The Chicago Convention & Tourism Bureau (CCTB) has excellent resources on doing just that. There's information on every part of the city. I am planning a trip to Boston, which I've heard great things about but have never been. I thought about planning an event for Boston and while looking at a map, realized that I still didn't have a clue. How far is point A to point B? Should my friend & I be renting a car? How easy is it to get a cab? I'm sure I can do my homework, but it's not the same as going and knowing for myself. So with that in mind, here are a few things to know about planning a trip to Chicago.
Chicago has crazy winters. Being positioned right along Lake Michigan means that it's constantly windy and the weather is more intense than other surrounding areas, particularly downtown. There's more humidity, more cold... It's also all over the place. Global warming aside, I remember earlier in the year when we went from 30 to 50 to 70 back down to 40 degrees in about a week. That was spring time and while that's not normal weather it's still not completely surprising.
Knowing this is important because your travel time can get backed up, especially in winter. This can affect your venue or activity plans. Obviously you can't not plan on doing things on the chance that the weather might be bad, but it's definitely something to keep in mind if you're at a time that's in-between seasons.
2. Sports, Conferences & Summer Festivals
This is a business dinner, why would I care about sports or conventions or festivals? Because they will block up the roads and suck up hotel space.
If you are a meeting planner or even a tourist but you're looking to come during a big convention, event or sports weekend (for example, the Ryder Cup will be bringing 200,000 people to the city who don't normally live here) then you should know that. It's a lot of restaurant reservations, a lot of hotels, a lot of transit... make sure you check what's in town. Lollapalooza, the giant music festival, practically shuts down anything in a mile radius of Grant Park. These type of things will affect pricing along with availability and possible congestion/detours/shut-downs.
Chicago has an incredibly efficient transportation system. If you're group is low key, or if it's not professional, I often suggest it. However, it can be confusing. Trains aren't labeled "north/south, east/west" they are labeled by stops. Make sure you know where you're going and don't hesitate to ask someone. If it's something you're using often, get a small map and make notes. For example, if you're taking the red line (which can drop you off at both Sox & Cubs Stadiums) you may want to know that the "Howard" direction is north and "95th/Dan Ryan" is south. Little details like that make life much easier. Trust me, when crowds are giant and trains are coming, you find yourself jumping on whatever train "feels" like the right choice. So if you have it written down, you'll make an informed choice instead of a panicked one.
4. Ask the People That Work There
When I work with out-of-towners, they often ask "how far are you from...?" I live here and work here, so I know. If you're planning for someone, don't hesitate to get on the phone with the concierge at a hotel or call anywhere you're booking to try to get as much information as possible. Your clients will appreciate the accuracy!
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