Discover Chicago's charm with this beginner's guide, perfect for a three-day adventure! From the iconic sights of Millennium Park and Magnificent Mile to the historic allure of Wrigleyville and Printer's Row, this curated map highlights the best of the Windy City. Explore vibrant neighborhoods, savor world-class dining, and soak in stunning lakefront views for an unforgettable urban experience.
Hotel Zachary
A unique hotel on Chicago's north side in Wrigleyville, located across the street from Wrigley Field, home of the Chicago Cubs.
Wrigleyville
The location of Hotel Zachary and Wrigley Field, with many options for dining and nightlife along Clark Street.
Wrigley Field
The famed home of the Chicago Cubs, where tours are offered when the Cubs are not playing or when there are no special events, blending into the surrounding residential area.
Printer's Row
A place to grab a quick coffee before heading out to explore Chicago.
Lincoln Park
A large park with a zoo, harbor, and scenic viewpoints of the city skyline at North Pond.
Bobby's Bike Hike
A tour company based in the Streeterville neighborhood that offers a variety of bike tours of Chicago.
Streeterville
The neighborhood where Bobby's Bikes is located.
River North
An area where a food and beer bike tour begins.
Lou Malnati's Pizzeria
A stop on the bike tour for a slice of pizza and local Summer Shandy beer.
Molly's Cupcakes
A cupcake shop on Clark Street with delicious cupcakes with batter-filled centers.
Clark Street
The location of Molly's Cupcakes and an area in Wrigleyville with many options for dining and nightlife.
West Village
A place to grab Molly's Cupcakes.
Lake View
The neighborhood streets through which the bike tour goes to see traditional Chicago architecture.
Wrigleyville Dogs
A place near Wrigley Field to get a Chicago style hot dog covered in everything except ketchup.
Murphy's Bleachers
A Cubs fan favorite bar for a local beer near Wrigley Field.
West Loop
A neighborhood transformed from a warehouse district into a hub for technology innovation with trendy food and shopping.
Chicago River
A river near the West Loop, with views from River Roast.
Morgan Station
A station on the pink line to get to the West Loop.
Time Out Market Chicago
A market in the West Loop that brings local cuisine under one roof.
McDonald's World Headquarters
The location of McDonald's World Headquarters and their Test Kitchen, where you can sample McDonald's menu items served in their stores in other countries.
Millennium Park
Chicago's newest park, home to the Cloud Gate sculpture (The Bean).
Buckingham Fountain
A grand fountain in Grant Park that erupts on the hour with a giant column of water.
Grant Park
The park where the grand Buckingham Fountain is located.
Michigan Avenue
The location of the Magnificent Mile and the Starbucks Reserve.
Magnificent Mile
A mile of shops on Michigan Avenue.
River North
The neighborhood on the side of the Chicago River where the Magnificent Mile is located.
Starbucks Reserve
A Starbucks location on Michigan Avenue that offers special blends of Starbucks roasts, tasty sandwiches and pastries, and an espresso Martini flight.
Water Tower
A nearby landmark to the Starbucks Reserve.
Oak Street
The city's fancy shopping street.
River Roast
A place along the Chicago River for light appetizers and a cocktail with a view of the river.
Navy Pier
A place to catch the free fireworks display near the lake on Wednesdays or Saturdays in the summer or Saturdays in December.
Lake Michigan
A beautiful lake with miles of bike paths and walking trails along the waterfront, east of Lakeshore Drive.
Lake Shore Drive
The area east of Lakeshore Drive is generally public parkland which is great for picnicking and gathering with friends to enjoy the outdoors.
North Pond Restaurant
An upscale meal option in Lincoln Park with iconic viewpoints of the downtown Skyline.
Belmont Harbor Dog Beach
A place near Lincoln Park where you can bring your dog to play in the water, especially on a hot summer day.
Collective Coffee
A place for a late lunch or coffee in Lincoln Park on Clark Street.
Bourgeois Pig Cafe
Another recommendation for lunch near Lincoln Park, further west on Fullerton.
Fullerton Avenue
The street where Bourgeois Pig Cafe is located, further west from Clark Street.
Marina City
Unique towers built in the 60s to be a city within a city, visible from the river walk.
Goddess and the Baker
A cafe along the river where you can grab sandwiches and salads for lunch, just over the bridge from The Mark.
Cafe Cremerie
A cute cafe in River North for an afternoon coffee, pastry, or refreshing Frozen Rosé drink, which serves good gelato too.