Fitness-friendly holiday rentals in Chicago

4.9 out of 5 average rating, 113 reviews

An outdoor pool is surrounded by lounge chairs in various colors, creating a bright and inviting atmosphere. Tall buildings are visible in the background, and the pool reflects the clear blue sky overhead.

Flat in South Loop

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.

4.92 out of 5 average rating, 143 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.

4.75 out of 5 average rating, 40 reviews

A bright bedroom features a four-poster bed with a sheer canopy, dressed in crisp white linens and a soft blue throw. A cozy blue armchair sits beside a small table, offering a comfortable seating area. A scenic landscape artwork adorns the wall, complementing the inviting space.

Flat in Uptown

13 mins DT | 4 mins Lake | Elegant Style Loft

Welcome to Uptown Chicago, proudly hosted by TIBO Ventures. Standout Features: • 𝗙𝘂𝗹𝗹𝘆 𝘀𝘁𝗼𝗰𝗸𝗲𝗱 𝗸𝗶𝘁𝗰𝗵𝗲𝗻 with modern appliances • 𝗦𝗺𝗮𝗿𝘁 𝗧𝗩 𝗮𝗻𝗱 𝗱𝗲𝗱𝗶𝗰𝗮𝘁𝗲𝗱 𝘄𝗼𝗿𝗸𝘀𝘁𝗮𝘁𝗶𝗼𝗻 — perfect for professionals or remote workers • In-unit washer/dryer and dishwasher for convenience • Rooftop area with breathtaking city views • Fitness center access to stay active during your stay • Steps from Montrose Beach, Aragon Ballroom, and Riviera Theatre • Parking available

4.86 out of 5 average rating, 203 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!

4.96 out of 5 average rating, 140 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

4.91 out of 5 average rating, 86 reviews

A modern living area is illuminated by natural light from large floor-to-ceiling windows. A comfortable gray sofa sits against one wall, accompanied by a coffee table. The open kitchen features a sleek marble countertop and stainless steel refrigerator, with minimalistic decor enhancing the ambiance.

Flat in River North

River North | Private Balcony With In&Out Parking

Enjoy a stylish experience at this centrally-located place ✨. Stunning 1,000 square foot modern two-bedroom, one-bathroom unit is perfect for corporate travelers and/or families looking for a stylish escape in downtown Chicago 🌆. 🌇 Rooftop Patio W/ BBQ 🍖 🚗 Free In/Out Parking - 5 Mins Walk To Garage 🌅 Private Balcony W/ Breathtaking Views 🛏️ 2 Bedroom | 1 Bathroom 👑 2 Queen Beds 🛏️ 1 Inflatable Airbed 👶 Portable Crib 📺 Netflix, Hulu, Disney Plus, and Prime subscription Included

4.98 out of 5 average rating, 217 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

4.89 out of 5 average rating, 145 reviews

A modern living area features a green sectional sofa and an orange armchair, complemented by a glass coffee table. Large windows provide city views and allow natural light to brighten the space. A potted plant adds a touch of greenery to the room.

Flat in South Loop

South Loop 2BR Apt Near Soldier Field & McCormick

🌆 Your South Loop City Escape Awaits Wake up to the golden glow of Chicago’s skyline streaming through your window. Sip your morning coffee as the city hums to life below — the perfect start to a day filled with discovery, excitement, or well-earned relaxation. Your Michigan Avenue suite isn’t just a place to sleep — it’s a place to live, unwind, and connect. Perfectly located just steps from McCormick Place, this 2-BR, 2-BA modern suite blends comfort, style, and urban convenience.

4.83 out of 5 average rating, 291 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 Chicago 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!

4.99 out of 5 average rating, 132 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.

4.84 out of 5 average rating, 154 reviews

A light-filled living area features a comfortable armchair and a stylish blue sofa. A modern coffee table sits on a textured area rug, with a decorative plant in the center. A wall-mounted television is positioned above a fireplace, complemented by large windows on either side.

