Fitness-friendly holiday rentals in South Loop, Chicago

Find and book unique fitness-friendly rentals on Airbnb

Top-rated fitness-friendly rentals in South Loop, Chicago

Guests agree: these fitness-friendly rentals are highly rated for location, cleanliness and more.

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Guest favourite

Flat in Uptown

4.9 out of 5 average rating, 516 reviews

Whole Flat in Private Club. Walk to L, Dining & Shows

Find unrivaled amenities in the newly restored Lawrence House, a Deco gem lauded a “unique architectural treasure” by the Chicago Architecture Foundation. Bask in an over-sized double lounger on the roof-top deck with 360-degree skyline views. Detox in the state-of-the-art fitness center with boxing gym. Soak in the 50-foot mosaic-tiled pool. Come home to a sunny, open-layout flat, with a cozy private bedroom, spa-like bathroom, fully-equipped kitchen, and free washer/dryer. Work or play in the terrazzo-floored Grand Lobby with club seating, adjoining cafe, craft cocktail bar and restaurant. Newly restored, sunny and spacious, immaculate, hotel-styled one-bedroom apartment with all new fixtures and appliances. Cozy bedroom with comfortable queen bed, flat screen TV, and large closet. Living room with couch that pulls out to a full-sized bed, club chair, large flat screen TV, and drop-leaf table for working. Stocked kitchen with everything you need to cook full meals, a new Smeg fridge, granite counters, and bar-stool seating. A queen-sized Serta air mattress allows up to 5 people to sleep comfortably. Central heat and air conditioning. Free washer/dryer in unit. Just-restored Art Deco building, called a "unique architectural treasure" by the Chicago Architecture Foundation. Unrivaled, private-club styled amenities. State of the art fitness center. Mosaic-tiled 50-foot pool. Roof-top lounge and deck with 360-degree skyline views, and tons of over-sized double loungers. Garden patio with fire pit, grills and picnic tables. Grand Lobby with cafe and craft cocktail bar, club seating, striking stained-glass skylight, ornate plaster moldings and terrazzo floor. Privacy guaranteed. The entire apartment is yours. You may also use the building's gorgeous amenities: fitness center, pool, roof-top lounge and deck, and garden patio. We have a self check-in and check-out system to provide you the most flexibility. However, we are always available to answer any questions, address any concerns, and provide recommendations. In the heart of Chicago's premier live-music and entertainment district, steps from two major concert venues and a legendary jazz lounge. Walk to dozens of restaurants and bars. Two blocks to the Beach. One block to the Red Line 'L' train, which goes straight to Wrigley Field in 5 minutes, and the Loop in 20 minutes. To learn more about the area, check out the Chicago Sun-Times feature on Uptown by googling: “sun times uptown neighborhood” One block to Red Line 'L' station. Free street parking with permits provided. Pets may live in the building but there are no pets allowed in this unit. In the heart of Chicago's premier live-music and entertainment district, steps from two major concert venues and a legendary jazz lounge. Walk to dozens of restaurants and bars. Two blocks to the Beach. One block to the Red Line 'L' train [temporarily 3 blocks while my station is rebuilt], which goes straight to Wrigley Field in 5 minutes, and the Loop in 20 minutes. To learn more about the area, check out the Chicago Sun-Times feature on Uptown by googling: “sun times uptown neighborhood guide”

Top guest favourite

Flat in West Town

5 out of 5 average rating, 6 reviews

Luxurious 3BD Penthouse- Private Patio+Gym+Rooftop

Welcome to The Ashbourne! This unit accommodates 6 adults (for families); otherwise, only 4 adults are allowed. To ensure the safety of all building tenants, ALL adult guests must submit ID proof via our verification partner, Authenticate. The building is fully keyless and guests must download the SALTO KS app to access digital keys for entry and access to all amenities like the Gym and our stunning rooftop deck. This is mandated by our building management, so please note this before reserving.

Guest favourite

Flat in Lincoln Park

4.89 out of 5 average rating, 9 reviews

Beautiful Condo in Lincoln Park w/ Rooftop

NEW LISTING! Make this Duplex Condo in the Heart of Chicago Your Home! Our condo features some of the most unique amenities, including: 🎥 150" Projection Home Theatre 🏋️‍♂️ Tonal Digital Gym & Nordic Track Treadmill 🌇 Patio with Grill & Gigantic Wall Mural 🌅 Access to Rooftop Deck with Spectacular Views 🏓 Ping Pong Table & Outdoor Mini Pickleball 🎹 Upright Acoustic Piano 🚶‍♂️ Highly walkable to top Restaurants and Shopping 🚇 Easily accessible via Public transportation 🚗 Free Parking

Superhost

Flat in Uptown

4.68 out of 5 average rating, 44 reviews

Sunny Modern 1BR Beach/City Views Rooftop WFH Gym

*PEACE* Escape to a serene oasis nestled in the vibrant heart of Uptown, Chicago. Enjoy a fully stocked kitchen, smart TV, and a dedicated workstation, ideal for traveling professionals or remote workers. Unwind in comfort with an in-unit washer/dryer, dishwasher, and access to a rooftop area for breathtaking city views. Stay in shape with a fitness center. Steps away from Montrose Beach, Aragon Ballroom, and Riviera Theatre, you can balance tranquility and urban exploration. Parking available.

