Chicago Travel Guide

Rachel BoucherTravel2 Comments

chicago, chi town, travel guide
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What an incredible city! My boyfriend Kyle graduated with his Bachelor’s degree in Architecture in June so as a gift from my family, we took an extra long weekend getaway to the beautiful architectural city of Chicago. We explored all of the touristy attractions, went to the most delicious restaurants, and stayed at a quaint Airbnb just outside the city. I’ve rounded up a list of everything we enjoyed while in the windy city! 

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If you plan on walking around the city all day, I would highly recommend buying this. We actually stumbled upon this deal while walking to Starbucks. We each bought a ticket for just $35 which was good for the next 72 hours, hop on and off all day/night! It loops around the city over and over again which was perfect because we were able to see incredible views and even learn a little bit of history. Plus, it saved us money on Ubers and time instead of walking everywhere.

Smith & Wollenksy

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Can you say delicious? Having grown up with my dad owning several restaurants, I’ve been to many steakhouses in my life and let me just say, this was one of the best steaks I’ve ever had. The atmosphere at this restaurant was incredible, as we requested a table right by the Chicago Riverwalk, overlooking the water. We sipped on some local beer and devoured our NY Strips in a hot minute, all while enjoying the hustle and bustle around us.

Deep Dish

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Of course you can’t go to Chicago without devouring a deep dish pizza. Lou Malnatis was a local hot spot (touristy, for sure) but delicious none the less! One of the coolest aspects about this restaurant is that while you’re waiting for your table, you can order your food ahead of time (something every restaurant should do if it were up to me). After we grabbed a drink from the bar and waited for our table, the hostess let us know about a website where we could check our place in line while waiting to be called for our table. What!? Genius. As I stalked the website and hit refresh every 5 seconds, before I knew it, I was devouring the most delicious deep dish pizza I’ve ever tasted. Best part? I even had leftovers. The whole experience was definitely worth it!

Willis Tower Skydeck

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I didn’t think I was afraid of heights, until I stood 1,353 feet above the street and looked down a glass floor from the skydeck. Oh. My. Gosh. Scary, overwhelming, amazing, breathtaking, and memorable are just a few words that came to mind as I stared out at the entire city of Chicago. If you are up for a little adventure and adrenaline rush, this is a MUST DO while visiting the city! I would recommend going during the day and as early as possible because the line does build up quickly. I would definitely do it again if we ever go back.

Buckingham Fountain 

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This fountain was something Kyle and I stumbled upon as we were hopping on and off the trolley. It was just a few blocks from Starbucks (obviously needed a 2nd Venti iced coffee that day). It was something so magical and beautiful, that it’s hard to put into words or even have the pictures do it justice..something you must go see in person!

Chicago Architecture River Cruise

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Even if you have zero interest in buildings, architecture, landmarks, or history (like myself) this is something every person who visits Chicago (and lives there!) must do at least once. The Chicago Architecture River Cruise was so beautiful and relaxing. After getting a few beers from the bar down below, Kyle and I took out our camera and started snapping photos as the boat made its way in and around the city. It was amazing learning about the history of the town and what the different buildings were for. The sun was blazing, the beer was ice cold, and the views were incredible – what more could you ask for?

Navy Pier

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We went here on our last night and it was beautiful. There was a giant ferris wheel (seriously, it was the biggest one I’ve ever seen) and we were taken up in a gondola-like box. We again got to see spectacular views of the city, this time, all lit up at night. There were a few little shops, several bars, and places to eat all along the navy pier. It was perfect for a date night out!


1. Stay IN the city! While we adored our Airbnb, it was just a bit too far outside the center of the city, and we ended up spending more in Ubers anyway.

2. Pack good shoes-always a mistake on my part. Make sure you’re comfortable. The city is large, but definitely all walk-able. Invest in something cute, but functional. 

3. Go for at least 3-4 days. Kyle and I were fortunate enough to spend 4 nights in the city, but we definitely could have stayed longer. There’s just so much to do and take in, you won’t want to rush by squeezing it in to just a short weekend getaway.

4. Visit in the summer. I am SO glad we chose to go in June and not in the winter months. While I’m sure its absolutely stunning in the middle of December, I’m also pretty positive it’s bitter cold. While we definitely had a scorcher of a weekend, it was nice to be able to see the beauty of the city surrounded by water, and walk around to all the many attractions. 

We had such a blast and cannot wait to visit again in the future. Time to explore a new city…

Take a trip to Chicago!

2 Comments on “Chicago Travel Guide”

  1. I so want to go to Chicago! Great info!!! My daughter and grandson went in the spring and had a great time. They did the ballparks

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