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Stunning 3BR Penthouse in the Loop | Roof Deck

[NOTE: The main rooftop is currently closed for seasonal repairs and is slated to reopen in Spring 2026. The 2nd rooftop remains open and available for guests to use.] 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 downtown Chicago. The penthouse is adjacent to the buil

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.

14th Floor 3Bd 3Bth Unit w/ Gym, Pool, &Amenities

Welcome to your spacious urban getaway in the heart of Chicago’s Printer’s Row neighborhood! This modern 3-bedroom, 3-bathroom unit is located in a stunning high-rise building, offering sweeping city views and access to premium amenities—perfect for families, business travelers, or groups looking to explore the best of downtown. Whether you're here for work or play, this retreat offers the perfect blend of style, comfort, and location. Book your stay today and experience Chicago like a local!

Luxury Designer Penthouse NW | 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!

Dtown Penthouse 11+Parking, Gym, Pvt Patio, Pool

Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional service along with “local vibes.” Guests love staying with us because: ✅ Central location near Grant Park, Art Institute, The Bean, Soldier Field, & more! ✅ 1 Free parking pass ✅ FAST WIFI ✅ En-suite Laundry ✅ The Lake & Park are only 2 blocks away ✅ KING beds ✅ Private Rooftop Deck w/ stunning views ✅ Amenity Floor (Gym, Pool, Lounge, Doggy Park) ✅ 1 block from Red "L" subway

Fun & cozy getaway w/POOL/game room/FREE parking

Enjoy our Pool & Play Getaway in hot Logan Square! Thoughtful upscale touches throughout. Conveniently located on a tree-lined Chicago Cul-de-Sac, just a 5 min walk to the L Blue Line. Relax in our extended outdoor living space, spend an afternoon lounging in the pool, al fresco grilling & dining on the deck or toast smores over the firepit in the yard. We're steps from all the hot restaurants and nightlife, including Chicago's #1 farmer's market. Free permit street parking for our guests.

Paradise with Pool & Games

Welcome to our home. Enjoy lazy summer days by our sparkling pool, where you can soak up the sun and cool off with refreshing dips. Our well-appointed kitchen is ideal for preparing delicious meals together, and the cozy living areas provide plenty of space for relaxation and bonding. With nearby attractions and easy access to downtown Chicago, our home offers the perfect balance of suburban serenity and urban excitement. We can't wait to host you for an unforgettable stay!

Sentral 1BR Premium Apt in South Loop Chicago

Indoor/Outdoor Resort-Style Pool • Grilling Station • Four-Story Indoor Garden • Fitness Center • Demonstration Kitchen • Pet Friendly w/ Amenities • Co-Working Space w/ High-Speed WiFi • Across from Grant Park • Steps to South Loop Dining & Nightlife • Breathtaking Views of Lake Michigan & the City Skyline Sentral Michigan Ave offers upscale comfort in the heart of Chicago’s South Loop, blending premium amenities with unmatched access to parks, culture, and entertainment.

Glamping Yurt&RV Gaming Room Pool/Hotub/Court more

GLAMPING FUN! April - mid Nov RV w/bathroom - 2 beds 20' Safari Yurt - 4 beds Gaming Room w/bathroom queen & sofa sleeper Gazebo w/2 twin beds (seasonal) Outdoor wooden Barrel-Sauna 27' above ground Pool 6-7 Person outdoor hot-tub Fresh Eggs (seasonal) mini golf 3-n-1 Court; Event Yurt add on $180 up to 15 additional non/overnight guest Contact me for Fall/Winter Glamping no more than 10. RV and Safari Yurt not included in Winter. Event Yurt is. It's heated!