Flat in Streeterville

Downtown Guild #4 | Mag Mile, Gold Coast

Feel at Home, Unwind, and Enjoy the amenities you deserve when you come to Chicago! Welcome to one of the best locations in Chicago. Guests love our home because: - You're SECONDS from the LAKE and MAGNIFICENT MILE - Steps away from the John Hancock - Gym in the Basement - Amazing location w/ many shops & restaurants nearby - Fast WIFI - KING bed - Charming, vintage Chicago building Please read our FAQs to answer any questions before booking.

4.96 out of 5 average rating, 24 reviews

A modern living area features a light-colored sofa with dark throw pillows, complemented by a sleek coffee table. Two abstract artworks adorn the wall above the couch. A plant adds a touch of greenery, while a large window allows natural light to fill the space.

Flat in Printer's Row

Spacious 3-Bedroom Urban Retreat in Chicago

Welcome to your spacious urban getaway in Chicago’s Printer’s Row! - Modern 3-bedroom, 3-bathroom unit with city views - Bright, open-concept living space with floor-to-ceiling windows - Fully equipped kitchen with stainless steel appliances - Rooftop pool and panoramic deck for skyline views - Managed by TheDreamRentals - Steps from cafes, parks, and museums - 1 parking spot available for sedans and small SUVs

Popular amenities for fitness-friendly rentals in Chicago

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Fitness-friendly apartment rentals

4.93 out of 5 average rating, 45 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)

5 out of 5 average rating, 12 reviews

A cozy lounge area features a modern orange sofa complemented by two green armchairs. A round wooden coffee table sits at the center. Large windows allow natural light to fill the room, while greenery is present in a woven basket, adding a touch of nature.

Flat in West Loop

Gym, Garage Parking, Balcony, Sleeps 4

4.98 out of 5 average rating, 120 reviews

A spacious light-filled game area is highlighted by a ping pong table at the center. Large windows frame the room, offering views of the outside. A comfortable seating area is visible alongside a decorative plant and wall-mounted mirrors, contributing to a relaxed environment.

Flat in West Town

King Bed • No Stairs • Ping-Pong • United Center

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

4.82 out of 5 average rating, 33 reviews

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

4.86 out of 5 average rating, 7 reviews

Flat in Chicago

West Loop | City Views With In & Out Parking | 1

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

5 out of 5 average rating, 62 reviews

An open concept living area is captured, showcasing a modern kitchen with stainless steel appliances and gray cabinetry. A cozy sofa with textured cushions faces a large window, allowing natural light to fill the space. A sleek dining table is positioned nearby.

Flat in Fulton Market

Fantastic West Loop 2 bedroom

4.9 out of 5 average rating, 121 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 Studio

Fitness-friendly apartment rentals

Apartment in West Loop

4.94 out of 5 average rating, 64 reviews

Bright&Modern Condo in the Heart of the Best Loop

4.9 out of 5 average rating, 69 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

4.93 out of 5 average rating, 209 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, 121 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, 46 reviews

Apartment in West Loop

Modern long-term luxury w/ spectacular view!

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

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, 123 reviews

Logan Square Spa

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

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

4.96 out of 5 average rating, 192 reviews

Home in North Park

Chicago River House -BBQ Oasis now open!

4.92 out of 5 average rating, 52 reviews

A wooden dock extends into the calm water, framed by lush greenery and trees. Two metal chairs sit on the dock, offering a serene spot to enjoy the lake views.

Home in Downers Grove

Lakefront View Getaway Home! Hot tub! Kayak!

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, 114 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

4.94 out of 5 average rating, 34 reviews

A brick townhome stands under a dusky sky, partially illuminated by a warm porch light. Lush trees frame the building, while an outdoor staircase leads to the upper level. A blue truck is parked nearby, and a patio area can be seen in the background.

Home in Avondale

Logan Sq/Avondale chic Townhome.