Holiday rentals in Boystown

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.

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.

Gothic-meets-mid-century in Lakeview

Welcome to our Lakeview hideaway—where gothic mood meets mid-century modern comfort. This updated 2-bedroom apartment is designed for guests who want something more than a standard rental: curated black-and-white artwork, warm lighting, and a show stopping emerald kitchen with bold checkered floors. You’re on a quiet, tree-lined street in the heart of Lakeview—walking distance to neighborhood favorites, close to Wrigley Field and Southport Corridor, and an easy “L” ride to downtown.

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.

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!

The Home Run: Modern 2BR Steps from Wrigley Field

Experience the heartbeat of Chicago in this spacious, modern 2-bedroom, 2-bathroom condo perfectly perched where the historic charm of Wrigleyville meets the upscale boutiques of the Southport Corridor. Whether you’re here to sing "Go Cubs Go" at the Friendly Confines or explore the city’s best dining, this is your premier North Side home base. The thoughtfully designed home offers a spacious gourmet chef's kitchen, and an inviting outdoor space!

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

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.

'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.

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.

Bustin’ a Mauve • Vintage Flat Near Wrigley

Stop scrolling! This 1920s studio in Chicago’s Wrigleyville/Southport Corridor has more personality than most full apartments. It’s cozy yet spacious, with vintage art, giant windows, and a glorious mauve-and-green palette that refuses to apologize. Just one block from Wrigley Field and close to Andersonville and the Brown Line, it’s a design-forward hideaway that actually feels lived in (in a good way).

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.