Trip Report – Chicago

We were in Chicago for approximately two and a half days over Labor Day weekend. There was quite a bit to do and we definitely want to go back at some point. The weather was ideal with the exception of Monday when it got significantly hotter and more humid. Overall, the weather was around 80 degrees or so during our stay.

Wrigley Field – Cubs vs. Giantsimg_3775

This was definitely one of the highlights of our trip. We aren’t fans of either team, but the Wrigley Field experience was unlike any other. If you like baseball in the slightest, you should definitely go to a game at Wrigley. We bought our tickets via StubHub.

Architecture River Cruise

This was recommended to us by many different people. We had pretty high expectations and I’d say it lived up to them. Our tour guide was wonderful and we learned so much about the city. This gave use a greater appreciation for the Chicago skyscrapers as we walked around the rest of the weekend.

SkyDeck Chicago

We initially visited the SkyDeck around 10am on Sunday, but the line was out the building and half way down the next block. We decided not to wait in line and figured we’d check back later that night. We came back later that evening and there was no longer a line out the building. However, when we entered the building we were told that it would be a 4 hour wait to get to the top. 4 HOURS?! Are you kidding me? No thanks. It’s not a theme park ride or something. We ended up showing up 15 minutes before it opened the following morning (Monday).


The line was out the building, but since it hadn’t opened yet we figured it wouldn’t be that long of a wait. From the time we got in line to when we actually got to the SkyDeck was about 40 minutes. It is worth noting that they have you take a elevator 1-2 floors above ground level where you wait in another queue for security, pictures, and buying your tickets. Then there’s another queue after this to get in the elevator to go to the top. After you get to the SkyDeck (103 floors up), there’s more lines to stand out on the glass boxes that extend outside the building.

Overall, there’s a lot of waiting for a view/experience that is average. Yeah it was cool to stand out on a glass box about a mile from the ground and look down. However, I’m not sure I would wait longer than 2 hours for this.

The Field Museum

This museum was pretty neat. There was plenty to see. We probably would have enjoyed it more had our legs not been so tired from all of our walking earlier in the weekend. The dinosaur fossils were pretty cool.


Walking Around

We walked a lot in Chicago. Since the weather was nice and Chicago isn’t covered with hills, it was pretty easy to walk several blocks to get around. 


To get from Midway Airport to Downtown Chicago we used the L train, which was fairly simple and cost effective. On the way back to the Airport, we ended up using Uber. We also used Uber to get to and from Wrigley Field. Usually we are able to strike up a decent conversation with our Uber drivers when were traveling. However, 4 out of our 5 Uber drivers preferred to drive in silence rather than chat with us. Maybe this is just part of the ride-sharing culture here in Chicago. I’m not really sure.

Cost Savings

We utilized a Groupon for the three Chicago attractions we visited. You can read more here about how I stacked a bunch of deals to save money. As you may have guessed, we utilized our companion pass to fly SEA > MDW and back. This flight dropped in price several times from the time we booked it. We were able to rebook it every time the price decreased. We ended up spending 19,005 miles + $22.40 for roundtrip flights for both of us. I didn’t get a chance to look at how much flights typically cost. Therefore, I’m not really able to compare to how much it would’ve cost us if we had paid cash for our flights. We used points for our hotel booking at the Hyatt Place Chicago/Downtown-The Loop as well.

Overall, our most expensive costs for this trip were restaurant and entertainment expenses. We had a great time in Chicago and it was one of our favorite U.S. Cities that we’ve visited thus far.