I had the awesome opportunity to go to Chicago in September and I have to say it was my favorite city I have been to! There were many “classic” things we didn’t do, but we took a leisurely approach to this trip and enjoyed every second of it! If you are planning a trip to Chicago, consider checking out a few of these places.
Where We Stayed
My mom booked us an Airbnb and upon arrival, we thought it was adorable! Then we tried to go to sleep at night and turns out it was an apartment over a nightclub in Boystown. Needless to say, we didn’t get much sleep on this trip. So, take my advice and don’t stay in Boystown (and also don’t book an Airbnb without reviews… Sorry to call you out, mom ;))
Things To Do
Go to a Chicago Cubs Game at Wrigley Field
The very first thing that I would recommend planning on your trip is watching a Chicago Cubs game at Wrigley Field. This was very special thing for us to do as my dad was a huge Chicago Cubs fan and always wanted to go to a game at Wrigley. However, even if the Cubs don’t hold a special place in your heart, it’s totally worth going! The way people came together was amazing and the energy in the stadium was contagious. It was definitely the highlight of the trip and some of the most fun I have ever had.
Check out Eataly
Eataly was foodie heaven for me. It’s an Italian market with many different little shops in one. There was a pizza counter, gelato and frosé , tons of desserts, an entire section of wine and you could get a glass to carry around with you. I also found a little corner on the second floor with an awesome collection of cookbooks, which was so fun to look through! Next to that, they even had a kitchen for cooking classes. Highly recommend checking out Eataly if you are a foodie like me.
The Magnificent Mile
If you like shopping, this place is for you! It was fun to walk around even though we didn’t go into all of the stores.
Millennium Park
I really wanted to go see Cloud Gate and I’m so glad we went to Millennium Park! Definitely a sight to see on your trip.
Dining
The Hampton Social
I scouted this place ahead of time t as it’s ranked as one of the most “instagrammable” spots in Chicago, with their “Rosé all day” neon sign. We had already eaten lunch, so we stopped by for a drink (and some fries if were being honest here) and I tried the Frosé , which is their signature drink. I was worried it would be super sweet, but it was perfection! We sat on the second floor and would have sat outside if it wasn’t raining. There was a ton of natural light on the second floor and it had an amazing atmosphere. Highly recommend for a classy place to get a drink with friends!
Mia Francesca
This was the first place we ate upon arriving in Chicago. It’s located in Wrigleyville, but our waiter told us there are a few other locations. We chose Mia Francesca randomly as it was in walking distance to our Airbnb, but we were pleasantly surprised! We got the bruschetta for an appetizer, which had whipped ricotta, tomatoes, basil, and honey drizzled on top, which was INCREDIBLE. I got a pizza and my mom and sister got pasta. All of it was delicious!
Harry Caray’s Seventh Inning Stretch
This was a really fun meal! Harry Caray’s Seventh Inning Stretch is a little hard to find on the Magnificent Mile, but the food was delicious and the atmosphere was really cool! They had Cubs memorabilia decorating the restaurant, a small Chicago sports museum, and the hallway to bathroom was lined with framed Cubs newspaper articles. I was also super stoked to find that they served a Beyond Burger! As someone who doesn’t eat meat, it is really nice to find an option other than salad on a menu.
Garrett’s Popcorn
My friends told me I absolutely HAD to stop by here while I was in Chicago and I’m glad I did. I got “the mix” and while it was so good, I couldn’t eat an entire bag by myself! Stop by here, but share with a friend!
The Berghoff
I can’t say enough about how wonderful our meal at the Berghoff was. If you like German food, you will love this place! I got a vegetarian option, but there is something for everyone, even if you don’t like traditional German food! We got the pierogis and a giant pretzel for an appetizer and I got the spinatknodel for my meal.
The Treehouse at Tavern at the Park
Really cute rooftop spot near Millennium Park to eat and have a drink! We had originally tried to go to Cindy’s at the Chicago Athletic Association (we’ll try that next time), but the line was insane! We chose this Tavern at the Park instead and enjoyed it! I got the Spritz Like A Glove which was Aperol, Watermelon juice, and Prosecco. Delicious!
Edit: After visiting again in 2019, this restaurant is now closed.
Native Food’s Café
Native Food’s isn’t local to Chicago, as they have several locations across the states, but I’m so glad I stopped in! They are a small fast-service vegan chain committed to serving sustainable food. Let me tell you, it was delicious! I got their BBQ burger and fries.
Stan’s Donuts
Everything you read online will tell you to go to a Stan’s Donuts while you’re in Chicago. Just do it.
In Conclusion
Chicago has been on my bucket list forever and I am so happy we went. Chicago is filled with awesome stuff to do and we didn’t even scratch the surface, but these are a few ideas for you if you’re planning on visiting!