Hmmm, it’s been a while since I actually lived in Chicago. Unfortunately the Lemur family-owned-and-operated establishments are north and south of your limits (though both are within a block of Metra, and Metra Electric does have nice-and-easy-to-reach Grant Park stations…). That said pretty close or directly off the Red Line there is:
—Vietnamese: You are a couple of stops north of the Argyle station, which is basically the Vietnamese cuisine stop.
Ba Le popularized bahn mi in Chicago.
Tank Noodle is good if you want a deep dive into Vietnamese food—also the waitstaff wears camo pants. For a
very nice French-Vietnamese meal there’s also
Le Colonial on Rush—go two blocks east from the Chicago stop and then a few north on Rush to get some window (or actual?) shopping in.
—Lawrence: One stop south of Argyle is Lawrence—here there’s another good Ethiopian place,
Demera, as well as a fun old-fashioned bar,
The Green Mill—they often have good shows (old-time jazz seems to be their specialty; attracted a big, classy retro crowd when I went there). Also close to the Aragon Ballroom, site if the infamous bathroom raw-dogging (RIP AVC Chicago local content).
—For a delicious breakfast (waffles and quiches especially), good sandwiches, or delicious M&M cookie + coffee there’s the
Bourgeois Pig off of Fullerton. My uncle works at DePaul University and I’d often meet him here—it’s in between where you are and downtown, though I wouldn’t get off just to eat here (there’s some stuff on Lincoln Avenue near here, but when I was there it was mostly just De Paul—though their new art museum, adjacent to the Fullerton stop, is quite nice—the old hospital, and nice homes, so not really much to see).
—The Intelligentsia Coffee at Jackson/Dearborn, one block west of the Jackson Red Line stop. Intelligentsia’s a local coffee chain, very good, but what’s nice about this location is that it’s an old-timey-styled coffee bar in the
Monadnock Building, the tallest load-bearing brick building ever constructed and last hold-out before steel frames completely took over Chicago skyscraper construction. Entering in between those broad pillars is almost like entering an Egyptian monument. Inside’s pretty cool, too, with a bunch of little shops (including a tobacconist, at least last time I was there)—a bit like a trip back to the nineteenth century. Close to a bunch of stuff downtown, too—I liked stopping here for breakfast when I had to switch between bus/Metra and Blue Line on my commutes, and it’s a good place to start the day.
You mentioned how far north and south you could go, but not how far
west. Here’s where the options really light up (and all these are accessible just by a flight of stairs or two from the Red Line stations on Lake, Washington or Jackson):
—You could go southwest on the Pink Line (getting out at the south exit of the Jackson Red Line and going to the at Van Buren and State elevated station) to 18th St. for Pilsen, which when I lived there was still very Mexican. Find the
places with least pronounceable/most pre-Colombian-looking names and get some of the best Mexican food—particularly mole—you’ll ever eat (this was more of a winter thing for me, though).
—There’s also the Blue Line, which heads northwest and can be reached via tunnel at either Jackson or Washington (Washington also gives you the opportunity to experience to Pedway which…really isn’t that interesting, but it has a Dairy Queen near where you get your driver’s license renewed under City Hall, which is nice). The Damen stop was…and still kind of is?…sort of the hipster epicenter of Chicago. This is where Reckless Records, inspiration for the film of
High Fidelity, as well as Myopic Books, a giant used bookstore. There’s Wormhole Coffee, which has (had?) an in-store DeLorean inside (but also very good iced tea, and was also the site of much Jean-Luc Lemur pre-Dissolve AVC quip-making). All of it is—was?—good for people watching.
Not hipster-y at all, though, is
Taxim, my favorite Greek restaurant in Chicago. Very authentic in its use of ingredients and portion size—i.e. not too large, not too showy, but very fresh and of high quality—and based on Greek cuisine of Ionia rather than European Greece, it is great. This was the last meal I had in Chicago (after unloading a chunk of my library with Myopic) before leaving for Amsterdam.
—A couple of stops out is Logan Square, which when I left was the mustache, meat, and beer central. I do not know how the waning of the traditional hipster in favor of the more normcore/agender look has affected this, but I suspect it’s much the same, just everyone’s a bit older. Anyway
Longman & Eagle is still a (according to Google) “farm-to-table fare & nose-to-tail…contemporary take on a traditional Chicago inn,” which is how I remember it.
—If you are willing to take a bus I’d also recommend going to
Borinquen, home of the jibarito—basically a Pueto Rican burger, but with fried plantains instead of buns. It’s a short bus ride west on North Avenue from the Damen blue line stop.