Our Chicago Adventure: 2019

Last year was a bit of a hectic year, but Chris and I managed to fit in one trip as a couple out to Chicago to see The Kooks. The stars definitely aligned for this one, as the concert dates were originally scheduled for November during my black out days at work and ended up rescheduled to this more doable time for us!

Pro Tip: I will never be unhappy about Kooks tickets as a gift. Bonus if I also get a trip out of it! Chris has clearly picked up on this <3

This was our third time visiting Chicago and the second time visiting for this exact purpose. Each time we’ve found something new to enjoy and this visit was no exception!


Chicago is one of the few cities that is extremely convenient to get to from the St. Louis area. It’s about a six hour drive, but parking (and driving) in Chicago was not something we enjoyed the last time we did it, so we opted to take the Amtrak–cheap tickets, same amount of travel time, and we both can sleep on the way. 


Uber, “L” Train, and walking! 

We only took Uber when it was absolutely necessary, as it seems to be the least cost efficient for us.

I am weirdly obsessed with public transport, so I enjoy when I have the opportunity to use it(seriously, if I lived in an area with a good system, I would LOVE to ride a train over driving). Our Airbnb had a station nearby, so we took advantage of the 3-day Ventra pass to get around.

Despite it being a much colder time of year compared to our previous visits, we did another one of my favorite methods of getting around–we walked! Granted, we may have had to walk our butts to a shopping mall for the sole purpose of getting winter hats at one point. It isn’t called the windy city for nothing! 


We visited in February, so it was a much colder time of year. I’m not one who is often bothered by the cold, but the wind can be biting. Snow was on the ground when we arrived from a previous dusting, but it was wet and rainy on top of the cold for the majority of our long weekend. 


Airbnbs are my go-to. They are often cheaper than hotels by a landslide and offer their own unique experience. I am not a high-maintenance traveler, so do understand that they may not be for everyone. 

We stayed in an Airbnb in a shared apartment near State Street. It was one we’d stayed in on a previous trip and we picked it again this time for some familiar territory.

This particular Airbnb had one private bedroom with a comfortable memory foam bed, a desk, ample closet space, and a private full bathroom. The shared space contained a full kitchen and living area with a tv and balcony.

No one was staying in the other bedroom for the first few nights and when a couple was going to be checking in late at around midnight, the host was sure to notify us so we wouldn’t be taken off guard. 


Oh vacation eating! Trying new restaurants is one of the things I love in this world, if only I could master the art of not over-indulging! 

Yolk – This spot was not new for us, as we visited last time we were here. A short walk from our Airbnb for a pleasant atmosphere for breakfast and generous portion sizes.

Burger Bar – This was another place we picked due to distance (hey, it was cold). Not to mention, the photos online looked GOOD, and out of any other foods, I love me a good burger. Chris and I each ordered a burger and shared fries and a milkshake. The burgers were amazing, but I think I’d skip the milkshake next time. Overall, I enjoyed the vibe of the place, but I wouldn’t say the food was mind blowing.

Devil Dawgs– Only steps away from our Airbnb, this was the perfect spot for a late night milkshake. The milkshakes were the only things we ordered (better than Burger Bar), but the food looked and smelled so good that I almost opted for a second dinner. I’d love to return for a late night bite some day!

Bulldog Ale House – We went here on a whim because it was around the corner. Our biggest travel obstacle is that Chris will spend hours researching restaurants to the point where I’m hangry AF, so after a bit of talking in circles, we just took the easy route. The service here was excellent, and the food was great! 

Stan’s Donuts– Donut shops are one of those random places I enjoy visiting, even though I have basic preferences and love a good old fashioned donut over any other kind. Sometimes I’ll branch out and try one of the more unique offerings, but that one’s always my standard. Stan’s didn’t have the best old fashioned donut that I’ve ever had, but it was still delicious! I wish I’d tried some other flavors, but I enjoyed hanging out at the counter looking out the window while munching on my donut.

Pequod’s – We’d tried Lou Malnati’s on a separate trip, so this time we did some research and picked Pequod’s as our pizza destination. We ventured there in the rain, got lost along the way, got sassy with one another, but it turned out to be worth our while. The place was packed and we had to wait outside for our table–thank goodness for awnings! We got in fairly quickly and, for shame, ordered a thin crust pizza instead of a deep dish with our tried and true toppings of pepperoni and bacon. We were served with impressive speed despite the crowd and we LOVED the pizza. It was super cheesy with a medium thickness in the crust that gave the best of both worlds. We were pumped to eat the leftovers the following day and would love to come back on our next visit to try their deep dish.

Fun Fact: Being from St. Louis, we’ve been relentlessly told by many Chicagoans that our pizza sucks and theirs is the best. Now, I could care less about our baseball rivalries, but don’t you DARE hate on my Imo’s (or STL style thin crust with provel in general). Chris and I both love thin crust, but pizza is pizza. 


The hardest part about trips is narrowing down the activities you’d like to fit in (no matter how long, it never feels like enough time to see it all). Luckily for this quick weekend trip, we already had some activities planned that helped to structure our days!

The Field Museum – It was during this activity that Chris and I decided that we cannot be trusted to manage our time wisely in museums. We did not come right when it opened, but we stayed up until they kicked us out for closing time. It was nowhere near enough time.

We are the types who love to read and look at everything, and the Field Museum had a lot to offer. Each exhibit was fascinating and we were shocked by how much time we spent in the ones we didn’t expect to be very interested in (the bird and animal section, really?!). I felt like I learned so much in each section of the museum that I hadn’t known before. Sue (the t-rex) and I have the same arm length!

Me VS. Sue

I will say that I didn’t find the movie included with our ticket worthwhile, as it took up 30 minutes of our time and didn’t provide us with any new information. The Bug Underground exhibit was also geared more towards children, but was not interactive, so I would have skipped that one as well.

If you’re in Chicago and love museums like we do, GO HERE! It was worth every penny, just make sure you allow plenty of time. I’m not sure if children will find it as interesting (I know our little one would have lost interest long before we did).

Riviera Theater Concert– This activity was the purpose of our little trip. I’d read horror stories about the venue online, but I experienced none of the issues myself. We got in line early and stood in the cold for four hours(Thanks, babe). I had no issues with employees, but I will say the sound quality could have been better in the room, as the speakers often drowned out the singers.

The Kooks put on an amazing show, as usual, but out of the two Chicago venues I’ve been to, I prefer Vic Theatre over this one.

Laser Tag (Schiller Park) – We’ve been hooked on iCombat style laser tag ever since we tried the one near our home town, so we decided to try out this location while we were here! We chose the Alcatraz map to try! Chris and I ended up on separate teams(like always). The map was awesome, but I struggled using the guns as they were different, older models than the ones at the location we are familiar with. They didn’t have the realistic kickback or manual reload which I thought eliminated some of the extra fun elements of the game. While different from what we were used to, we still had a blast! The 90 minutes always goes by too quickly.

We thought about seeing a comedy show during one of our free nights, but took too long making a decision and ended up missing the ones that were on. There is always next time!

We know there is still a lot to see and Chicago is a place we can easily pop over to for a weekend when we’re feeling like another adventure.

What things would you recommend seeing/doing on our next trip there? What restaurant do we absolutely have to try next time?! Any cool local spots we need to check out?

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