Having had some time to reflect on our experiences in Chicago and the hundreds of pictures we took, here’s what I’ve come up with to encapsulate the city and the time we spent there:

The History:

One of the main reasons that I wanted to visit Chicago was that I was fascinated by certain key pieces of its history.  I was completely enthralled by Erik Larson’s book The Devil in the White City, about the Columbian Exposition of 1893 and a serial killer who was operating in Chicago at the same time.  I’ve been fascinated by dinosaurs and archaeology for years, and I knew that there were lots of dinosaur skeletons at the American Museum of Natural History (with which I was intimately familiar) and the Field Museum (with which I was not).  And plus … you know … lots of crime history?  City of the big shoulders?  The windy city?

During our stay I learned that some darker parts of Chicago’s history got a lot of attention, or at least seemed to be embraced by the popular culture.  We took a “Devil in the White City” tour.  We saw a “Devil in the White City” ice cream soda flavor.  We saw Al Capone and gangster-themed stuff for sale EVERYWHERE.  At gift shops all over the city we saw Al Capone mugs, shot glasses, figurines, root beer, taffy, and more.  And yet, when my boyfriend googled the location of the Saint Valentine’s Day Massacre, we just found an empty parking lot.  That’s it.  Not a single plaque or anything to indicate that something of historical significance had taken place on that spot.

Other than that, there are bits and pieces of Chicago’s history all over the city, both in the buildings themselves (sometimes creatively repurposed and showing signs of their previous owners) and in the “at this spot used to be …” plaques.  In that way, it felt very similar to New York.

Oh, I almost forgot.  I did learn ONE more thing about Chicago’s history a few weeks before we were going to visit.  I had recently subscribed to a very cool, educational, and surreal podcast called The Memory Palace.  Each epsiode is just a few minutes long, and when you’re looking down at your iPod all you know is the episode’s title so you have to listen to the episode to know what it’s really about.  The length of the episodes made it possible for me to listen to a lot of episodes all in a row, and one of those episodes was called “Far Below Lake Michigan.”  Over the next minute and 18 seconds (I TOLD you these episodes were short!), I learned about something called the Eastland Disaster.  In which a ship that was supposed to leave Chicago and sail across Lake Michigan in 1915 capsized shortly after its departure, killing hundreds of people on board.

I’ll admit that it made me think about the Lake Michigan lunch cruise I’d booked in a whole new light.

The Museums and Other Attractions:

Like I said, one of the reasons I wanted to visit Chicago was that I wanted to see the Field Museum.  We had a lot of fun there, but it still paled in comparison to New York museums.  As in, not nearly enough dinosaurs and not nearly enough Egyptian stuff.  Honestly, it was very difficult not to flaunt my New York attitude and start yelling, “Well, it’s certainly no Temple of Dendur!” in a very haughty voice while exploring their comparatively small Egyptian collection.  Because, you know, that would have been rude.  So instead I just whispered it in my boyfriend’s ear.

The same day we saw the Field Museum we visited the nearby Shedd Aquarium.  I hadn’t heard of this place until about a month before we visited, so in some ways that was good because I had zero expectations and was pleasantly surprised … mostly by the building.  I mean, yes, the fish were very nice and all.  But since we saw the Field Musem first it was really crowded by the time we got to the aquarium, so every time we wanted to look at something there were a dozen people standing in the way.  What I saw of the wildlife was nice, but what I saw of the building was GORGEOUS.  The Shedd Aquarium is a very old building (it opened in 1929) and there are cool nautical elements EVERYWHERE.  Basically, every time I had to wait for a bunch of kids to get out of my way so I could look at some exotic creature, I stared off into space for a while until I noticed yet another cool design element in the building.

We had several people tell us that we should visit the Art Institute of Chicago, and the fact that they had a Roy Lichtenstein exhibit sealed the deal for me.  This was a great place to visit, and they had an awesome selection of sculptures, paintings, and lots of other cool stuff.  Plus they had a really great gift shop that featured all kinds of artwork on all kinds of objects.  What kind of design would you like on your tote bags?  Nighthawks by Edward Hopper?  Water Lilies by Claude Monet?  The Gashlycrumb Tinies by Edward Gorey?  You get the idea.

