Holiday rentals in Boystown

5.0 out of 5 average rating, 29 reviews

Private 2BR/2BA heart of Boystown walk to Wrigley

Enjoy a private entrance to an entire garden apartment in the heart of Boystown. Right on Halsted Street, across from Lark & Replay, 3 blocks to Wrigley Field, and on the Pride Parade & Market Days route. Walk to groceries, dining, and Elevate Coffee. Wi-Fi, street parking, full kitchen, 2BR/2BA. One bedroom includes a cozy bonus room with a small bed—great for one adult or kids. One room also has a desk with chair, where one can work. One full bathroom with shower, one half bath. Self check in.

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.

4.98 out of 5 average rating, 117 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.

Superhost

4.76 out of 5 average rating, 272 reviews

Cozy Bedroom in Wrigleyville (Entire Apt)

You can’t beat this location! Right in the middle of Boystown and steps from Wrigley Field, you’ll be surrounded by some of the city’s best bars, restaurants, and nightlife. Cubs Stadium is just one block away, and the Addison Red Line station is a quick 5-minute walk, making it easy to explore all of Chicago. No shared space: Due to updated COVID-19 policies, this unit is now 100% private. Once you book, the entire place is yours and the additional listing will be blocked immediately.

An open-concept living area features a dark leather sofa and a green armchair, both arranged around a round coffee table. A decorative rug lies beneath, while a modern kitchen with white cabinetry and a large island is visible in the background.

5.0 out of 5 average rating, 86 reviews

The G Estate

The whole group will enjoy easy access to everything from this centrally located place in East Lakeview. You will be steps away from great dining, boutique shopping, fitness studios, and the Belmont harbor where you can access the lake and Chicago bike path. This unit is a 15 minute walk to Wrigley Field where you can enjoy games, concerts, and other events. Easy access to public transportation with the Halsted bus stop at the corner and a 15 minute walk to the Belmont Redline stop.

4.96 out of 5 average rating, 608 reviews

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

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.

Guest favourite

A comfortable living area is presented, featuring a brown leather sofa and a dark wood coffee table positioned on a soft area rug. Two light chairs are placed near large windows, while a flat-screen TV is mounted on the wall above a rustic fireplace adorned with stacked firewood.

4.98 out of 5 average rating, 47 reviews

Mid-Century Modern | Walk to Wrigley

Experience stylish comfort in this beautifully designed, mid-century modern apartment in the heart of Wrigleyville. Enjoy a spacious back porch, perfect for relaxing, a chic dining area ideal for entertaining, and a dedicated desk space for remote work. Located just steps from Wrigley Field, Wrigleyville's bars and restaurants, and the Southport Corridor, with high end shops and dining. Parking is not provided and the street is prohibited from 6pm-6am and Wrigley Field events.

An elegant stone entrance is framed by lush green ivy, leading to a wooden door beneath a decorative awning. A charming fountain, featuring three tiers, adds a serene element to the outdoor area, surrounded by abundant foliage and creating a peaceful environment.

4.98 out of 5 average rating, 161 reviews

CASA NEWPORT

Second floor, one bedroom apartment, with an additional queen pullout couch located in a beautiful historic district in Lakeview. Just steps away from Halsted street/Boystown/Wrigley field. Conveniently located to shopping, restaurants, subway (EL) and grocery stores. Close to lakefront, jogging path and bike path. Complementary street parking passes available. The apartment does NOT have air conditioning. It does have a window unit in the bedroom from May to September.

A spacious living area is furnished with two leather sofas, a coffee table, and a decorative rug. A television is mounted above a tiled fireplace, and large windows allow natural light to fill the room. A comfortable armchair is positioned near the window.

4.99 out of 5 average rating, 167 reviews

Spacious 2 Bedroom in the heart of Lakeview!

Come enjoy this warm and spacious 2br/1ba vintage apartment in the heart of Lakeview! 10 Minute walk to Wrigley Field and steps away from many dining and shopping options. Fully stocked kitchen, dining room (seats six), decorative fireplace, TV w/ Fire Stick, two bedrooms with queen beds, office space for working remote, and large private deck with gas grill. Very close to Lake Shore Drive, short walk to the Belmont L, and easy access to many buses. Two night minimum stay.

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.

4.96 out of 5 average rating, 184 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.

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.

4.81 out of 5 average rating, 496 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.

4.82 out of 5 average rating, 179 reviews

Guest Favorite Getaway | Lakeview | Near Wrigley

Walk up two flights of stairs to the 2nd floor. Older building with radiant heat managed by the building. Enjoy a fully furnished home for longer stays, complete with WiFi and essentials. Just a 3-minute drive or 13-minute walk to Wrigley Field! This cozy 1BR/1BA apartment is perfect for business or vacation, featuring a full kitchen, comfortable bed, and modern decor for a relaxing Chicago stay.