Vacation rentals in South Loop

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Top-rated vacation rentals in South Loop

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Superhost

An outdoor pool is surrounded by a pavement area, featuring a few lounge chairs arranged along the sides. The building's modern architecture is visible in the background, with city high-rises and clear blue skies providing a vibrant setting.

Apartment in Near Southside

5 out of 5 average rating, 22 reviews

The Stadium Overlook

Within walking distance are world famous attractions including: Millennium Park, The Bean, Navy Pier, Riverwalk, Soldier Field, The Field Museum, and more. Additionally, guests are merely a couple blocks from an "L" train stop, which will transport passengers anywhere they could desire in the city. Located at the epicenter of Chicago's cultural, historical, and business attractions, this luxurious 1 bedroom apartment offers guests all the comforts of home, whether on the road for work or play.

Superhost

A stylish living area features a blue sofa with a decorative pillow, positioned against a coral wall. Light floods in through two large windows, illuminating a modern wooden table with metal chairs nearby. A small table with a plant and wall-mounted shelves completes the cozy space.

Apartment in Near Southside

5 out of 5 average rating, 3 reviews

South Loop 2BR Retreat | McCormick & Soldier Field

👋 Welcome to McCormick Oasis – Your Stylish South Loop Stay! We’re excited to host you in the heart of Chicago! Expect the best with our place! 🏠 Property Highlights: 🏢 9-min walk to McCormick Place 🏋️ Gym access 🌇 Rooftop + outdoor patio with lounge seating 🌐 Dedicated high-speed WiFi 📺 4K Roku TVs in every room w/ Netflix 🛌 2 Queen beds + Sofa bed (sleeps 6) 🚗 Optional parking for $30/day 🍳 Fully equipped kitchen 📍 Located right off Michigan Ave 💬 Message us for special rates!

Superhost

A modern living area features a comfortable gray sofa adorned with blue pillows, accompanied by a round glass coffee table with gold accents. The kitchen area in the background showcases sleek cabinetry, stainless steel appliances, and an organized countertop with dishes and a coffee maker.

Apartment in River North

4.82 out of 5 average rating, 285 reviews

Kasa | Nearby Millennium Park | River North

Halfway between Old Town and River North, our Kasa offers comfort, class, and convenience. Situated in a brand new high-rise, our modern apartments include state-of-the-art amenities as well as chic details like gourmet kitchens and high ceilings. You’re less than a mile from the Museum of Contemporary Art, The Wrigley Building, and more. Our tech-enabled apartments offer self check-in at 4 pm, 24/7 guest support by text, phone, or chat, and a Virtual Front Desk accessed via mobile device.

Guest favorite

A bright living space features a dark brown sofa adorned with orange cushions. A stylish coffee table sits on a patterned area rug, while two large windows allow natural light to fill the room. A corner mirror reflects the sofa and a cozy bed is visible in the background.

Apartment in Bridgeport

4.74 out of 5 average rating, 331 reviews

Bright & Spacious| Free Parking |Trendy Bridgeport

Step inside and be greeted by an open-concept space bathed in natural light. High ceilings, hardwood floors perfectly blend vintage charm with modern elegance. The living area invites you to unwind after a day of exploring our vibrant city. Relax on the sofa, watch your favorite shows on our large flat-screen TV, or indulge in book in the cozy seating nook. Whether you're a solo traveler, couple, or friend group looking for an unforgettable adventure, this is the ultimate urban retreat.

Superhost

A bright living area features large windows that allow natural light to fill the space. A modern green sofa is complemented by two matching chairs. A round wooden coffee table sits on a plush area rug, with decorative wall art adding character to the yellow-painted walls.

Condo in Near Southside

4.86 out of 5 average rating, 154 reviews

Luxe 2BR Cozy Suite | Skyline Views near McCormick

Welcome and Experience Chicago in style at our modern, luxury 2-bedroom, 2-bathroom suite located on iconic Michigan Avenue in the heart of the South Loop! Just steps from McCormick Place, our spacious 1,200+ sq ft suite is perfect for groups, business travelers, and families. This stylish apartment offers breathtaking skyline views, modern furnishings, and high ceilings that add a bright and spacious feel to every room. With sleeping arrangements for up to 8 guests.

Guest favorite

A cozy sleeping area features a four-poster bed draped with sheer fabric, creating an intimate ambiance. Bedside tables are positioned on either side, each topped with lamps. Natural light filters through multiple windows, illuminating the softly colored decor and inviting warmth.

