Located in the heart of Chicago’s Northwest Side, Wicker Park is where artsy charm meets big-city cool. In the summer, the neighborhood comes alive with patio dining, indie shopping, street festivals, and shady parks made for lingering. Whether you're craving culture, cocktails, or just some curated relaxation, this itinerary will guide you through the perfect 3-day getaway—just steps from your stay at Wicker Park Inn.

 

 

Start your escape by checking into the Wicker Park Inn, a boutique bed & breakfast on a quiet, tree-lined street—yet just around the corner from Milwaukee Avenue’s energy. Unwind in your chic, comfortable room, refresh with locally sourced amenities, and get ready to explore.

Ease into the evening with dinner at Big Star, a local favorite for tacos and margaritas served on one of Chicago’s best patios. Prefer something cozier? Try Etta for wood-fired plates and a buzzy dining room with warm ambiance.

Wrap the night with Dorian's Through the Record Shop, known for its live music, speakeasy-style vibe and expertly crafted drinks.

 

 

Kick off your day with cool 80's vibe coffee at Wormhole or a flavorful crepe from Bru, then hit the sidewalks for Wicker Park’s signature shopping:

Myopic Books: A multi-level indie bookstore.

Una Mae’s & Store B: Stylish boutiques for vintage fashion and home finds.

Reckless Records: Vinyl goldmine for music lovers.

No pool? No problem.

• Chill at The Robey rooftop (day pass or bar access).
  
  

• Visit the Flat Iron Arts Building to browse local artists’ studios in A/C comfort.
  
  

• Walk the 606 Trail early in the day or closer to sunset for breezy skyline views.
  
  

Dine at Paradise Park, a funky pizza joint with an eclectic outdoor setup. Or go upscale with Mott St, a Michelin-starred experience for foodies in the know.

 

 

Stroll to the Wicker Park Farmers Market (held Sundays at Wicker Park proper) for farm-fresh produce, pastries, and people-watching. Grab brunch afterward at Bongo Room for decadent pancakes or Handlebar for vegetarian-friendly fare.

Spend your last few hours exploring neighborhood murals, Victorian architecture, and quirky storefronts. Don't miss the Wicker Park Secret Garden behind the library for a serene send-off.

Back at Wicker Park Inn, freshen up, grab a complimentary coffee or tea, and take a few porch-side photos before saying goodbye to your Chicago summer escape.

 

 

At Wicker Park Inn, you’re not just booking a room—you’re stepping into a neighborhood experience. With walkability, local recommendations, and charming accommodations, we make it easy to live like a local.

Book your stay today and let Wicker Park be your home base for a summer getaway that blends culture, comfort, and cool Chicago charm.