I have to admit that I was pretty excited for our first trip to Chicago this summer, since it seemed like I'd heard nothing but good things about the city from friends and coworkers who are infinitely more well-traveled than me. Suffice it to say, I had developed a lot of expectations before landing in the Windy City, with descriptive words like "beautiful", "friendly", "clean", "pizza", and "steak" firmly planted in my mind. Okay, so those last two words are exactly descriptive words, but they were at the forefront of my attention.

Cayman Airways offers direct service (remember my obsession with direct flights?) to Chicago for part of the year, and of course we preferred visiting this northern U.S. city in the summer, so we linked it up with a trip to PA to see the fam in July. (Fabulous July. Oh how I love thee.) So after flying from GCM to O'Hare, going through immigration, collecting our bags, going through customs, and then taking the blue line train into the heart of downtown (our hotel was on Michigan Ave.), we were good and ready for our first taste of Chicago flavors.

For a first-time deep dish pizza experience, you can't go wrong with Giordano's.  First of all, they're located all over the place, and we were lucky enough to be able to see the closest restaurant from our hotel room.

Second of all, well, this picture says everything.

That crust is even flakier than it looks. Totally melt-in-your-mouth.
I am not enjoying the writing of this post while denying myself gluten.

We obviously only needed one pizza between the two of us, and I was thrilled to find out we could order different toppings on each half. He always gets Hawaiian or Meat Lovers. I always get Veggie. It's really hard to reconcile those two concepts.

But be forewarned: Masterpieces take time, and so do these deep dish delights. Don't expect to walk in and have a slice handed to you five minutes later. I think we waited for our food for about 40 minutes (as their menu indicated.)

Our next big check-the-box item was a Cubs game at Wrigley Field. We took the red line train to the stadium, which is located in a neighborhood (not on the outskirts of town, like many ballparks.) Due to the timing of the game, we had to use the metro during rush hour, cramming ourselves like sardines into cars with everyone in their suits and briefcases. But unlike my experiences in New York and London, people were smiling and friendly, joking about how this was such a cozy way to get to know each other. We had practically invited fellow riders down to Cayman for a visit by the time we reached Wrigley. 

Verifiable fact: Chicagoans are friendly people.

We had gorgeous weather for sitting in the bleachers, which was the recommended location for the most authentic Wrigley Field experience. Sitting in the cheap seats reminded me of going to Little League World Series games as a kid in South Williamsport, PA. Fond, fond memories.

Baseball really is such a classic American pastime. When everyone saluted the flag as the national anthem was sung, I got a little misty for a minute. This is what happens when you spend six months out of the country!

Loving the hand-turned scoreboard.

Confession: We're not really big baseball people, and the Cubs aren't actually "our" team, but thanks to a little paraphernalia given to us by the lovely Chicago-native SM, we fit right in.

Back at the hotel, we noticed that being centrally located on Michigan Ave. meant being within walking distance of not only Giordano's, but also Starbucks, Walgreens, Einstein Bros. Bagels, CVS, and tons of steakhouses. Ahhh the perks of city life. I know it sounds ridiculous, but a Walgreens run was almost euphoric for me.

We contend that one of the best ways to see a city in a short amount of time is on a bicycle. It worked so well on our Eurotrip last year that without hesitation, we booked a tour with Bobby's Bike Hike for the following morning, which was (surprise, surprise) within walking distance of the hotel.

We chose the Lakefront Neighborhoods Tour, which led us through the neighborhoods of Streeterville, Gold Coast, Old City, and North Ave. Beach.

Admiring the evidence of wealth in the Gold Coast district

Lincoln Park. They say it's bigger than Central Park - what?!

A house built with wood that survived the Great Chicago Fire. The owner says she can still smell the fire sometimes... Hmmm, no comment.
St. Michael in Old City

Much to our delight, the tour took a break at the Lincoln Park Zoo, which is free year-round. It's a well-established fact: Who doesn't love a zoo?

NS headed right for the monkey habitat.

City zoos are quite cool; it's like having a green jungle planted right in the middle of a concrete jungle. And due to the proximity of Lake Michigan, this concrete jungle even included a few sea gulls.

I've gotten so used to the year-round warm waters of the Caribbean Sea that the waters of Lake Michigan probably wouldn't hold much temptation for me, but I do love the cityscape/seashore thing they have going on.

