Mansion holiday rentals in Wrigleyville

Private Lincoln Park Condo with 2 Parking Spots

Built in 1895 and updated in 2025, the condo provides historic charm with modern convenience. The unit is light filled with ample space to spread out and relax. The bathroom has been fully remodeled and the kitchen is updated. The unit has a private balcony deck and a landscaped common patio. The unit includes 2 free off-street parking spots. Amenities include 60" 4K Smart TV, fiber internet, Nest Thermostat & Tuft & Needle/ Casper mattresses. Enjoy living in the heart of Lincoln Park.

Huge Bright Corner Home on Chicago's North Side

Enjoy a bright 4,100 sf home that can sleep 12-25 people. Located between Downtown and North-Suburban attractions. Half an hour to Chicago’s sites: Sears/Willis Tower, Millennium Park, the Bean, Beaches, Magnificent Mile, Art Institute, the Loop, Wrigley Field, Soldier Field, and United Center. Half an hour North to the Botanical Garden, Ravinia Festival, Northwestern University, Old Orchard, Baha'i House of Worship, LEGOLAND, and everything in Evanston, Highland Park, Skokie, Northbrook, etc.

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!

Spacious 3600 SQ Ft. Home next to Park & Transit

Large 3600+ sqft. home is perfect for group and family vacations. Sprawl out and relax after a busy day in Chicago with 6 bedrooms, 8 beds, 2 living rooms, 3 dinning areas, 3 full bathrooms, and kids play area. A Short walk to groceries, restaurants, coffee shops, Walgreens, CTA blue line train (20min ride to O’hare, 15 downtown), and across from an amazing park. Fast speed 1 GB Fiber internet for those working from home. FREE and easy parking on treelined street. Great Area! More pics coming.

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!

Large Remodeled Home in Lincoln Park, Sleeps 12!

Stay in this thoughtfully remodeled home in Lincoln Park. Sleeps 12 w/ complimentary access to 3 parking spots! Enjoy the spacious layout, massive bedrooms, 2 private decks, and front yard w/ a grill. You will be steps from the North & Clybourn Red Line station, Divvy stations, Starbucks, Binny's, Whole Foods, Trader Joe's, Alinea, Steppenwolf Theatre, and more! Our home is (conveniently!) located next to train tracks. If you are a light sleeper, this urban location might not be for you.

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.

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.

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.

The Broasis • 4BR W/ Parking Near Wrigley

Headed to Chicago with a crew that likes their personal space? This large nautical flavored space has room for everyone to manspread, unwind, and still like each other afterward. Spread across two full floors, it’s a spacious, design-forward home in Ravenswood. Minutes from Wrigley Field, Andersonville, and the Brown Line. White walls, black trim, Norwegian maritime banners, comfortable beds, great light, and....plenty of room for big groups to actually breathe.

Chicago Bootlegger House Sleeps 10-20

Walk to restaurants, groceries, shopping, Wrigley Field, Lake Michigan, Beaches, Boat Harbor, Lincoln Park Zoo, night life, bars, clubs, Red Line Train, Lakeshore Drive and more; all just a few blocks from your door. Giant house on 2 levels with over 3,500 square feet of living space and 6 bedrooms. Nicely decorated and lots of places to sit and mingle or watch one of the 85" TVs. Private 2 spot parking in garage and a parking pad for oversized vehicles.

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!