I referred a buddy to my blog post that I wrote last year about IML. He replied saying, "gosh, this isn't what I wanted to hear." My friend is going to IML, but his interest is hanging out with fellow gear-guys, not having a one-night stand. While my partner and I have no interest in returning to IML again, we are happy we went two years ago to see what it was all about. Call it "one of the things to do in a long career as leathermen."
To try to give some balance to what may be perceived as a dislike for IML or Chicago, which isn't true, here is what I said to my friend in an email reply:
You will LOVE Chicago. It is a great town to visit. It is a very walkable city (flat, few hills) and they're very leather-friendly. Feel free to go fully leathered while being a tourist.
There are lots of things to see and do in Chicago. And it's the best town in the USA for pizza. Lots and lots of choices, all over the place. (And every local has a favorite they claim is better than all the rest. Don't worry
, you really can't go wrong anywhere except perhaps Pizza Hut! LOL!) Try Lou Malnati's, which is just a couple blocks from the Hilton. Get "deep dish" which has more ingredients, not more dough. Definitely the pizza to get in Chicago!There are some great museums, though I have to admit that I am spoiled by having the Smithsonians, which are all free to enter. But admissions are part of the price of being a tourist.
Don't go see a movie! You can do that at home. Go see the city. It is vibrant, alive, and fun. It's also generally safe, especially along the Miracle Mile. That's the name of the section of Michigan Avenue with the high-end stores, shopping, restaurants, but also tourist stuff to see, like "the bean." "The Bean" is really cool and you should definitely boot up and go see it -- and take your picture reflected in it. See the pics on my website.
There are a fairly large number of panhandlers around. It's cruel, but hold your head up and walk on by. Don't look them in the eye or establish eye contact. Do not give one money; the rest will follow you worse than a flock of pigeons.
As in any city, keep your wallet in your front pocket, not in a back pocket or a jacket. There could be pickpockets around, too.
As for transportation, yes, there are lots of taxis. Plenty will be at the hotel. There will be some at the bars, too. However, we didn't use taxis when we were there. We didn't go to the local leather bars during IML, but I have been to them before. The Chicago leather bars are about 3 - 4 miles away from downtown. IML provides buses to the leather bars at night, late into the night. The bars are packed during IML, dark, loud, and hard to talk to anyone due to the crowds. We decided not to go to the leather bars during IML because the night would run waaaay too late for us. We're just not the night-owl types. We would rather just play tourist wide-awake during the day, staring with a great breakfast (There's a great breakfast diner "Yolks" just a few blocks from the hotel on Michigan Avenue; try it!)
The public transit system (subway and trains) is very good, and reasonably priced. We took the train from O'Hare Airport into the city and then walked to our hotel. For $2.25, we got to the hotel directly and inexpensively. The train trip takes about an hour, but it's still faster than using a shuttle or taxi, stuck in traffic.
I went to Chicago a few weeks ago and stayed in the very same hotel where IML will be held... note, it is about a 7-block walk from the train exit at Jackson to the hotel, and I wouldn't recommend it in the dark. But in daylight, it's fine. And an easy walk on the flat, wide sidewalks. Alternatively, you can use the train to get downtown and then get a cab from the train exit to the hotel. That would probably only cost $5 including tip. I'm cheap, and I walk! Be sure to have luggage with wheels!
IML itself is worth seeing. Don't skip out on the events you paid for with your registration. Go see the introductions, stroll through the leathermart and see things you wouldn't imagine existed. Get your boots shined (for only the cost of a tip) by one of the bootblacks competing for Mr. Bootblack. Go to the final fashion show (Mr. IML contest.) It's interesting, and honestly, you'll never be in a place with as many leather-clad guys anywhere else. It's kinda cool to be all leathered up and be around all those men.
It's also fun to hang out in the host hotel lobby and watch the leather clan come-and-go. Many of them are so funny. There are a lot of once-a-year leather dudes who worry more about their hairstyle or how straight their leather tie is than anything else. They'll stand there yapping away on their cell phones or texting trying to find their friends. They will watch other guys to see how they're dressed, who they're talking to, and what they're doing. Those kind of guys crack me up. My partner and I spent hours people-watching. We had a lot of fun -- only if they knew what was really on our minds. (My partner and I would exchange what we thought were "thought bubbles" for some guys, and then burst out laughing. I'm sure everyone around us thought we were nuts.)
Anyway, relax, have fun, go play tourist, and DO IT IN LEATHER AND BOOTS! And since you're flying there, be sure to check out my "Air Travel With Leather Gear" guide. It can help you decide how to pack.
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