After a red eye flight from PDX, I arrived early on a slightly delayed flight to Chicago. Just as with my last visit to Chicago, I was immediately reminded of the kindness of Chicagoans. From my seat at the back of the plane I could see the bags being unloaded from the plane and happened to see my own suitcase go down the conveyer belt, unzipped and broken. The zipper was finicky before I left, and perhaps came undone during travel. The crew was carefully unloading it to be sure that it was flat in the cart and even checked with someone else to see if there was anything else they could/needed to do with the broken suitcase. I rushed to baggage claim so that the rest of the world didn’t get access to my wide open suitcase, and luckily found that it had arrived just the same on the arrival carousel, everything still in tact. Kudos to Alaska Air.

Instead of the Blue line to my destination in Logan Square and cradling my broken, un-rollable suitcase, I decided it would be better to take the Lyft ride. $30 from O’Hare to Logan Square with some Thursday morning rush hour traffic. My driver was from Ghana and we talked about Ghanaian culture, and all the things he loved about living in Chicago. He then proceeded to carry my little broken suitcase out of the trunk and up the steps when we arrived.

I wondered what a post-covid Chicago might look like, as people start going about in a somewhat normal way again. Apparently it’s turned into at least 2-3 hour long waits at places that you used to be able to walk right into on the weekends, due to efforts to keep less crowding. It seems that especially on weekends and Fridays, reservations are essential.

THURSDAY

After a power nap, we tracked down the famous Woolly Mammoth Antiques and Oddities (an Atlas Obscura find), home to everything from taxidermy hounds, skunks, pets and more, to teeth, bones, hands, and life-size Bert and Ernie. It’s a tiny hole-in-the-wall, but worth a quick peek if you are in to weird things, like me. Just around the corner is a great little coffee shop, La Colombe Coffee Roasters, and HopLeaf Bar, where we stopped for lunch. I also found the best Pils I have had since Germany in this neat little stop, along with a fantastically paired beet and asparagus salad, and some pommes frites that also brought me back to my European outings. There were not a lot of vegetarian options at this one, but I’d still opt into HopLeaf for the vast assortment of European beers and sumptuous snacks, especially for those who like to reminisce over their years abroad.

For dinner we went to a local favorite called Parson’s Chicken and Fish. Friends explained that the cocktail slushie (Negroni) was the must-have drink, along with the fish sandwich, since I do not eat chicken. We started out with the best hush puppy plate I have ever had, paired with breaded shrimps and killer fries. The honey sauce is not to be missed here. The old diner vibes were real, and were really the only way to start our night out bowling.

In the evening we found ourselves transported back in time for a good old-fashioned game at Avondale Bowling. The 2nd floor bowling alley had a very original feeling 50’s retro bowling alley, complete with a vinyl DJ, endless fifties music and not-overly-shiny alleys. I have a strong affection for bowling shoes, and unfortunately my one disappointment was the velcro bowling shoes instead of the clearly sexier laced shoes. There is a great cocktail menu (and even cocktails to go in a bottle) to pair with your high school math skills – you have to add up your own scores. We had to learn how to self-score! A lot of time was spent counting here (far too much math for my post-cocktail, liberal arts degree brain 😉 ) . Electric score boards are certainly a luxury I have under appreciated in my modern bowling days.

FRIDAY

The next morning we started with coffee and donuts at West Town Bakery, then on to a tour at the Frank Lloyd Wright Museum, Home and Studio in Oak Park. Because I have spent so much time in Phoenix, I was well-accquainted with Wright’s Phoenix homes, but not as much with where he and his Prairie architecture all began, his home in Wisconsin and life in Chicago. I was excited to see that all of our tour group, except the two of us, were international visitors. Our tour guide, coincidentally also named Frank, was extremely knowledgeable and a great guide. He put many of Wright’s theories and reasons for success into vivid perspective during the tour of his home and through his life as an architect in Chicago.

We learned the tell-tale stamp of a Frank Lloyd Wright building, and the five pillars most important to Wright in his creation (the tour guide wanted to be sure we memorized this):

1. Connection to nature (something I also greatly value in his work)
2. Music (he had a baby grand piano that he played to inspire his six children to be creative)
3. Fröbel (building blocks meant to inspire creativity)
4. Japanese architecture and culture
5. Luis Sullivan (once his boss, and long-time friend)

One of my favorite parts about Wright’s homes, especially in Phoenix where his architectural design school is located, is his belief that nature should not be destroyed to build a home. It should be built with, through, and within nature.

At our guide’s recommendation, after the tour we drove the streets around the museum to find other buildings that had been designed by Wright by identifying his signature home traits – primarily discreet, unassuming, and geometric. We ended our adventure in the Oak Park area at the Unity Temple, which the guide described, “as if someone from Mars had dropped a building down to Earth.” As we pulled up in front of it, I thought, now this looks like a prison. Not helpful to its plight, it is greatly contrasted by the First United Church of Oak Park directly across the street. However, the interior of the church was much more Wright-esque, in his use of psychology in buildings and quintessential nod to nature.

