Chicago In One Day: My 18 hour under $300 journey

I had not been on a plane since the pandemic began, so I couldn’t pass up an offer from Southwest Airlines that I learned about through Thrifty Traveler: register for the promotion, take one round trip flight this season, and earn unlimited two-for-one status for travel this January and February.

(For those that don’t know about Thrifty Traveler, it’s founded by our friends Jared and Erika, and is a must-subscribe service for anyone who loves to travel. Sign up here.)

So I bought a round trip ticket to Chicago just to earn the promotion. My original booking was first flight out of MSP at 6:25am, land at Midway, maybe have time for a bathroom break, and take the next flight home back to MSP, landing at 11am, just in time for brunch with the family.

Then I started to see the weather reports, predicting a PERFECT day in Chicago. Being Southwest Airlines, they allow free ticket changes for everyone (which, along with two free checked bags, makes them awesome). So I changed the ticket and mapped out a whole day in the Windy City.

Here I’ll step you through my entire solo day in Chicago, Sunday October 17th 2021, through photos and stories, including wines consumed (and the best wine by the glass bargain I’ve ever found), food devoured, and total amount spent. Here we go!


OFF TO THE AIRPORT! It’s 4:45am, and I have barely slept because I always fear missing an early morning flight. I’m also one of those people that like to show up super early at the airport, not worry about anything, and enjoy some food and drink. So I’m already running on fumes.

BREAKFAST AT BARRIO in Terminal Two. The breakfast sandwich at Barrio is one of my favorite ways to start a day. It’s a delicious and absolutely perfect sandwich. The coffee was hot and strong. Awesome way to begin. $16.73.

ON THE PLANE! My first plane ride since January 2019. Full flight, early morning, quiet, and kinda weird feeling packed in with all these fellow travelers. My Covid anxiety started to go up, but I fell asleep pretty quick so that solved that.

ON THE TRAIN! I love flying into Midway and taking the Orange Line into town. We did this regularly when Spencer was going to school there. There’s a special deal right now for an all day CTA pass for trains and buses for only $5.00. Check!

INTO CHICAGO, AT THE ROOSEVELT TRAIN STOP, which is a main connecting hub for the other trains. This is also the neighborhood that Spencer lived in during college, so it was good to be back. I headed downstairs to the Red Line (subway) to go south into Chinatown.

8:30 AM. CHINATOWN! Not as big and busy as Chinatown in San Francisco, but still a wonderfully tight community and a fun morning walk. The goal was Dim Sum at Three Happiness, an insider’s secret 24 hour Dim Sum institution in Chicagoland.

Alas, Three Happiness was not open. Nor was most of Chinatown. By then it was 9:10 in the morning and most Dim Sum places don’t open until 10 or 10:30.

But I knew a secret!

IMPERIAL is a wonderful restaurant on the second floor of the Chinatown marketplace. It’s a little hard to find, but is a favorite of locals. What’s nice here is they don’t have Dim Sum steam carts, but rather everything is made ala carte to order. After breakfast at Barrio, and knowing I had a big day ahead, I only ordered a couple of items.


BBQ Pork Rice and Crepe Roll, plus a delicious order of Shrimp and Corn Dumplings. Total cost with tip: $13.42.

Back into the city and wandering around: the Bears were playing the Packers at noon at Soldier Field, so the fans were out and the tailgating was starting! Cornhole, beer, and music all around.

I found a nearby Peet’s Coffee and Tea for a few hours of work on the laptop.

From the Printer’s Row/South Downtown area I walked all the way up Michigan Avenue to see the sights. I love the Chicago Institute of Arts so much, but time was limited.

During the whole day the only transportation I took was the train from the airport to the city, and the quick jaunt down to Chinatown. Otherwise, it was all on foot and bike, at least ten miles or so. My feet are so sore!

Destination: Al’s #1 Italian Beef! Even after years of going to Chicago multiple times a year when Spencer lived there, I never made it to Al’s. Time to solve that problem.

I ordered it classic “Hot Beef, wet” meaning spicy peppers and the bun is dipped into the au jus before building the sandwich. This makes for great flavor but you have all of three or four minutes to eat it before it falls apart completely. Man, this was good! The French fries at Al’s #1 were equally fantastic, the best I’ve had since the State Fair.

POPS FOR CHAMPAGNE is still cranking, but I’ve always found them horribly expensive. Plus after the Hot Italian Beef I didn’t want to be burping all afternoon, so I kept walking.

TIME FOR EATALY! And also time for me to tell you what feels different there.

As many of you know, Eataly is one of my favorite destinations. It’s heaven for the lover of Italian wines and food. The marketplace along with all the restaurants have been consistently incredible, but this was the first time I’ve been back since the pandemic hit.

Things have changed at Eataly, as expected. You can see the impact of the labor shortage, and they have rearranged things quite a bit. The seafood and meat centered restaurants are not open, nor is the Birra beer garden. They are not serving wine by the glass in the wine shop area. Most of the restaurant area is now just the Pizza and Pasta concept, but strangely they don’t have the eat-at-the-bar area open.

And overall, things just felt kinda chaotic and messy. Bits of food on the floors. Abandoned glasses and cups around the space. Shelves not organized. Don’t get me wrong, I still had a blast, and it’s still a must-go destination, but it’s just different.

So I went downstairs to near the Gelateria to have a quick glass of wine, my first of the day.

That’s what a $15 “glass” of Gavi di Gavi looks like at Eataly.

My guess is that it’s about four ounces, maybe even three and half. The person at the counter poured it into a plastic cup even though she had stemware right in front of her. “Can I have it in a glass?”

