Wicker Park and the adjacent neighborhood Bucktown have some incredible residential architecture that's worth a self-guided walking tour! This PDF map will take you along some of the most charming and lovely streets and includes a short writeup about some of the neighborhood's most impressive spots.
This classic, chaotic used bookstore is a Wicker Park mainstay on Milwaukee, just across the six corner intersection from The Robey. Watch out if you're allergic to cats.
While definitely not even close to the best Mexican food in Chicago, Big Star is definitely a vibe. It may not be warm enough in May to sit outside on their giant patio, but Big Star is definitely worth a quick lunch or margarita stop.
Just down the street from The Robey on Milwaukee, this quintessential Chicago coffee shop is a good spot for a coffee and a snack (plus there's a DeLorean inside).
This Wicker Park bar arcade and event venue features classic games like pinball and Donkey Kong. Note: It's usually 21+.
Widely considered the best brunch in Chicago, Lula Cafe is about a mile northwest from the Robey Hotel in the Logan Square neighborhood—one of our favorite places in the city. It's across the street from the Logan Square monument and park, just a quick bus ride up Milwaukee Avenue or three stops north on the CTA Blue Line (toward O'Hare). Be warned though: They don't take reservations and wait times can be extreme.
Located about a mile northwest of The Robey, Giant is one of our favorite restaurants in the city.