His goal was to build “a temple to man, appropriate to his uses as a meeting place, in which to study man himself for his God’s sake.” Wright’s choice of concrete kept costs to a minimum while enabling the façade’s ornament to be cast in, rather than applied afterwards at additional cost. To reduce the noise from the street windows were eliminated at street level. Instead, stained glass skylights and clerestories provided light to the space in green, yellow and brown tones in order to evoke the colors of nature. (Frank Lloyd Wright Foundation)

It was officially snack time as we made our way towards the Ukrainian Village, home to Fatso’s Last Stand – where I sought to find an epic Chicago meatless hot dog. I heard they existed. You see, it is possible to match everything you need in a hot dog in a veggie dog – the taut outer layer crunch, the juicy, salty inside wrapped in the perfect bun and topped with great additions. Thus far, the only place I have found a hot dog that meets those needs, is in the Beyond Meat Sausage (and Fatso’s does sell a Beyond Burger!). However, the veg dog here taste more like tater tots rolled up in a hot dog shape and topped with the appropriate hot dog toppings. Which, is not by any means terrible, but it will not win my “world’s best Chicago veg dog” accolades. I need the hot dog juice and crunch. I cannot advocate for their standard hot-dogs whatsoever, but they were awfully popular and I can only assume, wonderful. The fries were on-point, and I assume their tasty looking milkshakes, were too!

That night we ended at the Boiler Room. Friday night’s post-covid in Chicago are no-joke. This was only after we walked into 2-3 places, ranging from noodles to sushi to pizza and were met with 3-hour wait times. And nobody has time for 3 hour waits after work when you’re hungry! The Boiler Room had a 30 minute wait, and a spot to drink a beer as we waited, at the bar. Lucky for me, it even gave me a chance to experience Chicago’s signature shot and apparent right of passage, Malört, a Swedish wormwood drink that Chicago apparently has a strong love/hate relationship and long history with.

“While Malört means “wormwood” in Swedish, the Russian translation of the word is “Chernobyl.” The infamous nuclear power plant was named after the native wormwood fields that once grew there… you know, before that whole radiation thing.” (Thrillst.com)

SATURDAY

We decided to begin our weekend with all you can eat sushi. You know, the food that fills you up really well at the time but you don’t feel completely stuffed for hours. The place that had a three hour wait the night before was much much subdued when we arrived just before noon, though it fulled up quickly. Sushi Taku boasts an impressive “all you can eat” lunch menu for $21.99. And yes. we. did. Delicious endless rolls, nigiri, and topped it all off with mochi. We took a quick wander down the street to the Steel Petal Press for some fun gift shopping (both local Chicago gifts and fun gag gifts) before hopping on the “L” downtown to find the Route 66 sign (which had been on my to-do list) and take an obligatory photo-op at the Millennium Park Cloud Gate.

Pro-Tip: We learned that you can in fact “tap” your credit/debit card at the entrance to the “L” Line and don’t even have to go to the ticket kiosks. It literally just charges it to your card.

We made reservations for Logan Square Improv in the evening for a fantastic free to $5 performance of some pretty great comedy. Although, even on a Saturday night, we didn’t necessarily need a reservation for the 7 pm show. It’s a low key, high comedy corner that was a great way to get the evening going with some hearty belly laughs. The intimate venue is BYOB, and beware, the seats are small and cozy. The show, “whose line is it anyway?” was just an hour, but we would have gladly stayed much longer or even for later shows if we didn’t already had reservations for Pequod’s Deep Dish pizza. We tried to walk in without a reservation the day before and were met with a three hour wait. Reservations, apparently since the pandemic, are suggested. And yes I did have pizza two days in a row. Pequods was rumored to have even better pizza than Chicago’s Pizzeria Uno or Giordano’s. I’m not an expert on deep dish, so I can’t compare. But the place does have a great vibe, was packed, super casual and full of that old-school pizza shop vibes that we loved from high school, you know, the red and white checkered plastic tables type?

Next, my friends were on a quest to find me a “traditional style cocktail bar,” after hearing of my intent in visiting the Violet Hour, which is certainly no secret speakeasy – hidden only by a door that matches the wall. We walked by and scoped out the wait for the Violet Hour, which we learned would be (you guessed it!) three hours, and you certainly can’t wonder too much about what the line of people outside would be waiting for. Supposedly they make some of the best cocktails in town. We made our way to the California Clipper, a 1930’s bar lounge with an impressive historic bar, drink list and a great Saturday night DJ. It had all the cocktail culture vibes. That evening it was filled with the usual characters you might expect, girls-night-out in luxurious coats and short skirts, low-key friend groups, Tinder dates, and some groups we couldn’t quite figure out.

