With the main downtown sights covered in day one, you can now venture out into Chicago’s unique neighborhoods. The truth is that most Chicagoans only go downtown when they have to, and most city life is lived out with this part of town. The city is the perfect mix of coastal sophistication and Midwestern manners and sensibility, and it’s in the residential areas away from the center that you experience it. In these neighborhoods, you’ll find out exactly why so many people choose to live here even with the brutal winters.

French breakfast

Café Marie Jeanne

Photo: Café Marie Jeanne/Facebook

Head to Humboldt Park for a decadent breakfast at Café Marie-Jeanne. You can go as simple as a coffee and a croissant, or try a rich omelet or French toast. If you want to get adventurous, try out the sweetbreads or calf brains on toast that often appear on the menu.

Humboldt Park

View of the Humboldt Park Lagoon in Chicago

Photo: James Andrews1/Shutterstock

A short walk from the cafe is one of the city’s best parks. Walk off your breakfast then head to the boathouse and rent a paddleboat and head out onto the scenic lagoon. This is a very non-touristy park and it’s great to wander around and see locals going about their day, having picnics, playing baseball, and enjoying being outside. You can also rent a Divvy shared bike and ride around the park and out to The 606, a bike trail along what were until recently abandoned train tracks. That path will take you straight to the next destination for lunch.


Small Cheval

Photo: Small Cheval/Facebook

A mile west in Wicker Park, pop into Small Cheval for an incredibly tasty burger that won’t empty your wallet. The patio out back is a great place to enjoy a beer, cocktail, or one of its delicious milkshakes.

Wicker Park and Logan Square

Two people on bench

Photo: Page Light Studios/Shutterstock

Check out the boutiques along Milwaukee Avenue in Wicker Park if you’re into shopping, then head to Logan Square (a short drive or just three stops on the Blue Line train). There are more cool boutiques there if you haven’t had your fill, but you should also check out the boulevards. These streets with wide grassy medians are part of an old urban plan that created much of the city’s green space. Along Kedzie and Logan boulevards right near the Logan Square subway station, you’ll see some beautiful old houses and get a sense of what residential neighborhoods in Chicago are like.


Lula Cafe

Photo: Lula Cafe/Facebook

Logan Square has tons of great restaurants. Lula Cafe is an excellent farm-to-table restaurant and was the first upscale restaurant that came to the neighborhood. For something a little different, check out the playful takes on classic Indian cuisine at the delicious Superkhana International.

Tiki time

Lost Lake

Photo: Lost Lake/Facebook

Half a block from Superkhana, Lost Lake is a tiki bar making excellent cocktails in a fun and trendy space. Careful though, because the drinks hit harder than you’d think.