Fitness-friendly vacation rentals in Cook County

Cozy 2 bedroom house/w garage in Skokie

Charming 2B/1.5B house in Skokie IL. This Airbnb boasts plenty of amenities including WIFI, Roku TV's, fully furnished, a beautiful backyard, workout gym and sauna in the basement and a kitchen with top of the line appliances. The house sits on a quiet residential street just 2 minutes away from the nearest interstate taking you to beautiful Downtown Chicago in about 25min . Downtown Skokie is a few minutes away, plenty of shopping options 5min to Village Crossing and 15min to Old Orchard Mall.

Couples Getaway, Jacuzzi, Sauna, Pool is Open

Couples Getaway | Private Suite w/ Jacuzzi, Sauna, Pool & Gym Indulge in a luxurious, private retreat designed for couples! This beautifully styled guesthouse suite is attached to the main house but completely private—you’ll have your own private entrance for total seclusion. Enjoy spa-like relaxation with a jacuzzi, sauna, pool access, and a fully equipped gym. Perfect for honeymoons, anniversaries, or weekend escapes, our space blends comfort, privacy, and elegance for an unforgettable stay.

RockStar Pad W3A BoysTown/Wrigley Field/Parking lot

HAVE IT ALL @ W3A Chicago Wrigley Field/Boystown/Lakeview -Newly renovated like new in safe centrally located East Lakeview. -10 min walk to Wrigley Field, Boys town, beaches, super markets, restaurants with late night dining. 5 min walk to Metro Sheridan Red Line (direct downtown), private enclosed parking $10/night & or free permits for street parking -600 thread count linens, fluffy soft pillows, house coats, high speed WiFi, Sonos speakers, stylish design & in unit washer & dryer

Kasa | Walk to Lincoln Park Zoo | 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.

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!

Hoosier Home - 5 min walk to the beach

Enjoy quiet, cozy, and spacious home just a short walk from the beach and local restaurants/bars. Located 2.1 miles from Indiana Dunes National Park (West Beach), 11 miles from Indiana Dunes State Park, and a few blocks from Marquette Park, which features a disc golf course and seasonal concessions. The Miller Beach train station, with direct service to Chicago, is also a short drive away. Please note: a 2-night minimum stay is required - single-night bookings are not accepted.

3bedrooms& 2 bath (king bed) in newly updated Home

Located in the West suburbs of Chicago you'll be far away from the chaos of the city, yet close to the highway to visit downtown whenever you like. You'll have a great night sleep in either the king, queen, or full size beds. All with brand new mattress and linens. Get ready for a night out in 1 of our 2 full size bathrooms. Enjoy a large backyard for kids to play and if you decide to have a family BBQ. Whether you're coming here for work or play we have you covered.

Modern Studio: Gym, Game Room & Home Theater

Modern, stylish, lake facing private basement studio in heart of Naperville with 2 bedrooms with 1 queen beds in each bedroom, 1 full bathroom attached to master bedroom, kitchenette, living room with electric fireplace, 165" projector, TT table, and more for perfect romantic getaway or business trip. Access via shared entry. Friendly hosts live upstairs. Ideal for a cozy stay for up to 4 adults.

Urban Oasis in Vibrant Gold Coast

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. ***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.***

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

Urban-Luxe experience at the Bliss of Evanston Condo. Elegant finishes and a sweeping Sky Terrace view of downtown Evanston. Resort-like amenities with fitness center, outdoor pool, free parking in indoor GAR, biz ctr, and much more. 2 bedrooms, 2 full baths, 2 roll-out beds welcome you to a comfortable stay near Northwestern University, Loyola, and Kellogg and minutes from Chicago Downtown.

Spacious Evanston Unit - Walk to Northwestern U

Welcome to my contemporary and spacious garden level unit located on a tree filled, serene residential block in Evanston. Walking distance to Northwestern University, retail areas, trains, golf, and the lovely beaches of Lake Michigan! A Walgreens and a local brewery restaurant are just a few steps away. Plentiful free street parking and free EV chargers one block away.

Breathtaking & Chic Oasis Loc in Desirable Old Twn

Enjoy a stylish experience at this centrally-located place. Our stylish 1-bedroom Airbnb, catering to all kinds of travelers. Whether you're looking for a restful stay, a productive workspace, a central hub to explore Chicago, a night of fun at the bars and nightlife, or a snug spot to unwind and connect, our place has everything you need.