Fitness-friendly holiday rentals in South Loop

A rooftop pool area is shown, featuring a clear blue pool surrounded by lounge chairs in red and neutral tones. Sunlight reflects off the water, and tall buildings are visible in the background, contributing to a lively urban atmosphere.

4.91 out of 5 average rating, 100 reviews

The Professional's Playground (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.

4.92 out of 5 average rating, 140 reviews

A vibrant living area showcases eclectic décor, featuring a colorful mural with artistic motifs on one wall. A round coffee table sits in the center, surrounded by cream-colored sofas adorned with green cushions. A wet bar with wooden stools is visible in the background.

Flat in South Side

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.

4.92 out of 5 average rating, 24 reviews

The communal lounge area boasts expansive windows that allow natural light to fill the space. A large dining table is accompanied by modern seating arrangements, including a sectional sofa and cozy ottomans. Lively greenery is distributed throughout, enhancing the modern decor.

Flat in Printer's Row

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!

4.96 out of 5 average rating, 188 reviews

A private outdoor patio is surrounded by wooden fencing, featuring a glowing sofa and two chairs placed on a patterned rug. A small table holds a plant, while greenery adds a natural touch to the tranquil setting, under a colorful sky at dusk.

Home in North Park

Chicago River House -BBQ Oasis now open!

Close to must see Chicago restaurants and nightlife, yet nestled in nature! This 1937 Print Shop is seated between the Chicago River & Forest Preserves, with trails & river walks, 3 miles to the beach, near Lake Shore Drive & 90/94, nearby Lincoln Square , Andersonville, and seasonal waterfalls, brunch nearby. This 2-bed, 2-bath home one level. 5star Chef's kitchen 9’ x 15’ HD projector, comfy beds, double shower head shower room, near nature. Relax on our private patio and glowing furniture

4.88 out of 5 average rating, 119 reviews

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

4.96 out of 5 average rating, 135 reviews

A modern chef's kitchen is shown, featuring an island with seating for four. Sleek dark cabinetry contrasts with light countertops and stainless steel appliances. A bowl of fruit adds a touch of color, while glass pendant lights provide illumination above the island.

Apartment in Gold Coast

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

4.99 out of 5 average rating, 210 reviews

A modern kitchen features sleek gray cabinetry and stainless steel appliances, including a refrigerator and oven. A neutral area rug complements the wood flooring. Natural light is provided by large windows, and stylish wall decor adds a contemporary touch to the space.

Apartment in Lake View

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

4.83 out of 5 average rating, 842 reviews

A serene bedroom features a spacious bed with crisp white linens and a light gray upholstered headboard. Natural light flows through large windows, illuminating the neutral walls and wood flooring. A small bedside table with a decorative lamp adds a touch of elegance to the space.

Flat in Near North Side

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.

4.89 out of 5 average rating, 146 reviews

A modern living area features a dark sofa adorned with colorful throw pillows. A wooden coffee table rests in front, and light streams in through large windows that offer views of the surrounding city. A dining table with chairs is visible in the background.

Apartment in Grant Park

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!

4.67 out of 5 average rating, 329 reviews

A spacious indoor garden lounge features abundant natural light streaming through large windows. Modern white furniture is arranged around a central coffee table, surrounded by lush greenery and decorative plants. The airy atmosphere is enhanced by hanging light fixtures, creating a serene and inviting space.

Flat in Grant Park

Sentral Premium 2BR Apt 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.

4.99 out of 5 average rating, 128 reviews

A modern living space features a light-colored sofa with decorative pillows and a woven throw. A warm-toned wooden accent wall complements a sleek electric fireplace below a mounted television. A patterned area rug anchors the room, while shelves in the background display decorative items.

Loft in South Side

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.

4.85 out of 5 average rating, 33 reviews

A rooftop pool area is showcased, featuring clean lines and modern architecture. The pool is rectangular and bordered by sleek railings. Surrounding urban buildings are visible against a clear blue sky, highlighting the vibrant city atmosphere.

