A Weekend in Chicago

“It’s not called The Windy City because of the wind,” a tourist father told his children as we walked behind him in Millennium Park. “It’s because they say the politicians run their mouths like the wind. That’s why it’s called The Windy City.”

Whatever you want to call it, Chicago was beautiful. Even in a hot July (temps in the 90s), the city still made us feel at home in the wild weirdness of its enchantingly vibrant boulevards, city parks, lakeshore, and street corners.
Let me trace our steps for you, not to acquaint you with Chicago in general but to recommend a few haunts to visit.

Would you rather watch than read? Check the vlog here:

We flew out of Austin-Bergstorm International Airport and, as a sidetone, would super recommend the Avocado Fundita (or something) and the Truffle Pomme Frites at Second Bar + Kitchen if you get stuck there.

We landed Friday night, rented a car, drove to the Whitehall Hotel, and crashed immediately. First thing Saturday morning, we got coffee and donuts from Stans Donuts.

Donuts: 10/10!

Coffee: 6/10. Meh.

Caffeinated and sugared-up, we hit the road to Indiana to explore USA’s most recent national park: Indiana Dunes National Park. We weren’t really expecting to get our toes in the sand on a trip to Chicago, but we did anyway. And it was lovely.

It was warm and muggy, but early in the morning wasn’t too bad. We were only on the lakeshore for about an hour. Just long enough to get sandy from head to toe, run up some little baby dunes, get my hair all nasty, and work up a sweat.

We drove back with plenty of day left to enjoy and worked on my road trip playlist (still a work in progress). We yelped a breakfast place that promised to serve eggs + potatoes and ended up at Lou Mitchell’s, claiming to have the world’s finest coffee. It was better than Stan’s coffee, that’s for sure. If you make it out to Lou Mitchell’s, get yourself an omelette “hobo skillet” style and white toast. Then put the skillet on the toast. Bite. Drink coffee. Repeat.

After brunch, we walked downtown and enjoyed the sights. The people were mostly friendly and the city surprised me with its variegated plant life amidst the glass and steel giants on the streets.

The star shape, with a more dramatic point on top and bottom, has always fascinated me. I couldn’t help getting a pic when I spotted that shape on what looked like staff lines in a bridge.

We wandered around downtown, taking new streets at every opportunity.

At some point during this early afternoon adventure, we stumbled across Dark Matter Coffee, which blew my mind. Check out my vlog to witness the absolute beauty of a coffee that I drank and, please, if you’re in the area,
grab yourself an iced aged mocha. Could NOT buy enough merch here…

I drank in the city until a headache pushed us back to the hotel room. I napped. Hard. There was drool, people. But when four o’clock rolled around, I was refreshed and ready for more Chicago. We got gussied up in our anniversary date night clothes and set out again.

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I snapped a pic with my favorite number before we headed to La Story for dinner. I got the eggplant something or other and it was phenomenal, but not as phenomenal as the meatball appetizer which I’m still craving.

We took an after dinner walk, scooping up some gelato at … While on a pier on Lake Michigan, we noticed a group of photography enthusiasts geeking out over light photography. I asked them if it was going well in passing, and, well, they ended up taking our anniversary pics. Thanks to @zo_after_dark and his crew of friends for memorializing our seven year anniversary trip!

Sunday morning we woke up with eggs + potatoes on the brain (again, like always). We strolled through a quiet city to Sunny Side Up, where we were very well cared for with the most perfect breakfast menu I’ve ever seen. If there are breakfast food experts, I’m one of them, and let me please tell you that I wanted to order every.thing.on.the.menu. It all looked so good. We ended up with cinnamon roll-inspired french toast and a carne asana hash that filled us up for our morning adventures.

We visited a church of Christ in uptown and then scooted back into downtown to check out of the Whitehall (with a quick stop to Joe’s Juice & Coffee).

Then we headed to a different part of the city on a mission to see Chagall’s boxcar, The Four Seasons. It was as abstract and quaint as the last Chagall I saw.

In our last few hours in the city, we ran through a library. I climbed into a window (pretty sure that was illegal, as far as library laws go).

I am happy to report that I got to see The Bean. Check.

Now, listen, if you want to try a deep dish pizza, go to Giordano’s. Everything we heard from friends and reviews told us to go there and it was not a mistake. It was our last meal in Chicago. What a send off.

On the way back to the airport, we snapped a few last shots in the city and then it was on a plane and back home.

What do you recommend in Chicago? I’ll go back for sure, so I want all the recommendations you’ve got.

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