A Packed Second Day in Chicago

Day two of our long weekend in Chicago was a little extra packed since we missed a couple of things on the first day, but the weather was gorgeous, so it was totally fine.

While we made our obligatory stop at Stan’s Donuts, I also bought a cup of coffee from Intelligentsia Coffee before we headed back to Cloud Gate for another round of photos with better sun and lighting.

As a reminder, most of the attractions and restaurants were comped per my work, so I will let you know everything I paid for (I paid for transportation, too).

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Millennium Park, Grant Park & Buckingham Fountain

After our stroll through Millennium Park, we wandered through Grant Park to see the Buckingham Fountain on our way to Museum Campus. The views from the fountain and the rose garden in Grant Park were stunning since the weather was really holding up! We also made a stop at the waterfront for some photos before first hitting up the Shedd Aquarium.

Museum Campus: Shedd Aquarium, Adler Planetarium & Field Museum

Shedd Aquarium

I really love aquariums because aquatic animals are just the coolest. Shedd Aquarium was a fantastic visit, and we would have stayed longer if given the chance—particularly to enjoy the shows since they were so fun and educational.

Adler Planetarium

Our next stop was Adler Planetarium, and right about here was when it started to get a bit rainy. Be careful when wandering the campus in the rain because there are some muddy bits around the trees, and when there is construction, the walk can be a lot longer than you think.

The planetarium had some fantastic exhibits, and it is especially great for kids! We had tickets for a star show; however, we were short on time to make it to our next stop, the Field Museum.

Field Museum

I realized later that, while I saw so much of the Field Museum, I totally missed out on Sue the T. rex and have regretted it ever since.

That said, the Field Museum was absolutely outstanding. There is so much to see, and the staff is ready and available to tell you all about the exhibits and help you learn more about the lobby, the fossils, and everything in between.

Art Institute of Chicago

Once we wrapped up here, we made our way to the Art Institute of Chicago, which was a big check on my friend’s list, and I was happy to grab tickets for this one!

The art here is stunning, and if you’re an art lover, you could wander the halls for hours. We sadly didn’t have hours, but we did manage to briskly make our way through everything.

Chicago Food Stops: Hot Dogs & Deep Dish Pizza

Chicago Dog at Millennium Tacos & Dogs

Obviously, by now, I was pretty hungry (my friend was holding out for our first slice of Chicago deep-dish pizza, which was coming up). I grabbed my first Chicago dog of the day at Millennium Tacos & Dogs. This subterranean spot is decent—not outstanding—but inexpensive (I think I paid around $5), and really hit the spot. I tried three hot dog shops on my trip, and my favorite might not be the one you would expect.

Deep Dish Pizza at Labriola

We got to our pizza spot next, a spot that we had been told to check out by some of the locals, Labriola (we literally just discovered it that day, so this was not a comp). The pizza was hot, fresh, and (for my friend who was still experiencing dull taste buds from a recent bout of COVID), particularly flavorful. It was a great spot to stop at to rest our feet and fuel up for the rest of the day.

Harry Potter Chicago & Snack Stops

We made a stop at Harry Potter Chicago since my friend is a huge Harry Potter fan, and, while I had no intention of spending any money there, it was pretty cool to see (and compare to the NYC location I had visited a few years prior).

We were about ready to head back to the hotel for a short break, but stopped at Beatrix Market (a great spot to grab soups, sandwiches, salads, and more on the go) and Do-Rite Donuts for some new room snacks (I love to keep a stocked room fridge, and the donuts were delicious and worth the cost).

Color Factory Chicago

After a little rest, we made our way to Color Factory, which is in the basement of Skydeck Chicago.

Color Factory is another spot I love to visit when I can find one—I’ve been to the NYC and Houston locations, and they were all so much fun. I visited the other two locations solo, and while the staff is always great, it’s extra fun with a friend.

If you are visiting, they make it super easy since there are cameras that can take photos for you that you can later download via a QR code they assign you upon arrival. There are also colorful snacks to enjoy throughout!

Dinner at River Roast

We had just two more stops, but by now, it was pouring. Like heavily.

We got lucky and hopped on a bus, and the rain calmed down a bit by the time we got to our dinner spot, River Roast. This spot is right along the river with an outstanding view, even in the rain.

Even better, the food was absolutely delicious. It was a great spot to enjoy a meal (everything from the mussels to the roast chicken was outstanding) and dry off from the torrential downpour we experienced before dinner.

360 Chicago at Night

Last, we stopped at 360 Chicago. I visited on my last trip in the dark as well, but this time was different and so much more beautiful. We caught the observation deck in the middle of a lightning storm, which made for some of the coolest photos.

Sadly, the rain started up again as soon as we boarded our bus back to the hotel, so the evening ended with a mad dash to the room and a lot of drying off.

Check out days one and three of my long weekend in Chicago here!