Chicago Insider Michelle Fasano on dinner at Ada Street, jazz at the California Clipper and the rooftop at the Robey Hotel
How long you’ve lived here: I grew up in the Chicagoland area, but I’ve lived in Chicago for the past four years, in both in Lincoln Park and Lakeview.
What you like best about Chicago: Chicago has all the perks of a major city while also being approachable. I love the various neighborhoods, each with their own feel and charm — all accessible by public transit! And no city does summer better.
Best meal you’ve had recently: Hay ice cream at Elske. It sounds strange, but it was refreshing and delightful!
Click Shoes along the Southport Corridor has a well-curated selection of shoes and clothes with a focus on brands that are both comfortable and trendy.
Favorite big-name restaurant: Café Ba-Ba-Reeba is a Chicago-staple, serving tapas food since 1985. The restaurant is large but feels smaller since there are so many different rooms. It is great for brunch or dinner, large or small groups, and there is something for everyone on the menu.
Favorite “hidden gem” restaurant: Ada Street. Tucked away in an industrial area next to Goose Island, it sees minimal foot traffic. It blends into the warehouses around it, except for a small sign and black awning. It has an intimate environment with an open kitchen, large selection of records and delicious American-fusion food.
Best sports bar to catch the game: Old Crow Smokehouse in Wrigleyville (they have a second location in River North) is a great place to catch a game, especially a Cubs game. It’s a huge spot with tons of TVs. If you like country music, they frequently have a live band. Also… retractable roof. Check.
A great night out with friends usually includes… trying someplace new for dinner and, ideally, live music. Millennium Park has a series of free outdoor concerts throughout the summer, and there are lots of small concert venues around town like Schubas.
Favorite store or best shopping area: Armitage (by the brown line stop) is quaint and walkable with a variety of small boutiques, but one of my favorite individual stores is Click Shoes along the Southport Corridor. They have a well-curated selection of shoes and clothes with a focus on brands that are both comfortable and trendy.
The California Clipper is a speakeasy-style bar with live jazz music and a small dance floor. I feel transported to another time when I go there.
The best way to spend a summer Saturday in the city: There really is no one best way — as long as you are outside exploring, you will have a great day. North Avenue Beach is a great option because there is a wide variety of activities available, including stand-up paddle boarding, kayaking, volleyball, hanging out at Shore Club or Castaways, or heading a few blocks inland to Lincoln Park, the farmers market or the zoo. In the evening, I would recommend enjoying a patio or rooftop for drinks and dinner. The rooftop at the Robey Hotel in Wicker Park would be great for this given its unique views of the city.
One thing every visitor must do here: Drive (or bike or walk) down Lake Shore Drive from Museum Campus up to Addison St. Some of the most beautiful views of the city are along this stretch. Each time I make this drive, I am awe-struck by the lake vs. city contrast. In addition to Museum Campus, this route also takes you past Millennium Park, Navy Pier, the edge of Michigan Avenue, several beaches, Lincoln Park and the harbors.
Secret Chicago spot: The California Clipper. It’s a speakeasy-style bar with live jazz music and a small dance floor. I feel transported to another time when I go there (heads up, it’s cash only).
Underrated activity in the city: Chicago has a lively comedy scene. The most famous is Second City, known as a feeder for Saturday Night Live, but there are tons of other great options including Zanies, The Laugh Factory and IO (Shakespeare improv at IO is a favorite).
What’s one place you hear great things about but have yet to try? Kai Zan — I’ve heard from multiple people that they have the best sushi in city.