Fitness-friendly vacation rentals in Downtown Chicago

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.

4.9 out of 5 average rating, 517 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”

The exterior of a modern duplex condo showcases a combination of wood and stone elements. Large windows allow ample natural light, while the upper level features a balcony. Lush green landscaping enhances the setting, contributing to the building's contemporary design.

4.89 out of 5 average rating, 9 reviews

Beautiful Condo in Lincoln Park w/ Rooftop

NEW LISTING! Make this Duplex Condo in the Heart of Chicago Your Home! Our condo features some of the most unique amenities, including: 🎥 150" Projection Home Theatre 🏋️‍♂️ Tonal Digital Gym & Nordic Track Treadmill 🌇 Patio with Grill & Gigantic Wall Mural 🌅 Access to Rooftop Deck with Spectacular Views 🏓 Ping Pong Table & Outdoor Mini Pickleball 🎹 Upright Acoustic Piano 🚶‍♂️ Highly walkable to top Restaurants and Shopping 🚇 Easily accessible via Public transportation 🚗 Free Parking

A spacious bedroom features a four-poster bed draped with a sheer canopy, complemented by turquoise bedding. A colorful accent pillow adds detail. The room includes a desk with a chair and a small decorative arrangement on the side table. Natural light enters through near sheer curtains.

4.68 out of 5 average rating, 44 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.

4.84 out of 5 average rating, 247 reviews

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

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.

4.96 out of 5 average rating, 113 reviews

Condo in Evanston

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

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.

4.98 out of 5 average rating, 203 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, 161 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.

Top guest favorite

The private patio showcases a cozy seating area with two chairs and a hammock, all set against a backdrop of a vivid sunset over downtown Chicago. The surrounding low wall offers an unobstructed view of the skyline, creating a serene outdoor retreat.

5 out of 5 average rating, 6 reviews

Luxurious 3BD Penthouse- Private Patio+Gym+Rooftop

Welcome to The Ashbourne! This unit accommodates 6 adults (for families); otherwise, only 4 adults are allowed. To ensure the safety of all building tenants, ALL adult guests must submit their email address and must submit ID proof via our verification partner, Authenticate. The building is fully keyless, guests must download the SALTO KS app to access digital keys for entry and access to all amenities. This is mandated by our building management, so please note this before reserving.

A stylish electric fireplace is framed by a white mantle with glass side panels. A television mounted above displays a nature scene. A small potted plant is placed on a wooden tray in front, complemented by neutral tile flooring.

4.76 out of 5 average rating, 17 reviews

Chicago/Beverly/Evergreen Park Home

This stylish unit... - Conveniently located 20 mins from Downtown Chicago. - 9 mins from Walmart, Target, Ross, Burlington, and other shops. - Offers a Keurig, Popcorn, Mini Fridge, Microwave, reading nook. - Comes with a Bath Bar stocked with Epsom Salt, face masks (pls do a skin test before using) and Bath bombs to throw into the relaxing Jacuzzi Tub. - Offers a photo wall for you to take great photos. - Offers a relaxing shared backyard area with seating (Warmer months only)

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.

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.

4.74 out of 5 average rating, 210 reviews

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

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!