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My 2007 trip to Chicago

I just got back from Chicago. I used to go there a lot, but hadn’t been since high school. Consider this my travel diary. I don’t expect it to be interesting to most people, but maybe someone else will find it useful.Lodging

We stayed at a hotel in Rosemont. The rates are much better in the suburbs, but to get to the Museum of Science and Industry when it opened at 9:30, we had to leave at 7 am. That’s counting the shuttle ride to get us close to the El station, the trip in the El with a transfer to another line, and a transfer to the bus line. So we were spending roughly five hours of our day traveling to and from the hotel.


We used public transportation because parking in Chicago is expensive and it’s difficult to drive there. We may reconsider that in the future. It’s also possible, though, that if we stayed downtown near the things we want to do, we still wouldn’t need a car. The trip to the airport would be longer, but we only make that trip twice.

The CTA tourist pass is a really good deal, and the more days you buy, the deeper the discount. And if you make a mistake and leave the station when you meant to change lines, the mistake won’t cost you any extra money if you have the pass. If you’re paying as you go, it will.

My sister and brother in law used a Water Taxi to go from the Field Museum to Navy Pier via Lake Michigan. That was after we had split up for the day, so we didn’t do the Water Taxi thing, but they said it was a fun experience.

We flew to Chicago. I love flying, or maybe I should say I used to. I’ve flown three round trips since Sept. 11–once to and from Dayton, once to and from Orlando, and once to and from Chicago. The “random” screenings are absolutely, positively not random. I’ve been flagged each and every time. I know why. My name sounds vaguely Middle Eastern (it isn’t–it’s Scottish). As I was being patted down yet again today, a thought occurred to me as well. Why would any Arab use the name “David?” That would be like a member of the Bush family using the name “Saddam.”

My bag set off alarms, so it must have tested positive for something. Other than shampoo or sunscreen I have no idea what, but they weren’t going to tell me what they thought it tested positive for. After all, with a name like Farquhar, I might be a terrorist. Can’t trust those bagpipe-toters.

I’m thinking the next time, we should consider Amtrak. Chicago is a 45-minute flight from St. Louis, but the TSA told us to get there 3 hours early because of security. Figure 3 hours sitting at the airport, whatever time the plane has to sit waiting to take off, the time in the air, and the drive to the airport, and you’re up over the 4-hour mark. Amtrak is about 5 1/2 hours. It’s longer, but it’s a lot cheaper (I found a rate of $88 for two adults round-trip) we won’t get as much guilty-until-proven-innocent treatment, we can carry more baggage, and as far as I can tell there are a lot fewer silly restrictions on what we can take. Since my wife is a diabetic, we have to keep some food with us at all times, which meant we had to buy a bunch of food at the only place within walking distance of the hotel. The quality of what we could get wasn’t very high, and the prices were double or triple what we would have paid close to home (think $5 for a box of Cheerios). And we had to throw away our leftovers since we couldn’t put them in our carry-on luggage. I guess there’s a bomb recipe somewhere that calls for Cheerios and apples. Oh, wait. No, bringing outside food in might hurt the airport’s profits. But we’ll call it “security” because that sounds better.

Driving is an option, of course, but I can’t drive to and from Chicago for $88 in a Honda Civic.

So I’m thinking Amtrak, and put the savings toward staying in a hotel in a less out-of-the-way place.

Things to do

As far as things to do, the City Pass is a good deal. For $50, you can go see the observatory, the Han*censored* Building viewing deck, the Shedd Aquarium, the Field Museum, and the Museum of Science and Industry. If you see four of those, you more than pay for the booklet. Plus you don’t have to wait in line. That can save you a couple of hours per attraction all alone.

We’d buy the City Pass again.

Where to eat

What’s the point of going to Chicago if you don’t get pizza, right?

We tried Gino’s East one night on a tip from a friend of my brother in law. Of course it’s good. The place has been around since 1966.

But we got to talking pizza with the bus driver as we were en route from the Museum of Science and Industry to the Han*censored* Building. He told us to try Giordano’s. As luck would have it, there was a Giordano’s within walking distance of the hotel.

Now that I’ve done some digging, I think Giordano’s was the place we tried back in 1989 on our second trip to Chicago.

I liked them both. They were both distinctive, and neither is something I should eat on a regular basis if I want to continue to weigh about 145 pounds. But on a future trip I wouldn’t mind eating dinner at one and then doing dinner the next night at the other.

