Jenn doesn't travel often for work, but when she does I try to tag along. We've been fortunate enough to go to some pretty incredible places like Seattle and Washington DC with these work trips. This year Jenn started a new job and sure enough a couple of months in and she was asked to go to a conference in Chicago a city we've never been to. We decided to take advantage of the opportunity and fly out a few days early and see what Chicago has to offer.
Day 1 -
A Sticky Delight
May 13, 2017
We oscillated between leaving Friday night late from Orange county and getting it bright and early Saturday morning or taking the earliest flight out of Orange County Saturday morning. We elected to go Saturday morning with a direct flight from John Wayne Airport to O'Hare. I woke up at around 4 AM to go for a run and by 5:30 AM we were out at the front of our apartment complex where our complimentary driver (through our apartment) took us to the airport.
We arrived a little before 6 AM, dropped off our bag, went through security, and grabbed some Starbucks before boarding the 3-hour flight to Chicago. The flight was pretty uneventful. Jenn got a little nauseated towards the end of the flight but nothing a good nap in our Uber ride couldn't fix. We arrived at the Hyatt Centric The Loop Chicago a little after 2 PM Central time and made our way to our 20th-floor room. The hotel is a tad on the older side but the room is great, super cozy, with nice amenities and a decent view of the Financial District in Chicago.
Once we finished our room tour and unpacking we went out and grabbed a burger at McDonald's (the worst food we will eat all trip) and just walked around. We didn't have anything on the agenda for today so we just walked aimlessly in the beautiful streets of Chicago enjoying the perfect spring weather. At around 4 PM we were back in our hotel room and finishing the third season of Amazon's Catastrophe and starting the second season of Netflix's Master of None.
I sort of lied, we did have one plan for today; dinner. When we went to Seattle last year I spent some time finding great places to eat and did a pretty good job, so I was tasked to do that again for Chicago. Tonight we went to dinner at a restaurant called The Kitchen which is set right up against the Chicago river. We both had a glass of red wine, Jenn a Pinot Noir and I had a Cab. We started out with fried cheese curds which were phenomenal. Think of them like an elevated mozzarella stick.
For our main entree, Jenn went with her all-time favorite meal, spaghetti bolognese and I had their spring gnocchi. Jenn's pasta was incredible, super fresh noodles, with a great sauce. My gnocchi (not something I've ever ordered) was out of this world. I don't often do this but I was literally scraping the bottom of the bowl to get ever last morsel of the sauce and lamb that came with it. What stole the show though was dessert. It took some convincing but I got Jenn to get the sticky toffee pudding which was one of the best desserts ever. It was nice and warm with delicious ice cream on top. We were fighting over the last morsels of dessert.
After dinner, we walked along the Chicago river and sat watching all of the tourist boats float by. Every once in a while we could hear bits and pieces of the random trivia that the tour operators were going on about. We sat there until a little after 9 PM before making our way back the couple blocks to our hotel and watching Master of None before falling asleep. Today marks not only our first day in Chicago but also our first day of traveling in 2017. And as always I'm pumped to see what the rest of this trip and our big trips this year have in store.
Day 2 - Biking to Chi Chi Land
May 14, 2017
We were so exhausted at the end of yesterday that it was beyond expected that we wouldn't get a fast start to our first full day in Chicago. I believe I was the first one out of bed a little after 9AM and went for a run and grabbed a cup of coffee at Starbucks before we got ready for the day.
Today we decided to start off our journey with brunch. I mean is there any better way to start a day? We passed by a restaurant called The Dearborn yesterday and were able to make a really last minute reservation for brunch. We got there a little after 11 and were seated not too far from a live 1920's style band. Jenn started off with a mimosa and I had a bloody mary. I'm always interested to see what accompanies a bloody mary and this one had sausage, shrimp, and a small Miller beer? Sort of odd right?
For our entree, Jenn went with the Duck Confit with Fried Rice. It was a nice serving of duck served with what we thought was some of the best fried rice we've ever had. I went with the Pastrami Hash and Eggs. Sort of a weird menu item but it was incredible albeit it needed more pastrami (I love pastrami). We were both loving the vibe of the place and the great live music that I got a cup of coffee and we sat and listened far longer than we expected.
After brunch, we were back out on the road and off to Millenium Park, the home of the iconic bean. We walked around the park for about an hour, took photos, sat on a park bench, contemplated overpaying for bad looking miniature golf, and all in all enjoyed a gorgeous day in Chicago. We decided after the obligatory pictures at the bean to walk along the lakeside. There we found bike rentals and decided what the heck and ended up biking for another hour or two along the lake and near the aquarium and history museum. We couldn't have asked for a better day to enjoy Chicago on a bike. At around 3 PM we dropped off our bikes at one of the stands littered throughout the city and were off to walk the 2 miles back to our hotel.
Along the way, we stopped at a Lids Outlet store and bought Cubs t-shirts and a hat for me for the Cubs game on Tuesday. We also dropped by a Starbucks and picked up our Chicago mug for the trip, another great mug to add to the ever growing collection.
We came back to our hotel, watched two episodes of Masters of None (well Jenn only stayed awake for 1 1/2 of them) and all in all relaxed. We went back out a little before 6 PM and walked the half mile to our dinner destination, Lou Malnati's one of the most popular deep dish pizza places in all of Chicago. When we got there the place was packed but we were lucky to grab two spots at the bar and enjoyed an incredible deep dish pizza with a Blue Moon for me and a glass of Chianti for Jenn. I didn't think I would love Chicago deep dish but we both raved about it. I seriously am contemplating getting one more pizza to go before I leave for home.