“No, we’re using cups now.”

“But other people have stemware, they are walking around with it. Like that person,” as I pointed out someone three feet away.

“Oh they got that upstairs. We’re not doing stemware down here.”

Okay, whatever.

The downstairs area between the pasta station, the coffee station, and the gelato was PACKED. Chicago is enforcing mask wearing in all indoor spaces including restaurants (no admittance without a mask on), but masks are not required when eating and drinking, which is what EVERYONE was of course doing there.

So my covid anxiety kicked in, and I was mad about the price of a tiny cup of wine, so I drank it quick and got out of there after buying some pasta to take home for Spencer.

Time to walk it off. Time to head to a good wine bar.

Oh no!!! What happened to The Purple Pig wine bar! It’s now a Chik-Fil-A … what the hell is the world coming to?

My frustrations with Eataly were still simmering when I came across what used to be the location of one of the top wine bars in America. Cue the sad face. 😞

Then I walked twenty steps further down the sidewalk …

Do I read that right?

The Purple Pig moved to new digs just across the way from the old location. They did this in December 2019, just ahead of covid hitting the US. The new location is laid out quite similar to the old, and as far as I can tell it’s the same tables, bar, and wall decorations. The main thing is a bit more elbow room (you couldn’t get tighter packed than you did at the old location), and a much larger kitchen. The energy is still the same, with the music blasting, and good (rich and filling) food being served.

I was still trying to sweat out my Hot Italian Beef sandwich, so I opted for a glass of wine. A nice white from Portugal. Look, it even came in a glass! How fancy!

If you take your cell phone camera out and scan this image, you’ll see their current wine list and menu.

Time to walk (and ride) off some of the day’s food and drink! I hoofed it to the Riverwalk, then sauntered in perfect weather to the lake.

By that time I my feet were screaming at me, so I picked up a Divvy Bike for a few miles.

It was a BEAUTIFUL day in the city, with loads of people out and about. The Grant Park area in particular was amazing at sunset, and I enjoyed about an hour of watching the kids at the skateboard park. My flight out was at 9:30pm, and I wasn’t opposed to getting to the airport early and just whipping out the laptop to work a bit, but why pass up time in Chicago?

Plus, I was feeling a bit stung by the costs of things at Eataly and Purple Pig. Maybe I’m just jaded after 18 months of not eating out, but the prices just kinda shocked me. Combined with the crowds, I was just not feeling what I wanted to from this trip.

I wanted one more stop. Maybe a bit more food.

Then I walked into one of my best travel wine moments … ever.

Aureilo’s Pizzeria is just off the corner of Roosevelt and Michigan Avenue, right where I happened to find myself after a couple hours at Grant Park and before hopping on the Orange Line back to the airport.

I wasn’t feeling like thick Chicago-style pizza (not after that afternoon sandwich!), but these guys offer a great thin crust and well as a “Lil” size six inch pie. Perfect.

Even better, the three people across the bar from me were WAY DRUNK. Just crazy shitfaced, laughing and swearing and being told by the bartenders and managers to keep it down. I love a good drunk show. Man they were loud! I should have shot a video but I was afraid they’d see me.

And then …

I’ve always said there is a bargain on every wine list. Sometimes “bargain” means an off the radar wine that simply delivers more than others. And other times “bargain” means BARGAIN.

Look at this. Kim Crawford Sauvignon Blanc for $11 a glass. Coppola Claret for $11 a glass. Santa Margarita Pinot Grigio for $12 a glass. And Duckhorn Cabernet Sauvignon for TEN DOLLARS A GLASS!!!!

What the hell?

I looked at the rack and there is was, so I ordered it.

Opening a fresh bottle for me!

So what’s going on here? How in the world are they pouring a $60+ (retail) Cabernet for $10 a glass? Most steakhouses in Chicago charge well over $100 for this wine.

Who knows. I don’t know if they have mis-priced it, or if the fact that Duckhorn is now publicly traded and only works with mega-distributors that will do whatever it takes to show depletions (sales) has anything to do with it, but I’ll take it.

To the tune of three glasses while I watched a football game and the drunk people.

Duckhorn Cabernet Sauvignon with a Miller Lite coaster. This picture says it all.

And the pizza was awesome. Total bill with a generous tip: $48.12.

One final stop at a favorite donut shop, Stan’s, to have dessert. $2.46 for a glazed donut.

Mmmmmm … donuts.

Back on the Roosevelt stop for the Orange Line to head back to the airport.

Arrival back at MSP Terminal Two. Exhaustion was just starting to really set in.

And back in the car just after 11pm.

What a day!

WHAT MY ONE DAY CHICAGO ADVENTURE COST

Southwest Airlines, MSP to MID round trip: $114.72
Breakfast at Barrio in Terminal Two: $16.73
CTA one day pass for trains and buses: $5.00
Dim Sum at Imperial: $13.42
Tea at Peet’s Coffee, with tip: $4.00
Al’s #1 Italian Beef sandwich with fries: $14.35
Eataly, one tiny little plastic cup of wine: $16.77
Purple Pig, one glass of Portuguese white: $16.53
Divvy Bike rental: $3.80
Aurelio’s Pizza Chicago, with small pizza and three glasses of Duckhorn Cab: $48.12
Stan’s Donuts: $2.46
One beer at Midway Airport before flying home: $13.00 (yikes, don’t buy beer at airports!)
MSP one day parking: $19.00

GRAND TOTAL: $287.90

Plus, now I have two-for-one Southwest Airlines flights during January and February. Florida, Arizona, California, and maybe Hawaii, here we come!!

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