Chicago (Day 2)

Our first full day in Chicago started off kind of rough. Walking around a city in heavy rain is not enjoyable…but a little rain never stopped us! (Even though it absolutely did make us kind of whiney.)
I don’t do the day until I’ve had coffee. After a little research on nearby coffee shops, my sis and I set out, but as soon as we walked outside the sky opened up. We waited it out as long as we could and made a mad dash to Big Shoulders Coffee on West Lake Street. I ordered a toasted marshmallow latte (go big or go home, amiright?) with a donut, and my sis ordered her routine sugar-free vanilla latte with an apple fritter.

Big Shoulders gets their pastries from Do-Rite Donuts, which is one of the popular donut places in Chicago that is always mentioned when you Google donuts in Chicago (I know this from personal experience).

Sorry sis, but this is too funny!

While we were finishing off breakfast, our friends came by to get us so we could walk to our bus stop. We bought a day ticket for the hop-on, hop-off Big Bus Chicago tour, which I think is always a good idea when you’re in a new city so that you can get an overview of everything. We also purchased this tour because the route took us close to the convention center where the expo for the race was being held and we needed to check in, get our numbers and shirts, and explore the expo. Our first tour guide was incredible – so funny, engaging, and totally looked like Pharrell – so we were kind of bummed when we had to get off early near the expo.


These towers are Marina City and are frequently featured in Transformers 3: Dark of the Moon, so I grabbed the shot since J is obsessed with those movies.

Even though it was rainy and gross, we didn’t want to stuff ourselves into the bottom part of the bus. The view is so much better on the top, and as we made our way up there we were extremely happy when they handed us free rain ponchos!

We got on the bus at the first stop which was Chicago Riverwalk. The next stops took us by the Chicago Theatre, Willis Tower and Skydeck, Millenium Park and Palmer House Hilton (which burned down thirteen days after it was built), the Art Institute of Chicago, the Hilton Chicago and Grant Park (the Hilton Chicago has been featured in a ton of movies, including Home Alone and The Fugitive!), Adler Planetarium and Shedd Aquarium (which is where we got off to walk to the expo).

The picture below is a prison in the middle of Chicago. I guess if you don’t have room to spread out horizontally, you just go up! Our guide said there were several underground tunnels so that police could escort some of the scarier people in and out.

Below is the stadium where the Bears play. It used to be on the list of historic buildings, but it got remodeled and they put what looks like a giant spaceship on top, so that didn’t quite go with the Roman style of the bottom. It’s definitely one of the weirdest/ugliest stadiums I’ve ever seen.


Soldier Field

While we were at the expo, we did have a great view of the Chicago skyline…when the clouds finally decided to go away!

We found out that there was a sailboat race going on right next to the expo. A few days later we also found out that someone had fallen overboard and died. The wind and the water was pretty intense, so I can’t imagine actually being out on it and trying to navigate a sailboat.

When we came back out from the expo, the sun had finally come out and it was turning into a beautiful day. The clouds had lifted and lots of people were cruising around on their boats blasting music. There was an Usher and Chance the Rapper concert going on that night, so I think everybody was psyching themselves up for a big night!

After we picked up our race swag, we were feeling a little hungry (although I had sampled some dairy-free cheese at the expo and just wanted something to clear my mouth out <ick>). We made our way back to the bus stop area where C had found positive reviews for a hot dog cart (Kim and Carlo’s Chicago Style Hot Dog Store, to be exact). We’d heard all the hype about Chicago-style hot dogs, so that was definitely on our list of things to do! A Chicago dog is an all-beef hot dog with mustard, onions, relish, tomato, celery salt, a sport pepper, and a pickle on a poppy seed bun. I hadn’t planned on being so daring, but when in Chicago, you gotta do what the Chicagoans do! And it was actually pretty tasty! I don’t eat tomato, raw onions, or relish, so I was kind of shocked that I enjoyed it as much as I did!

My sister is an all ketchup girl, but the sign on the cart said you have to dance for ketchup, so she just opted for a plain polish sausage…with a pickle on top 😂.

So cute with her little hot dog!

We ate our lunch on the steps of The Field Museum and while we were chowing down a wedding party rolled up to take pictures. We got lunch and a show!

Beautiful friends eating beautiful food!

After lunch we jumped back on the bus to finish our tour. Our plan was to get off at Navy Pier, but when we rolled up there were SO MANY PEOPLE. I don’t do well in crowds and probably looked horrified, so we just kept on going with the tour.

When you first get on the bus they give out tickets for free popcorn samples at Garrett Popcorn Shops, so we got off a couple stops after Navy Pier to redeem our tickets. One family told us that the samples were tiny, but we were actually really surprised at how big the samples were (we didn’t actually get ours because the line was long and we had a very early dinner reservation to get to). But don’t worry, we definitely got our Garrett fix. I was concerned that the popcorn wouldn’t live up to all the hype, but y’all, it’s SOOO GOOOD. If you go to Chicago, you MUST get Garrett popcorn, preferably the Garrett mix!

One of my work friends had highly recommended a restaurant called Girl and the Goat but C had checked on reservations there and said nothing was available until mid-August! We were there in July. While I was frantically looking for a place to eat that wouldn’t mess up our bellies for the race the next day, I stumbled across a diner that was opened by the owner of Girl and the Goat called Little Goat Diner. The only spots they had were at 5:15 or 9:00, so I thought early was better than super late.

Little Goat Diner is adorable. It’s definitely set up like a diner but more upscale and chic.

There’s a bakery in the back, which is where we sat, and we got to watch the pastry chefs and bakers while we had dinner (and we were mesmerized).

I saw pork belly on the menu, and if you’ve noticed anything about my eating habits, it’s that I never turn down pork belly. Their version was pork belly home fries – big chunks of potato and pork belly with pickled peppers, cilantro, and fish sauce vinaigrette. Yum.

Looking back at the menu, I’m surprised that I didn’t order one of the breakfast-for-dinner options. I’m a firm believer and supporter of breakfast-for-dinner. I think since we had an awesome placed picked for brunch the next day (stay tuned!), I must’ve thought that French toast or pancakes twice in two days was too much? I really don’t know what I was thinking.

But anyway, for my entree, I ordered a fancy grilled cheese, but when it came, I was super confused and really disappointed. There wasn’t a lot of cheese on it and there was a gross olive mixture on it (if you don’t know a word in a food’s description, you should look up that word because it might mean “gross olive mixture” instead of being a fancy cheese like you think). I ended up asking the waiter if my food was the right thing and he was so nice about it and immediately offered to get me something different. I hate being that person, but I just couldn’t eat that weird sandwich, so I asked for a patty melt and that ended up being so much better!

I had been annoying my sister about stopping by Nordstrom for the anniversary sale, so after dinner, since it was so early, she and N escorted me to Nordstrom, probably so I’d stop talking about it. We strolled around there for a bit and then decided it was time to hit the hay and get ready for a super early morning…and a 10k!

We had beautiful weather and some great light as we walked around that evening! I think the rain caused us not to give Chicago enough credit for being kind of beautiful!




Stay tuned for more information from Chicago, including our super interesting experience running the Rock ‘n Roll Chicago 10k!

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