I had to fly into Chicago for a training session for work, but we weren't able to spend very much time in the downtown area during the weekdays. Fortunately, my bf was keen to visit, and I extended by trip for about 4 days and we were able to spend more time in the city!
Pre-training Day 0 & 1
I left Honolulu with my coworkers and we flew from Honolulu on United Airlines through San Francisco with just a short layover. Our initial flight was delayed so we had to make some changes, but we all were able to make it on the same itinerary and arrived at O'Hare in the afternoon of Monday, Sep 23.
After renting our cars,
a handful of us stopped at the nearby Fashion Outlet Mall to visit a few outlets that we don't have in Hawaii.
We then eventually made our way further into Chicago so we could see a Cubs game! We didn't have solid plans for parking ahead of time, but luckily were able to figure out there was a free lot and shuttle available for the game at 3900 N Rockwell Street.
Due to traffic, we parked only a bit before the game started and when we arrived at the field, it was already under way! We stayed through most of the 8th inning before making our way out to beat the crowds with the score being pretty set at that point. (The Cubs won!)
Training Day 2, 3
Training took up most of Tuesday, but after work, we were able to quickly check out Lake Michigan
and then head to Trader Joes for some omiyage shopping.
We stopped at Olive Garden for dinner which is usually another big hit for Hawaii people since this chain didn't make it over to us yet.
Last stop of the night was Bass Pro Shops which my boss really wanted to visit. Apparently his friend had hyped being able to test shoot guns and use the poles and reels to catch fish in the store. This particular one didn't offer that, but we still had fun shopping and exploring the store which was so huge.
On Wednesday, we had another full day of training but several of us were pretty worn out by this point due to jet lag and weird sleeping hours. Some people branched off for more shopping and drinking but we opted for a simple dinner after we took about an hour to figure out where we wanted to go lol. We ended up at the Lazy Dog Restaurant and Bar which I didn't realize was a chain! We all really enjoyed our meals here and would definitely try it out again if I saw one on the mainland since the menu is quite extensive.
Training Day 4 (afternoon in Chicago)
I picked up my bf from the O'Hare in the morning before the training which was a bit of an adventure on my own while I took the wrong cut off (wtf lol) and once I got back, he rested in the hotel while we went to work.
We only had a half day of training this day, so after our last bit of mingling and networking, we were able to head out to downtown Chicago while it was still daylight. Unfortunately there was a bit of (roadwork) traffic and it took us over an hour to get to where we wanted to park, but we all made it in one piece!
First stop was lunch at a place that was just nearby the parking garage - Exchequer Restaurant. For the 5 of us, we got one large thin crust pepperoni pizza and then one medium "The Mob" deep dish and it was way more than enough food. I only really tried the thin crust at this place, but everything smelled delicious.
Once done with lunch, we started making our way to Millennium Park. We passed the garden and front entrance of Art Institute but didn't go in.
Also stopped at Crown Fountain
and finally made it to the Bean/Cloud Gate!
We also decided to do axe throwing at a place called Ragnorak Axe Throwing Chicago. Our coach was Neil the Viking! I've never done this kind of activity before, but I was surprised to find out how carefully guided it was. We were with 4 other people who were their own group but ended up merged with ours and took turns learning and then playing different games. I was not very good at it but Neil was really patient with everyone!
The group then separated as some people went to see Hamilton and the rest of us grabbed something to eat at this Latin food court in a mall before heading back towards our hotel.
Since it was Thursday, we stopped at a sports bar along the way to watch the end of the football game and also caught the end of the Cubs game as well!
Day 5 - Food tour and Buckingham Fountain
We woke up and left our accommodations for the training and drove with my boss towards O'Hare to drop off the rental car.
From there, we caught the shuttle to the airport and made our way to the Blue Line to get to Division station where a family friend was waiting to picking us up!
We had arranged to stay with her at her house in Lincoln Park for the rest of our trip which was really nice. Once we settled in and took a break, we headed back out but used the Red Line this time to get to Chicago/State.
We booked a food tour through Airbnb Experiences and met up with the group at 13:00. It included the guide ("Chicago Kelly"), a two other couples.
Our first stop was Downtown Dogs where we tried Chicago (style) dogs. (As I've mentioned a ton of times before, I'm a super picky eater, so you shouldn't take my opinion on food taste seriously. I literally asked for a plain hot dog here.) Our guide shared some of the history of the food with us as well.
Next on the tour was Pizzeria Due where we were able to try deep dish pizza from the place that invented it according to our guide! (Toppings were something like Chicago classic and included sausage, pepperoni, onions, bell peppers and more.) The crust was super buttery but apparently doesn't include any and gets the taste and texture from olive oil! This helps keep it from getting soggy.
We walked a bit more through what seemed like a super cool renovated McDonalds that had a ton of green features and also electrical outlets like a fancy airport lol.
For the Italian beef sandwich, we stopped at Al's. As I understand it, you can get this sandwich with the beef "dry" or "wet" and most people will recommend it "wet" for best flavor!
