What follows here is my subjective view of items of interest for people passing through Chicago. Certainly there are other travel guides on the web; what follows are some of my personal notes about several touristy bits a short walk from Chicago Union Station, and on Metra.
Metra: arguably the best-run transit agency in the US
My pal had an apartment in Orland Park. Some visits to the Metra website at http://www.metrarail.com allowed us to come up with a plan. He would drop me off at the 153d Street Metra station in Orland Park, where I would catch a morning commuter train. I would sightsee in Chicago all day, and catch an evening train back to 153d Street. This line is what Metra calls its "SouthWest Service" line.
I was not prepared for witnessing the Chicago Union Station afternoon commuter rush for the first time. What impressed me immensely was: a) the number of people utterly dependent on commuter rail and b) Metra's punctuality. Since I left Germany I had not seen trains where, if one was 20 seconds late, one could not board. I didn't think that happened anywhere in the USA!
In retrospect, given the complexity of railroad trackage around Chicago, I really shouldn't have been surprised. What is amazing is just how well the systems work on a daily basis. Metra express and local trains, in some cases, depart just two -- that's 2 -- minutes apart on different tracks down the same line. That these operations happen daily without incident stand as mute testament to the skill and professionalism of the Metra workforce on a daily basis. This is more amazing when one considers that up until the recent accident Metra had on the RI line, no passengers had been killed in the history of the agency.
Metra has embarked on an extensive campaign to rehabilitate former freight lines for commuter use. Plans were well underway during my trip to extend the SouthWest Service line, and construction on both stations and track was visible from my bilevel gallery car seat. The trains themselves were run push-pull. Cars were clean and well-kept. Fares were reasonable. Even so, because I was travelling through the week, and not on a weekend, I didn't want to do any railfan-serious Metra riding. For railfan-serious riding, consider riding the lines with weekend service with a Metra weekend pass, for $5.00. Even so, Chicago has enough other things to keep the traveller busy.
Around Union Station
As I said, there are any number of Chicago travel guides around. Plug into your favorite search engine as you like. Here are my hints.
*Coin lockers: Thanks to terrorists, the days of stashing your bag a couple hours for 50 cents are over. You may wish to check your baggage with Amtrak when connecting. If you're like me -- slightly paranoid about checking baggage -- renting one of the fancy-schmancy high-tech lockers at Union Station for an hour will cost you $3.00. Figure about $9.00 for the entire day.
*Sears Tower: the Sears Tower is a block or two. On a clear, sunny day, one can't go wrong making a trip to the observation deck. The view stuns, and on a clear day, you can see Wisconsin. You will have to pay for this view, however.
*The Federal Reserve Bank of Chicago: perhaps a four or five block walk from CUS. After passing through a security scan, you may enter the Chicago Fed's money museum. Interesting, and best of all is the cost: free. Better yet: the Chicago Fed allows visitors to take home a small baggie of shredded money. Great souvenir for the kids, and it's also free. What a deal!
If you feel like walking to the Chicago Fed, a CTA Red Line El station is nearby. For a traveller just passing through, the El expands sightseeing options immensely. I used it to head for the Apple Store on Michigan Avenue, on the Magnificent Mile (I did have to walk a bit from the station, though). Because I have a .Mac account, the associates there were happy to let me plug my card reader into a top-of-the-line Mac, and upload my digital pictures for family and friends via a university-grade web pipe. Even if you don't have a Mac, the Apple store's display machines will let you surf the web and check webmail accounts at no charge. Darn near every Mac had someone doing precisely that while I uploaded my pictures. Free is good.
Model railroad buffs should plan on a visit to the Museum for Science and Industry, which is about a 40-minute bus ride across town. I got confused looking for the direct line's bus stop, and just winged it on another CTA bus line that dropped me a couple blocks away from the MSI. The ride and walk were worth it; among other exhibits, the MSI has a massive HO scale layout depicting the BNSF from Chicago to the West Coast, NYC&HRRR 999, and the cab backend of a PRR K-4. Like the Sears Tower, you'll have to pay for this.
As much as OTOL posters like and use the full diner on Amtrak trains, there are some of you out there, who, for whatever reason, won't be able to take advantage of them. Hopefully, these hints will help you out while travelling Amtrak through Chicago.
For the classic "trucker breakfast", Lou Mitchell's at 565 W. Jackson Street, can hardly be beat in terms of both price and convenience. In business since 1923, Lou Mitchell's, a classic diner/breakfast/coffee shop, brags about "Serving the world's finest COFFEE" on its neon sign, and "the best scrambled eggs in the city" on the menu. I'm not sure about the coffee claim -- I did serve overseas, after all -- but I won't dispute the bit about the eggs. A breakfast here should carry you through in fine style until dinner. Don't bother stopping here, however, if you're on a diet. The fresh donuts and cinnamon rolls will make you break it.
Sundries: the Walgreens drugstore chain is headquartered in Chicago, and their store in the Bank One building up the street from Chicago Union Station reflects it. The store not only has all the headache, allergy, or digestive medicine a traveller could need, it also has all the munchie food an American traveller could desire. If you need candy, chips, or canned vienna sausages to sustain you during the next leg of your train trip, this drugstore is hard to beat.