Flat in Printer's Row

South Loop | Rooftop With In & Out Parking | 2

Enjoy a stylish experience at this centrally located place! This stunning 1,000 sq. ft. modern 2-bedroom, 2-bathroom unit is perfect for corporate travelers and families looking for a chic escape in downtown Chicago 🏡 🔥 Rooftop Patio W/ BBQ 🏊 Rooftop Pool 🚗 Free In/Out Parking (5-Min Walk to Garage) 🛏️ 2 Bedrooms | 2 Bathrooms 🛌 2 Queen Beds 🛌1 Inflatable Airbed 👶 Portable Crib (For Mini Travel Companion) 🎬 Netflix, Hulu, Disney+ & Prime Included

Popular amenities for fitness-friendly rentals in South Loop

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Fitness-friendly apartment rentals

4.95 out of 5 average rating, 40 reviews

A well-lit bedroom features a spacious bed with a blue patterned comforter. Large windows allow natural light to fill the room, and a simple desk with a chair is positioned near the window. Soft carpeted flooring complements the modern decor.

Flat in Chicago Loop

Luxury Loop Loft (2BD/2BA)

4.79 out of 5 average rating, 14 reviews

McCormick 2br/2ba Oasis Parking/Patio/Gym/sleeps 6

4.97 out of 5 average rating, 33 reviews

A bright and airy living area is filled with natural light from floor-to-ceiling windows, offering expansive city views. A plush sectional sofa is positioned on a soft area rug. Potted plants and a console with a television add to the inviting ambiance.

Flat in Fulton Market

Skyline Oasis: City & Lake Views

4.84 out of 5 average rating, 109 reviews

A modern living space is presented, featuring a comfortable dark couch adorned with textured throw pillows. A sleek arc floor lamp provides soft lighting, and a small dining table by the window offers a view of Lake Michigan. A framed artwork adds a splash of color.

Flat in Grant Park

Downtown Mich Ave #10 | gym+rooftop

4.96 out of 5 average rating, 54 reviews

A cozy bedroom features a spacious bed with hotel-grade bedding, complemented by warm tones on the walls. A green accent wall, potted plant, and stylish lamp create a calming atmosphere. Nightstands are placed on either side, enhancing the room's functionality.

Flat in West Loop

Gym | Garage Parking | Balcony | Sleeps 6

4.98 out of 5 average rating, 180 reviews

The bedroom is designed with a spacious bed centered against an accent wall featuring geometric patterns. A plush bench is positioned at the foot of the bed. Warm lighting illuminates the room, complemented by rich curtains and wooden flooring.

Flat in Magnificent Mile

Elegant Suite in Gold Coast

A bright living area features a contemporary design with large windows that provide ample natural light. An orange couch and green accent chair create a vibrant seating space, complemented by a dining table with black chairs and a television mounted on the wall.

4.62 out of 5 average rating, 58 reviews

Chicago get Away

5 out of 5 average rating, 20 reviews

A comfortable living area features a modern sofa, complemented by two stylish ottomans. A large window with sheer curtains provides natural light, while a wall-mounted TV is positioned for easy viewing. A piece of wall art adds a contemporary touch.

Flat in West Loop

Chicago Luxury Long Term 30+

Fitness-friendly apartment rentals

4.9 out of 5 average rating, 68 reviews

A cozy living room features a spacious sectional couch, complemented by an elegant coffee table and accent chairs. Large windows allow natural light to fill the room, with a vibrant green wall and a cityscape artwork enhancing the decor.

Apartment in Lake View

2BR Apt, Office, Parking & Backyard by Wrigley

A bright living area features a blue sofa adorned with yellow pillows, paired with two white chairs and a small round table. Natural light enters through large windows with blinds, highlighting the warm wooden floor and a textured area rug.