Guest favourite

Guest suite in Lake View

4.84 out of 5 average rating, 246 reviews

Wrigleyville/Boystown/Entire Private Floor!

1000 sq ft-entire private floor & door access. The perfect Wrigleyville/Boystown/Lake location. Zip to downtown Chicago in minutes via cab or public transportation options. Our friendly neighborhood is packed with fun bars, fabulous restaurants, unique boutiques & great music venues. Enjoy pool, ping pong and pinball and our 65" 4K flat screen TV or a seat at the bar. A Queen bed, 2 single beds in the main room, steam shower and bathroom. We have a mini fridge, microwave, coffee and home gym.

Guest favourite

Apartment in Evanston

4.96 out of 5 average rating, 112 reviews

Harmony of Evanston 1 BDR Exec Suite w/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. Harmony 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, BBQ and picnic area and beautiful landscaping. In the warmer months, Guests can enjoy the Clark Street Beach & Lighthouse

Guest favourite

Home in Wrigleyville

4.91 out of 5 average rating, 180 reviews

Soaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP

Say "WOW" in this top floor, IMMACULATE SPACIOUS with cozy FIREPLACE + ROOFTOP overlooking skyline! Open 2-story layout w/7 bed options, 3 bathrooms, private rooftop with skyline. Luxury flooring, soaring high ceilings, fully-stocked kitchen + huge island, keyless entry, 2 HD TVs, & outdoor grill. Perfect for SPECIAL OCCASIONS! Next to all Wrigley bars & restaurants. Train to Downtown <12 mins. Private parking for rent. As a "GUEST FAVORITE" we boast >1250 5-star reviews across listings!

Top guest favourite

Apartment in Lake View

4.99 out of 5 average rating, 160 reviews

RockStar Pad W3A BoysTown/Wrigley Field/Parking

HAVE IT ALL @ W3A Boys Town/Wrigley Field/East -Newly renovated/brand new in safe centrally located East Lakeview. -10 min walk from Wrigley Field, Boys town, beaches, super markets restaurants with late night dining. 5 min walk to the Metro Sheridan Red Line (straight shot downtown), 1 free enclosed parking plus free permitted street passes. -600 thread count linens, fluffy soft pillows, house coats, high speed WiFi, Sonos speakers, stylish furnishings & in unit washer and dryer.

Superhost

Flat in West Town

4.85 out of 5 average rating, 161 reviews

*Comfortable & Spacious Home Close to Downtown*

Comfortable & Spacious beautifully furnished home! 4 large bedrooms, and 3 large bathrooms. Fully equipped kitchen. This is a 2200 sq ft of a home away from home with in unit laundry. Free parking! The home is a few blocks from Humboldt Park! Blocks to the train and other nearby transportation. Easy to get a Lyft/Uber from the unit. Walking distance to restaurants, cafes and bars! Free Street parking directly in front of the building, there is no permit or parking pass needed.

Superhost

Loft in The Loop

4.74 out of 5 average rating, 210 reviews

Downtown Penthouse #5 | Vintage +gym & balcony

Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! We are a short walk to Millennium Park, Skydeck, Shedd Aquarium, Adler & many dining + shopping options! Most homes don’t provide professional service along with “local vibes.” Guests love staying with us because: ✅ It's Unique! ✅ High loft ceilings ✅ FAST WIFI ✅ Spacious layout ✅ Comfy beds ✅ Central Location ✅ Big Balcony! ✅ Close proximity to Grant Park, Soldier Field, Museums, and more!

Top guest favourite

Apartment in East Rogers Park

4.99 out of 5 average rating, 282 reviews

Cozy 3BR on Chicago's North Side & Free Parking

Enjoy this charming 3-bedroom condo with free on-site parking just three blocks from Lake Michigan. Convenient access to public transit, including the express bus to downtown (9 miles), Navy Pier, and Grant Park. The CTA Jarvis station is only three blocks away. Perfect for families, business travelers, and couples, this condo is also close to Loyola (1.5 miles) and Northwestern universities (2.5 miles). A great home base to explore all that Chicago has to offer!

Guest favourite

Flat in Oak Park

4.89 out of 5 average rating, 47 reviews

Charming 1BR/1BA Hideaway in Oak Park, IL

Welcome to our charming 1 bedroom apartment in the heart of Oak Park, IL! Perfectly located, this cozy retreat offers a comfortable stay for solo travelers or couples seeking a memorable getaway. For those who like to stay active, our property offers a convenient fitness center, allowing you to maintain your workout routine during your stay. After an invigorating workout, head up to the stunning roof terrace, where you can admire panoramic views of the cityscape.