We weren’t sure which of the skyscraper observatories we were going to visit, and we decided to go to the John Hancock Observatory.  You take the elevator — excuse me, the strangely CHATTY elevator — up to the 94th floor and you do what you usually do when you’re that high up.  You look down at the rest of the world, and you ooh and aah appreciatively.

The Museum of Science and Industry wasn’t on our “to-do” list at first.  But when I learned that, like in San Francisco, it was a modern science museum built into the shell of an old art museum, I decided that I wanted to check it out.  This was a very cool museum with lots of interactive exhibits.  It was both very educational and a lot of fun.  We went on several mini-tours inside the museum, and those were cool and entertaining, too.  The U-505 submarine tour especially was definitely worth the price, even if we weren’t allowed to take pictures on board and even if it was claustrophobic as all get-out.

I didn’t know that the Chicago History Museum existed until we passed it one day while driving back to our hotel.  Even though some of the exhibits brought me to tears (I remember that one of the exhibits was about the Eastland disaster, but I don’t remember what the other one was), I definitely enjoyed the visit.  There were lots of exhibits on highs and lows of Chicago’s history, from the White City to the Chicago fire to the gangland wars.  But then there were also exhibits devoted to Chicago’s creativity, from the Second City theatre to Lincoln Logs to Marshall Field to an ancient toy called Mr. Machine, which my boyfriend said that he’d owned as a child (way back in the 19th century, apparently).

And finally, if you go to Chicago you absolutely must visit Millennium Park and the Navy Pier.  Millennium Park is great for people-watching, whether they’re splashing around in the Crown Fountain or reflected in the Cloud Gate sculpture, affectionately known as “The Bean.”  The Navy Pier is basically designed to entertain you and your entire family.  By which I mean you can eat lots of food, enjoy alcoholic and non-alcoholic beverages, ride the Ferris Wheel, play miniature golf, or even go inside to cool off and get out of the heat while exploring the Smith Museum of Stained Glass Windows.  I’m not kidding when I say that it has something for everyone.

The Tours:

When we first booked this trip, I decided that I wanted to start the week with an architecture tour since several people had recommended that we take one of those tours.  I’d booked our hotel through Priceline, and one of the tours they sold was a River & Lake Architectural Tour through Seadog Cruises.  I later found out that there are a LOT of companies that offer boat tours on Lake Michigan and the Chicago River.  In any case, the Seadog cruise was a good match for us.  The first three-quarters of the tour was slow and stately, and we cruised along the river, waiting for locks to open and taking lots of pictures as we learned about Chicago’s architecture and history.  Our tour guide, Grant, was very funny and personable, and was entertained by each of my questions, from the one about whether or not Chicago hot dogs were worth trying (he’d probably heard that one before) to the one about which skyscraper the giant grasshoppers climbed in Beginning of the End (that was a first for him).  Oh, and according to wikipedia, in the super-duper special effect of making it look like giant grasshoppers are climbing up a skyscraper by putting regular-sized grasshoppers on a PICTURE of a skyscraper … director Bert I. Gordon used a picture of the Wrigley Building.

We also went on a lunch cruise aboard the Spirit of Chicago.  The lunch was served buffet-style as soon as we boarded, which means that by the time the boat set sail we were almost finished with the meal.  So technically, it was more of a digestion cruise than a lunch cruise.  The cruise was nice in terms of the food and in terms of being able to go out on the desk and check out the views of the Navy Pier and the Chicago skyline.  But the activities on board weren’t really our kind of thing.  There were lots of musical numbers (including several solos by our talented waitstaff) and lots of requests for people to get out on the dance floor.  Like I said, not really our thing.  But the food was good and the views outside were beautiful.

