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 $85 NZD 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 modern kitchen and living area are showcased within an open-concept space. The kitchen features stainless steel appliances and a large island with seating for three. The cozy living area includes comfortable seating and a low wooden coffee table, complemented by warm wooden flooring.
Apartment in West Rogers Park
4.99 out of 5 average rating, 108 reviews

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

Why stay anywhere when you can experience luxury during your travels. This brand new 1-BR apartment was designed with a touch of elegance and offers amenities to make your experience not just satisfying, but memorable. At your finger tips is a full kitchen; luxury bathroom with enormous walk-in shower; separate bedroom w/ queen bed (extra day bed in living room to sleep 3 total); garage parking; garden access; cozy workspace; 2-Smart TVs; bicycle; ample storage for longer stays; WIFI; 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, 111 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.

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Superhost
A spacious living area features an exposed brick wall complemented by large windows allowing natural light in. A sectional sofa is arranged around a round coffee table atop a patterned rug, and a modern light fixture hangs from the ceiling. A television is positioned on a clean-lined media console.
Condo in Lake View
4.87 out of 5 average rating, 150 reviews

Wrigleyville Condo 2 Blks from Lake & Train

I think you'll enjoy my spacious East Lakeview condo. The location is super convenient just 2 blks from Sheridan red line & 2 blks from the lake. Easy proximity 4 blks to Wrigley Field & restaurants/nightlife in Wrigleyville & Boystown. Amazing restaurant next door w/back patio- El Mariachi w/the freshest chips & guacamole! Starbucks, playground, and Divvy Bike station at the corner. 1 mi to Montrose Beach. All downtown sight-seeing easily accessible from Lake Shore Dr or red line 2 blks away.

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Top Guest favourite
A living room features a large bay window with multiple panes, offering a view of greenery outside. A comfortable sofa is adorned with colorful pillows, complemented by a contemporary armchair and side tables. Warm light is provided by a nearby lamp.
Apartment in Lake View
4.98 out of 5 average rating, 293 reviews

North Side Near Wrigley Lakeview Walk Everywhere!!

Located on a beautiful tree lined street one block from the thriving Southport Corridor, one of the hottest neighborhoods in Chicago. You'll love the convenience of being just steps from the Southport Brown Line "L" Stop, you can see the City without ever needing to drive. Steps to outstanding restaurants, bars and shopping. Going to Wrigley Field? Enjoy a 10 minute walk down some of the most beautiful streets in Chicago. Ideal for families seeking comfort, style and a convenient location.

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Top Guest favourite
A contemporary loft bedroom features a spacious bed with a light grey quilt. Exposed brick walls complement framed vintage Chicago artwork. Soft lighting is provided by string lights near the window. A green plant adds a touch of nature, while dark wood accents create warmth.
Loft in Lake View
4.96 out of 5 average rating, 597 reviews

Lakeview Loft-Vintage Chicago, Modern Amenities

The Lakeview Loft is a freshly remodeled loft space with a vintage Chicago theme and modern amenities. Located in the Lakeview neighborhood, it is 1/2 mile to the Brown & Red Line el trains, less than a mile to Wrigley Field and 1.5 miles to the lakefront. The Lakeview Loft will provide guests a true Chicago experience while staying in a great Chicago neighborhood. We believe in giving back to our neighborhood as well so for each booking we donate $5 to a local children's charity.

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Top Guest favourite
Home in Wrigleyville
4.99 out of 5 average rating, 165 reviews

Whole apartment! 2 Bed/2 bath steps from Wrigley!!

Newly rehabbed urban nest among the tree-lined streets of beautiful East Lakeview. Literally 60 seconds to Wrigley Field, close to bars, restaurants, El train/busses, and lakefront. You’ll have loads of space in this 2 bed, 2 bath, plus office and large laundry room with FREE full size W/D. Free parking passes! Owner lives near by and is happy to help with anything you need to make your trip the best it can be. Flexible check in/out times upon request.

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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, 114 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.

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Top Guest favourite
A spacious living area is presented, featuring a large gray sectional sofa. Natural light enters through expansive windows, illuminating the room. A fireplace and a mounted television are visible on the wall, with plants enhancing the decor around the space.
Condo in Uptown
4.98 out of 5 average rating, 359 reviews

Near Lake Michigan & Wrigley Field

Available 2B/2B condo with 2 King Size Beds. One block from the Aragon Ballroom and Riviera with great views of Uptown and two blocks from Lake Michigan. It’s also a perfect place to stay if your in town for a Cubs game. You can see the stadium from the rooftop deck. Walking distance to everything you need, 2 train stations, groceries, gym, restaurants/ bars. The perfect place to come and go as you please with easy key code entry.

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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, 179 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.

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Top Guest favourite
Apartment in Lake View
4.94 out of 5 average rating, 244 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.

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Guest favourite
The exterior of a garden unit is visible, featuring a red door framed by large windows. A locking fence surrounds the entrance, with low shrubs and a small area of gravel alongside the pathway. The building's brick facade provides a classic urban feel.
Apartment in Wrigleyville
4.81 out of 5 average rating, 492 reviews

'Secret Garden' Apartment in Wrigleyville

Small garden unit in the heart of Wrigleyville. Steps from both Wrigley and Boystown. The apartment has a queen bed in the bedroom and a sitting area with a TV and mini-dining area. In addition, the apartment has mini fridge, microwave, coffee machine w/ pods, and small dining table. There is no kitchen; fortunately Chicago has a multitude of amazing restaurants to choose from! Includes full bathroom with shower and linens.

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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, 73 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.

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Popular amenities for Wrigleyville holiday rentals