Fitness-friendly holiday rentals in The Loop

4.92 out of 5 average rating, 108 reviews

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.

Flat in South Loop

Professional's Playground (Fitness Center • Sauna)

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, 147 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.

4.86 out of 5 average rating, 207 reviews

A spacious living area features a large sectional sofa facing a media unit with a TV, accompanied by a coffee table. A dining table with four chairs sits nearby. Floor-to-ceiling windows provide bright natural light and a view of adjacent buildings.

Apartment in Gold Coast

2BD/2BA MAG MILE MASTERPIECE (+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 - Tranquil rooftop overlooking the Lake - Fast WIFI - Super comfy beds! - Custom chef kitchen - Located on a quiet street - Lake Michigan view from our floor-to-ceiling windows We look forward to hosting you!

4.95 out of 5 average rating, 151 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

5 out of 5 average rating, 9 reviews

Flat in Chicago

Upscale High-Rise Apt · Rooftop Pool + Views

Stay in this brand-new 2025 apartment with luxury amenities. Perfect for work or leisure, it offers everything you need for a comfortable stay. Building Amenities: - 24/7 concierge & secure entry - Rooftop pool & gym with skyline views - Rooftop lounge with a fireplace - Steps from grocery stores & restaurants - Paid parking nearby Unit Highlights: - Stunning views of the city - Work from home space - In-unit washer & dryer - Fully equipped kitchen - Fast WiFi - Modernly designed interior

4.83 out of 5 average rating, 305 reviews

A bright living area features large windows that offer city views, enhanced by natural light. Comfortable gray seating is arranged on a patterned rug, complemented by modern decor and greenery. A flat-screen TV is mounted on the wall, alongside a stylish coffee table.

Flat in The Loop

Spectacular 2BR Penthouse in the Loop | Roof Deck

This top floor corner penthouse is in a perfect location with panoramic city views in multiple directions. With over 1,200 square feet of space, 13 foot tall ceilings and oversized windows, this spacious penthouse is a true escape in the sky in the heart of Chicago. It's a two bedroom, two bathroom apartment with an additional sofa bed. The building has a pool and an amazing outdoor rooftop terrace with 360 degree views of the skyline and lake. This is the best location in the city!

4.81 out of 5 average rating, 259 reviews

A bright bedroom features a spacious bed with crisp white linens, complemented by an abstract wall art piece. A wooden nightstand with a lamp is positioned beside the bed. Large windows provide natural light, showcasing views of the city beyond.

Flat in Near North Side

Kasa | Explore the Neighborhood-Mag Mile | 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.

4.93 out of 5 average rating, 109 reviews

A spacious living area features a mustard-colored sectional couch, accompanied by a small side table. Large windows allow natural light to fill the room, illuminating the modern decor. A flat-screen TV is mounted on the wall, and a cozy reading nook is visible through an open door.

Apartment in Grant Park

Downtown Penthouse - Mich Ave 2bd | +gym & VIEWS

Feel at Home, Unwind, and Enjoy the amenities you deserve right next to Grant Park! Guests love staying with us because: -Central Location near public transit (no car needed!) -FAST WIFI -En-suite Laundry -Lake & Park are outside our front door -Comfy Queen beds -1 Closed & 1 Loft style bedroom -Shared Rooftop Deck with stunning views -Gym -3 blocks from Red "L" subway -Close to Grant Park, The Bean, Soldier Field, Museums If you're interested in booking, see our FAQs below.

4.82 out of 5 average rating, 90 reviews

The living area showcases a mix of modern and industrial design, featuring a plush gray sofa, a coffee table, and a flat-screen TV. Large windows allow ample natural light to illuminate the space, while a dining table with four chairs is positioned nearby against the wall.

Flat in Near North Side

River North | Rooftop With In & Out Parking | 3

Enjoy a stylish experience at this centrally-located place! ✨🏙️ Stunning 1,000 sq. ft. modern 2-bedroom, 2-bathroom unit—perfect for corporate travelers & families looking for a stylish escape in downtown Chicago. 🔥 Rooftop Patio w/ BBQ 🚗 Free In/Out Parking (5-min walk to garage) 🏠 2 Bedroom | 2 Bathroom 🛏️ 2 Queen Beds & Sleeper Sofa (Sofa Bed - Sleeps 1) 🛌 2 Inflatable Airbeds 👶 Portable Crib (For Mini Travel Companion) 🎬 Netflix, Hulu, Disney+, & Prime Included

4.74 out of 5 average rating, 182 reviews

A serene indoor pool area is highlighted by tall glass walls, allowing natural light to illuminate the space. Cozy seating with soft cushions is arranged around the pool, while overhead greenery and pendant lights create a calming atmosphere.

Flat in Grant Park

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.

4.99 out of 5 average rating, 136 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.