The highlight of the day (if the rest of the day wasn't amazing already) was our final stop for the day, the Jazz Showcase. Jenn and I love good old fashion music, and I will admit the movie La La Land sort of inspired us to go to a jazz club. I found one when I was looking for places to eat and got us VIP tickets for an 8 PM to see the Grammy-Nominated Cuban Pianist Alfredo Rodriguez. We got there a little before 8 PM after taking an Uber from Lou Malnati's. We got a couch in the front row off to the side. Jenn got a bailey's on the rocks and I had an old fashion. The set didn't start until close to 8:30 but for the next hour and change we were transported with some of the best live music I've ever heard. The nearly sold-out club was electric. It was an incredible show and one that made Jenn and I immediately start searching for Jazz Clubs in Southern California (which there are almost none) and start following Alfredo Rodriguez's music.
I'm so glad we went out of our comfort zone and did something different. We were the youngest in the club (outside of the musicians who were our age) by 20-30 years and yet the life found in the music was something I'll never forget. We walked the mile back to our hotel after the set and called it a night. Another incredible day in Chicago is in the books.
Day 3 - Bad Wine, Great Cocktails
May 15, 2017
I'm still amazed at how much Jenn and I have been able to pack into our first two days in Chicago. The weather (which looked from forecasts to be bad) has been phenomenal and we've been able to do most of what we wanted to do in Chicago in the two days we've been here. We took our time this morning getting going, Jenn worked, I went for a run and got us Starbucks.
We finally made our way out of the hotel a little before noon and went in search of lunch. This ended up being our first time getting lost in Chicago. We were trying to find a lunch place that was nestled within another building and caused us to do a couple of circles. When we found the restaurant it was packed so we ended up making a game-time decision and backtracked to a restaurant we saw on our search called Doc B's Fresh Kitchen. It ended up being a great decision. Jenn got a delicious egg, blue cheese burger that she devoured even if the egg went everywhere. I had the Corned Beef sandwich on a pretzel bun which was literally (not hyperbole) one of the best sandwiches I've had in a long time.
After lunch, we really had nothing planned so we stopped at a winery on the riverside. We should have known better that the wine might not be great given its location. But neither of us anticipated it being atrocious. We went from a great lunch to horrific wine. Luckily the view and the company was fantastic and we enjoyed the cool afternoon breeze sipping on two-buck chuck's ugly stepchild.
We went back to the hotel, exhausted, with a slight bad wine headache. We watched some episodes of Masters of None (amazing show) and resting. We went back out to get Chipotle for dinner a little after 5 and back out again for an evening stroll. Coming back from our walk we saw an advertisement at our hotel for a rooftop lounge. We went up to the 24th floor and had drinks just as the sun was starting to go down. Jenn had a Cosmo and I had an old fashion. We sat talking and we literally sat there talking until we were told the place was closing for the evening. It was the perfect end to a very relaxing day.
Day 4 - Take Me Out to the Ballgame
May 16, 2017
Reality reared its ugly head this morning at around 7 AM when our alarms went off. I went down to go for a run and Jenn got ready for the reason we came to Chicago, to begin with, the start of her conference. A little before 9 AM I walked Jenn a couple of blocks to her conference and went and grabbed a Cappuccino at a small local coffee shop. I enjoyed my coffee watching the locals hustle off to work.
Once I left there I went off for a couple mile walk to Soldier Field. We did almost no research for our trip to Chicago and it wasn't until a little after we got back to the hotel Saturday night that I realized that we were mere steps away from Soldier Field (the home of the Chicago Bears). I didn't want to miss at least seeing the stadium so I walked back down there took some pictures and walked back to our hotel.
I met up with Jenn for lunch and we went to this upscale food court where local chefs can pop up restaurants. We landed on a Mexican food place where Jenn got carnitas tacos and I had chicken tacos. They were phenomenal although I should have just copied Jenn rather than trying to be different because hers were way better. I dropped Jenn back off at the conference and went for another walk along the river before going back to the hotel and watching a couple episodes of Luke Cage.
Jenn got done with her conference at 4 and we went back to the same food court to grab a quick bite to eat. This time Jenn got ramen and I had fried chicken. The food court was such a cool idea and the food was really great. We didn't want to eat too much because after dinner we jumped on the Chicago subway and took it to Wrigley Field to see a Cubs game. We got there in about a half hour, jumped off the subway and walked a couple of steps and were at Wrigley.
It was surreal to be at Wrigley. I've seen so many games on TV and of course grew up watching Rookie of the Year. Walking into Wrigley and seeing the ivy laced outfield was something I'll never forget. We had great seats on the ground level and were captivated by one of the most intense baseball crowds we've ever experience. We bought some peanuts, I had a Bud Light and Jenn had a water. We got up with everyone and high-fived all the nearby fans whenever something good happened for the Cubs. We fit right in with our Cubs gear and had a great time at the ballpark.
We left a little early and took the subway back to our hotel before calling it a night. This was my last night in Chicago. In the morning I have a 7 AM flight from O'Hare to go home and back to work. Jenn has a couple more days of her conference before coming home on Friday. Although my time in Chicago is coming to an end, I'm struck by how incredible our time has been. I hope Jenn has another conference here as soon as possible because I'll be joining her.