Turning An $1800 Win Into An Action Packed Road Trip

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One Night In Chicago

One Night In Chicago

We asked this question a few weeks back on the podcast, how far have you gone for a deal? I have done some weird things in the past for travel hacking, or miles and points, but I never took a trip solely for it. That is, at least until now! Last month there was an amazing deal for a new Wells Fargo Business checking account. New members could earn a $1500 bonus by opening a new business account and depositing $5,000 for 60 days. The catch was you had to do it in branch. Well, there are no Wells Fargo branches in Michigan. The nearest one happened to be in Chicago, a four and a half hour drive away.

I decided this deal was worth the 9 hours round trip I would invest in it. I also decided to make it into a mini road trip and take the kids with me to spend one night in Chicago. The trip almost didn’t happen since I came down with covid, for a second time, the week before we were supposed to leave. Luckily there were still a few weeks left for the promotion so I was able to reschedule my appointment.

Stopping In Michigan City Indiana Was A Mistake

My appointment was for Friday afternoon and I didn’t think I would be able to make it in time leaving straight from Detroit Friday morning. Or, at least, I didn’t want to get up at the crack of dawn and fight traffic and rush to get there on time. Because of that we left from the kids school Thursday afternoon, which is of course a half hour in the wrong direction.

Knowing we wouldn’t get to Chicago until late in the evening I decided to stop about an hour outside of town in Michigan City, Indiana. I had booked a Hampton Inn that had good reviews and I had thought it was a hotel we had stayed in 15 years earlier. Well, both ended up not being the case, the hotel was filthy and it wasn’t the one we have stayed at before. Even after telling the desk the first room wouldn’t do the second room was no better. I was too tired to deal with it and the sheets / bed looked clean in the second room at least, even though everything else was nasty. So we sucked it up and I complained to Hilton Honors via Twitter.  They have always been extremely helpful and empowered in the past. They often end up helping more than the property would (pay attention IHG).

I am happy to say they are one of the few service areas that weren’t torpedoed during the pandemic. I sent them some pictures of the room and they credited me 30,000 points (the stay was 36,000 points). That was more than fair in my opinion and we were off to Chicago in the morning.

Thompson Hotel Chicago Valet Issues

We got on the road pretty early because we had some things I wanted to hit before our afternoon appointment at Wells Fargo. I figured there was a good shot that the hotel would have a room ready early since it was Friday and because of my Globalist status (that I still have for now). I was also aware of the $75 a night valet parking charge, which would be covered because of my status. This is probably the most underrated perk of Hyatt status. Can we take a second and realize how insane Chicago parking prices are. More so than anywhere else I have been, sometimes costing more than the room. It is gouging at its finest.

I pulled up to the valet stand and walked over to the attendant to hand over my keys with a few dollars tucked in underneath. He looked at me, and then at my car, and said, I am going to have to charge you $20 an hour to park here. For some reason he thought I just wanted to use the valet stand. I said, no I am staying at the hotel. He still looked confused and said, well that is $75 a night. I said well not for me but thanks under my breath and headed towards the door.

It was pretty obvious that he didn’t think my car, a 2012 Dodge Journey, was worthy of the hotel. It isn’t the best car, no doubt (it is actually my DoorDash vehicle), but it is the car we use for longer road trips. Especially when valet parking is involved which almost always leads to scratches. Shocker, it did this time too. I talked about this on the podcast and others reached out to let me know they had the same thing happen with a less than luxury car at that property. So be aware of that.

We had the same attendant when checking out and he was great and super welcoming. I will say that everyone else at the hotel we interacted with was excellent. So I wouldn’t let this deter you from staying there. I’ll try to put together a full review of the hotel though.

One Night In Chicago: Starbucks Reserve Roastery

The Thompson Chicago was able to check us in at around 10:30AM which worked out perfectly. We dropped our stuff and hit the road. Our first stop was the Starbucks Reserve Roastery.

