Unique to Chicago are certainly the hot dogs and deep-dish pizza. My favorite place for hot dogs is Portillo’s, but many people don’t realize that they also have some of the most amazing chocolate cake in the city. For deep-dish pizza, my go-to is Lou Malnati’s. Since deep-dish pizza can take 45 minutes to cook, many places let you order while you wait for your table so when you sit down the pizza comes out almost right away! There’s also a big dessert scene in the city. I would definitely recommend Do-Rite for donuts, Molly’s for cupcakes and Jeni’s for ice cream.
If you are up early enough in the morning, be sure to check out the Cloud Gate sculpture – better known as The Bean — at sunrise. This time of day, it is completely empty and the sunlight shines directly underneath The Bean. From there, you can rent a bike from one of many Divvy bike stations and head to Michigan Avenue for shopping and classic skyline views from the Michigan Avenue Bridge. After taking in the views, you can choose from multiple boats that offer architecture tours along the river. Each tour is slightly different; as the guides all share different facts about the history of the city and its architecture. Many locals, including myself, recommend a Chicago Architecture Foundation River Cruise aboard Chicago’s First Lady Cruises.
If you keep making your way north, you can head to Oak Street Beach to lay out or enjoy a drink from the beach bar. This beach also has incredible views of the city’s skyline. Adjacent to the beach is Lake Shore Drive, which has its own pedestrian and bike paths that run along the lake all the way north and south of the city.
Further along Lake Shore Drive is North Avenue Beach, which has some of my favorite views of the skyline. From here, I like to head west into the city where you will find Lincoln Park and its free Zoo. It’s easy to spend a few hours walking around here.
By this time, you are probably close to evening, a good thing since Lincoln Park offers amazing restaurants. For a more laid back, hipster and unique neighborhood, be sure to head over to Wicker Park for the rest of the evening to find pool halls, live music, and plenty of bars and lounges. Wicker Park for the rest of the evening to find pool halls, live music, and plenty of bars and lounges.