Apartment in East Rogers Park

4.67 out of 5 average rating, 46 reviews

3 Bed Apartment in Chicago by the lake

4.95 out of 5 average rating, 203 reviews

A living area features a blue sofa and a wooden coffee table in front of a window, allowing natural light to fill the space. A keyboard on a stand is visible, along with a comfortable chair. Black-and-white artwork of a cityscape adorns the wall, enhancing the room's character.

Apartment in Chicago

Cozy 3BR, 12 mins to W Loop

4.95 out of 5 average rating, 119 reviews

A bright living area features large windows that offer city views. Comfortable seating arrangements include a pair of teal sofas and a wooden armchair. A coffee table sits at the center on a soft area rug, accompanied by a flat-screen TV mounted on a nearby wall.

Apartment in Evanston

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

4.96 out of 5 average rating, 45 reviews

A relaxing living area is furnished with a sectional sofa, a modern lounge chair, and a plush area rug. A mounted television is positioned above the couch, while floor-to-ceiling windows allow natural light to flood the space, complemented by dark curtains.

Apartment in West Loop

Modern long-term luxury w/ spectacular view!

Apartment in Lower West Side

A comfortable living room features a light-colored sofa and two armchairs positioned around a decorative coffee table. Natural light floods through large windows dressed with sheer curtains, illuminating the space. A modern fireplace with a marble surround is positioned against a light gray accent wall, complemented by framed photos and decorative items.

5 out of 5 average rating, 11 reviews

East Pilsen Gem

4.99 out of 5 average rating, 294 reviews

A light-filled living room showcases soft gray walls and hardwood flooring. A comfortable sofa and armchair are positioned around a decorative area rug. A television is mounted on a console, while a lamp beside a side table adds warmth to the space.

Apartment in Chicago

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

Apartment in Humboldt Park

A living area features a large flat-screen television mounted on a low black media cabinet. A dog is comfortably resting on a patterned area rug. Two framed artworks are hung on the light-colored walls, and a tall green plant is positioned beside the television.

4.76 out of 5 average rating, 119 reviews

Logan Square Spa

Fitness-friendly house rentals

4.95 out of 5 average rating, 44 reviews

A spacious living area is illuminated by natural light, featuring large windows that frame views of greenery outside. A modern sofa and armchair sit around a round coffee table, while a sleek fireplace adds warmth to the elegant decor.

Home in Gold Coast

Gold Coast Home|Rooftop |PoolTable |Parking |Views

5 out of 5 average rating, 36 reviews

A modern living room features elegant curved sofas complemented by colorful cushions. A geometric coffee table sits on a round area rug, while large windows bring in natural light and showcase lush green plants. A fireplace adds warmth to the inviting space.

Home in Logan Square

Homer Street Hotel: Bucktown Upscale Designer Home

4.87 out of 5 average rating, 68 reviews

A spacious backyard is bordered by lush greenery and features a mix of colorful lawn chairs arranged around a fire pit. A large tree provides shade, and a fenced area offers privacy. The unit's deck is visible in the background.

Home in Portage Park

Luxe King Beds-Private Gym-Huge Backyard-Crib

4.91 out of 5 average rating, 188 reviews

Home in Wrigleyville

Soaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP

4.95 out of 5 average rating, 206 reviews

The living room features a spacious sofa complemented by decorative pillows and a wooden coffee table. A reading lamp provides soft lighting. A wall art piece with a 'W' symbol and stars is displayed above the seating area. Natural light enters through the windows, framed by wooden trim.

Home in Lake View

Wrigleyville Greystone

Home in Old Town Triangle

5 out of 5 average rating, 24 reviews

4 BR • Theater Room • Gym • Walk to Lincoln Park!

4.95 out of 5 average rating, 113 reviews

A single-story brick house is presented with a spacious front yard, featuring trimmed greenery and a walkway of stone steps leading to the front door. A driveway, visible to the right, accommodates a garage door with a dark finish.

Home in Skokie

Cozy 2 bedroom house/w garage in Skokie