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So, your boss calls you into his office in Milwaukee and tells you that he needs you to go to Chicago for a week and help implement some new software at another office. Sure, you think, sounds like a good way to get some face time with your co-workers that you don’t see on a regular basis. But, then, there’s the planning. How are you going to get there? Where are you going to stay? If you drive, where are you going to leave your car? What are some ways to save money? Planning any kind of travel, business or otherwise, can be stressful. Here are some tips and other information I have found that work to reduce that stress.

The first step in planning any trip is to figure out how you’re going to get there. Of course, when we’re planning a trip to somewhere warmer during the winter or back home to New York for Thanksgiving, the choices are narrower. But when we’re talking a distance as small as Milwaukee to Chicago, which is less than 100 miles, your options increase.

The first option, and I would think the first thing people think of would be to drive. This seems the most convenient, who wouldn’t want to have their car with them, but there are some limitations to consider. First, there’s the stress of driving to Chicago. Speaking as someone who lived there for two years, the traffic is awful and the drivers do not pay attention at all. I personally avoid driving in Chicago whenever possible. Second, there’s the cost to park. Parking in downtown Chicago is expensive. A quick search on my favorite parking spot locator,, came up with several options in the immediate area. The average cost at places like Tower Self Park or Traders Self Park is $100. More expensive options are available, like at the Franklin Center for $172. What the advantage is of spending more, I’m unsure. Overall, I find having a car in Chicago to be a pain and I avoid it whenever possible.

Which brings me to the second option, which is my personal favorite, and that is the train. The Hiawatha line departs several times a day from the Milwaukee Intermodal Station downtown and takes you straight to Union Station in downtown Chicago which is walking distance from the area surrounding Sears Tower. The cost of a round trip ticket varies based on your dates of departure but can generally be had in the $50 to $75 range. Prices and timetables may be found at Every time I have gone to Chicago from Milwaukee, I have taken the train. I cannot imagine a reason why I wouldn’t unless there was a pressing need for a car. Of course, taking the train means having to rely on public transportation once you are in Chicago so you want to keep those costs in mind as well.

Once you have decided how to get to Chicago, your next challenge will be finding a hotel. Your choices are numerous and the prices vary wildly. There are hundreds of hotel web sites that you can use. My personal favorite is as they do a good job aggregating all of these sites into one place so you can feel confident that the price you are paying is a good one. Based on travel dates of 3/28 to 4/1, they have prices of anywhere from $79.00 per night at the three-star Club Quarters which is 0.3 miles from Sears Tower, to the five-star JW Marriott at $299 per night which is 0.2 miles from the tower. Where you stay is going to be dictated by your own preferences but, probably more so, by the budget allocated to you for the trip. Keep in mind, you will primarily be using your hotel to sleep and get cleaned up. It doesn’t necessarily have to be the nicest place in the area. Also, just because something is expensive, doesn’t mean there’s anything special about it.

Your next consideration should be food. Now, this is Chicago. No matter where you are, there is probably a restaurant or grocery store within two blocks of you. Near the Sears Tower, your choices are practically limitless. Looking to impress a client? There’s the Metropolitan Club in the tower with gorgeous city views and impressive menu options. Keep in mind, though, that you will be lucky to get out of there for under $200.00. Just wanting a quick lunch? Every single fast food, sandwich shop, and pizza place you can think of is within five to ten blocks. Can’t find what you’re looking for? There’s probably a delivery service that will bring it to you. For a typical breakfast and lunch, you can expect to spend anywhere from $5 to $15. Dinners tend to run a little higher but, if you’re looking for something no-frills, you can generally eat for between $10 and $20. Chicago is a very easy city to splurge in so as long as you keep your budget, and your company’s credit limit, in mind, you should be ok.

If you are planning on making trips to Chicago on a fairly regular basis, you may want to consider some ways to cut down on costs. My favorite way to do this is through reward programs. Pretty much every business you walk into (hotel, restaurant, parking garage etc.) has some sort of rewards program in place that you can use to save money in one way or another whether it be a free night’s stay, a free night of parking, or a free meal. When you travel for business, the points you earn add up quickly and can save you quite a bit of money in the long run. I also, depending on the circumstances, will go to the grocery store for food rather than relying on restaurants. Let’s face it, take out gets old and you just can’t beat fresh food. I also recommend using a spreadsheet to track your costs. This can help you identify areas where you are overspending and cut down on your budget. An example spreadsheet can be located here.

Are you feeling prepared for your trip to Chicago yet? It’s a great city to both work in and visit. I hope that this information will help point you in the right direction once you get there and help you save some money and frustration in the process.