Mansion holiday rentals in Wrigleyville

NorthSide Chicago duplex 5-BD,2King size-free park

5-BD, 2-BR duplex; a combination of first floor and garden units. Just a 3-minute walk from the train, our property is the perfect place for your big gathering. Sleeps up to 12 guests with indoor Jacuzzi, full kitchen, free indoor parking( 1 car), and private patio. Access to grill, fire pit with big screen TV, and sound system. Keyless check-in and 24/7 active security cameras. Don't miss out on experiencing the best of Chicago from our beautiful and convenient duplex unit. Book your stay now!

Stunning 5 Bedroom Gem Steps from Wrigley Field!

One of a kind, beautiful 5 bed, 2 full bath two-level condo inside of an amazingly well-appointed all brick building, just steps from Wrigley Field. Exposed brick in the living area, incredible kitchen with all new appliances, island, and top of the line cabinets & countertops. A large group can comfortably enjoy the their time together spreading out in the two living spaces with large smart TV's, five bedrooms, two full baths, a back deck, and secure, private garage parking for two vehicles!

UP-SCALE Wicker Park 4BD/3.5BA HOME (+garage)

Escape into this Wicker Park Masterpiece! Guests love this home because: - Steps away from top-notch restaurants/entertainment on bustling Division St. - Close to every popular attraction that makes Chicago so great - Luxurious interior filled with natural light - Open-floor plan for entertaining! - City skyline views from top floor! - Fast WiFi (1,000 mbps) - Large attached garage! - Beautiful custom built-ins - Next to modern park and playground! - 10 minute walk from blue line (CTA L)

Soaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP

Say "WOW" in this top floor, DRAMATIC SPACIOUS Loft condo w/ PRIVATE ROOFTOP overlooking skyline! 45 seconds to Wrigley! Open 2-story layout w/7 individual bed options, 3 full bathrooms, fully-stocked kitchen + huge island. Enjoy luxury flooring, soaring high ceilings, keyless entry, 2 HD TVs, & brand new BBQ grill. Perfect for special occasions! Next to Wrigleyville bars & restaurants. Train to Downtown only 12 mins. Up to 4 parking spaces for rent. Over 1300 5-star reviews across listings!

The Urban Oasis | Outdoor Lounge • Sleeps 10+

Luxury 4BR/2.5BA residence featuring 3 private bedrooms and an open-concept bonus room with a queen bed and full-size bunk beds—perfect for upscale families or executive groups. The spa-inspired primary suite offers a soaking tub and rain shower with multiple settings. Enjoy a modern kitchen, stylish living room with a 76” smart TV, and a large covered patio. Located near UIC, West Loop, Chinatown, McCormick Place, the lakefront, and some of Chicago’s best dining and cultural attractions.

Lake View | Wrigley Designer House w/Patio

Between Wrigley Ville and Lincoln Park, our home is on a quiet street. We are surrounded by coffee shops, restaurants and nightlife. There is a Whole Foods less than a block away, a Target and other groceries stores within 5 minutes walk. The house is over 2,500 square feet spread over 3 floors, with 4 completely separate bedrooms. Extra tall ceilings in the common areas, artsy cathedral ceilings and skylights in the upstairs bedrooms and very comfortable mattresses will help you unwind.

Comfy/Elegant Home by Wrigley, Garage Spot & Yard

This chiq duplex home near Wrigley Field is a hidden gem. It features 6 beds, a garage parking spot; and a fenced yard; with 5 bedrooms, 3 baths, a spacious living & dining area and fast gigabit internet. In an unbeatable location close to many popular attractions, this home is the perfect base for your Chicago adventures. 6 min drive to: -Wrigleville -Andersonville & Boystown -Montrose Beach -Uptown, Green Mill, Riviera / Aragon Theaters 15-20 min drive: Cloudgate, Downtown, Loop!

Inspiring Stone Grotto Sleeps 10-20 & Free Parking

Imagine a stone castle, medieval style; except this one has an 85" HDTV, Wifi, 16' long granite bar with full kitchen and appliances. The warm glow of recessed lighting and polished concrete floors of this basement unit create a comfortable atmosphere. Lots of space with over 2,000 square feet; fully rehabbed with all newly appointed features. A secure building with a private entrance, free parking. Perfect for large groups of up to 20 friends and family; located in East Lakeview.

Spacious 4 Bedroom Condo

Located in West Town in the heart of Noble Square, just north of West Loop with access to all the best restaurants and only minutes away from River North and Old town, enjoy this 4 bedroom, 3.5 bath condo with private parking, 2 living spaces, heated floors throughout the entire lower level and steam showers. A gourmet kitchen stocked with everything you will need including an espresso maker. This home is perfect for families, couples, friends or traveling for business.

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.

Beautiful Chicago Greystone

Spacious, private, 4 bedroom condo 15 minutes directly west of the city center. Minutes away from the West Loop, Garfield Conservatory, Downtown, and United Center. Ideal public transportation access with multiple bus stops within 1 block radius, 2 blocks away from Blue Line CTA, 1 mile away from Pink Line CTA. Exquisite back porch and patio with access to grill and patio furniture. Onsite laundry per request Local hosts!

The Broasis at Wrigley

I took a perfectly nice flat on a beautiful street and filled it with great things...I want my guests to feel less like they are at an Airbnb and more like their 'very tidy but quirky friend' gave them keys to the flat for a weekend away. Super easy access to Wrigley Field, the bustling Southport shopping corridor, and all of the 'Boystown' nightlife.