
Fitness-friendly vacation rentals in Downtown Chicago
Find and book unique fitness-friendly rentals on Airbnb
Top-rated fitness-friendly rentals in Downtown Chicago
Guests agree: these fitness-friendly rentals are highly rated for location, cleanliness, and more.

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.

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 Unit Highlights: - Stunning views of the city - Black-out curtains & roller shades - Work from home space - In-unit washer & dryer - Fully equipped kitchen - Fast WiFi - Modern design

Luxury Designer Penthouse 3803 | Pool | Gold Coast
NEW PENTHOUSE IN THE HEART OF GOLD COAST! Enjoy your own penthouse in Chicago's Gold Coast-the city's center of nightlife, restaurants, and shopping. Sitting 38 stories in the sky, your 3 bedroom/2 bathroom penthouse offers some of the best views in all of Chicago. The highly secure building includes elevator, rooftop pool, full gym, and is perfect for families traveling to Chicago, professionals visiting the city on work trips, and everything in between. The cityscape views are unbeatable!

Mag Mile Penthouse + Lake Views! (+Rooftop/Gym)
Welcome! Incredible Gold Coast/Streeterville location SECONDS from the LAKE and MAGNIFICENT MILE. Located on a quiet street, this condo 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 generally 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!

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.***

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!

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.

Downtown Chicago Retreat 2BD 2BA Views Gym Rooftop
Experience downtown Chicago living at its finest in this stunning 2-bedroom apartment, Sleek black and gold accents, in the heart of the River West. Wake up to breathtaking city views and step out to world-class attractions just minutes from your door. Enjoy a gourmet kitchen with high-end appliances, stylish baths, in-unit laundry, gigabit Wi-Fi, and free parking. Building amenities include a rooftop lounge and gym—perfect for business or leisure.

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.

Level Junior Two Bedroom Suite | Fulton Market
Two bedroom, two bathroom suite featuring a king bed, queen bed, and sofa bed. Maximum occupancy is 4. Enjoy access to over 32,000 sq ft of unrivaled lifestyle amenities, including a seasonal outdoor pool, a relaxing hot tub, and a state-of-the-art fitness center. Take in stunning views of the Chicago skyline from our Cloud Lounge, grill meals at the BBQ stations, and enjoy movie or game nights in the media room.

Level ◆ Brand New Luxe JR Two Bedroom Suite
Space to live, space to play, space to call home. Our Junior Two Bedroom Suites boast 820 sq ft of modern living space and feature a fully-equipped kitchen, open concept living and dining area, two spa-inspired bathrooms, and an open-air balcony perfect for taking in the city views. All suites also feature in-suite laundry, premium appliances, flat-screen TV with cable, complimentary WiFi and local calling.

Modern 3BR Apartment Near North Ave Shops
Welcome to your bright and spacious 3-bedroom Chicago retreat. Enjoy an open living area, fully equipped kitchen, and cozy bedrooms designed for both comfort and privacy. Large windows fill the space with natural light, while modern furnishings and soft tones create a calm, welcoming feel - perfect for families, groups, or business travelers seeking room to relax and recharge.
Popular amenities for Downtown Chicago fitness-friendly rentals
Fitness-friendly apartment rentals

Top Floor Views + Central Comfort

Corporate Smart Home At River Walk

Apartment near McCormick w/ gym & workspace

Top of River West: Luxe Penthouse for Groups

Kasa | Studio, Walk to Grant Park | South Loop

Luxury South Loop Apt

Plymouth Collection: 3BD 2BA with Gym & Rooftop

1bd w/gym, game room, parking. Sleeps 3
Fitness-friendly condo rentals

2BR Apt, Office, Parking & Backyard by Wrigley

Luxe 2BR Cozy Suite | Skyline Views near McCormick

Stylish 3BR, 12 mins to Loop + Parking

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

RockStar Pad W3A BoysTown/Wrigley Field/Parking lot

Modern long-term luxury w/ spectacular view!

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

Pond View, Washer Dryer, Non Smoking, Pet Free
Fitness-friendly house rentals

Fun and Cozy Family Home Near O’hare Airport

The Chicago River House – GIANT wall projector!

Luxe Duplex-King Beds-Gym-Huge Backyard-Game Room

Jacuzzi|Movie Theater|Games|Arcade|Gym|Kid's Space

Wrigleyville Greystone

Cozy 2 bedroom house/w garage in Skokie

Logan Sq/Avondale chic Townhome.

Entire Luxury Home: Private Gym
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- Wrigley Field
- Lincoln Park
- United Center
- Soldier Field
- Grant Park
- Navy Pier
- Millennium Park
- Naval Station Great Lakes
- 875 North Michigan Avenue
- Indiana Dunes State Park
- Six Flags Great America
- Shedd Aquarium
- The Field Museum
- Humboldt Park
- Chicago River Walk
- University of Chicago
- SeatGeek Stadium
- Guaranteed Rate Field
- Lincoln Park Zoo
- Loyola University Chicago
- Donald E Stephens Convention Center
- Union Park
- Frank Lloyd Wright Home and Studio
- Garfield Park Conservatory
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