Guest suite in Near Southside

4.89 out of 5 average rating, 9 reviews

Hidden Gem in South Loop

Welcome to your hidden gem Airbnb efficiency, where comfort meets convenience in an unbeatable location! This cozy retreat features a private entrance, ensuring your peace and privacy with a fully equipped kitchen. Located just steps away from local attractions, cafes, and shops. Whether you’re strolling through the city or attending an event at Soldier Field or McCormick Place, this spot is a perfect base for your adventures. Parking is not included. It is $20/day

Guest favorite

A spacious living area is highlighted by large windows that provide ample natural light. A contemporary sofa faces a round black table, complemented by a vibrant red area rug. A striking mural adorns the wall behind the seating, adding a bold artistic touch to the space.

Apartment in The Loop

4.89 out of 5 average rating, 245 reviews

1BR South Loop Loft I SuperHost + Top Rated!

Enjoy Chicago in our modern & spacious 1-bedroom loft in the South Loop. Central location to Grant Park, Soldier Field, Museum Campus, McCormick Place and more! Our location has a walk & transit score of 97, providing easy access to all the hot spots on your itinerary! Expect lovely natural light, luxuriously tall ceilings and room to accommodate your entire group. Guests are always pleasantly surprised by the size of the space and the modern amenities we provide!

Guest favorite

A spacious bedroom features a king bed with a memory foam mattress centered against a decorative wall panel. Two potted plants add greenery to the room, with modern pendant lights providing illumination. Large windows allow natural light to fill the space, complemented by a comfortable chair and a mirrored wardrobe.

Apartment in The Loop

4.89 out of 5 average rating, 173 reviews

Lovely 1-bedroom serviced apartment near Museums!

Guest favorite

A modern kitchen features sleek black cabinetry and appliances, complemented by a contrasting white countertop. Stylish stools are arranged around a small kitchen island. The wall is adorned with a framed painting, while decorative items are displayed on open shelves above the countertop.

Apartment in Pilsen Historic District

4.87 out of 5 average rating, 274 reviews

Spectacular Pilsen Studio for 2!

This chic studio in the heart of Pilsen is the perfect space to kick back and relax during your visit to the Windy City! The vibrant neighborhood always has something to offer to any type of traveler, and it's a quick trip to see most of the iconic Chicago sights. Easily walk to historic Thalia Hall, or drive to the Loop in just 5 minutes! You'll love the thoughtful touches and modern decor in the apartment, as well as the bright and welcoming main space.

Guest favorite

A modern kitchen is showcased, featuring sleek cabinetry in dark tones and stainless steel appliances. An island with a light countertop provides ample space for meal preparation. Natural light enters through large windows, brightening the inviting atmosphere of the open layout.

Apartment in Pilsen Historic District

4.95 out of 5 average rating, 58 reviews

Pilsen Modern Chic Retreat

Welcome to your perfect getaway! This stunning 2-bedroom home is the epitome of modern chic; offering an unforgettable blend of style and comfort. Designed for up to 6 guests, the space is crafted with thoughtful architectural details and an eye for eclectic decor. Located in the heart of Pilsen, known for its vibrant art scene, trendy restaurants, & local culture, you'll be perfectly situated to explore everything Chicago has to offer.

Guest favorite

A spacious living area features a large sectional sofa, complemented by a light area rug. A flat-screen TV is mounted above an elegant fireplace. The room is illuminated by warm ceiling lights, with greenery adding a touch of nature. The open floor plan leads into the kitchen area.

Apartment in Near Southside

4.94 out of 5 average rating, 182 reviews

South Loop 3Br/2Ba Condo with Balcony & Parking

Welcome to our stylish 3-bedroom, 2-bathroom apartment in the vibrant South Loop neighborhood! Perfect for families, friends, or business travelers, this spacious unit comfortably sleeps up to 6 guests. With a private balcony, free parking, and all the amenities you need, it’s an ideal base for your Chicago getaway. Book your stay today and experience the best of Chicago from the comfort of this modern, spacious apartment!

Superhost

A spacious living area showcases a blend of modern comfort and rustic charm. Exposed brick walls complement sleek furniture, including a large sofa and two orange armchairs. A flat-screen TV is mounted on the wall, with a circular coffee table in front. Dining chairs surround a nearby table.

Apartment in Chicago

4.85 out of 5 average rating, 26 reviews

Loft-Inspired Retreat | Stylish Stay Near Downtown

Unwind in this loft inspired unit with soaring ceilings, ideally located just 10 minutes from downtown Chicago in the vibrant Pilsen neighborhood. Enjoy a fully-equipped kitchen, luxury bathroom with rain shower, cozy queen bedroom, and spacious living area with a pull-out sofa. Features include high-speed WiFi, central heat/air, Smart TVs, and washer/dryer access. Perfect for up to 4 guests–your chic urban retreat awaits!