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My first Greyhound trip (Milwaukee to Chicago)

What, Kev is talking about taking a bus trip? Yes, I booked my first Greyhound trip due to a recent event. Nothing terrible, but Greyhound fulfilled a need and gave me an adventure all in one. Sit back with your favorite beverage and find out how Greyhound saved the day and earned me some brownie points.

My first Greyhound Bus Trip
My first Greyhound bus

I didn’t plan on that happening!

Recently, my folks returned from an extended stay at my sister’s. She lives in the greater Omaha, Nebraska, area. My folks planned to take Amtrak’s California Zephyr from Omaha to Chicago, Illinois. They would transfer to the Hiawatha in Chicago, and that train would take them to Sturtevant, where I would pick them up.

As I was sipping my morning coffee, my folks’ were rolling through western Iowa. I thought it would be nice to call them to check in on their adventure.

I have faith that my folks could handle their whole trip independently, but I thought I would offer my assistance.

My dad said they were fine, and my mother gave a typical mom response, “it is up to you.” Knowing my mom is a nervous traveler, I realized I should dig a little deeper, so I asked, “what would make you happy?” She then admitted that she would feel better if I came to Chicago, and she and my dad would appreciate it.

Their train was coming in early, which meant there was a chance for them to take the earlier train. Depending on how early it got in, it could be too tight to do at the station, so they would need to call Amtrak. Typically, in non-pandemic times, they could have used their tickets on an earlier Hiawatha, but that is not the case.

Knowing the Hiawatha schedule, I knew I did not have much time to put this trip together, a little more than an hour. I also needed to buy my tickets quickly.

I logged into my Amtrak account, put in my station codes, and up came something I did not plan on; my train showed sold out!

Why did I pick Greyhound?

Amtrak’s Hiawatha at the Milwaukee Intermodal Station

I planned to take Amtrak down because it was quicker and got me to where I needed to go and start where I needed to end up at Sturtevant depot.

Due to the pandemic, the Hiawatha schedule is limited with no mid-day train, so I needed to leave earlier than I wanted, by several hours.

My natural second choice is Metra, but in this case, it was not an option because it would take longer. Since they were coming in early, I could change their Hiawatha reservation and get them home early with the 3:15 train instead of the 5:08.

So, how can I make this trip work?

Not wanting to disappoint my folks, I found another option, I could take Greyhound to Chicago. I found they had a bus that would fit my needs, and I could get to Chicago before them! Then came the new problem, I needed to get to Milwaukee.

While Amtrak inadvertently caused this issue, they also came to my rescue. A northbound Hiawatha could take me from Sturtevant to Milwaukee to catch a bus to head South. Conveniently, the Milwaukee Intermodal Station is the home to Amtrak and Greyhound.

A lot of work but worth it for my folks, right?

The Trip to Milwaukee

Amtrak Hiawatha in SVT
My first Hiawatha for 2021

This March trip was my first Amtrak trip of 2021, the latest first trip of the year since 2012! We are still in a pandemic, so things happen.

The Amtrak journey between Sturtevant and Milwaukee was not long and went well. The trip is 23 miles and has a 29-minute run time.

Over the years, I have taken this short trip many times. I found taking the train to Milwaukee to hang out with friends handy because having one less car makes things easier. Plus, I get a train ride.

So over the years, I got to know Milwaukee’s Intermodal station and the surrounding areas well.

My Milwaukee layover

Between the train and bus trip, I had around an hour and a half to kill.

I enjoyed doing something on this trip that I had not done in over a year; I went inside a coffee shop! Not just anyone, but one of my favorites, the Stone Creek Factory Cafe. The best part about this particular one is that it is halfway up the block from the station. Tasty and convenient means a happy Kev. Occasionally, before going to Chicago, I would go to Milwaukee to grab a coffee at Stone Creek before heading south.

It was nice to be there again, even if the cafe is grab-and-go. I missed the coffee, delicious pastries, and treats. However, it was odd how quiet it was because no one was in the shop but the workers.

With my caffeine and cream cheese monkey danish in hand, I took advantage of the beautiful day to incorporate a walk into my layover. It was also a great time to update my folks and ensure we were all on the same page.

beautiful rail cars
Charter Wire private rail cars

While walking near the station, I saw a few of my favorite private rail cars. Charter Wire owns them, and they keep them around the Milwaukee station. Charter uses them for client outreach and more. One day I would love to take a ride in these beautiful cars. Until then, I can dream about the experience.

Thank God and Greyhound

On greyhound
All masked up on Greyhound (wearing my Amtrak jacket).

After my walk, I headed to the station and prepared for the trip. It was odd to be on the bus side of the waiting area; typically, I am on the Amtrak side.

After waiting a while, they called for all the Chicago-bound travelers to line up behind door number one. Donning my pandemic gear and doing my best to distance myself socially, I waited in line with my future adventure seekers.

Have you ever noticed that time slows down when you wait in line? We were standing in line for about ten to fifteen minutes, but it seemed like a half-hour, I guess, because I was excited. Soon we marched out to our waiting coach to start our adventure.

As we approached the bus, the driver scanned our tickets, making my way to the door. By this time, not only was I ready but excited for this adventure. I had to wait a second for the cleaning lady to get off the bus, reassuring me that Greyhound thoroughly cleaned their buses (or at least they gave excellent optics). Once I climbed on board, I picked a driver-side seat and settled in. I think I was the only one using a seatbelt, but I am okay with that.