4.9 out of 5 average rating, 124 reviews

A spacious bedroom features large floor-to-ceiling windows, allowing natural light to fill the room. A large bed with neutral bedding is complemented by a contemporary desk and chair setup, which is arranged near a wood-framed lamp. A subtle area rug lies beneath the bed.

Flat in River North

50th Floor Mag Mile Views, Balcony, Pool, Gym

The Penthouses at Grand Plaza PH#12: Towering 50 stories above Downtown Chicago, this luxury unit features floor-to-ceiling windows and breathtaking skyline views. Enjoy sunsets, unmatched location, and true urban living. Walk Score of 100 with a grocery store in the building. Amenities include a fitness center, outdoor pool, kitchens, and business center. The city is at your feet—experience Chicago in style.

Popular amenities for fitness-friendly rentals in The Loop

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Fitness-friendly apartment rentals

4.83 out of 5 average rating, 196 reviews

A bright living area features large windows that provide panoramic city views. A comfortable gray sofa is positioned across from a 50" smart TV, with stylish accent chairs and a round coffee table nearby. Greenery adds a touch of nature to the space.

Flat in The Loop

Stunning Corner 2BR in the Loop | City & Lake View

4.76 out of 5 average rating, 203 reviews

A modern living area features large windows offering views of the city and lake. A dark sectional sofa is complemented by stylish accent chairs and a round coffee table. Indoor plants add greenery to the open space, which is adorned with a geometric patterned rug.

Flat in Streeterville

Chic Corner 2BR in Streeterville | Roof Deck | Lak

4.92 out of 5 average rating, 105 reviews

A rooftop pool area features a long, inviting pool bordered by lounge chairs in various colors. Sunlit trees are visible nearby, and the backdrop consists of modern high-rise buildings, creating a vibrant urban atmosphere.

Flat in South Loop

The Metropolitan Retreat (Fitness Center • Sauna)

The kitchen area features modern appliances, including a refrigerator, stove, and microwave. A marble-top table is surrounded by black chairs. A small floral arrangement and placed items are visible on the table, while a cozy seating area is adorned with a textured rug.

Flat in Uptown

4.84 out of 5 average rating, 37 reviews

Stylish Hidden Gem in the Heart of Uptown 1BD 1BA

4.97 out of 5 average rating, 34 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

4.85 out of 5 average rating, 118 reviews

Flat in Grant Park

Downtown Mich Ave #10 | gym+rooftop

4.83 out of 5 average rating, 180 reviews

The bedroom features two twin-size beds, each dressed in crisp white linens. A table lamp provides soft illumination between the beds, which are flanked by framed abstract artwork on the walls. Large windows allow natural light to fill the space.

Flat in Near North Side

Kasa | Walk Magnificent Mile | River North

4.98 out of 5 average rating, 126 reviews

A modern living room features a warm fireplace with elegant stone detailing. Comfortable seating is provided by a plush sofa alongside a stylish armchair. Natural light enters through multiple windows adorned with blinds. Decorative elements include a wooden coffee table and contemporary wall art.

Flat in Magnificent Mile

Chic 2BR Gem with Fireplace

Fitness-friendly apartment rentals

4.9 out of 5 average rating, 71 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 large windows that allow natural light to fill the space. A modern green sofa is complemented by two matching chairs. A round wooden coffee table sits on a plush area rug, with decorative wall art adding character to the yellow-painted walls.

Apartment in South Loop

4.84 out of 5 average rating, 171 reviews

Luxe 2BR Cozy Suite | Skyline Views near McCormick

4.92 out of 5 average rating, 212 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 + Parking

4.95 out of 5 average rating, 123 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

4.98 out of 5 average rating, 225 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 lot

4.99 out of 5 average rating, 296 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

4.92 out of 5 average rating, 51 reviews

A comfortable living area features a dark sofa, coffee table, and a modern TV stand with a large television. A dedicated dining space with a round table for two is visible. Sliding glass doors lead to a private balcony, providing natural light and outdoor views.

Apartment in Lombard

Pond View, Washer Dryer, Non Smoking, Pet Free

Apartment in Lincoln Square

4.68 out of 5 average rating, 28 reviews

Bright Bowmanville Studio with parking

Fitness-friendly house rentals

4.98 out of 5 average rating, 40 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

4.96 out of 5 average rating, 197 reviews

Home in North Park

The Chicago River House – GIANT wall projector!

4.85 out of 5 average rating, 72 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 Duplex-King Beds-Gym-Huge Backyard-Game Room

4.92 out of 5 average rating, 189 reviews

Home in Wrigleyville

Soaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP

4.95 out of 5 average rating, 210 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

4.95 out of 5 average rating, 115 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

4.97 out of 5 average rating, 60 reviews

The living area features a combination of modern and stylish furnishings, including a tufted brown sofa, blue chairs, and a glass coffee table. Colorful artwork adorns the walls, and natural light brightens the space through large windows.

Home in South Side

Entire Luxury Home: Private Gym