounded by top-notch restaurants/retail - Close to all popular attractions that make Chicago so great - Luxurious, newly-renovated interior filled with natural light - Open-floor plan for entertaining! - Gorgeous master en-suite with marble bath + walkout patio! - Fast WiFi (1000 mbps) - Very comfy beds! - Attached, private garage is huge bonus! - Red line (North/Clybourn) station 0.2 miles away (3-5 minute walk)

A serene garden space is presented, featuring green grass and a variety of plants and trees. Two light-colored Adirondack chairs are positioned on the lawn, surrounded by vibrant foliage. The backdrop includes brick buildings and a pathway, creating a welcoming outdoor environment.

4.8 out of 5 average rating, 201 reviews

Wicker Park Historic, Art-Filled, Urban Oasis #2

Entire 2 bedroom apartment in art filled,wicker park building 5 min from downtown Chicago. Quick walk to shops,restaurants,public transportation,parks,night life,etc. Space includes -Nice bathroom,walk in shower -1 bdrm w/ queen size bed,tv,desk,large closet -1 bdrm w/ single bed & closet -1 sleeper couch w/ full size pullout bed & mattress pad -1 foldable twin bed -1 queen size blow up air mattress -Fully equipped kitchen -Beautiful garden -1 parking space included + parking passes available

4.96 out of 5 average rating, 391 reviews

The living area features a comfortable blue sofa adorned with decorative cushions, complemented by a patterned rug. A soft pink armchair and a small round coffee table are present. A vibrant floral painting hangs on the wall, and natural light enters through the window covered by light curtains.

Guest suite in Chicago

Gorgeous, cozy 1-bedroom Suite in Andersonville

Our place is a short walking distance to everything. “Timeout” rated Andersonville #2 of the “worlds coolest neighborhoods”. Check out their Neighborhood Guide online for the best restaurants, bars & shops to visit. You’ll love your suite because of the quiet ambiance, location, complete privacy and NO cleaning fee. We are close to public transport and about 1 mile to the lakefront & Lake Shore Drive. 5 miles N of downtown Chicago. Perfect for couples, solo adventurers and business travelers.

4.99 out of 5 average rating, 268 reviews

An outdoor terrace features comfortable lounge seating and a grill. A panoramic view of the Chicago skyline is visible, showcasing various architectural styles and buildings under a clear blue sky.

Townhouse in Chicago

Spacious 4-Level/4-Bedroom Townhouse in West Loop

Spacious Townhouse in Chicago's Hip Foodie Neighborhood: West Loop/Fulton Market. This is a Private, 4-Story Townhouse on a Tree-Lined Street just Steps from the Action...while still quiet enough for a good night's sleep. Walk to some of the Nation's Top Restaurants (near Restaurant Row), Clubs, Pubs, Groceries, Parks, Coffee Shops. Easy Train Transit to O'Hare, Navy Pier, Mag Mile, McCormick Place, etc...Terrace w/Skyline Views & Attached Garage Parking for 1 Regular-Sized Vehicle Included!

A row of historic brick homes is set along a tree-lined street. Each home features ornate details on the facade, with stairs leading to the entryways. Greenery and flowers enhance the surrounding gardens, adding to the neighborhood's vibrant character.

5 out of 5 average rating, 104 reviews

Lincoln Park DePaul Rowhouse Historic Bissell St

Exclusive Lincoln Park location. Beautiful historic landmarked block. Perfect for a weekend getaway or longer stay. You will have your own apartment with a private entry and brick patio to relax and enjoy coffee in this vibrant and historic neighborhood. Just a couple minute walk to exclusive Armitage Shopping District and DePaul University. Short walk to the lakefront, free Lincoln Park Zoo, Peggy Notebaert Nature Museum and Organic Farmer's Market during summer months.

4.97 out of 5 average rating, 155 reviews

A modern living area features a green sofa positioned in front of a glass coffee table on a patterned rug. An open kitchen with white cabinetry and stainless steel appliances is visible in the background. Natural light fills the space, enhancing its welcoming atmosphere.

Condo in Chicago

Large 2BR, 2BA, patio, sunroom, W/D, L-kitchen

Welcome to our charming home in the peaceful yet centrally located Buena Park neighborhood, housed in an updated antique building. This prime location offers easy access to the Red and Purple train lines, as well as multiple bus routes, making it easy to explore Chicago. You’ll be within walking distance of Wrigley Field, Clark St. bars, Montrose Beach, Lakeview, Boystown, and the iconic Green Mill. A perfect blend of quiet comfort and proximity to Chicago’s best attractions.

A modern living area features a gray sofa with accent chairs set beside large windows, allowing natural light. A patterned area rug covers the floor, complemented by a minimalist coffee table. Wall art adds subtle elegance, enhancing the overall inviting layout.

4.98 out of 5 average rating, 112 reviews

Spacious&Modern Condo | Near Dwtn | Secure Parking

Your stylish city escape—unwind, explore, and experience Chicago like never before. Our modern, spacious condo is perfect for families, groups, and business travelers looking for a comfortable, stylish, and well-located stay. Whether you're in town for a concert, conference, sightseeing, or a weekend getaway, you'll find everything you need for a relaxing stay. ONE SECURE INDOOR PARKING SPOT IS INCLUDED❗❗❗ ✨ Book your stay today & experience Chicago in comfort and style! ✨

A well-appointed bedroom features a spacious bed with layered linens and decorative pillows. Soft lighting from two bedside lamps complements a small desk and chair positioned near a window. Rich wood tones and a colorful area rug enhance the room's inviting atmosphere.