Dear Ismael,
With summer in full swing, what are some good ways to get visiting family/friends/tourists out of The Loop and into neighborhoods in a way that can provide a more localized, interesting experience as well as (ideally) help give back to some of the communities around the city?
— Tour Guide in Avondale
Dear Tour Guide,
When I have people visit, I plan out the itinerary based on how many times my friends and family have been to Chicago.
The trick is to start strong with classic landmarks and experiences — get them a little tired of the spending and walking they aren't accustomed to — and then ease into Chicago-insider secrets of charming neighborhood gems that are also budget-friendly.
Yes, I'm advocating for some time in The Loop, but hear me out.
It's important to remember people do save up hundreds or thousands of dollars to experience things they don't have back home, such as huge skyscrapers, the Riverwalk and yes, even deep-dish pizza. We should try to not come off as city snobs, especially if it's their first time here, and give our out-of-town visitors the full tourist experience.
The Chicago architecture boat tour is my top pick for a tourists (and even locals) to experience. And before its closure, I knew my visitors would really enjoy getting a drink and a view of the Chicago skyline for only $14 at The Signature Room.
It's also nice to let tourists be curious and find things on their own. I almost became a city snob when my friend bought tickets to the Chicago Gangsters and Ghosts Tour. Inside, I was like, "Are you serious? How embarrassing." But, thankfully, I kept my mouth shut, and I actually really enjoyed the tour.
Tourists love to show off when they go back home. Not only through photos on social media, but by having that "Chicago cred" that comes with appreciating neighborhoods, bars and restaurants the average Loop visitor doesn't know about.
I think my friends love to say they stay with me in Pilsen because they can claim to have roots here, in some way, beyond a temporary and sterile hotel room. And that's a good way to give them a localized experience — let them stay with you or a nearby Airbnb, if your place can't accommodate a large group. That way they can wake up and eat brunch in your neighborhood, and also unwind with a drink at a nearby bar at the end of a long day of downtown activities.
Introduce them to a famous face in the neighborhood, even if they are just famous to you. In my case, I've taken my friends to my favorite snack store, Neveria El Sabor de Mexico, and introduced them to one of my favorite business owners, Juana. My friends still ask about her, every so often.
Also, based on their interests, I've taken friends to see other businesses that uplift the community, like Semillas Plant Studio, a Latina-owned shop where you can buy plants and also build your own flower arrangement. And to save money on a day we want to take it easy, there's always the admission-free National Museum of Mexican Art.
I've found that the more they visit, the more open they are to starting and finishing their day in the neighborhood. After they get a good feel of your neighborhood, it's time to get lost and branch out to other neighborhoods you might not know much about either.
Take your tour guide cap off, admit you don't know much about a specific place you've been curious about and maybe they'd be more encouraged to explore with you.
Write to Someone in Chicago at someoneinchicago@suntimes.com.
