Vacation rentals in South Loop, Chicago

5 out of 5 average rating, 4 reviews

The South Loop Suite

Located at the epicenter of Chicago's cultural, historical, and business attractions, this luxurious 2 bedroom apartment offers guests all the comforts of home, whether on the road for work or play. 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.

4.92 out of 5 average rating, 121 reviews

A submerged tunnel displays large sharks and various fish swimming gracefully in clear blue water. The vibrant coral and underwater foliage are visible below, creating a lively marine environment. Two individuals, one adult and one child, are seen observing the aquatic life.

Apartment in Chicago

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.

Apartment in Near South Side

4.85 out of 5 average rating, 103 reviews

Skyline 2BR in South Loop Chicago Near McCormick

Welcome and Experience Chicago in style at our upscale corner suite nestled in the dynamic South Loop district—just steps from McCormick Place and minutes from top city landmarks. This modern, metropolitan 2-bedroom, 2-bathroom suite features soaring 10 ft ceilings, a spacious open layout, and curated interiors that set it apart from the average stay. From custom furnishings to thoughtful amenities, we’ve created an elevated home-away-from-home for families, professionals, and long-term stays.

Top guest favorite

A vibrant mural adorns the exterior of a multi-story building, featuring colorful depictions of skeletons and bright flowers. The design reflects cultural significance and artfulness, bringing life to the urban landscape. The building is situated at a traffic intersection, enhancing its visibility in the community.

Apartment in South Lawndale

5 out of 5 average rating, 11 reviews

2B Midcentury Artist Loft w King Bed

Welcome to Casa D'Mi Amá, this vibrant mid-century loft style apartment is centrally located in Little Village, one of the most vibrant Mexican-American communities and thriving shopping district in Chicago. Our community is known for its colorful murals and hundreds of Latinx-owned businesses and restaurants. We are just 4 mile away from downtown & Midway airport, three miles away from Pilsen & UIC, with public transportation right outside your door making it easy to plan your visit.

Apartment in Pilsen Historic District

A modern bathroom features a spacious shower with a glass enclosure and wooden bath mat. Soft lighting brightens the neutral-toned walls and floor tiles. A framed picture hangs above a small toilet, while a complementary towel is neatly hung on a nearby hook.

4.82 out of 5 average rating, 22 reviews

Garden Apartment in Historic Pilsen Arts Area

This private garden unit is ideally located and well-equipped with everything you need for a comfortable homebase on your Chicago adventure. Come to Pilsen and experience one of Chicago’s most vibrant neighborhoods. With dozens of unique shops to explore, delightful coffee shops, Pilsen is a beating heart of arts and culture. Peruse charming streets filled with distinctive and historic architecture, admire beautiful street murals, and try one of Pilsen's many delicious taquerias.

A panoramic view of downtown Chicago is displayed, featuring a mix of modern and historic buildings. In the foreground, train tracks and parking areas are visible. The skyline is partially obscured by fog, adding a unique perspective to the vibrant cityscape.

5 out of 5 average rating, 9 reviews

South Loop | Rooftop With In & Out Parking | 1

Enjoy a stylish experience at this centrally-located place ✨. Stunning 1,000 square foot modern two-bedroom, two-bathroom unit is perfect for corporate travelers and/or families looking for a stylish escape in downtown Chicago 🌆. 🔥 Rooftop Patio W/ BBQ 🏊‍♂️ Rooftop Pool 🚗 Free In/Out Parking - 5 Mins Walk To Garage 🛏️ 2 Bedrooms | 2 Bathrooms 🛌 2 Queen Beds 🛌 1 Inflatable Airbed 👶 Portable Crib (For Mini Travel Companion) 🎬 Netflix, Hulu, Disney+ & Prime Included

A modern kitchen features sleek blue cabinetry complemented by marble accents. The space is illuminated by pendant lights above a kitchen island with seating. A round dining table is set nearby, surrounded by plush chairs, providing a welcoming area for meals and gatherings.

4.73 out of 5 average rating, 159 reviews

Sentral Studio Apt in South Loop Chicago

Experience a lifestyle where everything you need is right at your fingertips in the vibrant heart of Downtown Chicago. Explore the area effortlessly: ✔ Breathtaking views of Lake Michigan and the Chicago skyline ✔ Close to major business hubs and the Loop District ✔ Enjoy a walk along the scenic Lakefront Trail ✔ A lively array of world-class museums, gourmet restaurants, and iconic architecture ✔ Quick access to Millennium Park, the Art Institute of Chicago, and Grant Park

A modern kitchen space features dark cabinetry and a sleek countertop. Kitchen appliances, including a coffee maker and kettle, are visible alongside plants for a touch of greenery. The counter is set with white bowls and glasses, inviting guests to enjoy meals together.

4.88 out of 5 average rating, 243 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!

The building entrance is featured, displaying a modern façade with large glass doors. A blue awning marked with '1021 SOUTH STATE' provides clear identification. The entrance is flanked by red canopies, adding a vibrant touch to the exterior design.

4.89 out of 5 average rating, 166 reviews

Lovely 1-bedroom serviced apartment near Museums!

A clean and organized laundry area is equipped with a double stack of front-loading washers and dryers. Clear instructions for operation are posted on the wall above. The space is well-lit, featuring a simple, functional design for convenience.

