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.

Retro Designer Home | Walk to Wrigley, Bars & Lake

Stay in prime Lakeview East, one of Chicago’s most walkable and safest neighborhoods, perfectly located near everything. • 12 mins walk to Wrigley Field • 6 mins walk to Lake Michigan & lakefront trails • 2 mins walk to top restaurants, bars, nightlife, shopping & entertainment • 8 mins walk to CTA Redline, access to downtown Chicago & airport • Extremely walkable, safe & vibrant area Live in the center of it all while enjoying a stylish designer apartment in one of Chicago’s best locations.

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.

RockStar Pad W3A BoysTown/Wrigley Field/Parking lot

HAVE IT ALL @ W3A Chicago Wrigley Field/Boystown/Lakeview -Newly renovated like new in safe centrally located East Lakeview. -10 min walk to Wrigley Field, Boys town, beaches, super markets, restaurants with late night dining. 5 min walk to Metro Sheridan Red Line (direct downtown), private enclosed parking $10/night & or free permits for street parking -600 thread count linens, fluffy soft pillows, house coats, high speed WiFi, Sonos speakers, stylish design & in unit washer & dryer

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.

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.

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.

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.

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.

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.

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.

'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.