Mansion vacation rentals in Wrigleyville, Chicago

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Top-rated mansion rentals in Wrigleyville, Chicago

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Superhost

Home in Lake View

4.84 out of 5 average rating, 102 reviews

Big Wrigleyville Home, Great for Groups, 2 Units!

Traveling with a big group? There’s no better choice for your Chicago base than this spacious 9-bedroom home located right by Wrigleyville. The 2 separate apartments can opened up into one large home; it's close to attractions/entertainment and can sleep groups of 20. Perfect for business retreats, family reunions, and friend trips! 6 min drive to: -Wrigleville -Andersonville & Boystown -Montrose Beach -Uptown, Green Mill, Riviera / Aragon Theaters 15-20 min drive: Cloudgate, Downtown, Loop!

Top guest favorite

Apartment in Albany Park

4.97 out of 5 average rating, 151 reviews

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!

Top guest favorite

An expansive kitchen and dining area features exposed brick walls and wooden beams. A large island stands in the center, surrounded by a mix of contemporary and rustic furnishings. Ample natural light floods the space through large windows, illuminating the warm wooden floors.

Home in Logan Square

4.95 out of 5 average rating, 150 reviews

The Grand Kimball Lodge, Logan Square, Sleeps 14

Welcome to The Grand Kimball Lodge, a truly unique getaway featured in Architectural Digest's "21 Best Chicago Airbnbs for Your Next Windy City Trip." Located in the heart of Logan Square, this charming loft combines rustic elegance with modern comforts. With 4 themed bedrooms, 3 bathrooms, a chef’s kitchen, & spacious living & dining areas, it’s the perfect space for families, friends, & small groups to gather & make lasting memories. Visit my owner’s profile page for a 20-person listing too.

Guest favorite

The historic stone façade of the building features intricate architectural details, with large arched windows and a welcoming entrance. Flower pots are displayed on the balcony, and a wrought iron fence surrounds the property, adding to the charm of the exterior.

Apartment in Lake View

4.92 out of 5 average rating, 231 reviews

Stone Mansion Sleeps 10-20 Free parking & TV

Giant, 4 bedroom, 2,300 square feet apartment on 2nd floor, near Red Line Train, bars, cafe's, shopping, restaurants, Lakefront and everything else Chicago has to offer. Large living room with bar area, TV and fridge for socializing before hitting the town. Dining room has a large table and 8 chairs. 4 bedrooms with 2 private rooms with king beds and one with a double bed. 4 futons for in the living room for extra sleeping space two (2) parking spots in the west facing garage on premises.

Top guest favorite

Home in Wicker Park

4.98 out of 5 average rating, 103 reviews

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)

Guest favorite

The entrance of Wrigley Field is depicted, showcasing the iconic red marquee sign indicating the home of the Chicago Cubs. Flags flutter gracefully above crowds of fans, with a vibrant atmosphere highlighted by the greenery and historic architecture surrounding the entrance.

Home in Lake View

4.88 out of 5 average rating, 171 reviews

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.

Guest favorite

Home in Roscoe Village

4.92 out of 5 average rating, 285 reviews

Duplex Home RoscoeVillage/Wrigley Free St Parking

Upgraded luxury 2000 sqf living in this beautiful walkable, desired and safe Roscoe Village/Wrigleyfield, surrounded by shops+restaurants. 5min walk to Brownline Paulina station, Divvy Bike rental; 20min walk to WrigleyField, 3 miles to beaches/Lake Michigan, 5 miles to downtown Chicago; fast WiFi, a dedicated office room with a 22" monitor for your work hours; smart 65" TV in the Living room, smart 50'TV in Master bedroom, walk-out deck. Chef's kitchen, complimentary premium coffee

Top guest favorite

A modern living area showcases a coffered ceiling and stylish furnishings. Plush sofas and accent chairs are arranged around a coffee table, with a large wall-mounted television and a decorative painting enhancing the aesthetic. Natural light enters through multiple windows, illuminating the space.

Condo in West Town

4.98 out of 5 average rating, 164 reviews

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.

Superhost

Home in Avondale

4.84 out of 5 average rating, 112 reviews

The Logandale: HUGE Mid-Century Home, sleeps 15

Welcome to The Logandale! This 4 bed/3 bath mid-century modern home is ideal for families, professionals, and groups. Enjoy an open floor plan, private patio, game room, and bedrooms with memory foam mattresses. The fully-equipped kitchen, Smart TVs with Netflix, and a backyard fire pit ensure a comfortable stay. Located in the trendy Avondale/Logan Square, you're close to public transport, eateries, and attractions. Experience Chicago's best with us! 🌃🛏️🎮🔥

Guest favorite

Townhouse in Uptown

4.96 out of 5 average rating, 148 reviews

Spacious 4BR Townhouse + Free Parking Included

• 4 bedrooms (3 queens, 3 twins, and 2 futons) • free private dedicated outdoor parking space • close to popular neighborhoods such as Wrigleyville (6 min drive), Andersonville, and Uptown • easy access to public trains (Metra, Red line Wilson and Brown line Montrose stops) and buses • 20 min to downtown Chicago by car • Easy access to Evanston by Metra (Ravenswood train stop) - 4 stops • Close to Montrose Beach • 94/100 walking score

Top guest favorite

Condo in Andersonville

4.92 out of 5 average rating, 170 reviews

Warm & Comforting 4br/2ba In Andersonville

Our 4BR/2BA home offers the perfect balance of quiet and convenience. Step out the front door into the tree-lined streets and walk just minutes to the heart of Andersonville for some exciting and historic neighborhood culture or to the Red Line which grants access to everything the City has to offer! Whether you are in town as a tourist, visiting friends, or on business, you will feel right at home!

Superhost

Apartment in Lincoln Park

4.83 out of 5 average rating, 136 reviews

Stylish 2-Level Designer Home by DePaul w/ Parking

A design lover's dream! Spend your next trip to Chicago in a beautifully remodeled 4 bedroom, 3.5 bath apartment in Lincoln Park. ✔ Safe and vibrant neighborhood. ✔ Free parking - We have two spots directly behind the building. ✔ Easy self-check-in & keyless entry. ✔ Walk Score of 92 - Close to transit, dining, bars, shops, groceries, and DePaul University. ✔ Easy access to downtown