Native Chicagoans and visitors can both enjoy the architecture cruise this company offers. Travel along the river viewing all the great buildings in the city and learn about the history of Chicago's great architectural style. It's a bit expensive, but a great experience to see more of this great City.
Especially worth it when the weather is nice. Get tickets in advance, it's a touristy thing to do so cruises can and do sell out.
PROS: see Chicago's great architecture
probably most appropriate for kids, but adults can enjoy it too. the mini golf course is pretty standard, but has some more creative holes. a standard arcade and restaurants, not too different from any other arcade type place but still a good time, again, particularly for kids. it can get crowded on evenings, but that's just part of the environment. you have to drive to get there but there is plenty of parking, and numerous restaurants nearby if you want to eat somewhere else. the games are not too expensive, but you can easily spend a lot of money. a fun place, if not an especially different kind of arcade.
an amusing gift - simple concept, just call and give them your message, and they deliver it in song. reasonably priced, friendly staff, they'll get it right. not something you will use often, but for a birthday party or spontaneous prank it is good to know there is a service like this out there to have fun with.
Another great theater in Chicago - a classic feel, not an overdone nightclub style place. They bring in a diverse group of musical acts, and have plenty of seating, but the way it's built you always have a close, great view of the stage. There's also a balcony section. Not as accesible on the CTA / El so you might have to drive, but it's a decent location. Worth keeping tabs on the calendar. Not too expensive either. A fun theater that attracts a great crowd of music lovers.
I was very impressed the first time I saw a concert at the Vic. It's not a huge place so you get very close to the stage, and they bring in all kinds of bands. It's in a great location, easy to get to using the El. Attracts a great crowd of music lovers so anyone can feel comfortable inside. Not a pretentiously hip place, just a classy theatre with a lot to offer.
Check out the "Brew 'n View" to drink beer and watch movies on the cheap.
PROS: great environment
Great classic theater right in Chicago. Very intimate environment inside makes it great for music performances, and they have a large variety of genres of music. It's not a pretentiously "hip" music club, it's a down to earth, fun place to catch a show. Second level with a lounge and bar for people who just like to sit around, but if you like to get close to the music the Aragaon is the kind of theater you want. The theater attracts a diverse crowd of music lovers, anyone can fit in.
PROS: great classic theater environment
Good improv isn't easy, but the Comedy Sportz casts pull it off. This place is as good as Second City as far as consistently good comedy. Lots of audience participation, as is expected with improv, so it's a very energized show. Very talented performers, a lot of fun to watch.
Anyone who loves comedy will fit in - there are special nights for kids, an open mic night, and BYOB so no silly drink minimums. Very worth the cost of admission, one of the best Chicago's comedy scene has to offer.
PROS: top notch performers
Great place to check out when you're in the mood for comedy. Better than average comedians, great location, easily accessible by public transportation. I don't like that they have a drink minimum, but it is what it is. There is a lot of average stand-up out there, but Zanies is among the better places to go, and great to see up-and-coming comedians. Fun to be in, true comedy club atmosphere. Worth a visit with a date or friends.
PROS: good comedy
There are plenty of places in chicago you can go to to see average stand-up. But Second City is one of the few that offers consistently funny shows by professionals. There's always a couple shows running, and they are very impressive. Well written, well acted, just funny. Some sketches are hit-or-miss, but that's comedy. They usually do some improv after the show, giving you a free second show.
Food and drinks are kind of expensive, but no more so than any other bar. The shows are about $17 each, which is quite reasonable considering the quality. Great place to take a friend visiting the city, or just to go with friends.
The seating is kind of cramped, because they squeeze a lot of people into a fairly small room, but that also means everyone is pretty close to the stage, which is a nice effect.
PROS: inspired comedy