Fitness-friendly vacation rentals in Downtown Chicago

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Top-rated fitness-friendly rentals in Downtown Chicago

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

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Guest favorite

The lounge area features large windows that open to the rooftop deck, offering views of outdoor seating and the city skyline. Modern furniture includes plush couches with colorful cushions and a vibrant area rug, creating a comfortable setting for relaxation.

Apartment in Chicago

4.9 out of 5 average rating, 519 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”

Guest favorite

Home in Carol Stream

4.86 out of 5 average rating, 7 reviews

Spacious 4 Bed/3.5 Bath Sleeps 8+

Just 30 minutes from downtown Chicago! You will love this gorgeous 4-bedroom home perfect for a vacation, staycation or business travel! Walking distance to the playground & walking trails, restaurants and even the local gym! Home has free parking, 3.5 baths, fully finished basement equipped with work-out room! May-Sept you can enjoy the deck, gazebo, outdoor gas grill & heated 27’ pool! Home is pet free and smoke free. Wi-Fi to enjoy your programs on the Smart TV inthrough your personal apps

Superhost

The rooftop area features a spacious deck with modern stone flooring, surrounded by metal railings. The sunset casts warm hues over the city skyline, providing a panoramic view that stretches beyond the horizon. Large windows are visible on the building's brick exterior.

Apartment in Chicago

4.7 out of 5 average rating, 47 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 favorite

A green felt pool table occupies the foreground, accompanied by cues and balls. A dark leather chair is positioned nearby, while a mini bar with various bottles is visible in the background, along with a glimpse of a brightly colored bedroom through an open doorway.

Guest suite in Chicago

4.84 out of 5 average rating, 248 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 favorite

Condo in Evanston

4.96 out of 5 average rating, 113 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 favorite

A modern living area features a cozy seating arrangement with large windows showcasing panoramic views of the Chicago skyline. The stylish bedroom is adorned with elegant decor, while a luxurious bathroom displays sleek fixtures and essential amenities for comfort.

Apartment in Chicago

4.88 out of 5 average rating, 200 reviews

Stunning Panoramic Chicago Views & Free Parking

Indulge in the epitome of luxury at our exceptional property with a host of amenities: 24-hour door attendant, heated parking, hot tub, modern workout and rec room, and stunning Chicago views. Situated in a secure, scenic South Loop neighborhood, our upscale abode grants swift access/steps to McCormick Place and Wintrust Arena. Discover the best of Chicago from this ideal spot, with easy public transport and airport commutes. Your remarkable experience begins in this lavish urban retreat!

Top guest favorite

A private deck features a wooden overhang and is furnished with two comfortable chairs and a small table. A decorative planter sits at the center, surrounded by a striped outdoor rug. The area is bathed in natural light, with a view of nearby neighborhood homes.

Apartment in Chicago

4.98 out of 5 average rating, 204 reviews

5* City Oasis: Logan Square/Avondale Neighborhood

Indulge in our two-bedroom one-bath retreat accommodating up to 4 guests. This space goes beyond relaxation; it's a revitalizing escape, catering to both tranquility and activity with a private deck. Your comfort, ease, and well-being are our focus. This isn't just a stay; it's a realm for crafting cherished memories, unwinding in luxury, discovering new facets of the city, and thriving in every sense. Reserve now and let our haven be your canvas for an extraordinary Chicago escapade.

Top guest favorite

Condo in Chicago

4.99 out of 5 average rating, 164 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

A spacious bathroom features dual sinks set within a dark wood vanity, complemented by modern fixtures. A large mirror reflects natural light from a nearby window. A walk-in shower with glass doors and elegant tile surrounds provides a clean and contemporary aesthetic.

Apartment in Chicago

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

A spacious living area features a large, curved yellow sofa adorned with various textured pillows. A wooden coffee table sits at the center, accompanied by a decorative plant. The high ceiling and artwork on the walls enhance the open feel of the space.

Loft in Chicago

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!

Guest favorite

A rooftop terrace features modern seating arrangements with colorful cushions. Lush potted plants are placed around the area, complementing the expansive city skyline visible in the distance. The terrace is bathed in natural light under a clear blue sky.

Apartment 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.

Top guest favorite

A charming first-floor porch features a metal roof and a decorative umbrella, offering shade to a small seating area adorned with potted plants. The entrance is flanked by stone steps and greenery, characteristic of a classic Chicago Greystone building.

Home in Chicago

4.95 out of 5 average rating, 184 reviews

Wrigleyville Greystone

First floor guesthouse ideal for 6+guests 1 block from Southport brown line station, 1/2 mile from Wrigley Field & red line station. Open floor plan with full kitchen, DR, double LR with 55” TV & foosball table, 3 bedrooms with queen size beds, 2 full bathrooms with bidet toilet, exercise room & back patio with sofas, table & koi pond. Since we live here and have another guests house in the building, we do not allow parties or large groups.