I have lived in Chicago the better part of my life so am pretty familiar with the city and what it has to offer but figured there are enough Chicago Dopers here to be worth picking their brains too.
In short a very special lady is coming to visit me this Sunday and Monday and I’d like to make her trip a memorable one. Granted you all do not know my (or her) particular tastes and interests but for this I am just looking for unique ideas. Be they interesting restaurants, museums, parks…whatever. Sure I could take her to Ambria (very fancy shmancy restaurant) but I’d rather take her somewhere cool and different (Halfshell…a dive seafood place…occurred to me for example).
Of course if you have a “Perfect Day” plan in your back pocket ready to go glad to hear all of it. Whatever anyone can offer would be great!
As great an idea as this is, I’ve always taken issue with the fact that there’s no way in hell Ferris could’ve done half the stuff he did on that lovely afternoon, even twenty years ago when Chicago was only somewhat crowded rather than ridiculously congested. You’d be lucky to do a handful of the stuff he did in two days, let alone one afternoon. Of course, IANFB, so I don’t have his magic powers, but nobody I know can get downtown, go to a game at Wrigley, hit the museums, scope out the action at the Board of Trade, dine at a fine restaurant (Sausage King or no), participate in a parade, and then come home and go for a swim with plenty of daylight still left over. Alas, it is a movie, but just so you know, it takes much longer to get places in Chicago than Ferris would have you think.
I always suggest a trip up to the Signature Lounge in the Hancock at night for a drink for those visiting from out of town. The Sears Tower Skydeck may be higher, but that can’t change the fact that it’s a touristy gimmick. The Signature Lounge is another story. When the city’s all lit up at night, it’s an incredible view to the southwest, and there aren’t a whole lot of places you can go to have a drink with that sort of view. Keep in mind that the restaurant is on the 95th and the lounge is on the 96th, and that you’re certainly not obligated to order [pricey] food with your drinks. It tends to be much busier in colder months (nobody wants to be outside for obvious reasons), but I’d be willing to bet if you make that your last stop of the evening on a clear summer night that’s not too busy, it’s guaranteed to be a particularly memorable cornerstone of her visit with you.
Beautiful indeed, but don’t take it as actual advice unless your friend likes to pay fines - alcohol is illegal in Chicago parks.
A perfect Chicago day for me is so dependent on the time of year and the weather. Right now, I’d love to go to one of the organic markets (there’s a nice one just across from Lincoln Park Zoo) and get lunch fixin’s, then make a picnic event near the beach. After that, some window shopping (or real shopping) before catching a trad session at Barleycorn or Old Town or a local play, and then a late dinner at some little ethnic restaurant.
One stupidly practical tip: if your friend has long hair, bring along a hair band (the elastic kind, not the music kind). Most out of towners don’t realize that “Windy City” is not a metaphor, and wrestling with unruly locks all day gets tiresome real fast. They’ll turn it down at first - just stick it in your pocket; it’ll be requested before lunch.
