Fitness-friendly holiday rentals in Downtown Chicago

An outdoor swimming pool is featured, surrounded by a spacious patio area. Lounge chairs are arranged around the pool, with tall buildings visible in the background under a clear blue sky.

4.93 out of 5 average rating, 108 reviews

The Metropolitan Retreat (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.

4.96 out of 5 average rating, 28 reviews

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

The entrance to a well-maintained building is framed by elegant arched architecture. Large glass doors lead into the interior, while a canopy overhead provides shelter. A valet parking sign stands beside the sidewalk, indicating nearby parking options, and vibrant storefronts enhance the urban ambiance.

4.99 out of 5 average rating, 144 reviews

Chic 2BR Gem with Fireplace

Discover urban luxury in our 2BR, 2BA Gold Coast haven. This stylish apartment boasts a warm fireplace, sleek granite countertops, and a cozy layout. Immerse yourself in city living at its finest, right in the heart of Chicago's prestigious Gold Coast neighborhood. ***Please note that from March until the end of September 2026, there will be construction on the upper floors of the building that may cause noise during the daytime hours. Construction will not be happening on the weekends.***

An indoor pool area is visible, featuring clear blue water and light gray tiled flooring. Large windows allow natural light to flood in, complemented by modern lighting fixtures. Lounge chairs in bright yellow and a wooden deck area create inviting relaxation spots alongside the pool.

4.93 out of 5 average rating, 109 reviews

Dtown Penthouse 11+Parking, Gym, Pvt Patio

Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional service along with “local vibes.” Guests love staying with us because: ✅ Central location near Grant Park, Art Institute, The Bean, Soldier Field, & more! ✅ 1 Free parking pass ✅ FAST WIFI ✅ En-suite Laundry ✅ The Lake & Park are only 2 blocks away ✅ KING beds ✅ Private Rooftop Deck w/ stunning views ✅ Amenity Floor (Gym, Lounge, Doggy Park) ✅ 1 block from Red "L" subway

An outdoor rooftop terrace features comfortable seating arrangements, including lounge chairs and patterned cushions. Lush planters with vibrant greenery add to the inviting atmosphere. A panoramic view of the city skyline is visible in the background, offering a perspective on Chicago's architecture.

4.82 out of 5 average rating, 338 reviews

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!

Superhost

4.81 out of 5 average rating, 294 reviews

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.

4.95 out of 5 average rating, 141 reviews

A modern kitchen space is illuminated by large windows, showcasing a view of the building's exterior. A round dining table with four chairs is positioned beside the kitchen, which features stainless steel appliances and sleek cabinetry. A decorative plant adds a touch of green to the design.

Condo in Chicago

GLORIOUS GOLD COAST GETAWAY

Welcome! Amazing Gold Coast/Streeterville location SECONDS from the LAKE and MAGNIFICENT MILE. Located on a quiet street, this apartment is tucked in between Michigan Ave and Lake Michigan. Steps away from the famous Drake Hotel, yet closer to the lake and Oak Street Beach. This spot is considered the best location in the city-- steps away from the best stores/restaurants in the world located on Michigan Ave (Mag Mile) and just north of Navy Pier. We look forward to hosting you!

4.99 out of 5 average rating, 142 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 Chicago

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.

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.

4.85 out of 5 average rating, 72 reviews

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

4.9 out of 5 average rating, 188 reviews

A spacious rooftop deck is adorned with a large sectional sofa in blue upholstery, offering panoramic views of the surrounding skyline and Lake Michigan. Glass railings enhance the open atmosphere, providing an unobstructed sightline to the water and buildings in the distance.

Condo in Chicago

MARVELOUS MAG MILE 2BD/2BA (+Rooftop)

Amazing Gold Coast/Streeterville location SECONDS from the LAKE and MAGNIFICENT MILE. Located on a quiet street, this apartment is tucked in between Michigan Ave and Lake Michigan. Steps away from the famous Drake Hotel, yet closer to the lake and Oak Street Beach. This spot is considered the best location in the city-- steps away from the best stores/restaurants in the world located on Michigan Ave (Mag Mile) and just north of Navy Pier.

Superhost

4.79 out of 5 average rating, 158 reviews

Level ◆ Brand New Luxe One Bedroom

Designed with you in mind, our One Bedroom Suites range from 560 – 698 sq ft of spacious living space boasting fully-equipped kitchen, comfortable living area, spa-inspired bathroom, bedroom with king bed and open-air balcony. Perfect for couples and corporate travelers alike, all suites also feature in-suite laundry, premium appliances, flat-screen TV with cable, complimentary WiFi and local calling. Welcome to the suite life.