For Chad’s birthday this year, I surprised him with a quick overnight trip to Chicago. It’s been long overdue: Milwaukee is incredibly close to Chicago (about an hour and a half away, either by car or train) and we’ve been waiting for the perfect time to visit.
I’ve been to Chicago twice previously: once in the fourth grade, when my brother graduated from Naval basic training, and then a few years ago over New Years, when that same bro was living in a suburb at the time. Chad, on the other hand, had never been.
So, the two of us packed as light as possible and headed to the Amtrak station to board the 8 a.m. train; we spent a whirlwind day and a half in the windy city, trying to cram in as many first-timer experiences as possible.
The train
Our first train ride was a successful one! Chad and I felt very excited and capable after getting to know another travel option. As far as booking and scheduling went, the Amtrak system was extremely easy. Milwaukee’s station was pretty straight forward, and our ride was teeming with excitement as we watched through the windows and reviewed our plans.
On the way back home, Chicago’s Union Station took a little more preparation to understand the layout and lines, and it was busy with vacationers returning home. It was still pretty easy, but I’m glad we arrived about 45 minutes early (enough time to grab food beforehand, too).
Saturday morning
After arriving, Chad and I started walking right away to a coffee shop. It was about a twenty minute walk through downtown and toward the river, and we were instantly blown away by the architecture and gleam of the buildings around us. It was about 9:30 a.m. and not busy at all, which seemed like a rare treat.
Because I misread the meeting time for a tour reservation (I thought we had to be there an hour earlier than necessary), Chad and I were hustling. We stopped at Caffe Umbria nearly out of breath (lol), but found instant delight in iced coffees and lattes and a very necessary croissant.
From there, we walked another twenty minutes or so to the riverwalk docks, even stumbling across an Indian wedding party that involved a very stylish man on a white horse and a crowd of dancing and cheering (it was incredible!). After finding out our boat tour was an hour away still, we went for a leisurely stroll on the riverwalk and absolutely loved it: the clarity of the water, the benches and steps, the business stalls, the beer gardens, the endless stream of dogs. It was so lovely and the energy was summery and exciting.
Boat tour
Up next, Chad and I did the Chicago Lake and River Architecture Tour by Wendella. Phyllis was our guide (she’s a lifelong Chicago local and has been doing tours for 38 years!) and she was fantastic.
Our 90-minute boat ride was full of countless facts regarding the history and architecture of the city. My favorite was learning about the World’s Fair and the lasting contributions, especially with cultural items like the Ferris Wheel.
We walked away extremely sunburnt (big oops!), but also full of new appreciation.
Saturday afternoon
The rest of the afternoon flew by. Chad and I had grand plans of fitting in more iconic stops, but we felt a time crunch. Instead, we fit in lunch at a nearby English-themed pub, Elephant and Castle. I had a shephard’s pie and a refreshing Moscow mule, which hit the spot.
After lunch, Chad and I went back to the Riverwalk to grab drinks with one of Chad’s former schoolmates at Colorado School of Mines, who was originally from the Chicagoland area. Ryan met us at the Northman cider and beer garden, where we spent several hours catching up and soaking in even more sun. Chad surprised me with a few fun drinks, including a fruity rum punch and a lemonade-based seltzer.
When we wrapped up, we were able to walk to our hotel to check in—which also meant finally, finally, taking off our backpacks, lol. It was about another half-hour walk north to the Magnificent Mile area, which is known for grand-scale shopping.
Saturday evening
After getting maybe twenty minutes in our hotel to recover (lol), Chad and I needed to start heading toward the John Hancock building for our reservation on the 94th floor’s observation deck and bar. There were a few lines to wait in, but the views at the top were worth it. Incredible!
We grabbed margaritas and sipped them to sprawling, 360-degree views of the city. I loved this part, even fully recognizing how touristy it was.
From there, Chad and I made plans to meet up with my childhood friend Annie, who lives in Chicago. She recommended we eat at Paulie Gees in Logan Square and we had the most incredible Detroit-style pizza, amazing drinks, and then even Malört shots when Annie joined us (lol, it’s horrible – do not recommend).
Annie then took us to a nearby bar called Spilt Milk, where we drank cash-only cocktails on the patio. Though we were exhausted (I think Chad was falling asleep, lol), we met several of Annie’s friends and ended up getting back to the hotel around 2 a.m. It seemed like the local experience we needed.
It was so much fun.
Sunday
If we’re being honest, the next morning was much less fun.
Somehow (probably out of necessity), we survived. Chad and I packed up our things and once again braved the city with our backpacks in tow, albeit a little slower at first. We grabbed food at Sunny Side up, which had a lengthy line out the door but was worth the wait: beyond a delicious hash, the vibe of the diner was classic, bustling, and vibrant, and our waitress was as charismatic as humanly possible.
We then set our sights on Navy Pier. We walked about half an hour there, and felt ourselves coming back to life post-coffee and food. It was a pleasant walk, though it started getting warm once again. Navy Pier was nearly identical to how I remembered it from childhood: great views, family vibes, lots to see and do. We mostly just walked from one end to the other and tried to take it all in, though on a different day we would’ve stopped for a drink or snack.
Afterward, Chad and I decided to keep walking to Millennium Park—the last attraction on our itinerary. It was about forty minutes, with a few hills, but mostly on a paved path for both foot and bike traffic. We loved the accessibility of walking and biking in Chicago, and were impressed by the sheer amount of people taking advantage of the summer weather.
By the time we arrived at Millennium Park, we were pretty exhausted, hot, and sweaty. However, we saw the Bean, admired the botanic gardens, loved the bridge and the amphitheater, walked through the splash pad area, and even crashed in some grass with a coke. I could’ve spent all day there, if we had the time.
Somehow the day flew by, and we had to start making our way to Union Station for the 3 p.m. train ride home. The last walk through downtown was a little sad, though it became clear with every step that this wouldn’t be our last trip to the city.
Chicago is beautiful and bold and exciting. I loved it, and can’t wait to return.
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