It seems I’m writing more and more about travels lately, but I suppose that’s a good thing. All of these were on my goals list and I like sharing them with you all should you want to go. This exploration was with my usual travel partner/cousin and another cousin who is making our duo into a trio. We sporadically planned a trip to Chicago with a day trip into Milwaukee. Two cities and states we’d never been to before.
As we researched flights and times and everything that goes into planning a trip, we obviously were gaining insights left and right on what to do once we got there. One of the first things that comes to mind when hearing Chicago is of course the Cubs. Luck would have it they were playing a home game the same day we were to arrive. So, we bought those ahead of time and splurged on the tickets (thankful for this later).
It was a very early morning and after some flight delays, I was on my way from Austin to Chicago. Upon arriving it was raining and dreary – can’t kill my vibe. My cousins were driving a rental in from a wedding in Iowa, so they were coming straight to the airport. Surprisingly as non-hectic as the inside of the airport was for me, I can’t say the same for the passenger pick-up area. If anyone was watching us, it was essentially a slowdown, throw my suit case and jump in while never putting the car in park. Hugs would have to wait.
We had about an hour to game time, and fortunately our Airbnb was only 2 blocks from Wrigley Stadium, so we were on our hunt for where we were staying. This was difficult. Directions weren’t very helpful because roads run together, and we were told to turn down alleyways that didn’t make sense. Not only are there alleyways everywhere, we weren’t familiar with this kind of housing construction. Truthfully, it was a clustered mess, but some nice people looking for a “Roberta” helped us out and pointed us where we should be.
We also didn’t pack accordingly. This is our fault. We were later told that Chicago will have all 4 seasons in one week. When we saw the degrees projected, we also think of the humidity that comes with it. That wasn’t the case with Chicago. It was raining and a little chilly. We’re good sports though. So here I go to the Cubs game in a bathing suit, Chaco’s, and a raincoat. The only water repellant clothes I have. We get to the game and (bless) those seats we splurged on are covered seats – yes! We all love baseball and it was a great experience. Unfortunately, the Cubs lost, but we had a great time. Even saw a [fan] take the field and avoid at least 5 security officers before finally being taken down. We stayed the entire game and it was well worth it. Following that we walked back to the house to warm-up and figure out our game plan.
We understood that Chicago’s famous deep-dish pizza was going to be our dinner. We headed to Pequod’s (recommended from a friend) for dinner. We got 2 pizzas and tried some local ciders and put together our itinerary for the rest of the trip, after catching up and enjoying being together.
Monday would prove to be our heavily touristy day. It started with what would be hands down my worst Uber experience to date, but 45 minutes after entering that vehicle, we were free and ready to experience this incredible city. We started with breakfast at The Eastman Egg Company and headed over to the Willis (Sears) Tower to experience the Skydeck. We were told at arrival that visibility was at zero percent – ok, we’ll be back! Instead we headed over and experienced the infamous, Bean. From there we’d heard so much about the Chicago Riverwalk and the Chicago River/Architecture Tours. We booked our tour, which at first glance looks expensive – it is SO worth it. Our tour was absolutely incredible not only learning about the history of Chicago, the river, and all of the buildings/architecture, but our volunteer tour guide was an absolute treasure.
From there we walked along the mouth of the river and Lake Michigan, out to Navy Pier. In my opinion Navy Pier is a bit of letdown. It’s prime real estate and I thought they’d really capitalize on restaurants, bars, and make it a touristy pier – it’s a bust. We meandered down Magnificent Mile and headed to a couple happy hours. We started at Cindy’s Rooftop, which is incredibly popular, and we had to wait in a line for – however, super friendly staff and beautiful views of the city, river and lake. After a couple drinks there, we headed down just a few floors to The Game Room before going to dinner at Miller’s Pub. We had a great time here for dinner, but it wasn’t our first choice. Time got away from us and truly we went there because it was still open serving full menu.
The following day was our day trip into Milwaukee. Surprisingly to me, Milwaukee is only about an hour and half north of Chicago. We put on Lakefront Brewery as our destination and headed that direction. After arriving, we went in and the brewery sits right on the Milwaukee Riverwalk. After a very helpful and pleasant staff, we grabbed some brews and sat out on the river just talking. From there we walked down the river into town, seeing the Bronze Fonz and going to the Milwaukee Public Market, where we enjoyed some delicious desserts. Per recommendation we walked to Harbor House, where we enjoyed a cocktail and had a photoshoot on Lake Michigan. We went back to the Milwaukee Public Market for dinner and had all the cheese in Wisconsin, with some other indulgences. On the way back to the car, we saw where the Milwaukee Bucks play, and the new stadium being built for them.
Arriving back to Chicago it was still important for us to experience Willis Tower, so we headed there just an hour before they closed. I mention this because I totally recommend going then. Not only was there not a line, but we weren’t rushed to take pictures on the Skydeck and leave for the next people. We could take our time, and seeing the city lit up at night is beautiful.
Unfortunately, then it was time to head back to the house and pack for us to get just a couple hours (literally) of sleep before having to go to the airport. After we all got through (separate airlines and terminals), we were able to meet for breakfast and say our goodbyes – already planning the next trip for us.
All in all, Chicago was an incredible city that I can not wait to return to and experience more of. I feel like Milwaukee would be such a blast if they were celebrating a sports win – the city just had that feel with all their breweries and bars.
“We travel, some of us forever, to seek other states, other lives, other souls.” – Anais Nin
The Narrative of a Merman 