Holiday houses in South Loop

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

Why stay anywhere when you can experience luxury during your travels. This brand new 1-BR apartment was designed with a touch of elegance and offers amenities to make your experience not just satisfying, but memorable. At your finger tips is a full kitchen; luxury bathroom with enormous walk-in shower; separate bedroom w/ queen bed (extra day bed in living room to sleep 3 total); garage parking; garden access; cozy workspace; 2-Smart TVs; bicycle; ample storage for longer stays; WIFI; and more.

The Executive's Escape (2BD / 2BA)

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.

Pro Cleaned & Isolated West Loop Coach House

Mimi & Paul's historic ivy-covered two-level coach house has a private entrance and an airy queen bedroom. The renovated kitchen is outfitted with European-sized appliances, though you'll probably have no time to cook since you're surrounded by the best restaurants Chicago has to offer. All of the essentials are provided to make your stay easy and comfortable...paper products, soaps, shampoo/conditioner/body wash, towels, linens and even coffee/tea! (See layout in "Other Details To Note" below)

Vibrant, Spacious Chinatown Home

Conveniently located in Chicago’s vibrant Chinatown, this spacious 2-bedroom apartment is perfect for both families and groups of friends. Enjoy a spacious yet cozy escape while being steps away from the city’s best dining, shopping, and cultural experiences. Minutes away from downtown Chicago by car and walking distance to the CTA train, the convenience is unmatched. Whether you’re here to explore the area or unwind after a day of adventures, this is the perfect base for your stay in Chicago.

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

Downtown Park #11 - Mich Ave PH | gym+rooftop

Feel at Home, Unwind, and Enjoy the amenities you deserve when you come to Chicago! Guests love staying with us because: -Central Location on Grant Park (no car needed!) -FAST WIFI -En-suite Laundry -Did we mention the Lake & Park are outside our front door? -Comfy Queen bed -Loft style bedroom -Shared Rooftop Deck stunning views -Gym -3 blocks from Red "L" subway -Close to Grant Park, The Bean, Soldier Field, Museums If you are looking for a special place, you've found it!

McCormick Place Cozy Studio Sleeps 4 | Opt Parking

🌆 Welcome to McCormick City Studio! Step into a space where comfort meets city energy — where mornings begin with soft sunlight streaming through tall windows, and evenings end with the glitter of Chicago’s skyline just outside your window. Whether you’re attending a convention at McCormick Place, exploring the Museum Campus, or simply taking a well-deserved getaway, this stylish studio suite offers the perfect mix of modern design, cozy ambiance, and unbeatable location.

Sentral Studio Apt in South Loop Chicago

Indoor/Outdoor Resort-Style Pool • Grilling Station • Four-Story Indoor Garden • Fitness Center • Demonstration Kitchen • Pet Friendly w/ Amenities • Co-Working Space w/ High-Speed WiFi • Across from Grant Park • Steps to South Loop Dining & Nightlife • Breathtaking Views of Lake Michigan & the City Skyline Sentral Michigan Ave offers upscale comfort in the heart of Chicago’s South Loop, blending premium amenities with unmatched access to parks, culture, and entertainment.

Lovely Garden Studio in Chicago

Kick back and relax in this calm, stylish space. Located in historic Bronzeville, our modern studio boasts open-plan living, stylish finishes and plenty of room to accommodate up to 3 guests. Our garden studio is located walking distance to the Green Line station, a 10 minute drive to downtown loop, 15-20 minutes away from Midway Airport, 5 minutes to Lake Michigan, and 5 minutes away from McCormick Place Convention Center, IIT, and Hyde Park/University of Chicago.

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!

Modern Stylish 1BR, Free Parking, Prime Location"

Just a few blocks away from Downtown Chicago, The Loop, and popular attractions, this property is the ideal spot for your stay! Carefully designed and fully furnished, the unit offers excellent amenities for both comfort and entertainment: Fully equipped kitchen In-unit laundry Roku TV in the bedroom (bring your own Netflix/Hulu login) Fast WiFi Perfect for healthcare workers, corporate employees, and all travelers seeking a convenient and cozy place to call home!

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.