Chicago, My Kind of Town Not on a Budget

But oh, so worth it

“My heart beats differently when I’m in Chicago. It slows down and I feel more at ease.” — Jeremy Piven

Photo by Aveedibya Dey on Unsplash

We celebrated my husband Carl's birthday this week. We originally planned to rent a pontoon boat and hit the waters of Lake Michigan to swim and picnic.

But.

For weeks now, I’ve been gearing up to go to Chicago by myself. It’s been 5.5 months and three days since I hit a major metropolitan city. I’ve all but lost my street smarts and intuition needed to immerse myself in crowds of people, honking horns, street walkers, and the hustlers who prey on the weak.

If you don’t use it you lose it.

Practicing navigating metropolitan cities is also keeping me polished for scouting potential relocation sites later on this year. Since my Spanish is lagging, self-confidence is all the more important for the endeavor.

This was the perfect reason to go to Chicago—to celebrate Carl’s birthday in style. We were going to spend the time and money anyway. The cost of the pontoon for four hours was $546, with an additional $25 per hour if we brought a dog. (Rolling my eyes, I still don’t have my own dog.)

Carl's such a good guy that he offered to take me to my new favorite city, the one he isn’t crazy about, instead of spending a few hours on the lake.

“I’ll do whatever you want to do. I’ll get the room; you make the plans and let’s go. We’ll stay for a couple of days,” my husband said, cheerfully.

Did I mention my husband is a good guy?

We booked an architectural boat tour, added a nighttime Cubs baseball game, and planned a Chicago dive bar crawl on the way to the game.

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Our 3-hour drive started with a quick stop at the Blue Chip Casino in Michigan City, Indiana. We ordered two $19 chicken salad croissants, two steaming hot cappuccinos, and a small bag of jalapeño potato chips. We hit the nearest blackjack table with a $40 buy-in, and walked away with a $400 win. The perfect way to begin our trip, booking a winner from the start

Checking in

The Warwick Allerton was located in the heart of downtown Chicago, just steps from Saks Fifth Avenue and Neiman Marcus (otherwise known as "Needless Mark-Up" by my husband).

Apparently, the needless mark-up wasn’t confined to the retail shopping; it also extended to our hotel room.

The room was $350 a night, with parking costing an additional $65 a night, plus deposits. The room was 274 square feet and barely held the queen-sized bed. We originally booked a king and confirmed. The first clue this hotel may have been a mistake.

One more not-so-interesting detail to note: When Carl booked the room, he specifically asked if their pool was in working order; it was the main reason he chose this particular hotel, that and its location. The reservationist confirmed it was open, and indoors.

The Warwick Allerton has no pool on-site. What they didn’t say was that the nearest lap pool was 1.3 miles away.

So much for luxury in a 4-star historic hotel on Magnificent Mile.

We didn’t have time to complain. We needed to find public transportation. Our riverboat architecture tour was in less than half an hour.

We’d make it work.

The boat tour

The blend of historical and modern buildings creates a visually stunning cityscape, and for me, best appreciated from the water. The cost was $63 per person for a 90-minute tour. While the architecture is Chicago’s stunning signature and looks beautiful from a distance, I needed a more personal connection. There is no better perspective than from the water, weaving in and around the bends of the Chicago River.

View of the Harry Weese River Cottages from the Kinzie Street bridge Image Credit: Andrea Bauer

The skyscrapers were magnificent in stature, but this strange and rather ugly gem truly captivated me. Designed on a human scale, the cottages are more approachable and not so overwhelming.

I dream of living in Chicago in another life. One of the cottage condos would be perfect, and fit into my imagination nicely.

Built in 1988, each unit initially cost around $300,000. The only one I could find that sold did so in 2015 for $2.25 million. These cottages were designed by Chicagoan architect Harry Weese. What’s unique is their combination of urban and waterfront living in the heart of Chicago, embracing the challenges of old man winter.

I did more research and found a bit more about the one that sold; and the short article does share a short video and a few images of inside the Nautical River Cottages, which makes the building even more fascinating to me

I learned a lot on the tour about Chicago, namely information on trying to navigate direction, and how difficult it is, even for those who live in the city.

Think of Chicago as a coordinate plane of sorts.

The origin is State and Madison. State runs North/South and tells you how far East/West you are (0 in this case) and Madison runs East/West and tells you how far North or South you are (also 0 in this case). The intersection of State and Madison is 0, 0. From there, you can go out in any direction into any “quadrant”. How far you go will determine the new values. Say you take State north 2 blocks and end up at Lake (200 N) You’re now at 0 E/W and 200 North. (1 block = 100 numbers and 8 blocks or 800 numbers is roughly a mile). Take a random intersection, say Fullerton (runs E/W) and Central Park (runs N/S). Fullerton is 2400 N (24 blocks, or about 3 miles north of Madison) and Central Park is 3600 W (36 blocks, or about 4.5 miles west of State)… …….Hope this makes sense.—polar_chimp, Reddit

Huh?

The city is built around the river, with streets designed on a grid system. Originally built for commerce, manufacturing, and shipping, today it is geared more toward tourists, retail, and recreation. It's also more bike- and pedestrian-friendly than any other US city I've visited, except maybe San Francisco (I haven't been to NYC or the boroughs yet).

It's going to take many more trips to figure out how to get around Chicago without getting lost all the time.

Cubs win, Cubs win, Cubs win (5-3)

I haven’t been to a professional baseball game since the '80s. I’m dating myself. So what?

We caught a cab and stopped for Italian appetizers ($109) at a mom and pop, and then walked to hit a few sports bars in Wrigleyville. Along the way to the ball field, we bumped into hustlers, hawkers, and even saw a few shooting up in the alleys.

Some things never change.

Tickets to the game were $233. Two bottles of water cost $18, and two hot dogs were only $16 (the latter was a bargain). The cab ride both to and from the game was around $35 (another bargain, considering the time and convenience). The five beers we took up to the room after the game cost $45.

We couldn’t have asked for a better night spent at the ballgame. The seats were perfect and our neighbors were a hoot.

Image: Courtesy of the Author

After the game, we headed out of the stadium and soon realized the train was packed (not that we knew how to catch the train or even where we were going), and cabs were absent. With over 37,000 of us leaving the park at once, what to do?

We got lucky. Pure and simple. A policeman had the road blocked, so traffic was rerouting. A cab was turning the corner, and the driver saw us hail him down and stopped in the middle of the busy intersection.

Did I say I love Chicago?

Saying goodbye early

We woke up the following morning and agreed it was okay to cut our stay short. What I didn’t mention earlier was that my husband forgot his C-PAP machine, the one that keeps him from stopping breathing in his sleep all night.

I stayed up in case he stopped breathing so I could nudge him. He tossed and turned all night because I was nudging him.

We browsed through "Needless Mark-Up," where I found a shirt dress I couldn't live without but was forced to leave behind. Then, we checked out of the hotel early with the promise of getting a refund for the night we missed. They refunded the parking fee and the deposit, so there’s that.

“Needless Mark-Up”

We stopped for a quick breakfast. For the money, was it worth it?

Yes, it was worth the money spent!

I included the cost of this birthday celebration to underscore the growing disparity between the rich and the middle class in the U.S. It's becoming increasingly difficult for many to afford even a modest getaway. The middle class finds itself edged out, struggling to justify the expense of vacations that were once considered attainable.

Next time I head into Chicago, I’ll be visiting on a budget to prove that you can have an incredible time for under $100.

See you next week!