Fitness-friendly 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.

5 out of 5 average rating, 5 reviews

High Rise Unit w/ Parking, Gym, Pool & Game Room

Welcome to your spacious urban getaway in the heart of Chicago’s Printer’s Row neighborhood! This modern 3-bedroom, 3-bathroom unit is located in a stunning high-rise building, offering sweeping city views and access to premium amenities—perfect for families, business travelers, or groups looking to explore the best of downtown. Whether you're here for work or play, this retreat offers the perfect blend of style, comfort, and location. Book your stay today and experience Chicago like a local!

A modern sleeping area features a comfortably made bed with crisp white linens and a dark upholstered headboard. A small side table holds a vase with fresh greenery and a magazine, while floor-to-ceiling windows reveal a view of Chicago's skyline.

Apartment in Near South Side

4.53 out of 5 average rating, 231 reviews

Sonder South Wabash | Two-Bedroom Apartment

Welcome to South Wabash — your modern South Loop sanctuary. Where each sophisticated space includes a fully equipped kitchen, in-suite laundry, and stunning Chicago views. Colorful art pieces complement the industrial exposed concrete ceilings. And floor-to-ceiling windows burst with natural night. There’s always something to do in the Windy City. Whether you like jazz, opera, or dive bar karaoke, the South Loop has entertainment for everyone. At South Wabash, experience the best of the city.

A communal area features comfortable seating, including a pair of gray armchairs with decorative throw pillows. A low coffee table is positioned between them. In the background, a beverage station with a coffee machine and snacks is visible, alongside a plant for added detail.

4.8 out of 5 average rating, 299 reviews

Kasa | Studio, Walk to Grant Park | South Loop

It’s easy to get a taste of Chicago’s culture and cuisine at Kasa South Loop Chicago, located within walking distance of the Museum Campus, McCormick Place Center, and a variety of restaurants and shops. Our Kasas are the best choice for your trip to the Windy City with our spacious floorplans, full kitchen, laundry facilities, and parking. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text, phone, or chat, and a Virtual Front Desk accessed via mobile device.

4.96 out of 5 average rating, 45 reviews

Apartment in River North

River North | Private Balcony With In&Out Parking

Enjoy a stylish experience at this centrally-located place ✨. Stunning 1,000 square foot modern two-bedroom, one-bathroom unit is perfect for corporate travelers and/or families looking for a stylish escape in downtown Chicago 🌆. 🌇 Rooftop Patio W/ BBQ 🍖 🚗 Free In/Out Parking - 5 Mins Walk To Garage 🌅 Private Balcony W/ Breathtaking Views 🛏️ 2 Bedroom | 1 Bathroom 👑 2 Queen Beds 🛏️ 1 Inflatable Airbed 👶 Portable Crib 📺 Netflix, Hulu, Disney Plus, and Prime subscription Included

The image captures a view of Chicago's skyline during dusk, with high-rise buildings reflecting on the water. The vibrant lights of Navy Pier and the giant Ferris wheel are visible, along with boats docked along the shore, creating a lively urban scene.

4.96 out of 5 average rating, 27 reviews

Luxury Loop Loft

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 block from an "L" train stop, which will transport passengers anywhere they could desire in the city.

Apartment in Near North Side

A spacious living area features large floor-to-ceiling windows that frame city views. A comfortable bed is positioned beside a stylish nightstand and lamp. A modern desk is arranged with office supplies, and a soft area rug adds warmth to the space.

4.9 out of 5 average rating, 99 reviews

50th Floor Mag Mile Studio

This Downtown Chicago unit is towering 50 stories above the city, with floor to ceiling windows in the living areas. This unit gives you the ultimate in Luxury urban living. It's all about the views and location. The city unfolds before you with amazing sunsets; nowhere in Chicago can you stay with views like these. The building provides the very best in amenities. A state of the art fitness center, Outdoor pool, Outdoor kitchens, business center, are available to our guests.

4.9 out of 5 average rating, 127 reviews

A rooftop deck features modern lounge furniture, including a cozy sectional and colorful seating. A grill is positioned near vibrant potted plants. The skyline view shows striking high-rise buildings with Lake Michigan visible in the background under a bright blue sky.

Condo in The Loop

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!

Apartment in Near South Side

A prominent fountain is showcased in the foreground, with multiple water jets arching upwards and illuminated in orange during twilight. The backdrop features a skyline of modern skyscrapers, including the Willis Tower, against a softly overcast sky.

4.84 out of 5 average rating, 118 reviews

McCormick 2B/2Ba w opt parking for up to 6 guests

• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 2 shifts Security officers in the building • 2 Queen size beds + Sofa bed for 2 extra guests • Comfortable stay for up to 6 guests at a time • Access to the Gym in the building • Fast dedicated Internet • 4K smart HDTVs in ALL ROOMS(Netflix and Roku) • Fully equipped & stocked kitchen with Coffee & Tea • EV charging stations available • Optional Parking space for only $30/day

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