Holiday houses in Wrigleyville

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Quick stats about holiday rentals in Wrigleyville

  • Total holiday rentals

    Explore 130 holiday rentals in Wrigleyville

  • Nightly prices starting at

    Wrigleyville holiday rentals start at $71 AUD per night before taxes and fees

  • Verified guest reviews

    Over 12,330 verified reviews to help you choose

  • Family-friendly holiday rentals

    80 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wi-Fi availability

    130 of Wrigleyville holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Wrigleyville rentals

  • 4.9 Average rating

    Wrigleyville stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated holiday rentals in Wrigleyville

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A comfortable living area features a cozy seating arrangement with soft cushions surrounding a wooden coffee table. A fireplace is positioned against a brick wall, with shelving displaying books and decorative items. An open kitchen is visible in the background, providing a warm ambiance.
Apartment in Wrigleyville
4.98 out of 5 average rating, 109 reviews

Grace Place in Wrigleyville

Unique, spacious, family friendly apartment 1 block from the home of the Chicago Cubs, Wrigley Field! Walking distance to Clark St. "strip", Halsted St. nightlife, Southport Corridor shops and restaurants, The Music Box vintage movie theatre, The Metro concert venue, and CTA red line for quick access to DePaul University, Loyola University, Michigan Ave Magnificent Mile premium shopping, Museum Campus and Soldier Field, Orchestra Hall, The Art Institute and so much more in the City of Chicago.

Guest favourite
A bright living area features large sliding glass doors that open to a balcony. Two elegant chairs and a cozy couch are arranged around a coffee table. Greenery adds a fresh touch to the space, with softly colored walls creating a calming ambiance.
Apartment in Lake View
4.93 out of 5 average rating, 280 reviews

Designer 3br with Balcony & Elevator on Clark!

My 3 bedroom apartment in Sheridan Park is a stunning place to call home in Chicago! You'll love the neighborhood; its vibrant food and art scene is uniquely diverse in Chicago. A mile north of Wrigley Field - Just to the east, Montrose Beach is a nice break from the city. If work is what brings to you to town, the nearby Brown line will take you right to the Loop. I provide all the essentials to make your stay easy and comfortable. (Balcony maintained for Summer Season, Memorial Day-Labor Day)

Top Guest favourite
A vibrant garden is visible with two blue Adirondack chairs placed on lush green grass. Potted plants are scattered on a table in the foreground. In the background, a domestic cat can be seen among greenery and flowering plants, creating a serene outdoor setting.
Apartment in Lake View
4.97 out of 5 average rating, 356 reviews

The Garden on Wayne

Located in one of the top 3 neighborhoods in Chicago, a great spot for a couple, a small family, business travel or a weekend with the girls. Close to high end shopping, a world famous and historic theatre and dozens of restaurants, our quaint garden apartment offers a quiet spot in a great area for weekending - and is also the midpoint between O'Hare and Downtown. The Lakefront is a quick 20-minute walk; the Lincoln Park Zoo is 20 minutes in an Uber. Please see below for further detail

Top Guest favourite
An inviting living space features large windows allowing natural light, framed by exposed brick walls. A round dining table is surrounded by modern chairs, while a comfortable sectional sofa is positioned near a cozy fireplace, enhancing the warm ambience. Stylish decor elements add character to the room.
Apartment in Lake View
4.96 out of 5 average rating, 273 reviews

Modern vintage chic steps from Wrigley: park free

Vintage touches and modern updates in the heart of Wrigleyville! Includes off street parking. Close enough to see Wrigley Field from the building, yet the block is charming and quiet. Close to the lake and Boystown. Charming vintage DNA meets modern amenities. Large deck. You will love the exposed brick and original millwork while enjoying huge new windows, an open floor plan, chef's kitchen, stylish decor, and spa like bathroom. Chicago Shared Housing Registration: R22000093584

Top Guest favourite
A spacious seating area is defined by a dark upholstered sofa with yellow accent pillows. A modern gold-toned coffee table sits in front, resting on a textured woven rug. Art pieces adorn the walls, contributing to the room's thoughtful design.
Apartment in Lake View
5 out of 5 average rating, 374 reviews

An elegant Chicago Northside Getaway

Welcome to Bluebird Inn, an intimate, thoughtfully designed urban inn that will serve as an oasis as you embark on your exploration of Chicago. Nestled above the Long Room, a beloved neighborhood tavern and coffee house (Bad Johnny's, Nice Guy Food Co., Cash's Kitchen and AJ's Bakery & Diner), you can start your day downstairs with breakfast and coffee and stop in for a nitecap before heading up to retire for the evening. Settle in & enjoy the amenities and approachable luxury.

