I just moved away from Chicago but it took me a few years to appreciate the city (and I never found visiting that compelling). I miss it now though, I think the best way to learn to appreciate the city is to go out and do things in the city and find the stuff you like. There is tons of great music, food, art museums, shows (especially improv, idk if the IO Theater is back running but the Improv Shakespeare that they did was amazing). You can find pretty much anything there, the only thing I struggled with is I like the outdoors and there isn't good hiking (but Chicago actually has really good birdwatching in the city).
The easiest bit of advice is to get out of the Loop; the city Chicago boosters won't shut up about is mostly out in the neighborhoods. Also: our real pizza is thin-crust.
Tavern style is what I always saw there (though I like deep dish). Also I'm surprised people always talk about deep dish pizza and not the clearly superior Chicago food: dipped Italian beef with hot peppers.
This is a bit of my own biases showing but I've found being very into deep dish or calling the loop "downtown" were ways to know who is new to Chicago
> You can find pretty much anything there, the only thing I struggled with is I like the outdoors and there isn't good hiking (but Chicago actually has really good birdwatching in the city).
Lincoln Park north is not what I would call "good hiking", but I think it's nice for those who like the outdoors. Good for daytime walks, large beaches, dog beach, bird sanctuary, some small natural areas, lakefront trail (paved).
For good hiking, yes you'll have to drive out of the city.
You don’t have to go too far out of the city - more than 10% of the county land area is forest preserve. Inside the city, the far northwest side (along the river) and the far south side (big marsh/beaubien woods) are probably the best bets.
I know that the wooded section between the IC tracks and LSD from 47th street up to Oakwood/Pershing is a hiking trail very popular with birdwatchers. You can keep walking up to the 31st street beach parking lot, but I think it might technically be trespassing ;)
Naturally, if you want really good hiking, there is a daily train from Union Station that stops at the front gate to Glacier National Park. You can also take the South Shore train eastwards - there are 3 stops adjacent to the Indiana Dunes (both the state and national parks).
No problem. You know, the whole area is very flat. There’s no getting around that, and some people will never accept that any hiking trail can be good if there isn’t a lot of elevation change. That’s their loss.
I remember going to a talk at the cultural center ~10 years ago where some lady, who was apparently very famous in her line of work, talked about moving to Chicago because of her husband’s new job and spending many years hating the natural surroundings. Until one day she was in a prairie west of the city and decided to really look at the wildflowers. And that was the spark that got her to start drawing the flowers, and eventually made her famous for it.
Anyway, it’s no Coastal California or Colorado mountain meadow. But if you go out and explore with a desire to find beauty in it, you will :)
Edit - and by the way, on the South Shore train, Dune Park and Beverly Shores have trails you see from the train platform. Ogden Dunes is a bit trickier, the open space west of the train station is all national park service land, east is private property except closer to the lake. The town itself tries very hard to make it look like a private gated community but the roads are all public and you are free to walk right in. Miller Beach I’d say the train is too far from the parkland, but if you have a car, the area due north starting about a mile from that train station will blow apart every stereotype you’ve ever had about Gary, IN.
Hah, there's my only lament about Chicago: no pet-friendly public transit if you have a large dog. I don't really have the stomach for the loopholes either: service dog lies or carrying her in a duffel bag NYC subway-style.
I liked to bike the lake there, the lakefront in Chicago is pretty underestimated by people who don't live there. For hiking there's the dunes or Starved Rock but those are super busy a lot of the year (and at this point I've been to both a million times). I ended up needing to drive at least like 2.5 hours into Wisconsin for long hikes, which is a longer drive than I want for just a day trip. That means for the outdoors I up mostly just went birding in parks in the city, generally Montrose Point Bird Sanctuary or Jackson Park, which were really nice but not the same vibe as a good hike (there are some birding groups that will meet around the city that were nice to go with).
I just moved out from Chicago. Don't miss it. Been to hundreds of big cities, Chicago is weak. There's not much to do for tourists compared to other cities. There is a decent theatre scene. Deep dish pizza is good. Lakefront can be nice.
As a lifelong native, I highly recommend one of the architecture boat tours. Never gets old, and the guides usually manage to pack in a fair bit of history. I know it changed my personal connection to the city.
I’m also convinced that if someone hasn’t connected to the city yet, they just haven’t been to the right neighborhood. They are many, and cater to many tastes.