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Chicago!

  • Writer: Taylor Solorzano
    Taylor Solorzano
  • Aug 24, 2022
  • 4 min read

Here is my take on how to spend the perfect 3 day weekend in beautiful Chicago!

We went in August and the weather was absolutely perfect. Put on your walking shoes and get ready to EAT! Be advised - I enjoy cheesy touristy stuff. I know.

Itinerary:


Day 1: I highly highly recommend doing an architectural river boat tour first thing to start your trip. It gave such great insight to the city and it was fun to reference things we learned on our tour throughout the trip. The tour lasts about 90 minutes. We purchased our tickets on Groupon for about $29 per person. Make sure to get Hillary as your tour guide. She's hilarious, and has the best food recs. She really knows her stuff. They sell alcohol, snacks, and water on board which is always a bonus.

You'll likely be hungry after your boat tour. I think its safe to say you NEED to start off your trip with a Chicago dog. It's iconic. You must. We tried Devil Dawgs, but I also wanted to try Superdawg Drive In. Honestly you wont have a hard time finding a Chicago dog anywhere, there's no shortage in that category. Try one. Try them all.


Next, we headed over to the Museum of Icecream. It's not reaaaaallly a museum, but it's cute, fun, and has unlimited icecream. We drug our husbands to this, but I would say this is definitely a great girls trip idea or would be fun with kids. There was also the Museum of Illusions which would be a good alternative. Be ready to take tons of photos because everything is so cute. There's mini golf and fair games inside along with a giant inflatable sprinkle pool. This is a pop-up museum so we were excited it was in town when we visited!

Now its time to walk off all that icecream you just consumed. Head down the street and stroll along all the shops and massive buildings on Michigan Avenue and the Magnificent Mile. Walk until your feet hurt. Look for buildings you saw on your river boat tour. For one of the best views in the city head to the former John Hancock center, now known as 875 N Michigan Ave. Walk inside and ask to go to the restaurant or the bar on the 96th floor. You're not really going to the bar though, you're heading to the women's bathroom. Yes, the bathroom. The view was stunning and best of all, free.


To end the night it would be only right if we had some deep dish pizza. After a lot of recommendations we decided on Pequads, who are famous for cooking cheese on the bottom of the crust, so you end up with a crunchy, chewy, cheesy shell for your deep dish. It was delicious. We also saw it on Somebody Feeds Phil, and I trust Phil with my life. Make reservations in advance for dinner, it gets very busy.



Day 2: Alright I know this itinerary is jam packed. Feel free to spread it out.

To start our day with a quick brunch we headed to Steingold's, a Jewish deli near Wrigleyville. My husband got a delicious pastrami sandwich, I opted for a breakfast bagel. The fries on the side were unreal.

Next, of course, a Cub's game! We walked over from Steingold's. If you are visiting Chicago during baseball season, it's a must. Coming from San Diego, we have one of the coolest baseball stadiums in my opinion. However, this one felt like we took a step back in time. Pro tip: the later you purchase your tickets, you're more likely to get them at a cheaper rate.

After the Cubs game, we took an early evening stroll around Millenium Park. Home of cloudgate, aka "The Bean". The bean is a sculpture made of 168 stainless steal plates with no seams. I never realized how large it was until I saw it in person. You can get lost in Millenium Park - there is a ton to look at. I'd plan at least 1 hour here.


To end the night we found ourselves in China town. It is massive. Come hungry. We headed there to try one specific restaurant, Lao Sze Chuan. Everything is served family style. This is a meal that everyone on our trip can't stop talking about. We got spicy fried rice, lo mein, green beans, orange chicken, and one dish in particular we came to try - dry spicy chili chicken. Everyone went crazy for it. Add this to your list now. Don't forget, k?


Day 3: We definitely slept in on day 3 because we were putting in 12,000 steps everyday. It was glorious. We headed down to the riverwalk and and just followed the path as long as it went. If you wanted to, you can rent bikes and cover more ground. The walk is beautiful, lots of restaurants and little parks along the way. We walked all the way down to Navy Pier where the ferris wheel is. Navy Pier was a little too cheesy for our taste but it was cool to see once. It would be great if you have littles on your trip. Enjoy a nice lunch on the water and marvel at all the buildings up close.

For dinner we drove over to Johnnie's, for the most amazing italian beef sandwich sent from heaven. I went down the rabbit hole on Reddit and after thorough research I decided we needed to get Johnnie's, not Al's. IT WAS SO GOOD! I got spicy peppers on my sandwich, but I think half spicy half sweet would be good too. It's messy, it's juicy, it's glorious. The beef had such good flavor. The fries taste like Mcdonald's fries which is the highest compliment. Wash it down with a soda. God is good everybody.


Whew! That wraps up a whirlwind 3 days in Chicago. I loved it here and I know there are so so many more things to see and eat! Let me know what you think of all my recs and what you would add to the must dos.


Gonna go eat a salad now brb,

Taylor





 
 
 

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