4.97 out of 5 average rating, 32 reviews

Downtown 2bd #4 - Near Grant Park, Museums, Lake

Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional service along with “local vibes.” Guests love staying with us because: -Central Location near public transit (no car needed!) -FAST WIFI -En-suite Laundry -Lake & Park are 1 1/2 blocks away -Comfy Queen beds -Gym -3 blocks from Red "L" subway -Close to Grant Park, The Bean, Soldier Field, Museums If you're interested in booking, see our FAQs below.

Apartment in Pilsen Historic District

An ornate entrance gate welcomes visitors with the phrase 'Bienvenidos a Pilsen,' crafted in bold lettering. The intricate ironwork frames the entrance, reflecting the vibrant character of the Pilsen neighborhood. Light filters through the transparent doors, hinting at the lively atmosphere beyond.

4.87 out of 5 average rating, 263 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.

Top guest favorite

A modern living area features a green velvet couch and a round wooden coffee table atop a patterned area rug. A television is positioned on a media console, with natural light coming through multiple windows. Artwork adorns the walls, adding character to the space.

Apartment in Chicago

4.99 out of 5 average rating, 230 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.

Vacation rentals for every style

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Popular amenities for South Loop, Chicago vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near South Loop, Chicago's top sights

Millennium Park213 locals recommend

Shedd Aquarium122 locals recommend

The Field Museum95 locals recommend

Other great vacation rentals in South Loop, Chicago

A spacious balcony view is captured through large glass doors, revealing a cityscape with rooftops and street scenes. A comfortable dark sofa is positioned nearby, adorned with a light throw and decorative pillows. Natural light brightens the interior space.

Private room in Chicago

5 out of 5 average rating, 3 reviews

Room w/ Private Bath | Chicago

MarkRating, 5 stars6 days ago

Daniel was a fantastic host! He made me so comfortable in his home and yet, I had all the privacy I could want. He described the area in great detail and offered lots of good suggestions on where to go for different meals. His place was exactly as described in his listing and the photos were an exact match. Daniel was a really friendly, helpful guy and I would stay at his place again any time! Thanks, Daniel!

4.88 out of 5 average rating, 51 reviews

A five-story building characterized by its vintage brick facade and decorative ironwork. An outdoor fire escape extends along the side, while large glass windows offer views of the bustling street below. A prominent sign displays the name 'South Loop Club.'

Hotel room in The Loop

South Loop Studio Hotel (305)

MarkRating, 5 stars2 weeks ago

Perfect stay for our night in the city. Thanks very much!

A clean bathroom area is featured, showcasing a spacious vanity with a mirrored wall above. Soft, white towels are neatly folded beside a green plant on the countertop, creating a refreshing and organized space. Neutral colors contribute to a calming ambiance.

Private room in Little Italy

4.78 out of 5 average rating, 79 reviews

Beautiful Private Room 5 min to the City

IngridRating, 5 stars2 weeks ago

Super close to UIC, located in a quiet and safe neighborhood. It’s also not far from downtown Chicago. The apartment has five rooms, with a toilet on the first floor and a full bathroom on the second floor. It can get a bit crowded on weekends, which might make the bathrooms busier, but in my experience, they’ve remained clean despite being shared. That said, cleanliness may vary depending on the tenants. Also, the walls are a bit thin, so noise from the first floor can sometimes be heard upstairs. However, people generally keep quiet after 11 p.m.

Private room in Chinatown

A clear blue sky provides a backdrop for branches adorned with vibrant pink blossoms. The trees are lush and full, creating a serene and inviting environment enhanced by the cheerful colors of spring.

4.95 out of 5 average rating, 117 reviews

China Tours

AdamRating, 5 stars1 month ago

I was in Chicago for a conference and Heidi's place was exactly what I needed. Clean, well-located and private. Easy access to Chinatown for great food and ambiance. Rest of Chicago is easily accessible through Subway or even by walk when weather is good. Heidi was a great host.

5 out of 5 average rating, 10 reviews

A modern bathroom showcases a walk-in shower with textured stone flooring and glass paneling. A small sink with sleek fixtures is positioned beside a large mirror, reflecting the neutral tile design. Warm lighting enhances the clean and functional layout.

Private room in Chicago

Sweet Pea - blue Key - Place 3

NeilRating, 5 stars1 week ago

Very nice and clean and close to the subway

A modern rooftop lounge area features stylish seating arranged around a sleek fire table. Green accent pillows add a pop of color against the gray sofas. Glass walls provide panoramic views of the surrounding cityscape and sky, enhancing the inviting ambiance.

Hotel room in Near South Side

4.65 out of 5 average rating, 37 reviews

modern design with VU Skyward rooftop bar

TaviasRating, 5 stars1 week ago

I arrived earlier than my booking time and they were available to get me a room. It was right across the street from the event I was going to as well.

A modern lounge area is adorned with hexagonal shelving displaying books and plants. Comfortable seating options include a blue velvet sofa, tan armchair, and patterned lounge chairs. Natural light filters through sheer curtains, enhancing the inviting ambiance.

Hotel room in The Loop

4.76 out of 5 average rating, 244 reviews

A polished, modern affair on iconic Michigan Ave.

StephRating, 5 stars2 weeks ago

good location, close to transit, room was as described.