One morning we went on a “Devil in the White City” tour offered by the Chicago Architecture Foundation.  We didn’t even know this tour existed until I read about it in a brochure I picked up at the Chicago Welcome Center.  Well, my boyfriend and I both loved that book to pieces, so we just HAD to go!  It was listed as a bus tour, but we also spent some time sitting and watching a slideshow (so we could see the way things used to look back in the 1890’s) and a lot of time walking.  The main problem with going to visit something that wasn’t meant to be permanent is that most of it isn’t there anymore.  A lot of the bus tour was spent going over the terrain of Jackson Park, driving past the places where those white buildings and the tawdry Midway used to be.  So we spent a lot of time looking out of the bus windows and using our imaginations.  Of course, when we got to the parts of the Columbian Exposition that survived until the present day — namely the Palace of Fine Arts Building (now the Museum of Science and Industry) and the Wooded Island, we got very excited because we got to walk around and look at things and touch things that had been there BACK THEN.  If you’re into history, you’ll enjoy this tour.  If you love that book, then you’ll LOVE this tour.

One word of warning, though: If you think that you’re going to visit H.H. Holmes’ murder castle on this tour, it’s not gonna happen.  It’s gone now, and they don’t drive you over to the site so you could … I dunno.  Look around?  Throw a rock?  Kick something?  Stomp on the ground and curse Holmes’ name?  Anyway, it’s not part of the tour, and if it was, it probably would be anticlimactic.

We spent one evening on a “pizza and cocktails” tour, which promised to take you around to several different pizzerias in Chicago where you could have pizza and a cocktail (wine or beer) at each location.  I figured that I would switch from booze to soda at some point in the evening — I like wine, but four glasses is too much for me.  I’d been on a pizza tour once before, and that was through Scott’s Pizza Tours in New York City.  That was one of the best tours I’ve ever taken, and that was in part because Scott was a funny and knowledgable tour guide, because he taught you something at each location, and because we sampled the same kind of thing (i.e. a plain cheese slice) at each location so that you could make equal comparisons and appreciate how the same kinds of ingredients could be interpreted differently.

The Chicago tour was much less organized, and the disorganization was heightened by the fact that many of the pizzerias were loud and dark and by the fact that members of our group were getting drunker as the evening wore on.  Let’s see … several of the places didn’t have tables set aside for us, and I had a feeling that at least one of them wasn’t expecting us at all.  Instead of tasting plain cheese slices at each place, most of the pies had lots of STUFF on them.  Pepperoni?  Sausage?  Kielbasa and sauerkraut?  Check.  So the end result was that we filled up a lot faster, and by the time we got to the final stop (where we were going to be having a deep dish pie at last) I was so full that I could hardly move.  I could only swallow a few bites, and I definitely couldn’t appreciate the flavor of the pizza anymore.  Then they brought out the special surprise bonus, a DESSERT PIZZA, and I couldn’t even look at the damned thing.

I clearly wasn’t in the right spirit, though, because most of the group ate some of everything, some of them drank alcohol at every stop (some of us switched to soda or water part way through, but some of us might have started drinking BEFORE the tour), and when we were sitting around the table at Pizano’s at the end of the night everyone started taking out their phones and sharing their Facebook account information.  And my boyfriend and I were suddenly the odd ducks at the table because we were the only ones who weren’t on Facebook.  BTW, is this the way that grownups act when they meet other grownups nowadays?  I mean, I see people wanting other people to friend them on Facebook all the time … but those are kids in the children’s room at my library.

Anyway, in conclusion, I learned very little about pizza on this tour.  But I did get to look into a pizza oven and I did get to eat a lot of food.  If you’re in NYC, though, I can’t recommend the bus tour from Scott’s Pizza Tours highly enough.

The Food:

Oh, man, we had a LOT of good food in Chicago!  There were certain foods that I just had to try, namely deep-dish pizza and Chicago-style hot dogs.  In fact, I had one particular hot dog place that I wanted to visit called Superdawg.  I found out about this place in a very unusual way.  I’ve been a fan of bad movies and bad-movie websites for years, and I always enjoyed reading on Jabootu and other websites about an annual celebration of bad movies in the Chicago area called B-Fest.  And Ken from the Jabootu site mentioned that part of their tradition every time they went to B-Fest was that they would all go out to Superdawg together.  So I knew that if I ever visited Chicago, I’d definitely have to check this place out.