North Ave. Beach

All in all, the bike tour accomplished what it set out to do, which was to show us around several of the popular neighborhoods and provide some background and history to each one. If I'm being completely honest, I don't think the tour quality was quite as high as the Fat Tire tours we took in Europe, but we still enjoyed seeing the sites on two wheels.

Just around the corner from the bike shop, I spotted a gourmet grocery store that interested me. We spent some time browsing Fox & Obel's produce section and other all-natural offerings, and ended up having lunch in their attached cafe. I do miss the variety that can be found on every corner in big cities.

Later, we visited the Museum of Contemporary Art, to get in our cultural enhancement for the day.

Gettin' cultured.
I have to say, I really enjoy art museums, but modern art is entirely a hit or miss experience for me. Either the exhibit is eye-catching and creative and memorable, or the piece is just downright weird and moody. Here are two of the former variety:

Andy Warhol silkscreens of media photographs Jackie O. leading up to and after the assassination.
But then, who doesn't love a photo of Jackie O.?
I think that was his point.

I like this next painting because the colors absolutely jump off the canvas. They're also some of my favorite colors to wear.

The painting is almost as 3D as NS.

The museum wasn't huge, but just big enough for us to see 90% of what they had. I included more photos of the various exhibits in the link to the full photo album below.

No trip to a major city would be complete without a view of the skyline from above.

The trick in Chicago is to skip the lines at the Sears Tower (or whatever the new-fangled name of that building is now) and go to the sky bar on the 95th floor of the John Hancock building.

For the price of a drink, you get incredible views (which include the Sears Tower) and a fruity drink to sip on. Now that's smart tourism.

On our way back to the hotel, we stopped off at a Chicago must-do: Garrett Popcorn. Founded in Chicago and made famous by their interesting blends (like The Chicago Mix: caramel corn and cheesy corn), we had to get ourselves a bag.

But if you can't wait to go to Chicago to sample their tempting offerings, they do ship to the U.S. and Canada. And they cater events - even weddings! How fun would that be?

Our evening almost ended on a super high note. Chicago is well known for tremendous steak houses, any number of which were recommended to us and would have been fabulous. But we decided to go with a steakhouse that we've tried in New York, Philly, Naples, and Cherry Hill and have never had a bad experience. I really don't know if I'll ever have a better steak than what they consistently serve at The Capital Grille.

We used to swear by their Kona-crusted Delmonico. Based on N's facial expressions below, I think you'll agree that our new favorite is what our server recommended that night: The Porcini-rubbed sirloin. Un. Believable.

Only complaint: Make it last longer! Is it possible to nurse a steak?

Our server was so warm and helpful, and by the end of the evening, I think we believed we were actually lifelong friends. Well-fed and excessively happy, we started the walk down Michigan Ave. to the hotel. Of course, the shutterbug that I am, I couldn't help but take a couple photos as we sauntered along. 

This is the last photo I took right before... super trusty three-year-old Canon Rebel t1i gave me an error message. And would not take another shot. Would not.

A quick Google search confirmed my worst fears: Basically, the shutter/mirror mechanism had malfunctioned and would require professional repair, which would probably require a $200-500 to fix, which was basically equivalent to the current price of the camera.

So not only did I have a broken camera that was barely worth fixing, but this was at the start of a 12-day vacation in the States. How to vacation without a real camera? I mean, I had a 4-year-old iPhone 3G and a 6-year-old Sony Cybershot point-and-shoot, but certainly nothing that compared to having a DSLR around my neck.

Hmmm.... what to do....

Fortunately, I'm married to the world's best procurement expert. He's decisive, budget-conscious, and technically-savvy.

In other words, N made a decision that very night, placed an order, and got my "second-born" on its way to PA before I could get a word in edgewise. More on that later. In the meantime, you'll have to feast your eyes on the photos taken with my less-than-ideal equipment in the next Chicago post. Creativity couldn't wait for the UPS man!

And for all my favorite Chicago photos, check out the full Google+ photo album.


  1. gorgeous. just an awesome tribute to the windy city! can't wait to visit Chicago ourselves! so glad that you were able to make an "emergency upgrade", although RIP CRSmith. ;)

    1. You'll love Chicago! Great place to visit; maybe even to live!

  2. love it! i think i could live in chicago...
    sad we don't have camera twins any more, but happy for you that you've moved on the bigger and better things!