
Fitness-friendly holiday rentals in South Loop
Find and book unique fitness-friendly rentals on Airbnb
Top-rated fitness-friendly rentals in South Loop
Guests agree: these fitness-friendly rentals are highly rated for location, cleanliness and more.

Stunning 3BR Penthouse in the Loop | Roof Deck
[NOTE: The main rooftop is currently closed for seasonal repairs and is slated to reopen in Spring 2026. The 2nd rooftop remains open and available for guests to use.] Beautiful 1,400+ square foot penthouse apartment on the top floor with 13 foot tall ceilings, oversize windows, and panoramic city views. This bright and airy three bedroom, two bathroom space is perfect for travelers looking for a luxurious escape in the sky in the heart of downtown Chicago. The penthouse is adjacent to the buil

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.

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.

Luxury 2BR | McCormick, Lakefront, Parking & Gym
Welcome and Experience Chicago in style at our upscale corner suite nestled in the dynamic South Loop district—just steps from McCormick Place and minutes from top city landmarks. This modern, metropolitan 2-bedroom, 2-bathroom suite features soaring 10 ft ceilings, a spacious open layout, and curated interiors that set it apart from the average stay. From custom furnishings to thoughtful amenities, we’ve created an elevated home-away-from-home for families, professionals, and long-term stays.

14th Floor 3Bd 3Bth Unit w/ Gym, Pool, &Amenities
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!

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.

Modern MAG Mile 2BD/2BA (+Parking/Rooftop)
Welcome! Guests love our home because: - You're SECONDS from the LAKE and MAGNIFICENT MILE - You're steps away from the famous Drake Hotel and Oak Street Beach. - Walk to every popular attraction that makes Chicago so great! - Newly remodeled interior with an open floor plan layout - Parking spot on-site in/out access!! - Tranquil rooftop overlooks Lake - Fast WIFI - Super comfy beds! - Custom chef kitchen - Located on a quiet street - Lake Michigan view from our floor-to-ceiling windows

RockStar Pad W3A BoysTown/Wrigley Field/Parking
HAVE IT ALL @ W3A Chicago Wrigley Field/Boystown/Lakeview -Newly renovated like new in safe centrally located East Lakeview. -10 min walk to Wrigley Field, Boys town, beaches, super markets, restaurants with late night dining. 5 min walk to Metro Sheridan Red Line (direct downtown), private enclosed parking $10/night & or free permits for street parking -600 thread count linens, fluffy soft pillows, house coats, high speed WiFi, Sonos speakers, stylish design & in unit washer & dryer

Kasa | Views from your Private Balcony | Chicago
When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.

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!

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.
Popular amenities for fitness-friendly rentals in South Loop
Fitness-friendly apartment rentals

Skyline 2BR in South Loop Near Museums & McCormick

Spectacular Corner 3BR in the Loop | City Views

52nd Floor MagMile Penthouse VIEWS Fireplace Pool

The Professional's Playground (2BD / 2BA)

Gym | Garage Parking | Balcony | Sleeps 6

Chic 2BR Gem with Fireplace

Beautiful,Spacious & sunny w/Parking-Logan Square

Stylish 2BR Corner Unit Near Downtown & McCormick
Fitness-friendly apartment rentals

2BR Apt, Office, Parking & Backyard by Wrigley

3 Bed Apartment in Chicago by the lake

Rarely available 3BR, 12 mins to W Loop

Modern long-term luxury w/ spectacular view!

East Pilsen Gem

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

Logan Square Spa

Bright Bowmanville Studio
Fitness-friendly house rentals

Gold Coast Home|Rooftop |PoolTable |Parking |Views

Homer Street Hotel: Bucktown Upscale Designer Home

Chicago River House -BBQ Oasis now open!

Luxe King Beds-Private Gym-Huge Backyard-Crib

Soaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP

Wrigleyville Greystone

Cozy 2 bedroom house/w garage in Skokie

Entire Luxury Home: Private Gym
When is the best time to visit South Loop?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ₹10,586 | ₹11,380 | ₹14,115 | ₹16,937 | ₹21,172 | ₹22,583 | ₹19,496 | ₹24,083 | ₹21,260 | ₹23,113 | ₹14,644 | ₹13,762 |
| Avg. temp | -3°C | -1°C | 4°C | 10°C | 16°C | 22°C | 25°C | 24°C | 20°C | 13°C | 6°C | 0°C |
Quick stats about holiday rentals that are fitness-friendly in South Loop

Total holiday rentals
Explore 330 holiday rentals in South Loop

Nightly prices starting at
South Loop holiday rentals start at ₹3,529 per night before taxes and fees

Verified guest reviews
Over 15,670 verified reviews to help you choose

Family-friendly holiday rentals
180 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 130 rentals that welcome pets

Holiday rentals with a pool
140 properties feature pools

Rentals with dedicated workspaces
220 properties have a dedicated workspace

Wifi availability
320 of South Loop holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across South Loop rentals

4.8 Average rating
South Loop stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
- Pet-friendly rentals South Loop
- Rentals with a firepit South Loop
- Rentals with an EV charger South Loop
- Rentals with lake access South Loop
- Family-friendly rentals South Loop
- Rentals with a hot tub South Loop
- Rentals with a patio South Loop
- Apartment rentals South Loop
- Flat rentals South Loop
- Rentals with a sauna South Loop
- Rentals with a fireplace South Loop
- Rentals with pools South Loop
- Rentals with outdoor seating South Loop
- Rentals with a washing machine and dryer South Loop
- Smoking-friendly rentals South Loop
- Fitness-friendly rentals Chicago
- Fitness-friendly rentals Cook County
- Fitness-friendly rentals Illinois
- Fitness-friendly rentals United States
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- 875 North Michigan Avenue
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- Oak Street Beach
- The Field Museum
- Wicker Park
- Frank Lloyd Wright Home and Studio
- Garfield Park Conservatory
- Lincoln Park Zoo
- Brookfield Zoo
- Museum of Science and Industry
- Willis Tower
- Illinois Beach State Park
- The Beverly Country Club
- Washington Park Zoo
- Raging Waves Waterpark
- The 606