Neighborhood 48H guide
Wicker Park: Where to Stay & What to Do in 48 Hours
The six-way corner at North, Damen and Milwaukee, Big Star tacos, Myopic Books and The 606 trail.
Wicker Park grew up around the six-way intersection of North, Damen and Milwaukee avenues. Today it is known for independent shops, bars and restaurants, with The 606 elevated trail along its northern edge.
Photo gallery
Photo: Victor Grigas · CC BY-SA 3.0 · Wikimedia Commons 
Photo: Victor Grigas · CC BY-SA 4.0 · Wikimedia Commons
Why stay here
Indie shops, bars and restaurants, with the Blue Line to downtown and O’Hare.
Who it's for: Repeat visitors, shoppers and travelers who want a neighborhood feel.
Pros
- Independent shops and bars
- Blue Line to downtown and O’Hare
- The 606 trail
Cons
- Few hotels
- Busy on weekend nights
- Far from the lakefront
48H in Wicker Park
Books, tacos and a trail walk.
10:00 – The 606
Walk or bike the elevated Bloomingdale Trail west.
12:30 – Myopic Books
Three floors of used books on Milwaukee Avenue.
18:00 – Big Star
Tacos and whiskey on the patio facing the ‘L’ tracks.
Named recommendations
Real places with links to their official site or a Maps place page. We do not invent hours, prices, or ratings.
Eat
Shop
Shop
Myopic Books
1564 N Milwaukee Ave
Long-running used bookstore with three floors.
Official site / map →
Outdoors
Outdoors
The 606 (Bloomingdale Trail)
Access at Damen Ave
A 2.7-mile elevated trail on an old rail line.
Photo: Victor Grigas · CC BY-SA 4.0 · Wikimedia Commons Official site / map →
Where to stay
Specific named properties—not vague city-wide searches. Expedia stays use tracked Creator links; others open the hotel's official site.
Roam48 may earn a commission when you book a stay through Expedia or Vrbo links on this page, at no extra cost to you. All commercial stay links use rel="sponsored nofollow".
Hotel · Expedia
Wicker Park Inn
1329 N Wicker Park Ave
Small bed and breakfast on a residential street near the six-way corner.
Check rates on Expedia →
Vacation rentals
Prefer an apartment or whole home in this neighborhood? Browse Vrbo listings for Wicker Park.
Chicago requires short-term rentals to be registered with the city, and some buildings and precincts ban them. Look for the city registration number on the listing before you book.
Browse vacation rentals in Wicker Park on Vrbo →Other ways to spend 48 hours in Chicago
- The Loop — The Art Institute, Millennium Park’s Bean, the Riverwalk and a rooftop above Michigan Avenue.
- River North — Marina City’s corncob towers, deep-dish pizza, a Portillo’s Italian beef and hotel rooftops.
- Magnificent Mile / Streeterville — Michigan Avenue’s shops, the 1869 Water Tower, the Billy Goat Tavern and Navy Pier.
- Gold Coast — Astor Street mansions, Oak Street Beach and the Drake’s Palm Court.
- West Loop / Fulton Market — Randolph Street’s Restaurant Row: Au Cheval’s burger, Girl & the Goat and Fulton Market’s old warehouses.
- Lincoln Park — The free Lincoln Park Zoo, the glass Conservatory, Pequod’s pan pizza and late-night blues at Kingston Mines.
- Lakeview / Wrigleyville — Wrigley Field’s red marquee, Murphy’s Bleachers and a hotel across the street from the ballpark.
- South Loop / Museum Campus — The Field Museum, Buckingham Fountain and live blues at Buddy Guy’s Legends.
- Hyde Park — Frank Lloyd Wright’s Robie House, the Museum of Science and Industry, the new Obama Presidential Center and Promontory Point.