Fitness-friendly holiday rentals in South Loop

Cozy 2 bedroom house/w garage in Skokie

Charming 2B/1.5B house in Skokie IL. This Airbnb boasts plenty of amenities including WIFI, Roku TV's, fully furnished, a beautiful backyard, workout gym and sauna in the basement and a kitchen with top of the line appliances. The house sits on a quiet residential street just 2 minutes away from the nearest interstate taking you to beautiful Downtown Chicago in about 25min . Downtown Skokie is a few minutes away, plenty of shopping options 5min to Village Crossing and 15min to Old Orchard Mall.

2BR Downtown Elmhurst | Pool, Gym, Kings, Garage

A professionally managed 2-bed 2-bath apartment in downtown Elmhurst, providing the perfect balance of luxury and comfort for business travelers and families. Walk to the cafes, restaurants, and shops of downtown Elmhurst, nearby classy Oakbrook (8 mins), O'Hare airport (12 mins), and blocks to the Metra train station with easy access to downtown Chicago! Enjoy the pool, fitness center, garage parking, courtyard with firepits, pool table, and movie theater - convenience is at your fingertips!

Music Hotspot 2nd Floor

Urban-style suite with Fiber Wi-Fi walking distance of 4 music venues. Crawling distance from Fitzgerald's music venues. 2 blocks from Autre Monde and other restarnats/stores. 3 blocks to the CTA Blue line & 6 blks CTA Green/Pink line. Close to parks, pools, the zoo, and Thatcher woods/river. Many amenities, including a unique landscape, a fire pit, a furnished patio, kool artwork, smoker, grills, two furnaces and more. Must be 25 years or older to book. Only get togethers - no parties!

Guest suite with separate entrance and cozy gym!

Charming and private basement level retreat in Wilmette. With your own entrance, bathroom, mini fridge, microwave, and a small gym, this space is designed for comfort and independence. Relax in the beautiful yard with a fire pit, enjoy free parking, and take advantage of quick access to public transit, Northwestern, Evanston, and downtown Chicago. I live on the top floor and I have two dogs who will most likely bark when they see you come in and out. It’s their way of saying hello :-)

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

Eco-Friendly, modern, sleek, condo with modern finishes and a sweeping Sky Terrace and resort-like amenities are just steps from Northwestern University, Loyola, and Kellogg and minutes from Chicago. Joy of Evanston features granite countertops in the kitchens, 9 ft ceilings, and designer plank flooring. Enjoy luxury amenities such as a fully equipped fitness center, outdoor pool, BBQ and picnic area and beautiful landscaping. Guests can enjoy the Clark Street Beach & Lighthouse

2 Mi to Northwestern: Updated Home w/ Game Room!

Kid Friendly | Home Gym Equipment | Washer/Dryer | 2 Mi to Purple Line Treat your loved ones to a memorable Chicago area retreat at this 3-bedroom, 2.5-bath Evanston vacation rental! The home features a sleek interior with thoughtful furnishings, a fully stocked kitchen, and a game room for the kids. Explore Northwestern University’s campus, visit Clark Street Beach and relish the views of Lake Michigan, or take the Purple Line downtown for sightseeing and live entertainment!

3bedrooms& 2 bath (king bed) in newly updated Home

Located in the West suburbs of Chicago you'll be far away from the chaos of the city, yet close to the highway to visit downtown whenever you like. You'll have a great night sleep in either the king, queen, or full size beds. All with brand new mattress and linens. Get ready for a night out in 1 of our 2 full size bathrooms. Enjoy a large backyard for kids to play and if you decide to have a family BBQ. Whether you're coming here for work or play we have you covered.

Wonderful 1BR Retreat with Balcony in Oak Park

3rd-floor unit with elevator access and a balcony. This stylish 1BR/1BA apartment offers the perfect blend of comfort and practicality. Enjoy a fully equipped kitchen, a cozy yet spacious living area, and sleek, contemporary finishes throughout. Guests also have access to building amenities, including a fully equipped gym and a rooftop with beautiful views. Just 15 minutes from Chicago, it’s an ideal home base for a relaxing and convenient stay.

Agave Escape | 6 BR/2BA | 20 Min to Downtown

Agave Escape is a modern, spacious home in a great neighborhood, just 20 minutes from downtown Chicago. Features 6 bedrooms, 2 full baths, and flexible sleeping for families, groups, or work trips. Open living and dining area, fully equipped kitchen with bar seating, fast Wi-Fi, and smart TVs. One bath includes a deep soaking tub. Laundry room accessible to guests. Clean, comfortable, and easy access to highways, dining, and essentials.

Near ORD & Rosemont • Game Room • Sleeps 10

Modern 3BR/2BA retreat near O'Hare International Airport with PS3, Pac-Man, foosball, darts & a mini gym. Relax on the large deck & patio with grill, enjoy the fully equipped kitchen, and unwind in thoughtfully updated spaces. Sleeps 10 and pet friendly ($60 fee). Minutes from Allstate Arena, Rosemont dining, and nearby Metra access to downtown Chicago. Perfect for families, group trips, concerts, airport stays, and Chicago adventures.

New Chic 6bd 2 bth Ranch Home, Skokie w/basement

Spacious 4BR Home w/ 6 Beds, Gym & open space- Near O’Hare & Downtown! Perfect for families or groups of 10+, this centrally located gem offers 2 full baths, an open basement loft, a private gym with treadmill & free weights. Just 20 mins from O’Hare (ORD) & Downtown Chicago, with easy access to I-94 & CTA Yellow Line. Cozy up this winter with a perfect home base to explore Chicago’s winter attractions, dining, & events!

Close to Navy Pier + Restaurant. Bar. Gym.

Tucked just off the Magnificent Mile, Hotel Saint Clair gives you front-row access to Chicago’s must-sees—think Navy Pier, Millennium Park, and late-night eats around the corner. Sip your morning coffee, grab your camera, and hit the lakefront in minutes. The rooms are pet-friendly, WiFi’s on the house, and everything you want to see is walkable. It’s your laid-back launchpad for big city adventures.