Vacation rentals in Boystown

5 out of 5 average rating, 23 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.

LocationFamilyAccuracy

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

4.86 out of 5 average rating, 148 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.

FamilyValueParking

Superhost

Apartment in Wrigleyville

4.76 out of 5 average rating, 267 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.

LocationFamilyQuiet

4.96 out of 5 average rating, 597 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.

FamilyValueAmenities

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.

4.99 out of 5 average rating, 155 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.

ValueLocationCleanliness

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, 162 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.

FamilyValueGetting around

The living area features a neutral color palette, highlighted by curved seating and a sleek entertainment unit. Three large windows allow natural light to fill the space, while a ceiling fan provides airflow. Minimalist art adorns the walls, enhancing the room's modern aesthetic.

4.96 out of 5 average rating, 94 reviews

Guest Favorite Newly Renovated 1BR Near Lakeview

2nd-floor unit with two flights of stairs. Older building with radiant heat managed by the building. Welcome to your stylish 1BR/1BA apartment in vibrant Lakeview, Chicago! This cozy retreat features a comfortable living space, a fully equipped kitchen, and a serene bedroom. Close to top dining, shopping, and entertainment, and just a short walk to Wrigley Field, lakefront trails, and public transit. Perfect for a getaway or extended stay—book now!

LocationValueKitchen

The contemporary kitchen features sleek stainless steel appliances and quartz countertops. A stylish overhead light fixture illuminates the space. A cozy dining area is positioned nearby with high-backed stools contrasting against the light cabinetry and textured wall.

4.85 out of 5 average rating, 533 reviews

Sleek and cool garden loft in East Lakeview

Cool loft 1 bedroom, queen bed in bedroom, 2nd queen bed in living area. Contemporary custom kitchen with quartz counters and stainless appliances. In unit laundry with central heat and air. Within walking distance to Lake Michigan, Belmont Station, Wrigley Field, Briar Street Theater, The Vic, Belmont Theater District, too many restaurants to mention and lots of retail shopping. 24 hour Starbucks nearby, Free Wifi and Netflix

ValueLocationWalkability

Apartment in Wrigleyville

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, 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.

LocationFamilyView

Apartment in Wrigleyville

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, 490 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.

ValueFamilyQuiet

4.99 out of 5 average rating, 124 reviews

The facade of a historic greystone building is showcased, featuring intricate stonework and large windows. A wrought-iron fence adorned with vibrant pink flowers is visible in the foreground, adding a touch of natural beauty to the entrance.

Condo in Wrigleyville

Wrigleyville Inn. Historic Greystone, Free Parking

Have fun with the whole family at this stylish place. Completely rehabbed 3 bedroom 2 bathroom high end, 1st- floor condo in a historic greystone, 5-minutes walk to Wrigley Field. And only 2 minutes walk to Clark or Halsted Streets. New open back porch for your enjoyment. Parking included. Old Grey Lady being reborn. Total gut rehab of classic Chicago 3 flat located in Historic Newport Avenue District.

FamilyLocationAmenities

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.