I am disappointed I did not play the song Thank God and Greyhound; it is on my phone. While the song has nothing to do with my trip, it is the only Greyhound song I own.

On my first Greyhound trip to Chicago

Waiting inline
Waiting in line for my first Greyhound trip

We left right on time, actually a minute or two early.

As my first Greyhound trip got underway, our driver got on the PA and informed us of the rules. I did not realize that drinking alcohol on Greyhound is prohibited. It makes sense, but I never thought about it before. I also discovered I could take the bus to the Cumberland CTA Ave Station to catch the Blue Line to O’Hare.

My favorite announcement the driver gave: when making a phone call, please keep them quiet because we do not want to be in your business.

After leaving the Milwaukee Intermodal Station, I tried Greyhound’s onboard entertainment. While the entertainment selection was limited, I found something, Toy Story 4, which made me happy. The movies streamed to my iPad well, and I thought Greyhound offered a little something for everyone. If you expect Netflix, you will be disappointed.

As we traveled down I-94, a Wisconsin State Trooper flew by us with his lights flashing. I thought, where are you going, buddy? Because it does not look like you are chasing anyone. A little further down the road, there was his destination, a car accident: at least two cars were in the middle of the road going the wrong way, and the other was on the side. The accident closed the North lanes of the interstate, with backups for miles. Good thing we are going south!

We were early!

After leaving our intermediate stop, we headed to the central bus station in downtown Chicago. I was glad I was not the one driving; the traffic was too much for my comfort level, and I could not imagine navigating a bus through that mess. My favorite time to drive through Chicago is about two or three in the morning when it is primarily truckers.

We arrived at the station a few minutes early, not bad for my first Greyhound trip. Because I had never traveled to this station before, I thought I would check it out. So a quick walk-through did the trick. A while back, I read reviews of the bus station, which seemed mixed. For what it is, I thought it was nice enough. It seems there are too many people out there with unrealistic expectations.

I arrived, and now time to get the folks.

The California Zephyr is backing into the station; my folks were on this train.

I will brag here a little because I am proud of myself; after leaving the Greyhound station, I walked to Chicago Union Station without GPS. Well, I did use one street sign for assistance. Over the years of traveling to Chicago, I have walked through this area a few times, although never to the Greyhound Station. Once I saw the old Post Office, my North Star for this walk, I knew where I needed to go.

While walking to the station, I called my folks and discussed food. Because they had less time between trains, I suggested grabbing something for them. Subs seemed to be not only tasty but portable. Doing this achieved a few things; it made me look like an excellent and thoughtful son, and I could eat; by now, I was hungry!

We had one last obstacle for the day; we needed to switch my folk’s tickets to an earlier train.

I called an Amtrak agent, and she made the required changes for them. Since I had the email from the original ticket, I could print out their updates.

About fifteen minutes later, I saw the California Zephyr backing into the station on track sixteen. Through the crowds of travelers were the ones I came to get. From there, we made our way down the hallway to the North waiting area for the mighty Hiawatha. After fifteen minutes or so, it was time for the “All aboard” for our final train of the day.

The pluses and minuses of my first Greyhound Trip

The pluses

  1. Greyhound filled a travel void.
  2. We arrived early and safely.
  3. The transfers worked well. Milwaukee’s was more convenient than Chicago’s and wasn’t too bad for a beautiful day.
  4. The entertainment selection was small but free; it worked well, helped to make the time fly, plus I finally got to watch all of Toy Story 4.

The minuses

I will admit this is a list of first-world problems, and none of them are deal-breakers for me. Take them as observations and not complaints.

  1. The WIFI was slow.
  2. A small try to hold a tablet or something would be awesome, for I have been on other buses that had one.
  3. The legroom on the bus was just enough, but a little more room for the knees would be fantastic. I am 6’2″, slightly above average, so I am accustomed to this problem across most transportation forms.
Chicago views from Greyhound
The few from my Greyhound window as we came into Chicago, IL.

I believe Greyhound uses two types of buses. A regional bus may have less legroom than Greyhound’s long-haul buses.

Overview of my first Greyhound trip

Overall, the trip went very well, and it helped to break up the day.

My first Greyhound trip cost more than I planned, but nothing outrageous. If I could book a ticket on the 332 Hiawatha, I could have saved $9.

It cost $11 to take Amtrak from Sturtevant to Milwaukee, $19 (about $22 with tax) for Greyhound to Chicago, and $24 to take the train home. Not too horrible, and making your parents less stressed out, priceless.

If the original plan had played out, I would have waited several hours for my folks. More than likely, I would be spending them at Union Station working on the website and maybe sipping a few PBRs, or I could have walked down to watch trains. But on days like this, I enjoy being on the move with the world passing by my window. So the bus worked out perfectly.

Thanks for coming along on my first Greyhound journey. If you are interested in my other adventures, check out this page to learn more about me, what I do, and how I do it!

Safe Travels!


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Kev has been traveling with Amtrak since 2012, celebrating his tenth year this year. Over those years, he has been on over 700 trains covering over 200,000 miles of rail. Kev enjoys helping others achieve their travel dreams by assisting them to get started. Kev enjoys making music as an organist.

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