And yes, I also suspected that Chicago might be a good place to find a great steak.

We had a lot of good and great food throughout the week, but my highest kudos have to go to breakfast at Yolk (a meal worth waiting for, and you WILL have to wait!), deep-dish pizza at Pizzeria Due, hot dogs at Kim and Carlo’s Chicago-Style Hot Dog Store, Italian Beef at Portillo’s, the banana cashew eggroll with salted caramel gelato at Big Bowl, pierogies at Berghoff, tortas at Xoco, the apricot jam and pistachio butter croissant at Grahamwich, and burgers and hot dogs at Superdawg.

We’ve had several people ask us about our favorie meal in Chicago, and after much deliberation I finally settled on the meal we had at The Purple Pig (motto: “Cheese, Swine & Wine”)  They had really nice wines, and a great selection of meats and cheeses in different forms — as appetizers, on toasted bread, or cooked in a wonderful homestyle way.  We managed to save some room for dessert, which also turned out to be superb.  So while I loved a lot of restaurants in Chicago, The Purple Pig gets my highest recommendation.

The People:

Okay, I was born and raised in New York City.  I was taught to always be careful of my surroundings, and never to talk to strangers.  I am very shy, I usually keep my eyes down, and I tend to keep my thoughts and opinions to myself.  I definitely THINK a lot of things, both positively and negatively, about other people.  But while I might whisper those opinions to my boyfriend or whomever I’m with, I will never express my thoughts to strangers.

Now imagine me transplanted to the Midwest.

First off, I guess I never realized how cool my T-shirts were.  New Yorkers tend to appreciate things with their eyes, but Chicagoans kept TELLING me how much they liked what I was wearing.  They liked my Fringe shirt, my MST3K shirt, and my Gashlycrumb Tinies shirt.  The closest I got to an insult was a guy who said, “That shirt is really … interesting.  Don’t know what it means, though.”

But my ultimate experience of Midwestern friendliness took place while I was sitting at the Superdawg waiting for my boyfriend to bring our food over.  I was sitting on a stool in the small dining area, and I was near a woman who was talking on her cell phone, having one of the single most inappropriate public conversations I’ve ever heard (keep in mind that I’m a New Yorker who works in a public library).  It got so weird that when a spot opened up on the other side of the room, I got up and took it so that I could get away from her.  Not that it made a world of difference; this woman was not well-versed in the difference between an “inside voice” and an “outside voice.”  Anyway, people came and went, and the woman went on and on with her soap opera-like saga.  Finally she got up and left, and within SECONDS all the other people in the room started talking about how rude and inappropriate she was.  And yes, it does occur to me that in a New York crowd, there definitely would have been people who would have started yelling at her, or at least wouldn’t have waited until she left before talking about how rude she was.

A woman sitting next to me at the counter looked at me and said, “You’re not from here, are you?”  I stared at her in bewilderment for a second before realizing … Oh, right.  My huge Nikon d80 camera sitting on the counter is probably a dead giveaway.  I told her that no, I was visiting from New York City.  To which she replied, “Well, I want you to know that we are NOT all like that!”  And then several of the men sitting behind me chimed in as well, saying that the woman who left was very rude and not a typical Chicagoan at all.  I was really overwhelmed by the whole conversation.  They were just so NICE to me, and they cared about what I thought about them and their city.  Then the lady next to me started asking me which sights I was going to see, and she started giving me recommendations for places I should see while I was in town.  By the time my boyfriend showed up with the food, I knew that I was in a very special place indeed.

Don’t get me wrong; I’m not about to start making eye contact with or (God forbid) talking to strangers in New York any time soon.  But it was definitely a nice experience to let my guard down for a little while with a couple of strangers who wanted to stick up for Chicago and the Midwestern ideal.