Chicago Travel Guide

Chicago. The homeplace of deep-dish pizza, the nation’s first skyscraper, and world-class architecture, Chicago is a must-have on any bucket list. The third-largest city in the U.S., Chicago is one of the greenest, cleanest, and friendliest big cities. From the Willis Tower to the Michigan Mile, ChiTown has a little something for everyone. Because it’s such a bustling city, you’ll probably benefit from a Chicago travel guide.

Hailey Almsted sitting and smiling at an indoor garden in Chicago.

Day 1

My first day in the city was a little hectic, but only because I decided to see a lot of sites. On today’s list: The Art Institute of Chicago, Skydeck Chicago, Cloud Gate, and Maggie Daley Park. So, my day began at 10 a.m. at Gepade Cafe with a delicious ham, egg, and cheese bagel sandwich and a latte (of course!). And as a (slight) art-enthusiast, I was excited to check out the Art Institute – even though I had no idea the famous “Ferris Bueller” painting was in that very Institute. Full of beautiful paintings, extravagant sculptures, and interactive exhibits, the Chicago Institute of Art was absolutely amazing. The Art Institute took a full four hours, but I wasn’t tired of sight-seeing, it felt like my day was just getting started.

Next on my list: Skydeck Chicago. I was most excited about being able to take infamous pictures in the glass boxes and I’d have to say it was everything I thought it would be (and not as scary!). I definitely took my time at Skydeck; it was hard to get over the breathtaking views. But, I eventually had to move on. What you know as “The Bean,” Chicago knows as “Cloud Gate,” and that was next up. There weren’t too many tourists around the Bean, so I was able to snap a few pictures.

Just across a windy bridge was Maggie Daley Park, a children’s park that is probably more fun for adults. It’s a perfect photo spot and might have been one of my favorite parts of the day. After this extravagant (and exhaustive) day, I was ready for bed. But, I finished this perfect day with a scrumptious milkshake from Devil Dawgs.

Day 2

Pier day! I was very excited to visit the pier, although it was very cold (as a Minnesotan, that didn’t stop me). The pier was just over a mile walk from my hotel, though it felt like much longer. However, Lake Michigan was quite the sight, as it was the color of a clear, sunny day sky. The pier had an interactive gem-exhibit, which was one of my favorite parts of the pier just second to the Sky Wheel. Though a bit nervous, I was excited to see all of the city from the Sky Wheel. It was definitely quite a different view from Skydeck Chicago – I could see all of Lake Michigan! After the ride, I went into an inside garden.

The garden was immensely and made for the perfect photoshoot spot. Nearly 100 photos later, I decided to venture over to the Michigan Mile and head into Eataly, a two-story Italian dream. Inside Eataly was a gelato and cannoli bar, a coffee shop, a pizza, and pasta shop, oil-tasting, a full wine bar, and my personal favorite: a Nutella cafe. Of course, I had to take a bite of something and so I delved into a Nutella filled croissant and it did not disappoint. After Eataly, I stopped in the Sugar Factory, Dylan’s Candy Bar, and Ghirardelli, where I got a delicious hot chocolate to warm up. I finished up day 2 by meeting up with some friends who happen to live in Chicago, we ordered Lou Malnati’s – the most delicious Chicago style pizza.

Hailey Almsted smiling in front of the Bean statue in Chicago.
Hailey Almsted posing at the Bean statue in Chicago.

Day 3

My last day in the city was a relaxing day, as my first two days were fairly hectic (though, a lot of fun!). Breakfast started off at the Little Branch Cafe where I had a fantastic “flamingo” shake (a mix of strawberries, raspberries, and other fruit) and a bacon, egg, and cheese croissant. This was probably my favorite breakfast stop. Just after breakfast, I went over to the Field Museum, Chicago’s history museum. I couldn’t wait to see Sue the T-Rex, the largest t-rex ever discovered, only to find out that she was in the process of being moved and wasn’t on display. However, the museum still had plenty of interesting exhibits and I enjoyed my time there.

I went on over to the Field Museum’s neighboring museum, the Shedd Aquarium. I was lucky enough to have seen the water show, and it was amazing! The dolphins were adorably smart and the beluga whales were breathtaking. After checking out the museums, I walked through Grant Park and went to Taco Madre for dinner. While the tacos were delicious, I had a craving for something sweet. So, off to (another) Nutella Cafe, I went! This cafe was different than the one in Eataly, and I got Nutella Gelato, which was drool-worthy. Let’s just say, it was the perfect ending to this trip.

While I was only in Chicago for three full days, it was one of the best trips I’ve ever taken. Chicago was truly just as beautiful as it is in the TV shows and movies, I didn’t want to leave! I think it’s safe to say that I was made for the city. Let me know if you use my Chicago travel guide! (and check out my other travel guides here!)

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