Vacation rentals with outdoor seating in West Side

A spacious living area showcases warm wooden floors and a dark brown accent wall. A blue sofa is complemented by colorful cushions, while a wooden coffee table sits in front. Artwork and decorative pieces adorn the walls, and natural light filters through large windows.

4.92 out of 5 average rating, 208 reviews

iKlektik House Chicago/BlueJay

Enjoy the warm heated floors and check out this home's amazing craftsmanship and artwork. Custom made built-in king size bed. Large custom kitchen, butcher block and claw foot tub in bathroom. WE DO NOT RENT ON "CL" DO NOT WIRE $ IT'S A SCAM The apartment is located in West Town. CLOSE TO THE UNITED CENTER New restaurants and neighborhood favorites, along with cocktail bars and music venues. Metra, Cta {buses and trains} close by. Metra: Western & Hubbard Free Street Parking Right Out Front!

A bright living room features large windows allowing natural light to fill the space. Comfortable seating includes a spacious couch and decorative poufs. A smart TV is mounted on the wall, and plants bring a touch of greenery, enhancing the relaxing environment.

4.98 out of 5 average rating, 112 reviews

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

4.97 out of 5 average rating, 330 reviews

A cozy living area features a gray sofa adorned with patterned cushions, complemented by a light-colored coffee table. Wooden flooring adds warmth, and large windows are draped with sheer curtains, allowing natural light to brighten the space. A small workspace is visible in the corner.

Apartment in Cicero

COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy

Located on a tranquil city side street, this property is walking distance to numerous restaurants and stores. Enjoy easy access to public transportation, including Metra train, CTA Pink Line, and a direct CTA bus to Midway Airport. Downtown Chicago is a mere 20-minute drive away, with the United Center and Soldier Field just 15 minutes away. Ideal for a quick getaway, an overnight stay before your flight, or an extended work assignment. Unwind on the patio, complete with a fire pit and grill.

4.97 out of 5 average rating, 306 reviews

A spacious bed is adorned with layered bedding, featuring a variety of pillows in soothing hues. Soft light from a nearby window creates a serene atmosphere, and a decorative stained glass piece adds a touch of artistry to the room.

Guest suite in Chicago

Private Suite w/ offstreet pkg, at Logan Sq Blu Ln

Cozy English garden apt (300 sq ft) w/ priv. entrance & free offstreet prking. 4 min walk to Blue Line. Brightly lit / high ceiling. Adjustable Tempupedic memory foam QUEEN bed plus futon in lvng rm. Kitchenette w/ mini-frig, Nespresso & Keurig, toastr ovn, microwv, and waffle maker w/maple syrp. Designer bath. 30+ restaur/bar nearby (see GUIDE BK in LOCATION). Self check-in. Flexible cancel. Early lugg. drop. A space to unwind in -- art-filled and artistic in design, NOT bland or IKEA like!

4.93 out of 5 average rating, 391 reviews

A charming brick two-story home is framed by lush greenery and colorful flower beds. The entrance is adorned with light fixtures, and steps lead up to a welcoming porch. The well-maintained garden features a variety of blooming plants, enhancing the inviting ambiance.

Guest suite in Chicago

Luxe, Private Suite w/Own Entrance-2023 Renovated

Newly remodeled private city oasis! Professionally designed cozy suite with private keyed courtyard entry & small lighted covered patio w/table and chairs (work outside!) New ensuite bathroom w/heated floor, bespoke vanity & fab water pressure. Quiet tree-lined street with free parking, great restaurants, old pubs, shops & transport walkable. Great launch to all Chicago has to offer while enjoying charming Bucktown. Close to Downtown, DePaul, Zoo, Lincoln Pk, Wrigley, United Ctr, Lakefront.

An aerial view of a swimming pool surrounded by a spacious wooden deck. Six comfortable loungers are positioned around the pool, with additional seating areas visible. An umbrella-covered table is set for outdoor dining, harmonizing with the greenery in the yard.

4.98 out of 5 average rating, 129 reviews

Fun & cozy getaway w/POOL/game room/FREE parking

Enjoy our Pool & Play Getaway in hot Logan Square! Thoughtful upscale touches throughout. Conveniently located on a tree-lined Chicago Cul-de-Sac, just a 5 min walk to the L Blue Line. Relax in our extended outdoor living space, spend an afternoon lounging in the pool, al fresco grilling & dining on the deck or toast smores over the firepit in the yard. We're steps from all the hot restaurants and nightlife, including Chicago's #1 farmer's market. Free permit street parking for our guests.

4.98 out of 5 average rating, 160 reviews

A living room features a mid-century velvet sofa in a rich green hue, paired with a tan leather chair. Natural light streams through large windows, illuminating a glass coffee table and a decorative wall with layered wooden frames. The original brick fireplace adds character to the space.

Home in Berwyn

Retro Modern Bungalow | free parking | fire pit

Experience the city in style at our 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 backyard. 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.

4.9 out of 5 average rating, 332 reviews

The living room features a spacious teal sofa paired with a simple black coffee table in front. A window with sheer curtains allows natural light to fill the area, complemented by a floor lamp and potted plants. Hardwood floors add warmth to the room.

Apartment in Berwyn

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.

4.91 out of 5 average rating, 493 reviews

A charming house is framed by a lush garden filled with various shrubs and flowering plants. The exterior features a mix of wood siding and prominent windows, while a white picket fence lines the front yard, enhancing the home's inviting presence.

Guest suite in Oak Park

Entire upstairs in Arts and Crafts Oak Park home

You have the use of the entire upstairs (with a separate, lockable private entrance). With two bedrooms, bathroom and a common area with a futon, fridge, microwave, coffee maker and kettle, it is flexible for individuals or small groups of no more than 4 people. Free overnight parking. We're a quick walk to the CTA Blue line, coffee shops and restaurants, parks, musical venues, the Oak Park Arts District, and a quick drive to downtown. Our home is cozy, in a friendly neighborhood.

A green sofa is positioned in a bright living area, accompanied by a round coffee table. A decorative bowl and a potted plant sit atop the table, while a piece of wall art featuring a tree landscape adds character. Natural light enters through nearby windows.

4.99 out of 5 average rating, 243 reviews

Modern Apt with style & comfort in Pilsen Chicago

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.

4.94 out of 5 average rating, 142 reviews

A lounge area features a curvy orange sofa, complemented by a black circular coffee table resting on a textured cream rug. Natural light filters through large windows, illuminating framed wall art with subtle hues. Minimalist decor creates a cozy and inviting atmosphere.

Guest suite in Chicago

Logan Square Garden Suite

Creative and quiet light-filled garden unit with lots of books, accompanied by comfortable lounge furniture and touches of nature for cozying up and relaxing after long travel or late nights. This is a perfect space for solo travelers or couples. This is also a great space if you are traveling with a small child or infant. The place is set up much like a hotel room in that it does not have a kitchen but we do provide a mini fridge and Nespresso machine.