Fitness-friendly vacation rentals in Chicago River

A bright living area features a comfortable gray sofa and two modern chairs set around a round coffee table. Large windows provide expansive views of the city, while greenery adds a touch of nature to the space. The warm lighting creates a welcoming ambiance.

4.75 out of 5 average rating, 288 reviews

Stunning 3BR Penthouse in the Loop | Roof Deck

[NOTE: The main rooftop is currently closed for renovations and is slated to reopen in Summer/Fall 2026. The 2nd rooftop remains open and available to use, including the pool which typically opens around Memorial Day]. Beautiful 1,400+ square foot penthouse apartment on the top floor with 13 foot tall ceilings, oversize windows, and panoramic city views. This bright and airy three bedroom, two bathroom space is perfect for travelers looking for a luxurious escape in the sky in the heart of down

5 out of 5 average rating, 5 reviews

Plymouth Collection: 2BD High Floor w/ Gym,Rooftop

Welcome to The Plymouth Chicago, a historic 1899 landmark in the heart of Printers Row. Beautifully renovated in 2018 and thoughtfully redesigned in 2026, this stylish studio blends classic Chicago architecture with modern comfort. Enjoy top-floor living on the 10th floor, with added privacy and abundant natural light. The space includes a full kitchen, cozy living area, and in-unit laundry—perfect for longer stays. Play pool in the lobby, head up to the rooftop to grill, or workout in the gym!

4.96 out of 5 average rating, 24 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 exterior of a modern high-rise building is visible, featuring large glass windows and a curved architectural design. Surrounding trees line the street, creating a blend of urban and natural elements. The image showcases the building's height against a clear blue sky.

4.8 out of 5 average rating, 364 reviews

Kasa | Studio, Walk to Grant Park | South Loop

It’s easy to get a taste of Chicago’s culture and cuisine at Kasa South Loop Chicago, located within walking distance of the Museum Campus, McCormick Place Center, and a variety of restaurants and shops. Our Kasas are the best choice for your trip to the Windy City with our spacious floorplans, full kitchen, laundry facilities, and parking. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text, phone, or chat, and a Virtual Front Desk accessed via mobile device.

A serene bedroom features a spacious bed with crisp white linens and a light gray upholstered headboard. Natural light flows through large windows, illuminating the neutral walls and wood flooring. A small bedside table with a decorative lamp adds a touch of elegance to the space.

4.81 out of 5 average rating, 998 reviews

Kasa | Views from your Private Balcony | 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.

A modern living room showcases large windows providing natural light and city views. A cozy sectional sofa is positioned adjacent to a sleek flat-screen TV, complemented by a dark coffee table and decorative elements. Exposed brick walls add character to the airy space.

4.89 out of 5 average rating, 103 reviews

River North | Rooftop With In & Out Parking | 6

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

4.89 out of 5 average rating, 168 reviews

A shared rooftop deck with views of the skyline features modern seating arrangements and vibrant flower planters. A stainless steel grill is available for outdoor cooking, complementing the comfortable lounge chairs and table set on the spacious tiled surface.

Condo in Chicago

Downtown Park #11 - Mich Ave PH | gym+rooftop

Feel at Home, Unwind, and Enjoy the amenities you deserve when you come to Chicago! Guests love staying with us because: -Central Location on Grant Park (no car needed!) -FAST WIFI -En-suite Laundry -Did we mention the Lake & Park are outside our front door? -Comfy Queen bed -Loft style bedroom -Shared Rooftop Deck stunning views -Gym -3 blocks from Red "L" subway -Close to Grant Park, The Bean, Soldier Field, Museums If you are looking for a special place, you've found it!

Top guest favorite

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

4.99 out of 5 average rating, 140 reviews

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 modern studio apartment is featuring a spacious bed with white linens, positioned next to a cozy gray sofa. A flat-screen television is mounted on the wall, with framed artwork adding subtle décor. Light wood cabinetry complements the neutral color scheme.

4.75 out of 5 average rating, 60 reviews

Level Studio | Fulton Market

Our Level Suite, approximately 500 sqft, features an open concept studio layout with fully equipped kitchen with gas cooktop, comfortable living area, king or queen bed, storage closet, and private balcony. Many of the suites also feature designated workspaces and sofa beds. Designed for comfort and convenience, all suites boast in-suite laundry, premium appliances, smart TV with access to your favorite streaming apps, complimentary Wi-Fi and local calling.

4.8 out of 5 average rating, 154 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.

4.83 out of 5 average rating, 64 reviews

LIVN West Loop Chicago Queen Studio Apartment

Experience modern city living at LIVN West Loop Chicago, a stylish loft-style apartment studio at 555 W Jackson Blvd in one of the city’s most connected neighborhoods. This newly renovated studio features a full kitchen, in-unit washer and dryer, and clean, modern interiors. Walk to Union Station and Willis Tower. You are minutes from top dining, offices, and transit, ideal for business trips, weekend stays, or longer visits.

Top guest favorite

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.