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.

Top guest favorite

A rooftop terrace is showcased, featuring a comfortable seating area with white lounge furniture and a vibrant green rug. A large umbrella provides shade, while planters with greenery add a touch of nature. The urban skyline is visible in the background.

Townhouse in Near South Side

5 out of 5 average rating, 43 reviews

Chic Townhouse: 2BR, Rooftop, Free Parking, Secure

Welcome to our luxurious 2-bedroom, 2-bathroom townhouse located in the heart of south loop Chicago! Our home is perfect for travelers who desire being in close proximity to all the city's major tourist attractions. Enjoy breathtaking views of the city from our rooftop terrace, where you can relax and unwind after a day of exploring. Our secure complex ensures your safety and peace of mind throughout your stay, while free parking provides a hassle-free experience for those traveling by car.

Loft in Pilsen Historic District

A sunlit kitchen area with white cabinetry and stainless steel appliances is showcased. A bright yellow wall complements mid-century-style furniture, featuring a light blue chair. Large doors open to the balcony, allowing natural light to fill the space.

4.9 out of 5 average rating, 390 reviews

Pilsen Modernist, Creative, Lightfilled Loft

Take morning drinks through the sunshine-yellow room to the back porch, or watch light dance on translucent walls and glossy black and white hardwood floors. Eclectic design includes a mix of new and vintage furniture, and a collection of art and design books for guests to enjoy. This unit is owned by an artist couple who split their time between Tucson, AZ and Chicago. This is their personal unit when they're in Chicago. Come stay here to get away, be comfortable, relax, and be inspired.

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.

4.81 out of 5 average rating, 21 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

Top guest favorite

The exterior of a historic brick building is framed by lush green trees and plants. A decorative wrought-iron gate leads to a set of stairs, which rise to a large wooden front door. Sunlight filters through the foliage, creating a serene entrance.

Home in West Loop

4.98 out of 5 average rating, 356 reviews

Cozy garden apartment historic Jackson Bvld.

Just a short walk to the United Center our cozy 1 bdrm garden apt is located on Historic Jackson Blvd's tree lined st. Stop back & warm up by the fireplace before heading out to near by shopping & restaurants. Less than an hour from Midway or O'Hare. Walking distance to Randolph St. Restaurant Row, Little Italy, Greek Town, Union Pk, Fulton Warehouse Dist, Rush Hospital and UIC. A quick train/bus to The Loop, Theater Dist, Mag Mile, Wicker Pk. Free, convenient street pkg.

A modern living area features a gray sofa, white coffee tables, and a dining space with four chairs. Floor-to-ceiling windows provide expansive views of the Chicago skyline, with natural light illuminating the open layout. A sleek kitchen area with a bar counter is visible in the background.

4.67 out of 5 average rating, 309 reviews

Sentral Premium 2BR Apt 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

Apartment in Near South Side

A spacious rooftop terrace is displayed, featuring multiple seating arrangements with dark wicker furniture and red cushions. The area is surrounded by railings and offers a view of urban buildings under a clear blue sky.

4.78 out of 5 average rating, 143 reviews

McCormick Place Studio/parking/sleeps up to 4

• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 2 shifts Security officers in the building • City view • Queen size bed + Queen size air mattress 2 extra guests • Comfortable stay for up to 4 guests at a time • Access to the Gym • Dedicated Internet • 4K smart HDTV(Netflix and Roku) • Fully equipped & stocked kitchen with complimentary Coffee & Tea • EV charging stations available • Optional Parking space for only $30/day

A modern entryway features a textured stone wall with large, bold numbers displaying '1021 South.' Illuminated ceiling lights highlight the contemporary design. A glass door leads outside, showcasing a glimpse of the street beyond.

4.93 out of 5 average rating, 182 reviews

Lavish 2BR/2BA Loft I Next to Grant Park & Museums

Enjoy Chicago in our modern & spacious 2-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!

A well-lit bedroom features a spacious king-size bed with a memory foam mattress. A desk and chair are positioned near large windows, providing views of the city skyline. Complementary plants enhance the modern decor, while the room's light walls create a bright atmosphere.