Fitness-friendly vacation rentals in South Side

Cozy 2BD Lake Apt Near Downtown, McCormick & More

Enjoy your getaway in this cozy solar powered and eco-sustainable garden apartment 5 minutes walking to Lake Michigan where you can access beaches, bike paths, prairies, parks & more! We are less that 8 min away from downtown, the University of Chicago, Soldier Field, the Field Museum and more. Our home is located in the historic Oakland neighborhood, central to so much of what Chicago has to offer. We love welcoming guests to our garden apartment where making your stay relaxing is our pleasure

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.

Stunning 2bd 1bath w/free parking, W/D & fireplace

Whether you're here to visit family or friends, to attend a conference in the city or a quick getaway, your family will love renting our entire flat. It has all the comforts of home located on a beautiful block in the historic Frank Lloyd Wright District in Oak Park. Here, you will be close to The Frank Lloyd Wright Home/Studio, downtown Oak Park, amazing restaurants and attractions, the Green and Blue line trains that will take you to downtown Chicago, and major highways and shopping centers.

Elegant Suite in Gold Coast

Established in 1927 as the first headquarters for Elizabeth Arden in Chicago, the Walton Residence is located in the heart of the Gold Coast neighborhood of Chicago. Steps away from the Magnificent Mile, and the high-end boutiques of Oak and Rush Street, we are perfectly situated in the middle of the action for your Chicago adventure. ***From Sept. to beginning of Dec. 2024, there will be repairs to the exterior of the building. We do not expect this to cause major interruptions to your stay.

Stylish 2BR Corner Unit Near Downtown & McCormick

Welcome to your modern 2-bedroom, 2-bathroom corner suite offers unbeatable convenience and comfort, located just steps from McCormick Place. 📍 Prime Michigan Avenue location 🏙️ Corner unit with South Loop skyline views 🛏️ 2 Queen beds + sofa bed (Sleeps 6 total) 🔥 65” Smart TVs in every room (Netflix + Roku) 🚀 High-speed dedicated Wi-Fi ❄️ Central heating & cooling 🍳 Fully equipped kitchen 🚗 EV charging + optional parking 🏋️‍♂️ Fitness center access 🧺 Washer/Dryer on the same floor

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!

River North | Private Deck With In&Out Parking

Stay in style at our brand-new, upscale retreat in the heart of downtown Chicago ✨ This stunning 3-bedroom, 2-bathroom unit blends modern design with luxury comforts ,perfect for families or corporate travelers 🌆 🌇 Rooftop Patio w/ BBQ 🌿 Private Deck w/ Lounge Seating 🚗 Free In/Out Parking – 5 Min Walk 🌅 Balcony w/ Gorgeous City Views 🛏️ 3 Bedrooms | 2 Bathrooms 👑 3 Queen Beds + 2 Airbeds 👶 Portable Crib for Little Ones 📺 Netflix, Hulu, Disney+, Prime Included

Sentral 1BR Premium 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

Entire Luxury Home: Private Gym

Welcome to our contemporary, luxurious living experience! This 4BR Chicago home with a gym is ideal for an unforgettable family vacation, a trip with friends, or a group of digital nomads. Our home is conveniently located near downtown Hyde Park, the University of Chicago campus, Lake Michigan, and the upcoming Barack Obama Presidential Center! This elegant home features 4 bedrooms, 3.5 bathrooms, and a gym. The entire house can comfortably accommodate 8 guests.