My buddy Han said we should check this place out. I wasn’t going to but our next planned activity wasn’t open yet so we headed here to burn some time. I am glad we did. As soon as I saw the line outside I knew this was a big deal to people. It appears there are only a few of these and it is massive. If you like coffee, or Starbucks, then check it out for sure. A lot of locals frequent it too, so it isn’t just a tourist trap. Each floor has something unique to offer, including a bar that serves coffee infused alcoholic beverages. The kids thought it was pretty cool and my daughter loved the old school train flicking sign they had.

American Girl Doll Store

This is how I convinced my 9 year old daughter to go on the trip and miss Friday specials (the fun classes) at school. I had made an 11:30AM lunch reservation in their dining room and figured we would walk around the store. We didn’t have a ton of time because of our 1:30PM Wells Fargo appointment.

This place was pretty cool if your kids are into American Girl dolls. They have a huge store with a bookstore, snack shop, ear piercing, salon, displays for all of the dolls and the cafe. You could spend hours here and I’ll try to do a write up giving more details on the place. The cool thing is everything the doll can do your kid can do too. They can get their hair done or nails painted together. Yes the dolls can even get their ears pierced with your child. It is a pretty unique experience and my daughter was in heaven.

After walking around for a bit we headed up to the cafe for our reservation. If you decide to partake in this experience then be prepared for it to take a while. It was a four course meal that took over an hour. I even had to rush the waitress along a bit since we were running out of time to get to the bank. The unique thing is they have a high chair that your doll sits in, right at the table next to you. You get to keep hair ties they use as napkin holders and a plastic tea cup and saucer to take home. The entire meal costs $25 per person, which I thought was well worth it. They even had champagne and beer for the adults etc. It gave me Bibbidi Bobbidi Boutique vibes for sure.

My daughter enjoyed it so much that she wants to go back with my wife for her birthday. We didn’t have time to do any of the other activities but it worked out that the two of them will get to do that stuff together.

On the way out my daughter picked up some matching jammies for her and her doll.

Wells Fargo Appointment

We ran back to the hotel from the American Girl Doll store to grab the car. You do get in and out privileges at the Thompson hotel. The bank was about 30 minutes away and I figured that was a bit far to Uber each way. Plus, we would be able to hit dinner on the way back and save that Uber trip as well.

The appointment took about an hour. I had the kids sit in the lobby with their tablets and it went by pretty quickly. I was even offered a $300 after spending $3,000 pre approved business credit card offer that I took. That brought my total win up to $1800 for the weekend!

One Night In Chicago

Pequod’s Pizza

Han gave us this tip for a good pizza place too. We headed there after the appointment. I had a reservation (recommended) but figured we would be able to get in an hour earlier at 4PM. It can’t be busy at 4, right? Wrong!

They were turning people away at the door and said they would try to get us in early. We went across the street to the Barnes & Nobles Bookstore to burn some time. After about 40 minutes we headed back over but they still couldn’t fit us in. Even though we say them squeezing in walk ins from off the street, but whatever.

One Night In Chicago

We were starving by the time we got to order the pizza. In true Chicago style, it would take about an hour to get it. We ordered some apps to fill the time which were very good, especially the fries. I would say this pizza is a mix between Detroit style and Chicago style. It isn’t a full deep dish like normal Chicago pizza and has the burnt cheese edges like Detroit style. It was really good and everyone loved it. We tried their thin / tossed pizza too, which was pretty horrible, don’t get that.

One Night In Chicago

Finishing Off The Night At Navy Pier

After getting back to the hotel we headed to the Navy Pier, which was a mistake. Since it was early May, and still kind of cold, it was pretty dead. The atrium was closed for remodeling and it was too late for the kids museum. I still wanted them to see it but they didn’t want to ride the Centennial Wheel either. We decided to just grab some overpriced ice cream and head back to the hotel for the night.

Another place where Chicago seems to be the priciest I have seen, Uber. It was $20 each way to ride a mile and a half and took like 5 minutes. I’ll drive people around for $240 an hour!

Hitting The River Walk Before Heading Out Of Town

We were leaving the next morning to get home for Mother’s Day but wanted to check out the River Walk area before leaving. I couldn’t convince my daughter to jump on an architecture boat tour for an hour even though the weather was perfect. My son and I plan on doing it together this fall when the girls are American Girl’ing. We walked around and checked out the buildings, hit a park and walked back to the hotel after paying another $20+ to take an Uber from the hotel down to the river front. Good thing I had those $75 Uber vouchers. It was a perfect finish to our whirlwind trip.

