Fitness-friendly vacation rentals in Downtown Chicago

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.

4.89 out of 5 average rating, 99 reviews

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.

Top guest favorite

The bedroom is designed with a spacious bed centered against an accent wall featuring geometric patterns. A plush bench is positioned at the foot of the bed. Warm lighting illuminates the room, complemented by rich curtains and wooden flooring.

4.98 out of 5 average rating, 163 reviews

Elegant Suite in Gold Coast

Established in 1927 as the first headquarters for Elizabeth Arden in Chicago, the Walton Residence is located in the heart of the Gold Coast neighborhood of Chicago. Steps away from the Magnificent Mile, and the high-end boutiques of Oak and Rush Street, we are perfectly situated in the middle of the action for your Chicago adventure. ***From Sept. to beginning of Dec. 2024, there will be repairs to the exterior of the building. We do not expect this to cause major interruptions to your stay.

A spacious living area features a blue sectional couch positioned near large windows, allowing natural light to fill the room. A glass coffee table sits in front, accompanied by a decorative plant and two accent chairs. Views of the cityscape and nearby streets are visible beyond the windows.

4.84 out of 5 average rating, 124 reviews

Modern 2BR/2BA Corner Suite Near McCormick Place

Welcome to your modern 2-bedroom, 2-bathroom corner suite offers unbeatable convenience and comfort, located just steps from McCormick Place. 📍 Prime Michigan Avenue location 🏙️ Corner unit with South Loop skyline views 🛏️ 2 Queen beds + sofa bed (Sleeps 6 total) 🔥 65” Smart TVs in every room (Netflix + Roku) 🚀 High-speed dedicated Wi-Fi ❄️ Central heating & cooling 🍳 Fully equipped kitchen 🚗 EV charging + optional parking 🏋️‍♂️ Fitness center access 🧺 Washer/Dryer on the same floor

A comfortable living area features a modern sofa, complemented by two stylish ottomans. A large window with sheer curtains provides natural light, while a wall-mounted TV is positioned for easy viewing. A piece of wall art adds a contemporary touch.

5 out of 5 average rating, 16 reviews

Chicago Luxury Long Term 30+

Enjoy a stylish experience at this centrally-located place. This home is a lovely city terrace modern loft in a quiet nook of the Fulton Market / West Loop Area. Furnished beautifully for working from home or coming home. Very walkable with all of the best smart home features: digital light controls, Sony 65” TV, Sonos BEAM, smart lock, solid marble dining table with modern chairs, comfortable bed and pillows, and quality sheets for a great night sleep! Ultra high speed internet at 500mbps

A spacious living area is framed by floor-to-ceiling windows, showcasing views of the Chicago skyline. A black leather sectional sofa and a glass coffee table complete the space. A modern fireplace sits against a neutral wall, providing an elegant focal point.

4.91 out of 5 average rating, 54 reviews

52nd Floor MagMile Penthouse VIEWS Fireplace Pool

The Penthouses at Grand Plaza PH#5 Experience elevated city living from this stunning penthouse, soaring 52 stories above Downtown Chicago. Enjoy floor-to-ceiling windows, a designer fireplace, and breathtaking views of Lake Michigan. Perfectly positioned between the elegance of the Magnificent Mile and the vibrant charm of River North, this residence offers refined comfort and an unforgettable stay in one of Chicago’s premier locations. The Penthouses at Grand Plaza. License #2210737

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.

4.82 out of 5 average rating, 757 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 spacious living area features two soft, tufted sofas arranged around a low coffee table. A separate dining area is visible with a sleek table and dining chairs. The modern kitchen, equipped with stainless steel appliances, complements the open layout, enhancing the inviting atmosphere.

5 out of 5 average rating, 6 reviews

River North | Private Deck With In&Out Parking

Stay in style at our brand-new, upscale retreat in the heart of downtown Chicago ✨ This stunning 3-bedroom, 2-bathroom unit blends modern design with luxury comforts ,perfect for families or corporate travelers 🌆 🌇 Rooftop Patio w/ BBQ 🌿 Private Deck w/ Lounge Seating 🚗 Free In/Out Parking – 5 Min Walk 🌅 Balcony w/ Gorgeous City Views 🛏️ 3 Bedrooms | 2 Bathrooms 👑 3 Queen Beds + 2 Airbeds 👶 Portable Crib for Little Ones 📺 Netflix, Hulu, Disney+, Prime Included

4.9 out of 5 average rating, 130 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!

A serene indoor pool area is highlighted by tall glass walls, allowing natural light to illuminate the space. Cozy seating with soft cushions is arranged around the pool, while overhead greenery and pendant lights create a calming atmosphere.

4.73 out of 5 average rating, 161 reviews

Sentral Studio Apt in South Loop Chicago

Experience a lifestyle where everything you need is right at your fingertips in the vibrant heart of Downtown Chicago. Explore the area effortlessly: ✔ Breathtaking views of Lake Michigan and the Chicago skyline ✔ Close to major business hubs and the Loop District ✔ Enjoy a walk along the scenic Lakefront Trail ✔ A lively array of world-class museums, gourmet restaurants, and iconic architecture ✔ Quick access to Millennium Park, the Art Institute of Chicago, and Grant Park

An open living area features a comfortable sofa and stylish accent chairs, arranged around a glass coffee table. A large flat-screen TV is mounted on the wall, reflecting the light from the expansive windows that provide a view of the exterior building and greenery.

4.88 out of 5 average rating, 40 reviews

Chic 2BR 2BA Condo with Balcony - River North Chic

Welcome to @TheDreamRentals chic 2-bedroom, 2-bathroom condo located in the vibrant River North neighborhood of Chicago! Perfectly situated in the heart of the city, this stylish and modern space offers everything you need for a comfortable stay. Whether you're in town for business, a weekend getaway, or an extended stay, our condo is the perfect home base to experience everything Chicago has to offer. We can’t wait to host you! Chicago Registration Number: R24000119721

4.9 out of 5 average rating, 162 reviews

A modern kitchen with white cabinetry features stainless steel appliances, including a refrigerator and microwave. An island with seating for three is complemented by decorative vases of flowers. Natural light fills the space through large east-facing windows.

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.

A bright living area features a deep green accent wall and polished concrete floors. A plush dark sofa with decorative pillows is positioned facing a television on a wooden stand. A window offers a view of an outdoor space, enhancing the natural light in the room.