Last stop was Portillo's for a chocolate cake dessert! This is where the tour ended and we were both really full (which was what the tour promised) even though we only had a fraction of each item. Apparently if we were still hungry, more food would have been provided to us at that point.
This Airbnb Experience was called "Classic Bites in River North" and I think it was priced appropriately for what we were promised and the name of the tour is very accurate. There were other tours with more "exotic" options for food (better for adventurous eaters and foodies), but what we were really looking for was a local guide to take us to places we probably wouldn't go to ourselves for these very specific "classic Chicago" food items. We were able to check them off our list and know that we ate a good representation of the dishes and anticipated that if we liked them, we would go and try them elsewhere in the future. It was just generally a good way to get an introduction to these local classics!
We had been hoping to make it on an architectural tour in the afternoon, but unfortunately they were all sold out for the day from the vendor we wanted. Instead, we purchased our tickets for Sunday and had lots of time to roam and explore the city.
We made our way to Buckingham Fountain where the water feature was off when we first arrived but we were able to see it turn on while we were taking photos!
For dinner, we were still pretty full from the food tour, so we were mostly looking at desserts. After looking through Yelp, we settled on La Bodega. We ordered the churro mix soft serve with glitter, brownie and chocolate covered pretzel toppings. Unfortunately the churro cone itself was pretty stale and didn't taste good but I did enjoy the soft serve and the abundance of toppings! If you try it, definitely skip the churro cone!
Day 6 - Field Museum and Art Institute of Chicago
We purchased the Chicago City Pass in the morning online and then caught and Uber directly to the Field Museum.
(There was a little bit of rain when we arrived but all the exhibits are indoors!)
There's so many different features and exhibits at this museum that I think it's impossible for me to highlight them all, so here's a photo dump. Most notable exhibit is probably SUE the most complete T-Rex!
It's really more fun to just look and interact with the exhibits rather than try to take photos, so sorry if it's just a random assortment.
Next major item on our itinerary for the day was the Art Institute which we had passed briefly on Thursday. It's included in the City Pass and highly recommended by our family friend, so we wanted to actually give it a try! It's a bit of a walk from the Museum Campus, so we decided to try out the Divvy bike system.
Seemed easy enough but in trying to avoid riding on the streets with the cars too much, we ended up going way around the Art Institute and the docking station we wanted to stop at had no available stations! Because of that, we had to keep looking around for one with vacancies and didn't make it within our 30 minutes and had to pay for another lol. Oops :O
For lunch we stopped at a nearby Shake Shack! We don't have this in HI, so we wanted to try it.
The Art Institute was nearby but by the time we got in, there was only about 2 hours left before it closed, so we knew we had to make the most of it.
The City Pass admission included an audio guide.
Here's another photo dump of a few examples of the exhibits at the Art Institute. We didn't nearly get to everything, so we tried to focus on what we were most interested in seeing. If you love art, I definitely recommend giving yourself a lot of time here!
We stopped back at the house to pick up our jackets and regroup/recharge a bit and then headed back out to quickly grab something to eat at Wiener's Circle nearby.
From there, we caught an Uber to the United Center for a preseason Blackhawks game which I think had a bit of surge pricing on the ride and pretty backed up traffic on the roads lol.
We made it inside just a handful of minutes before the start and were able to be seated just before the national anthem. This was both of our first times seeing an NHL hockey game and both didn't know exactly what to expect. We don't know all the rules and how the game play flows exactly but it was still pretty easy to follow for the most part. I was pretty impressed with the stadium itself which seems really well maintained and clean, plus the seats were comfortable and we had a largely unobstructed view!
Day 7 - Architectural Boat Tour and Hamilton
We caught the train in and got breakfast at one of the many Stan's Donuts locations in Chicago. It was pretty busy in there, but the staff seemed to have a good handle on things and we were able to find a table to sit at easily as well. We got a glazed pretzel donut to share and my bf also got some cold brew.
The tour we booked was from the Chicago Architectural Center via Chicago's First Lady.
There are many different companies offering these types of tours but this one seemed the most highly recommended from the people we talked to. It was requested to be there 30 minutes prior to the start of the tour and when we went down to the riverwalk, there was already a small line forming. Since there's no assigned seating on the boat, the order you enter the boat determines when you get to choose your seat. We didn't board until closer to 15 minutes prior to departure, but by then a significant line had formed, so we were glad we got there when we did.
I didn't take photos of every building, but here's a small sample. The full 90 minutes is well used and you get to explore all the architecture along the river (both sides) with an extremely knowledgeable and enthusiastic guide. Like most people, I would definitely recommend doing this if you visit!
We stopped for lunch at Ajida which was a bit more of a walk away than we expected from the Riverwalk, but I was pretty tired of eating heavy American and Italian food at that point lol. We both got the Shoyu Ramen and it was a nice change of pace for a meal.
From there, we made our way to CIBC Theatre for our 14:00 showing of Hamilton!
We chose the cheapest ticket tier which meant we had a bit of an "obstructed view" but we figured it wouldn't be too big of a deal. We were basically just missing the far stage right section from our angle. We were pretty enthusiastic when we first sat down, but really the issue wasn't the angle of the seats but rather that the people who ended up sitting in front of us blocked most of the stage itself lol. Especially when they moved or sat forward.