Top Guest favourite
A modern dining area features a wooden table surrounded by six chairs. Natural light enters through large windows, highlighting the grey walls and stylish cabinetry. A chandelier hangs above the table, while a wall-mounted art piece adds a decorative touch to the space.
Condo in Wrigleyville
4.9 out of 5 average rating, 175 reviews

Foosball, Steps from Wrigley, Private Parking

Our apartment is ideally located near Wrigley Field and just steps from the Red Line, making it extremely convenient for exploring Chicago. Because of this prime location, occasional train and street noise can be heard. To help you sleep comfortably, we provide ear plugs. Many of our guests still enjoy the vibrant city atmosphere while finding the apartment cozy and restful. Perfect For: Guests who love being in the heart of Chicago and don’t mind a bit of city life sounds.

Guest favourite
The living area features a mix of modern and industrial design, with exposed brick walls and hardwood flooring. A cozy sectional sofa, accented by colorful pillows, complements a stylish area rug. A kitchen area with dark cabinetry and stainless-steel appliances is visible in the background.
Condo in Wrigleyville
4.81 out of 5 average rating, 282 reviews

Can't Beat This 2min Walk to Wrigley!

My home is a half block from Wrigley Field. You can be to the ballpark in 2 minutes (or Murphy's)! Enjoy your pregame afternoon feeling the buzz of the neighborhood from the private deck. Room for 6 to sleep comfortably in a Queen, 1 Twin plus a Twin over Full Bunk Bed and a Murphy Bed. I provide all the essentials to make your stay easy and comfortable. Toilet paper, soaps, shampoos, towels, linens and even coffee and tea! I have extensive information for you - let's chat!

Top Guest favourite
The brick exterior of the three-story home features large windows that provide natural light, framed by dark accents. A set of stairs leads to the black front door, showcasing a modern design. The surrounding area includes concrete walkways and mature trees.
Home in Wrigleyville
4.99 out of 5 average rating, 111 reviews

Wrigleyville Single Family

Private single family home one block from Wrigley Field! Enjoy three levels of living all to yourself. Totally gut renovated home with a chef's kitchen, central heat/air, washer/dryer, and three full bathrooms. Three bedrooms on the second level with a full basement/ bedroom with its own bathroom. Large back deck off the kitchen with a gated parking pad for one large vehicle included. Have an amazing time in the very heart of Wrigleyville.

Top Guest favourite
An open-concept living area is featured, showcasing a dark sofa complemented by light-colored pillows. A round coffee table sits on a patterned rug, and a dining area for four is visible nearby. Modern kitchen appliances are neatly arranged against the backdrop of sleek cabinetry, with natural light flowing through a large window.
Apartment in Wrigleyville
4.96 out of 5 average rating, 172 reviews

Beautiful Remodel in Sought After Wrigleyville

Modern comfort meets unbeatable location in this freshly renovated 1BR/1BA Wrigleyville gem. Enjoy the "new unit" feel with fresh paint, new appliances, and soaring 10-ft ceilings. Nestled in Lakeview, you're steps from top restaurants, bars, theaters, and iconic attractions. Perfect for travelers seeking style, convenience, and a true Chicago experience. Public transit is a block away and Spothero parking behind the building.

Top Guest favourite
Apartment in Lake View
4.94 out of 5 average rating, 239 reviews

Quirky Quarters at Wrigley

I think you are just going to love my apartment. The space features wonderful large street level windows in the living room and has all of the quirky charm that vintage buildings offer up. The location literally can't be beat, with the apartment a ten minute walk from Wrigley Field, the bustling Southport shopping corridor, and both the red line and brown line subway stations. There is no parking available with the apartment.

Top Guest favourite
A dining area showcases a long wooden table surrounded by six metal wire chairs. Natural light enters through two large windows, highlighting the warm wood finishes of the space. A sideboard with glass cabinets is visible against the wall, complemented by decorative art pieces.
Condo in Lake View
4.98 out of 5 average rating, 445 reviews

Prime Lakeview Apt: Walk to Wrigley Field

Escape to our bright & airy 2-bedroom apartment on a quiet, tree-lined street in Chicago's vibrant Lakeview. Perfect for 4 guests, this stylish retreat features a full kitchen, cozy fireplace, and is just a short walk from Wrigley Field, Lake Michigan, Boystown and the 'El' train for easy downtown loop access. Enjoy the best of Chicago from this classic home! Street parking passes available upon request.

Guest favourite
The living space features exposed brick walls that blend with modern kitchen elements. A spacious light-colored couch is arranged around a round black coffee table on a patterned area rug. A wall-mounted TV is visible, alongside sleek kitchen appliances, enhancing the contemporary design.
Apartment in Lake View
4.93 out of 5 average rating, 72 reviews

Full Luxury Home in Wrigleyville

Enjoy your stay in Chicago like a TRUE "Chicagoan" would. Enjoy the charm of exposed brick in a historic Chicago brick walk-up building steps away from the Left Field wall of Wrigley Field. Home features a king bed, pull-out couch, Amazon Fire TV, and exposed brick. This quiet tree-lined street is walking distance to the lake, Red Line, Clark Street bars / restaurants and Wrigley Field.

Popular amenities for Wrigleyville holiday rentals

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  4. Cook County
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