SUNDAY

Sunday was a low key day. We started with the classic Chicago Dinner, a refreshingly vegan classic style diner. I was extremely tempted to try their famous vegan take on the Chicken Fried Steak that had such rave reviews, but after eating so much fried food this trip, I opted for a little bit more diversity and ordered the breakfast bowl. I also ordered the award winning vegan milkshake (this splurge was non negotiable), which was in fact just as life changing as I had hoped. It was creamy and unassuming, and topped with the perfect dollop of whipped cream. I ordered the strawberry because I ate too much in general, but they also had very rich sounding cookie dough and peanut butter flavored, and a variety of others. Afterwards, and to settle breakfast, we made our way to Dark Matter Coffee. I had my heart set on taking home some of Chicago’s finest local brew, and was sent to Dark Matter to fill that bill. If their artwork and design and coffee names don’t win you over, their variety of flavors certainly will.

To conclude the trip did some sight-seeing and beer. We head over to the Gold Coast because my heart was set on finding the very first apartment that Ernest Hemingway and his first wife Hadley had lived in. As I stood in front of the brownstone row house from 1887, my mind flickered back to the pages of The Paris Wife, by Paula McLain, one of my favorite stories.

“Hadley’s married life began in a cramped, shabby apartment in a poor neighborhood. The grimy, top-floor walk-up was at 1239 North Dearborn Street in a run-down section of Chicago.”

That poor neighborhood eventually turned into Chicago’s Gold Coast, now a ritzy and high end area of Chicago where the Chicago’s rich and elite make themselves at home. After all, the original Playboy Mansion is just around the corner.

We drove past Oz Park to see the character statues, because why not, and then ventured on to some of the local breweries to get a better taste of Chicago. Half Acre Brewing had a great set up, an impressive event space and beer garden circled by aging barley wine barrels, and a well-lit, open and friendly bar. I chose the taster flight, as I do, to get a wider array of what a brewery has to offer. Lighter and fresh in flavors, I can only imagine what a great hangout this place is in the summertime. It was a bit too cool for my Arizona bones to sit outside on that particular breezy Sunday afternoon in April.

Then it was on to Spiteful Brewing, a quick walk around the corner from Half Acre. This cozy tasting room ended up being where we spent the rest of the afternoon. I tried many of their beers; Spiteful Radler, Farthing Dark Mild (you guessed it – an English Ale), Cubby Bear Lager (this oh-so-Chicago beer came back to Oregon with me), Spiteful Hefe, Bleacher Bum (a most unique blonde ale with peach), Turnstile Hopper and the The God Damned Pigeon Porter, to name a few. I was impressed with the assortment and variety of flavors they had to offer. After looking into their story a bit, I was excited to see that they had roots to both Tucson, Arizona and Boulder, Colorado!

MONDAY

I arrived back in Portland on Monday morning, just under the radar before the official Covid mask mandate in airports and airplanes was lifted. I had a new carry-on suitcase to get my belongings home and it passed its first flight test without a scratch. It is my first carry-on with 4 wheels and a hardshell. I know, I’ve been old school for a long time.

It was now my chance to try the Amtrak route I had wondered about, especially for friends making their way to visit. I knew that the trains were about the same amount of time as a car for some routes with traffic and such, and they certainly are much more scenic, but I wanted to test out the real experience.

Having just stepped off of a terribly cramped, 4.5 hour flight from Chicago where the Wi-Fi was “down” and the plugin to charge my phone was essentially non-functional, the accommodations and experience of the Amtrak starting at the Portland Union Station were very welcome. I am convinced the airline seating is getting smaller by the year. I took a $28 Lyft from PDX to Union Station, a quick hop over the river, and was dropped off at the grand entrance to the historic Union Station, an impressive historic building built in 1896. The seating in the waiting area is that of the movies, with the long wooden benches and grand ceiling overhead.

The train ride cost $21 from PDX to Albany, Oregon, offered free high speed Wi-Fi, a plugin at my seat, ample leg room with plenty of space for bags overhead, a fantastic window view of rivers, greenery, and some housing, and very friendly staff. I learned that the 503 Cascades train does not have the upper deck which I was hoping for for a better view (I believe the Coast Starlight does). But it was the 503 Cascades south that happened to be going where I needed to go at that time. The Cascades didn’t arrive until 2:22 pm, and I needed to leave before noon. There were both seats of two, and seats of four facing each other options within the car, but far more two seaters. Bring a blanket or cozy jacket, the train was rather cold. I will absolutely make use of these trains in future travels across Oregon and Washington, you can even book tickets on their app, and gather points! There were no foodie opportunities on my somewhat short train ride home, but I do believe there was a bar at Union Station, which I did not have the opportunity to investigate.

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