Before this trip, we had never been to Chicago. I had heard so many positive things about the city, from both family and friends. Some even said it was comparable, if not more enjoyable, than New York City.

We left Friday after work, and didn’t get in until really late.  After ditching our bags at the hotel, we realized how hungry we were.  Nearby, was a pizza place Zach’s sister and my Dad has recommended, Gino’s East Pizza. We spent that evening enjoying our first Chicago deep-dish style pizza. Ho-lee-shizzle…

This pizza had crust about 3″ high. The pictures do NOT do this baby justice.  Thank heavens we ordered a small, because we were nearly comatose after each eating only one piece. The garlic breadsticks didn’t help before the pizza came either.

A friend recommended we get a three-day railway pass, which conveniently are sold at Walgreens, a block away from our hotel. As if the sticks and pizza weren’t enough, we stocked up on treats for our room and got our ticket through the city.

The next morning, Zach slept in and I hit up the Westin Workout. I literally am saying that, not because I am like, “look at me, I am so cool…I worked out on vacation”…I say that because I am pretty sure that pizza made me gain 4 whole pounds.

We then took the subway to Wrigley Field for the Cubs Game. If you are wondering what Zach’s highlight of the trip was, look no further…

Two things I didn’t know: Wrigley Field has a very serious relationship with Wrigley Chewing Gum. Yeah, didn’t know that. Second, Wrigley Field was built in SIX weeks. For those of you whole live in the design/build world like me can marvel at that accomplishment.
We got our gear on and settled in out seats. I LOVE Wrigley Field; the brick, the ivy outfield wall…it is iconic American Baseball! Second favorite ballpark – after Yankee Stadium. (I have never been the Fenway, so that may change in the future).

Soon after we sang “Take Me Out to the Ball Game” at the 7th Inning Stretch, it began to POUR. This was no drizzle, my nizzle. Soon, ponchos became priority number one.

After we got these glam get-ups, we braved the walk back to the rail. We looked very attractive.  Of course as soon as we stepped off the subway, the rain had dissipated. How convenient for me that on our walk back to our hotel were centrally located shopping destinations – H&M, Zara, JCrew, and so much more…
You can guess what we did until out dinner reservation.

We ate at an amazing Steakhouse, Wildfire (thanks Gina!) for dinner. Probably my favorite meal of the trip. And HOW CONVENIENT that Pinkberry was a block away? Steaks and frozen yogurt – Zach was sky high.

Every night before we retired to our hotel room, we walked around a different part of the city.  We got in comfy clothes and explored.  I must say, Chi-Town is MUCH cleaner than NYC and the people are a tid-bit more pleasant.  It was a big city, without a big city mentality.

But we didn’t stay out too late this night, because we had an early (for us) tour date in the morning.

Sidenote: I am obsessed with the Prohibition Era. The boot-legging, the scandal, the MAFIA! So of course when we planned this last minute trip, a Gangster Tour was a must for me. I am serious, we’ve seen pretty much every gangster movie out there. Call me a whacko, but I am so intrigued.

So that morning we took a Chicago Untouchables Tour! How hilarious, the men are dressed in period clothing, fedoras and all, and they pick you up in an old-school black bus!?  We drove around the entire city, stopping at various locations of interest: where John Dillinger was shot, the site of the Valentines Day Massacre, Al Capone’s favorite night club, and my personal favorite: the Holy Name Catholic Church, where you can still see the bullet holes in the exterior of the building! Yup, LOVED it!  By the way, they don’t call it the “Mob” or the “Mafia” in Chicago, it’s called the “Outfit”…just FYI because I knew you were dying to know that.

After the tour, we discovered Sprinkles.  Zach waited in the line that ran down the block, while I shopped at various locations in the vicinity. Once again, #1 Husband Award goes too…
But in all seriousness, Zach liked his S’mores cupcake just as much as I enjoyed my Famous Red Velvet. It’s worth the wait people!!

Zach was completely shopped out after we made a few more stops.   In my defense, I must add we didn’t miss much College Football.  We managed to work in segments of the BYU and USU games throughout our Saturday.  Just saying, you know…because of the cupcake thing.

We had to take a brief time out at our hotel before heading off to our Italian dining experience, inspired by our Gangster tour, of course.  Volare was delish, once again a referral. If it wouldn’t have had the flat screens playing sports highlights it would have been pretty authentic.

It was late and we decided to walk off our dinner all the way back to the hotel. Suddenly, after our delicious meal, Zach informs me he wants popcorn. Chicago is a culinary mecca, and my husband wants stale greasy popcorn! After convincing me that microwavable popcorn is not sufficient, he tells me he has found a movie theater nearby.  I agree to go out of our way to get him his popcorn.  We are walking to the location, via GPS on his phone, and we can’t find it.  We ask a Bell Hop if he knows where the theater is, he says, “Ah just 5 blocks down Rush Street, can’t miss it.”  My father, whom has traveled to Chicago numerous times for business, told us specifically to avoid this street. But…popcorn won the battle.  So we walk 5 blocks, then 8…no theater.  We ask another Bell Hop at a sketchy hotel where the theater is, he tells us about 3 blocks left and then 5 more up.  So we are walking…and it starts to dump rain on us.   POURING RAIN!  We find refuge under the ghetto-ist bridge, full of riffraff.  Zach tells me if we can find a taxi that is not occupied, we can go back to the hotel.  I refused! All that, and no popcorn?  We braved Rush street and the hoodlums, we could do it!!   So you know what we did??  We found a taxi, told the cabby to take us to the theater and wait outside until Zach could run in and get his bag of popcorn.  I decided to wait inside cab, just in case he decided to take off.  It is still pouring rain at this point. THIS is where I receive the Best Wife Award….(no, not the that, for what’s coming….)

Zach is inside the theater ordering his popcorn, and I am still in the cab with this weirdo man.
A late movie must have just let out because people suddenly start flooding out the front doors. They see the downpour, then they see a cab standing by. Suddenly people are surrounding our cab, waving and trying to open our doors. Knowing it was raining and cabs were going to be highly coveted at this point, the cabby had locked the doors. These people are freaking out! They can’t see me behind the tinted windows, and are now banging on the doors and windows for the cabby to unlock them. It was seriously like a zombie movie!! We were under attack! Finally I see Zach running, spilling kernels as he approaches us…and I yell to open the doors. Zach jumps in and we speed away! Yeah, all that for a bag of…you know what.

Officially the most expensive bag of popcorn we’ve ever purchased, after the cab fare.  But look at that face…how could I turn that face down?

The next morning, we set off for one last and EARLY educational experience: the Architectural Boat Tour! I was on cloud nine. The Art Deco skyscrapers, the Post Modern structures, the story of the Chicago Fire…it was awesome!

Chicago is definitely ahead of us weather wise, and it felt like Fall! It was perfect. We ended with one last stop: Millennium Park. We had planned to go the night before, but the weather and popcorn drama delayed our visit.

We had to stop and get a photo op at “The Bean”.  I have no idea what it is really called, but I’ve always wanted to go.  The sculpture has a reflective surface so you can see the architecture of the city behind you.  Each view of Chicago is different as you walk around, it was one of my favorite things about the entire city!

We had a fantastic trip, and we will definitely be returning to the Windy City again.  As for NYC vs. Chi-town?  I say it is a toss up.  What’s not to love about a city with kind-hearted people, amazing architecture, top notch food, that has an amazing story to tell?