Fitness-friendly holiday rentals in Libertyville

Chicago's Treasure "Heart of Evanston" 2bdr +1 Ba

Eco-Friendly, modern, sleek, condo with modern finishes and a sweeping Sky Terrace and resort-like amenities are just steps from Northwestern University, Loyola, and Kellogg and minutes from Chicago. Heart of Evanston Condo features granite countertops in the kitchens, 9 foot ceilings and designer plank flooring. Enjoy luxury amenities such as a fully equipped fitness center, BBQ and picnic area and beautiful landscaping. In the warmer months, Guests can enjoy the Clark Street Beach & Lighthouse

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.

Hidden Gem:Artsy Speakeasy in Historic Bronzeville

Enjoy this fun and unique 1-bed 1.5-bath speakeasy in the heart of Chicago's Bronzeville District. This artsy vibe features eclectic décor, hand-painted murals, Smart TVs, wet bar, wellness studio, remote workspace, free street parking, and ground-level-step-free access. This cozy space is perfect for fun couples, solo adventurers, business travelers, and game night aficionados. Easy access to Downtown (6 miles to Mag Mile, Navy Pier, Millennium Park), Beach (1 mile), Museums, & Sports arenas.

Lakefront, beautiful views, spacious and private.

With panoramic views of the lake, you’ll love the stunning sunsets, private beach, pier, and kayaks. Experience outstanding fishing and walk to downtown for restaurants, bars, shopping, theater, and concerts in the park. Skiing at Wilmot/Vail is just a short drive away. Inside, unwind by two fireplaces, three TV screens, or play a game on the pool table. The large wet bar and expansive kitchen are perfect for gatherings, with additional space in the dining areas, private office, and gym.

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.

Tropical Bungalow Getaway in Quiet Neighborhood

Located on a quiet tree lined street, the bungalow's garden level design was influenced by the rumpus rooms of the 1950's. A private side entry, a few steps down from the rear courtyard, leads into your tropical get away. Heywood Wakefield furniture and thatch palm leaf wall covering enhance the Tiki vibe of the sitting room. An exercise area, private bedroom and bath are all accessed from this main space. While the suite is at garden level, it is always bright and airy.

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.

Cozy 3BR on Chicago's North Side & Free Parking

Enjoy this charming 3-bedroom condo with free on-site parking just three blocks from Lake Michigan. Convenient access to public transit, including the express bus to downtown (9 miles), Navy Pier, and Grant Park. The CTA Jarvis station is only three blocks away. Perfect for families, business travelers, and couples, this condo is also close to Loyola (1.5 miles) and Northwestern universities (2.5 miles). A great home base to explore all that Chicago has to offer!

Wrigleyville Greystone

First floor guesthouse ideal for 6+guests 1 block from Southport brown line station, 1/2 mile from Wrigley Field & red line station. Open floor plan with full kitchen, DR, double LR with 55” TV & foosball table, 3 bedrooms with queen size beds, 2 full bathrooms with bidet toilet, exercise room & back patio with sofas, table & koi pond. Since we live here and have another guests house in the building, we do not allow parties or large groups.

Stunning Corner 2BR in the Loop | City & Lake View

Dramatic 1,250+ square foot corner apartment with 12 foot tall ceilings, massive windows, and panoramic city and lake views in multiple directions. This stylish light-filled two bedroom, two bathroom space is perfect for groups looking for a luxurious getaway in the sky in the heart of downtown Chicago. Centrally located in a historic building close to everything you want to visit, this is the best location in the city!

Elegant Suite in Gold Coast

Steps away from the Magnificent Mile, and the high-end boutiques of Oak and Rush Street, this generous one-bedroom apartment is perfectly situated in the middle of the action for your Chicago adventure. ***Please note that from March until the end of May 2026, there will be construction on the upper floors of the building that may cause noise during the daytime hours***