Thursday - Travel Day (aka Chicago weather said “not today”)

We left at 6:35 a.m., picked up my mom and her friend (we will refer to them as “the moms”), and headed to the airport thinking we were very on top of things.

Parking and the shuttle immediately humbled us, being a bit slower than normal.

TSA was fine, breakfast by the gate was quick but expensive, and we even boarded on time, feeling mildly smug about it.

Then Chicago weather showed up.

We circled O’Hare for a while learning about the storm do its thing below us, until the pilot basically said, “Yeah… we’re gonna divert to Grand Rapids for fuel.” So we did that. Very normal start to a trip.

We eventually landed about two hours late, slightly reset as people.

By sheer luck, my mom’s friend’s son was in town for work and picked us up, which is still kind of amazing when you think about it, but maybe a not-so happy birthday for him. He drove us to the Embassy Suites Downtown North near the Riverwalk.

Check-in was where things started to feel like a bit of a prank.

We booked a two-bedroom suite. We got… not that. I went down to fix it and was basically handed a different version of “also not that.” At some point you just accept the room is what it is, and start mentally rearranging furniture for survival.

Four adults. One smaller-than-expected space. It was going to be fine. Probably.

Dinner at Osteria Via Stato next door, completely redeemed the night. Really good food, fast service, and the moms were very confident the wine was “the best ever,” which is always a strong post-travel claim (or they were just tired).

Back at the hotel we discovered the safe didn’t work, the phone was dead, and the lamp outlets were decorative. We decided not to investigate further.

Lights out around midnight.

Friday - Hyde Park, Frank Lloyd Wright, and Deep Dish Pizza

Hotel breakfast (omelets included, which helped morale), then Uber to the Frank Lloyd Wright Robie House.

We got there early and walked around Hyde Park, which is one of those neighborhoods that just feels calm in a very intentional way. Big trees, old houses, University of Chicago energy everywhere, and that quiet reminder that the 1893 Chicago World’s Fair basically left history scattered around the area.

Then into the Robie House, where our guide, an architecture student, made Frank Lloyd Wright feel way more interesting than anything I remember from school.

My son met us there, which made it even better.

After that, we trained over to the Avondale neighborhood to meet my sister, who had just landed and immediately got initiated into Chicago traditions via Giordano’s deep dish.

Everyone politely agreed it was “interesting,” which is Midwest for “we have thoughts.”

But honestly, the food mattered less than the fact that everyone was finally together.

We later hung out at my son’s apartment, met the cats (who clearly run the place), and eventually drifted back toward the hotel. Drinks and appetizers at the hotel basically turned into dinner without anyone formally deciding that was the plan.

We ignored the room issues again. Growth.

Saturday - The Bean, museums, and a ghost tour that actually delivered

We asked the hotel to fix everything while we were out. They said they would. We chose to believe them.

We walked to Millennium Park, met up with my son and his girlfriend, and stopped at The Bean (Cloud Gate).

It’s one of those things that’s hard to explain until you’re standing under it. The skyline wraps around you in a way that makes it hard to tell what you’re looking at directly and what you’re seeing reflected. You kind of lose track of edges. Everything blends together in a way that feels slightly unreal but still grounded enough that you’re just standing there like, “okay… this is cool, but also what is happening.”

From there we went to The Field Museum of Natural History, which ended up being way better than expected. You start with the smallest pieces of life and end up staring at dinosaurs thinking about how long ago everything actually was. You could spend a whole day there easily.

Dinner at Gordon Ramsay Burger was next, simple, good, no drama (no one got yelled at - that we heard).

Then the Chicago Hauntings Original Ghost Bus Tour.

We met at the Congress Plaza Hotel, which already feels like it knows something you don’t (and it does - look it up). The bus itself was actually great, comfortable, clear audio, not at all the chaotic situation we were bracing for.

The guide was the real deal: decades in Chicago, background in paranormal investigations, even appeared on Ghost Hunters. He knew every story and every stop.

We went all over the city, haunted locations, historic crime sites, and places tied to major tragedies like the Eastland Disaster and the Iroquois Theatre fire. At a few stops we tried EMS devices in the cold, which felt very “we are doing this now”.

It was freezing outside, but the bus stayed warm and made everything tolerable again.

Really good tour. Worth it.

Sunday - Surprise brunch & the river cruise goodbye

We pulled off a Mother’s Day surprise at The Gage. The moms thought we were going to hotel breakfast until we rerouted them across the park. My son and his girlfriend were already there waiting, which made it even better.

After brunch, we walked to the Chicago Architecture Center River Cruise Aboard The First Lady.

That guide was incredible, just nonstop knowledge. You float down the river and suddenly the whole city becomes a timeline. Marina City, Willis Tower, Wrigley Building, Tribune Tower… everything stacked together in glass and steel.

It was beautiful, and also very cold once you were in the shade between buildings.

By the end, it was time for the part of trips that never really gets easier: everyone splitting up.

Saying goodbye to my son always hits in a way that sneaks up on me. Even when you know it’s coming.

A nice dinner at Andy’s Jazz Club with the ladies ($20 cover at the door. You need to make a reservation a few weeks in advance) and back to the hotel to pack for an early morning departure.

Monday - Head home

Uber to the airport with four women and luggage was the obvious choice at that point.

Everything went smoothly, which honestly felt a little suspicious after the rest of the trip.

Flights home were easy.

Round Up

A few hiccups, a lot of walking, some questionable room assignments, and a whole lot of time together.

We used Viator to pre-book everything more than a month ahead of time, and I am glad we did. Even in the off-season things book up. Doing so worked out great. One note though, for the Robie house, the Viator booking got you a ticket but not a day or time. In early May it didn’t end up being a huge issue, but it would be wise to call them when you buy your tickets to lock down a time.

Give yourself plenty of time as it takes a bit to get the train down as well as get your bearings in a new city.

Chicago did what Chicago does. It’s beautiful, friendly, spacious and clean. I highly recommend a very long weekend or short week in the city!

O’Hare Delays, Haunted Hotels, and The Bean Confusion