I remember the very first time my family went to Chicago was in 1985. We wanted to get Chicago style pizza, and somehow or other we stumbled on this place called Perry’s. I have absolutely no idea where it was. I found a website for a place on Devon Avenue in Park Ridge by that name that’s been around since 1967, and the menu features the Gutbuster, which I vividly remember Dad pointing out to me on the menu in 1985. So it’s possible this was the place.

Being our first experience with Chicago-style pizza, Perry’s is now a family legend. And you know how legends go. They get bigger with each passing year. I think within a couple of months the pizza in our memory had become a foot thick, or at least six inches. And nothing we’d had before, and nothing we’ve had since was half as good.

Part of me would love to find Perry’s again, but part of me thinks it would be best to just let legends be legends.

For lunch, a good choice is the nearest hot-dog stand for a Chicago-style hot dog. Let me preface this by saying I normally do not eat hot dogs. I don’t care much for the taste, and I know they’re one of the least healthy things on the planet for you to eat. But I liked these. A traditional Chicago-style dog has onion, tomato, pepper, pickle relish, mustard, chile pepper, and celery salt served on a poppy seed bun. If you put ketchup on it (the person at the counter won’t), the ghost of Mike Royko will come haunt you, and he’ll undoubtedly have some other disgusting ideas for things you could have put on the hot dog instead.

I wouldn’t eat them on a daily basis due to health concerns, but I’ll eat one every time I go to Chicago from now on.


There aren’t many places on the Magnificent Mile that I can afford to walk into, let alone shop at, and I’ve never been much for shopping anyway. I hear Chicago has lots of really great train stores. I stayed away from those, putting my short-term financial goals ahead of my hobby.

But if you like to shop, there are tons of places to do it.

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6 thoughts on “My 2007 trip to Chicago”

  1. Hi Dave,

    I was just in Chicago about three weeks ago for a business trip (actually out west a little in Oak Brook). I had to decide how I was going to get there and ultimately decided to drive! Taking the get to the airport way too early, flight time and transit time from airport to hotel, it seemed the logical thing for me to do. No hassles about too much luggage or bringing shampoo on the plane, total freedom to go where I wanted in my free time (a decent grocery store for example), etc. Since Southwest has very low fares from Louisville to Chicago it ended up costing me about the same price but the time involved was fine (about 5 1/2 hours from here, St Louis looks closer on a map) plus the freedom! I think my drive vs. fly tolerance is up to about 8 hours or so, meaning I’ll definitely drive if it takes 8 hours or less instead of flying.

    My daughter took Amtrak to Austin, TX from St Louis last year and the restrictions are less but there are some. She did not like the experience but it was WAY longer than your trip to Chicago would be.



    1. Hi Bruce,

      One concern about driving is paying for parking. Some hotels charge $40 a night just to park, so that’s one reason I’m weighing taking the train versus driving. It’s about 4 1/2 hours to drive, versus about 5 1/2 to take the train. Being able to read, sleep, or otherwise do whatever I want (within reason) during the trip would make the extra hour worth it, for me at least.

      Now that we can actually afford to take more than one vacation a year (finally!) we’ll probably be heading back quite a few more times, so eventually we’ll get a good process down.

      1. Hi Dave,

        Excellent point about the parking if going into downtown Chicago. I suppose it probably is like New York in that there are almost no "free" or inexpensive parking places even if you are staying in a downtown hotel that has parking (they will still make you pay). So Amtrak makes good sense for that, plus – as you said – you get to totally relax on the train there and back!

        – Bruce

      2. One other advantageous aspect to the train is the frequency with which they now travel between St. Louis and Chicago. There are now five round trips due to the state of Illinois giving Amtrak more funding last year. You can leave St. Louis now at 4:35, 6:35, and 8:30 am, plus 3 and 5 pm departures.

  2. My wife and I attended the VMWare symposium in Chicago at the end of May. It was held at the Rosemont Convention Center, but we stayed in Schiller Park (about a mile away). We did eat at the same Giordano’s as you – and yes, it was incredibly good!

    We spent one day playing tourist, driving into downtown and parking at the Sears Tower ($28). Driving in from the Rosemont area wasn’t great, but about an hour as opposed to 2.5 hours.

    One other transportation option is MegaBus. They travel between St. Louis and Chicago for $21 per person,. each way. Very close to your Amtrak price, although recently I have seen discount rates at $8 or even $1 per person.

    1. Ooh, I forgot about Megabus. Comparable price, and it might be a little faster. I like having options.

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