Overall, it was still a great show. I'm not sure if my experience would have been improved by paying approx $150 more for center front of the mezzanine, but I would consider it in the future for seating in this theatre just because there doesn't seem to be enough rise between the rows going back.
Day 8 - Shedd Aquarium, Willis Tower and Navy Pier
One of the attractions I was most looking forward to in Chicago was visiting the Shedd Aquarium! This is the main reason we started looking at the City Pass since the admission is a bit pricey. We waited for the rush hour surge to die down a little bit and then Ubered straight to the entrance and started our day there.
Here's another photo dump from the various exhibits at the aquarium!
We opted against going to the 4D movie experience as well as one of the other animal attractions (I think it may have been a dolphin show) even though they were included in admission because there were just other things we were interested in seeing instead. Otherwise, I was impressed with the different kinds of environments featured at this aquarium and found it different and interesting!
After our slight screw up biking from the Museum Campus area 2 days prior, we tried to plan our Divvy ride a bit better this day. Especially because we were aiming to go further inland (away from the lake) where there would be a lot more cars and intersections. I was also a bit nervous about how I would do riding in a dress, but knew it wasn't going to be impossible.
We had several intended docking stations we were aiming for, but of course, our primary target had 0 vacancies by the time we got there. How did this happen to us multiple times in one trip? Luckily, this time we were able to find an alternate before the 30 minutes were up because someone was taking a bike out at the same time we were trying to return.
Needed a small break, we stopped at McDonalds for a frozen Coke and a small cone.
Then we sought out a place to eat lunch and settled on Revival Food Hall which offered quite a few options and lots of seating. I got a stromboli from the Italian place and my bf got a ramen and also some hot chicken.
Last item we wanted to do using the City Pass (especially in order to get our money's worth) was visit the Skydeck at Willis Tower.
We had pretty much no wait to get up to the 103rd floor but ofc it was quite busy once we arrived.
The 2 lines for the glass boxes were quite long with the anticipated wait being around 35-45 minutes. (They were also advertising a "fast pass" where you can skip the line for $30/person.) I think you get approximately 90 seconds in a corner of the box (another party gets the other corner) and it goes by
quickly especially because it feels like there's a lot at stake after waiting for so long. I didn't even have time to think about being up so high!
I actually had pretty high hopes for the "professional" photo but the one in the glass box came out so dark, especially compared to the photos of the guests preceding and following us wtf. It's just as well because the photo set is $30 but I definitely wasn't paying for it for a poorly lit photo that seemed specific to us lol.
My parents had decided to come to Chicago to visit their friend (the one who's home we were staying in) as well and they came in in the early afternoon. They had biked over and we agreed to meet them at the Navy Pier.
It's not really close to Willis Tower, but when looking at the ride share pricing, we decided it would be best to just try to Divvy again lmao. They were waiting for us at the Navy Pier, but of fucking course, there were 0 vacancies at the docking station near them by the time we arrived.
We ended up having to keep riding to find an alternate and then walk back to where they were.
We walked around the area and explored a little bit.
Then we decided to get tickets for the giant ferris wheel since the line wasn't too long and it would offer a great view of the city.
After getting some refreshments in the food court nearby, my parents got on their bikes and we hopped on Divvy bikes again to go back to Lincoln Park. It was a long ride along the lake, but a defined bike route which made it much easier to ride through even though most people were speeding past us. At least we didn't have to worry about getting hit by a car and navigating!
And finally, when we got back there were actually spaces at a docking station!! Lucky too, because we had only about 4 minutes or so to spare for our half hour.
We regrouped and then went out to dinner at Parson's Chicken and Fish with our family friend's family, my parents and us altogether. It was a really nice end to the trip!
Day 9 (travel)
We woke up, got ready and got a ride to Division station on the Blue Line on Tuesday. Unfortunately, the trains going towards O'Hare on the Blue Line weren't stopping at this particular stop on the day we were leaving so we had to catch the train away from the airport and then switch to an O'Hare bound train from Chicago station. A minor delay but relatively uneventful as we were able to still get seats and ride to where we needed to go with plenty of time.
Stopped for some Garrett's popcorn of course. Although this was my first time really IN Chicago, I have had short layovers at this airport before and always stop to get some caramel popcorn. (Sorry purists but I'm not into the cheddar mix lol.) Also makes great omiyage, especially right before heading home.
According to the seat map, our plane wasn't nearly full and we had gambled on taking a window and aisle seat, leaving the middle vacant. Luckily, this paid off and we had the three seats to ourselves for nine hours!
All in all, this was a trip full of new experiences. Traveling to the mainland US is so much different than going interisland and way different than Japan obviously even though the plane ride is a similar length. It does usually get a little tiring it to eat so much heavy "American" food after a while, but thanks to Yelp these days it isn't so hard to find nearby options in big cities. I'm not sure I'd be ready to go to Chicago again for a little bit just due to the distance and most likely having to fly United, but there's definitely a lot we weren't able to do during our 4 days despite how full they were so if I had training there again, I wouldn't say no!
