The Chicago Sun Times posted a "bucket list" for things to do in the city of Chicago. I've given some thought to mine. I'm excluding from this list the obvious choices, like the museums, aquarium, and planetarium. Those are kind of duh things. My personal favorite is the Museum of Science and Industry. Since I generally stick around the north and near north side, this list is hugely biased in that respect.
1. Lincoln Park Zoo. It's free, and it's a damn good zoo. If you visit in the winter at starting just after Thanksgiving until around Christmas, they have "Zoo Lights" where they decorate the zoo with Christmas lights and you can wander around. Not many animals out at that time of year (except inside at the lion house), but it's very pretty and romantic if you are into that kind of thing. Or you can just bring a flask and holler at the animals.
2. Go to a Chicago Bears game in December or January at Soldier Field. You really don't get the true Chicago football experience until your beer ices over before you can drink it.
3. Watch a Cubs game from the rooftop seats across the street from Wrigley Field. After the game is over, go for a bar crawl along Clark Street. Don't forget to go upstairs at Sluggers, where you can hit the batting cages and play skeeball. 3540 N. Clark.
4. Play a board game and enjoy a drink at Guthrie's Tavern. They have pretty much any board game you might want to play. 1300 W. Addison St.
5. Order a "chocolate milkshake" at the Weiner Circle. Make sure it is late night (after 1 a.m. or so), and you are appropriately drunk. This will cost you $20, and is not recommended for children, but is certainly a sight to behold. 2622 N. Clark St.
6. Stay out at the bars until 5 a.m. (It was amazing to me when I moved here that there are bars open that late.) You have multiple options for late night bars, but my favorite is Burton Place. 1447 N. Wells.
7. Go kayaking on the Chicago river. There are many different types of tours available, all both for newbies and experienced kayakers, both at night and during the day. They teach you how to do it prior to the tour, so don't worry if you have no idea what you are doing. The Fireworks Paddle is a favorite. Kayak Chicago, 1501 N. Magnolia.
8. See a concert in Millenium Park or Grant Park. The city views are amazing, and there is no place better to watch a concert in the city. You can accomplish this by attending Lollapalooza, but other than that there are always concerts going on in the park.
9. Take a cruise on Lake Michigan on one of the tall sailing ships. I like the Red Witch at Tall Ship Adventures of Chicago.
10. Have breakfast -- and cinnamon rolls -- at Ann Sather. 909 W. Belmont.
11. For something a little more classy, hit Pops for Champagne for an after dinner drink. 601 N. State St.
12. If you are in your early to mid twenties, do a bar crawl up Lincoln Avenue. Start at Lincoln and Armitage (Gamekeepers, Stanley's) and work your way north all the way up to Wrightwood (The Grand Central) -- if you can make it that far. (You hit a block or two of residential here and there, but keep going. There are lots of bars along this strip, most frequented by DePaul students.) This is also fun in your thirties, but the crowd on this strip is generally younger. For a slightly (at times, and some bars) older mix, try a crawl up Southport from Belmont or Roscoe up to around Byron or so. Make sure to hit Cullen's (next to the Music Box) for the macaroni and cheese if you are hungry.
13. If you like to shop luxury, hit Michigan Avenue and Oak Street. That's where all the big hitters are -- Louis Vuitton, Ferragamo, Burberry, Chanel, Neiman Marcus, Prada, Marc Jacobs, Hermes, etc.
14. For easy access to beer, hit the Bull & Bear, which has taps at the tables. 431 N. Wells.
15. For great sushi, in my humble opinion, go to Sai Cafe. 2010 N. Sheffield.
16. To see some beautiful historic buildings and attend to some boutique shopping (as well as all of your make up and hair needs), go to Armitage between Racine and Halsted, and then north on Halsted between Armitage and just north of Webster. It's a historic district, pretty, and easy to drop a lot of money.
17. Go to a rooftop bar in the loop for a great view over appetizers and/or drinks. I recommend either the roof at The Wit Hotel, 201 N. State, or for a little lower of a view (but a great view of the Library), try the Plymouth at 327 South Plymouth Court.
18. If you are in town around Christmas, go to Christkindlmarket in Daley Plaza. It's like Octoberfest at Christmas with all kinds of good food and little shopping booths. It smells delicious. You get the bonus of seeing the Chicago Christmas tree and the famous Chicago Pablo Picasso statue right there also. 118 N. Clark.
19. If you desperately need to watch your favorite college team play football or basketball, many of the bars here are themed to specific teams, so you don't want to end up at an OSU bar if you are a Michigan fan. Google to find out where to go on Saturday. There are too many teams to list to tell you where to go in this post, but there is nothing quite like being in a bar full of people rooting for the same team as you, and where they play the team fight song on every score. If you need your football fix while in town, you can find the appropriate watching place. There are also themed NFL team bars, so keep that in mind when you are choosing where to watch your game.
20. Go and watch live Blues at Kingston Mines. It's a true blues experience, and well worth the cover charge. 2548 N. Halsted.
You know what? There are just too many fun things to do in this city. I'm stopping there.
Hmmm....I guess this isn't really my "bucket list" so to speak, because I've done all of these things. Number one on my list to do is one of the architectural tours on the river. I hear great things about them, but I've never done it. I usually just kayak up the river and observe on my own. I actually look forward for people to come visit me, because then I get to do all the touristy stuff around here that I would never do on my own.