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Soak Up Mid-Century Style in Wrigleyville and Boystown

This is an architecturally significant (3-bedroom 3.5-bathroom) home by noted Las Vegas architect Homer Rissman. We are located in the heart of East Lakeview, just half a block from Lake Michigan and Lincoln Park, and blocks away from Wrigley Field and Boystown. Smart TVs (with Netflix, Hulu, Amazon Prime) are located in the shared main level TV lounge, and also the lower level lounge. Entire home I like in-person check-in but full privacy is offered You will receive a link with detailed instructions within 24 hours of your check-in. If you have a U.S. mobile number, you will also receive a text message FULL DISCLOSURE: If you haven't used a lockbox (or don't know how to), self-check-in isn't for you. Your check-in should be in person. Lakeview is home to two of the most vibrant sports, nightlife, and theater scenes in Chicago: Wrigleyville and Boystown. Explore souvenir shops and casual eateries by day, and hop from bar to bar along Clark, Addison, and Sheffield Avenues by night. You walk to Treasure Island (half block), Jewel Osco (2 minutes), Whole Foods (4 minutes), Lakeview Athletic Club (4 minutes), XSports Fitness (5 minutes), Walgreens (3 blocks), bars and restaurants aound the corner. Close to multiple buses on Lake Shore Drive. Grab a bus to downtown in 15 minutes You will have to climb one flight of stairs for all bedrooms Street parking is free on the east side of Broadway. The west side requires 383 permits. Please, read the signs.

Amazing Location! Spacious Duplex Getaway

Welcome to your perfect getaway! This beautifully renovated duplex is ideally located, just steps away from charming coffee shops, local restaurants, and Lake Michigan. Only 2 blocks from Metra and CTA stops, you will have convenient access to downtown Chicago, Wrigley Field, Northwestern University and much more. With a free off-street parking spot, comfortable king-sized beds and fast wi-fi, whether you're here to explore or just relax, you'll love the convenience and comfort this home offers.

*New* Luxury Wrigley Penthouse, Free Parking

✨ NEW Guest Favorite in Chicago Wrigleyville! SPACIOUS 3BR, 2.5BA DUPLEX, UP TO 12 GUESTS w/ NEW FURNITURE, BEDS & GAME ROOM ✨ A standout stay in Chicago — nothing else like it! Just a 5-min walk to Chicago Red Line Station (10 mins to Downtown Chicago!) & only 5 mins to Wrigley Field. Walk to cafes, shops, parks & more. Includes FREE parking, fast Wi-Fi, foosball & arcade games. Perfect for friend groups, families, corporate housing, and digital nomads! A perfect score in the heart of Chicago!

Ideal Group Getaway: Best Location, Parking, Patio

Unique opportunity to rent an original Victorian home in historic Old Town. Only listing of its kind! Within walking distance of Downtown, the Magnificent Mile, restaurants, bars, boutiques, Lincoln Park, and beach. Enjoy an open floor plan with a spacious living, dining, and sitting area with a cozy fireplace. The home offers 3 bedrooms, 2.5 baths, a fully stocked kitchen, 2-car garage, backyard, and laundry. Pets are welcome! Perfect for a relaxing city escape. Message me with any questions!

Opulent 3bdr2bth Old Town Luxury + Parking prmts

Luxurious home in the heart of Historic Old town triangle. Fantastic location! Steps to restaurants, shops, Lincoln park Zoo, Lake Michigan, Brown line. Pristine craftsmanship throughout, with no expenses spared. Sleeps 4 people. Internet speed 1G. 3 smart TVs. Essential baby gear. Key-less self-check-in. Bicycles with locks for the guests to explore the city. Complimentary guest parking permits. Pet friendly This home is perfect for business and pleasure!! Event allowed with host approval.

3 floor 2000 sqft home, deck, w/d, central

Welcome to my stylish, bright, & renovated home! 3 floors of spacious & comfortable living with new furniture. 3 big bedrooms with queen beds, each located on their own private floor. All floors have a bathroom (2 full & 2 half). Groups can enjoy together in the big living room or open dining area. Or there’s lots of space to do your own thing. 2 separate workspaces. Roof deck w/ great view & seats! Walk to lake, zoo, park, top-rated eats & public transit. *Ask before if parking is available*

Gold Coast Home|Rooftop |PoolTable |Parking |Views

Luxurious Gold Coast Townhome – Offers Indoor Games, Rooftop, Parking & More! Experience the best of Chicago in this stunning 4,000 sqft Gold Coast residence. Perfect for groups of up to 12, this home features 4 spacious bedrooms, 4.5 bathrooms, and a ceiling-length window with incredible views. Enjoy a variety of indoor games and make use of the convenient rooftop. Whether you're here for leisure or work, this property offers modern amenities and unforgettable comfort in the heart of City

Bronzeville 42: Art & Hospitality Mins to Downtown

Bronzeville 42 (B42) is a vibrant space where art meets hospitality! Featuring art from the owner's private collection, B42 is beautifully decorated and conveniently located in the historic Bronzeville neighborhood just 5 miles from Downtown and minutes to Hyde Park, the lakefront beach, and the upcoming Obama Presidential Center (opening June 2026). Dining Table seats 6 Kitchen Table seats 4 Sleeps 8 -BR1: King bed -BR2: 2 Twin beds -BR3: 2 Queen beds 2 Full Bathrooms

Spacious Two Story Luxurious Home w/Outdoor Deck!

Our home is in a quiet neighborhood, on a corner with abundant space and natural light. There are two spacious levels with two bedrooms upstairs and one downstairs. The large outdoor brand new deck was designed for barbecuing, star-gazing or just relaxing. Beautifully polished wood floors with a modern kitchen make this home ideal. A claw foot soaking tub is perfect for the end of a day and truly ensures a relaxing stay and a deep, refreshing sleep. Free parking!

Historic Old Town, Fabulous 4 Bedroom Home

Lovely Historic 4 Bedroom, 3 bathroom home in Old Town, walking distance of restaurants, boutiques, coffee shops, the lake front and excellent public transportation. 2nd Fl. Master Bedroom has a King size bed and Twin plus private bath with bathtub, walk in shower, w/d; 2nd Fl. two room "suite" with a Queen size bed in each room and private bathroom. 1st Fl. bedroom with Queen bed and private bathroom. Off Street Parking and Private Deck! License Pending.

Sleepy sanctuary

A spacious, modern and comfortable 2 bedroom, 1 bathroom flat situated in the quiet and relaxing Evanston neighborhood, Kingsley. This corner property comfortably sleeps up to 6 so whether you and your sweetheart need a change of scenery or the family wants a getaway spot close to Lake Michigan beaches, we can accommodate a variety of guest sizes. Includes a laundry room, garage parking for one vehicle, two work spaces with monitors, and large backyard.

Modern South Shore Retreat Near Lake and Museum

Stylish South Shore Escape | Walk to Lake, Near Hyde Park & Downtown. Welcome to your home away from home in South Shore, Chicago, just a 5-minute walk to Lake Michigan and a quick drive to Hyde Park, the Museum of Science and Industry, and the future Obama Presidential Library. Perfect for group stays, business travelers, or relaxing getaways, this stylishly updated space offers modern comfort in a peaceful neighborhood steeped in Chicago history.