Vacation rentals in West Side

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Top-rated vacation rentals in West Side

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An open living area features a comfortable grey sofa against a textured wall, with a flat screen TV mounted nearby. A small side chair and a decorative plant add to the space. Natural light enters through two windows, enhancing the room's bright and airy feel.

Apartment in Cicero

4.69 out of 5 average rating, 124 reviews

108 Mid-Century Rustic Studio

This is a BRAND NEWLY RENOVATED SPACE! It is a cozy apartment studio with ability to sleep 3 if needed. There are laundry facilities on site. A large flat screen smart tv with free wifi and a connected keyboard. Have access to a full kitchen with all the items needed for food prep and clean up. The CTA pink line, to and from Chicago, is a few blocks south for easy commuting. A Dollar General is across the street for groceries. There are many restaurants within a block and many other chains near.

Superhost

Apartment in Chicago

5 out of 5 average rating, 3 reviews

New Building in Med District - Modern 2Bed 2Bath

Welcome to your modern retreat in the heart of Chicago's vibrant Tri-Taylor neighborhood! This stylish 2-bedroom, 2-bath apartment is perfectly situated near the Illinois Medical District and the University of Illinois at Chicago, offering a blend of modern comfort and urban convenience. Explore the nearby historic Little Italy district with its authentic Italian restaurants and cafes, or easily access downtown Chicago via the CTA Pink Line, just a block away. Enjoy amenities like air conditioni

Top guest favorite

The exterior of a classic Chicago brownstone is presented, showcasing a welcoming entrance with stairs leading up to an ornate covered porch. Flowers in planters and hanging baskets add color, and an American flag hangs proudly from the porch.

Private room in Chicago

4.96 out of 5 average rating, 630 reviews

NEW,Roscoe Village,Cubs, Pvt Bath, Pvt Entrance

Gorgeous, classic Chicago brownstone with a private entrance and private bath. It is your own private apartment with a private kitchenette, private en suite bath and a private entrance. In the heart of a great city with every amenity and over 500 five star reviews! Walk to Wrigley or ride one of our free bikes. This suite is located 5 minutes from the "el" and many restaurants, boutiques and taverns. TOP 1% of all Airbnbs in Chicago after a DECADE of helping our guests in every way we can.

Guest favorite

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

4.9 out of 5 average rating, 334 reviews

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.

Top guest favorite

A well-lit sleeping area is featuring two spacious beds with crisp white bedding. A dresser is positioned nearby, and a round mirror is mounted on the wall, reflecting natural light from a window. A bold blue accent wall adds a pop of color to the room.

Home in Oak Park

4.97 out of 5 average rating, 144 reviews

Garden: Quiet & Near Train, Walkable & Parking

Our Oak Park, recently remodeled garden unit is 3 blocks to the train with free parking in upscale, safe, walkable Oak Park. Enjoy some time in our little urban farm. Check out the gardens and visit our 6 friendly hens. This non-smoking studio with a kitchenette is perfect for tourists, families, or business travelers. We require no check-out chores. Easy highway and airport access. No parties, 4 guests max. Booking age, 25 or at least one 5 ⭐️ review. Visit profile for more units.

Superhost

The spacious bedroom features a large bed dressed in crisp white linens, framed by soft side tables with gold accents. A piece of abstract artwork adorns the wall above the bed, and natural light enters through a large window with unobstructed views.

Apartment in Chicago

4.72 out of 5 average rating, 1,155 reviews

Kasa | Spectacular City Views | 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.

Superhost

A spacious sleeping area is featured, showcasing a large bed with crisp white linens. A soft, beige upholstered headboard complements the warm tones of the room. A bedside lamp stands on a wooden nightstand, and natural light filters through sheer curtains.

Hotel room in Chicago

4.79 out of 5 average rating, 383 reviews

All-glass gem by Chicago architect Harry Weese

$29.35 Resort Fee to be collected on property Swissotel Chicago is an award-winning luxury hotel overlooking the Chicago River and Lake Michigan, and just steps from the Magnificent Mile. The distinctive 4-diamond, all-glass hotel offers spectacular wrap-around views from Navy Pier to Millennium Park and has a state-of-the-art penthouse fitness center. The room may not look the same as the room in the photo as this room is run of house and selected by the hotel at check in.

A spacious bedroom features a large bed dressed in crisp white linens. Two bedside lamps provide soft illumination on either side. An abstract piece of wall art adds a modern touch, while natural light enters through the window, enhancing the clean lines of the room.

Apartment in Chicago

4.68 out of 5 average rating, 350 reviews

Sonder Market Hall | King Studio Apartment

Overlooking Union Park, Market Hall is the perfect blend of city and seclusion. You’ll have leafy green views, paved walking trails, and endless global cuisine options on Randolph Street. Each room includes a fully equipped kitchen, in-suite laundry, and a Roku for streaming. And take advantage of the free weights or machines in the fitness center. The West Loop is a trendy hot spot for foodies and entertainment seekers. Enjoy the best of the Windy City at Market Hall.

Superhost

Private room in Chicago

4.82 out of 5 average rating, 205 reviews

ChicagoRiver Double Room

Nicely decorated Private (10x11 sq ft) Room w/designated work station, well-lit, *shared common bathroom* (other guests may be in the premises). This is NOT a full condo rental; just 1 room. Quiet & clean, 2 miles from downtown, walking distance to dozens of restaurants in Taylor Street & Little Italy. Perfect location in a quiet neighborhood, but still close to the city to enjoy food& music festivals, free concerts in Grand Park, Museums, Broadway shows, etc

Top guest favorite

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.

Apartment in Chicago

4.99 out of 5 average rating, 245 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.

Top guest favorite

Two hanging chairs are positioned on a covered patio, surrounded by lush greenery and decorative plants. A small garden structure adds privacy, while the floor features a vibrant red surface. Ambient light filters through the overhead structure, creating a relaxed outdoor space.

Home in Chicago

5 out of 5 average rating, 14 reviews

Chicago Row House Garden Apartmt

This stylish urban garden apartment is a comfortable stay just a few blocks from the United Center and 1 mile from the very popular West Loop and Fulton Market areas! Street parking is readily available and free! We are a 3 mile straight shot down to Millennium Park in the Loop. Take the “L”, bike or walk there and hit Greek Town, the Lyric Opera, the Sears (Willis) Tower, the Art Institute and the Bean (Cloud Gate) along the way!

Guest favorite

The kitchen area showcases wood cabinetry, a sink, and a stove with an oven. A microwave is mounted above the counter, and utensils are neatly arranged in a holder. Colorful tiles add a decorative touch to the backsplash, while natural light illuminates the space.

Apartment in Chicago

4.85 out of 5 average rating, 137 reviews

*A Happy (City) Glamping- walk to train FREE park

Totally private NO shared spaces. Full amenity City Camper . FREE street parking (no permit needed) One block walk to (Green Line) train. - Two stops to trendy West Loop bars, restaurants & shops. 12 minute ride to downtown Chicago City Center. 5 min to United Center/Union Park. Air con & wi-fi. NOTE No visitors No smokers you must agree on my first message. Please CLICK "SHOW MORE" BELOW FOR MORE INFO....