One Night In Chicago: Final Thoughts

When a deal is too good to pass up sometimes you need to do something crazy to take advantage. I know people drove from Cleveland to Chicago to do this deal, others flew somewhere solely to grab it. The bankers in Chicago made a joke that MtM was sending them all these people since they were packed with appointments. I know of at least 5 people that went to that very branch, so it was kind of true.

When going out of your way for a great deal, mileage or mattress run it never hurts to make the best of it. I was able to have an amazing quick weekend trip with the kids all while racking up $1800 in wins. That will help my yearly $15,000 earning goal for sure. Even if I left it some of the money behind in Chicago it was well worth the time and money investment to get this done.

What is the craziest thing you have done for a miles and points win? Would you spend one night in Chicago and drive 9 hours for $1800? Let me know in the comments.

Mark Ostermann
Mark Ostermann is a father, husband and miles/points fanatic. He left the corporate world after starting a family in order to be a stay at home dad. Mark is constantly looking at ways to save money and stay within budget while also taking awesome vacations with his family. When he isn't caring for his family or taking a weekend trip, Mark is working towards his goal of visiting every Major League Baseball ballpark.

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14 COMMENTS

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14 COMMENTS

  1. We have been making trips to Mayo, so most times we stay somewhere in MSP using all kinds of free stays and mattress runs. I think Chicago has more to see than MSP.

  2. Wow, thanks for this piece! Until now, I wasn’t aware sure if I could open an account in a state other than where I’m living. Some of these bonuses can at least cover the cost of a road trip. Do you know if this can also be done with other banks that may not in my home state?

  3. Looks like a great trip to me! I’m not sure how much your son and daughter are into aviation, but there’s a really cool museum called the Museum of Science and Industry in the South Shore area. It has a United 727 inside the museum that you can walk into, so it’s an awesome experience.

  4. LOL. As somewhat less dedicated travel hackers, we often end up in the reverse position: taking a road trip just to use up free hotel nights before they expire. Our first trip to Chicago was built around using up a couple of free Hilton nights. Although I live in Minneapolis, I had never traveled to Chicago and was surprised to discover what an exciting destination it is. We took the Empire Builder to Chicago (using up some of those Amtrak points and avoiding having to drive in Chicago) and stayed in the historic Palmer House, a treat in itself. Did the usual tourist things (yes, the Architecture Boat Trip is absolutely worth it!) Had a blast, and have been back twice, staying free at two more historic properties.
    Probably our craziest “burn the nights” expedition was a trip to beautiful downtown Des Moines (because it was the closest city that had a Hyatt hotel). Had a wonderful time. Brought our bikes and biked on the spectacular Trestle Trail north of Des Moines, visited the Children’s Museum (walking distance from the hotel) and toured the state capitol (one of the most beautiful in the Midwest, if you’re into state capitols). On the way home we found a surprisingly good sushi restaurant in Owatonna, MN, and enjoyed a free bandshell concert in a cute little park with ostentatious historic plaques everywhere. Did you know there’s a Louis Sullivan jewel box bank building in Owatonna? Betcha didn’t. Small towns in Minnesota have to really work at distinguishing themselves. Usually it’s with a giant fiberglass fish or Paul Bunyan statue, but Owatonna really does have some architecture to show off.

    • Chicago is a very underrated city in my opinion. Much cleaner than many of the more popular destinations like NYC etc. too.

  5. It think this made sense. That is not a bad drive at 4.5 hours away. Chicago is a cool city, so glad the kids had fun. I live in Alabama, but I just flew to Chicago 2 weeks ago. I missed the Archecture River Cruise too, but the Lake Michigan one was surprising ok with beautiful views. You take it from Navy Pier. It was late May, so weather was ok. Sounds like profit & fun!

    • Yup not a terrible drive. I looked at flights to just go quickly myself but the prices were of course crazy so we opted for this instead.

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