One great way to explore Chicago is by bicycle. In fact, if you have a day to kill and some energy, I highly recommend you start in Rogers Park where the lake front trail starts, and ride it as far South as you can. Or, take it until you get a little tired, get off it and you'll probably be in the middle of one neighborhood or another. Ride
west and check the neighborhood out or get back on the trail.
The trail will take you through Lincoln Park, past the Zoo. Goethe admirers will enjoy the giant statue of Faust in a park near Diversey. Keep riding South to North Avenue Beach, where tons of people gather when it's nice out, play volleyball, swim, all that stuff. You can ride through the Loop past Navy Pier and even ride out onto the pier if it's open.
Keep riding further South and you will pass the Field Museum of Natural History, the Oceanarium, which has this seawall path that's really fun to ride around on, ride by the Adler Planetarium and eventually you'll pass legendary Soldier Field, home of DA BEARS! GO BEARS!
Keep riding on the trail and you'll pass old harbors and many interesting buildings. The trail is probably my favorite thing about Chicago. It's wonderful for a city to have its entire beach front open to the public and bicyclists in particular.
During weekend days when it is nice out, the trail can get pretty congested. When it's like that, it's better not to try to ride too fast because it's kind of dangerous for everyone.
If you're looking for a peaceful, quiet journey to clear your head and maybe ride really fast , get on the trail at night. There is barely anyone on it but it's well lit and the lights of the city look very pretty from the quiet lake front.
The trail just keeps going on and on. You can ride through Hyde Park, where there's an old lighthouse, ride further South and the trail sort of ends but picks up again after you pass through a neighborhood called South Shore. Last time I rode through there were grown men relieving themselves in the bushes in the afternoon, a victimless crime I've been busted for twice and jailed for once, so who am I to judge them?
If you've ridden from Rogers Park and are in South Shore, you're probably getting a little tired. The wind may be at your back or you're really intense and you want to keep going. Do it, I urge you. You can take the el most of the way back. Don't be such a coward!
Keep riding under the skyway and through industrial boatyards and eventually, you will end up in Northeast Indiana, the land of Axl Rose.
For those starting their ride from the South Side and going North, read this article in reverse.
“Well, there’s a North Side and a South Side and they’re very much separated. The North Side is chic and all that, and we’ve always lived over there, at least for many years, but lots of old families, old Chicago families, if you know what I mean, still live on the South Side. The University is there. I mean it’s stuffy to some people, but anyhow it’s different from the North Side. I don’t know whether you understand.” -F Scott Fitzgerald (From Tender Is The Night)
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