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Point
1. The 606
 (Free Entry) 8.5
stay time indicator 0.5-1.0 hr stay Open now Check Hours of Operation
Trail, Scenic, Hike

Local Favorite, Trendy, Dog Friendly, Hiking, Biking, Breathtaking Views, Street Performance, Family Fun, Free Entry, Lush, Exhibitions, Walking Around, People Watching, Photography, Romantic

1805 N Ridgeway Ave, chicago

The 606 is a former elevated rail line, the Bloomingdale Line, converted into a combination walking, jogging, and biking path from Ashland Avenue to North Ridgeway Avenue. The trail connects to ground-level neighborhood parks, an observatory, art installations, and other amenities. There is a lot to see architecturally, lovely plantings along the way, with many entrances and exits along the route.

Point  (Free Entry) 8.6
stay time indicator 0.5-1.5 hr stay Open now Check Hours of Operation
Scenic, Architecture, Hike

Local Favorite, Wheelchair Accessible, Dog Friendly, Breathtaking Views, Famous, Family Fun, Free Entry, Lush, Sightseeing Tours, Walking Around, People Watching, Romantic

Riverwalk, chicago

The 1.25-mile path from the lakefront to Lake Street, Chicago Riverwalk, is an open, pedestrian waterfront located on the Chicago River in downtown Chicago. It connects four distinct districts; The Confluence, The Arcade, The Civic, and the Esplanade, with many places to stop and relax, various tours, and food vendors. The riverwalk offers glamorous architectural views of the city and refuge from the city's hustle and bustle.

Point  ($$) 8.4
Brunch, American (traditional), Breakfast

Dog Friendly, Vegetarian Options, Coffee Tea, Cafe, Take Outs, Outdoor Seating, Mid Western

2051 N California Ave, chicago

It started as a food truck, Bang bang pie and biscuits; true to its name is an award-winning pies and biscuits institution. Visitors and locals flock to this celebrated spot in Logan Square for its Midwest comfort food. They sell seasonal varieties of pies and biscuits along with additional comfort food staples.

Point  ($) 8.5
Mexican Restaurant, Lunch, Dinner

Dog Friendly, Vegetarian Options, Vegan Options, Gluten Free Food, Take Outs, Outdoor Seating, Byob, Tacos

2234 N Western Ave, chicago

Located in Chicago's Bucktown neighborhood, Taqueria Chingón is a Mexico City street-style taqueria focused on one of Mexico City's favorite street foods: the Al Pastor. They've developed a menu with classics that stay true to their origins and some tacos that create a new tradition. All the items on the menu are tasty treats, especially tacos.

Point
5. Kasama
 ($$) 8.8
Fine Dining, Lunch, Filipino Restaurant, Bakery

Trendy, Dog Friendly, Famous, Dine In, Asian Fusion, Cocktails, Full Bar, Romantic, Desserts, Cozy

1001 N Winchester Ave, chicago

The world's first Michelin-starred Filipino restaurant, Kasama, is a bakery and modern Filipino restaurant by chefs Genie Kwon and Timothy Flores in the East Ukrainian Village neighborhood of Chicago. The place is small, with 14 tables, but it's modern and inviting, with an open kitchen and impressive tile work. There is also an outdoor patio to accommodate (weather permitting!) additional quests.

Italian Restaurant, Pizzeria, Lunch, Dinner

Trendy, Dog Friendly, Romantic, Vegetarian Options, Salad, Pizza, Gluten Free Food, Take Outs, Outdoor Seating, Italian, Date Night, Takes Reservations, Pasta

3719 N Harlem Ave, chicago

Forno Rosso Pizzeria Napoletana brings the flavor of authentic Italian Neapolitan Pizza to the city of Chicago with the hand-picked freshest ingredients from Italy. Chef Nick Nitti applies learning and inspiration from his first-hand travel experience with his family from his childhood in Italy. There are currently two branches: one on Harlem Ave and another in West Loop on Randolph Street.