What to Do in Chicago (Travel Diary + Vlog)

Last week, my husband and I took a weekend trip to one of our very favorite cities which happens to be the one I was born and raised in! We both love the city of Chicago and wanted to make a mini vacation out of our stay there. Let me start by saying it was COLD. Since I lived in Chicago for 17 years, I am aware that it gets very chilly there, but I had forgotten just how cold it gets in the city right by Lake Michigan. If you are planning a trip to Chicago anytime soon, make sure to pack lots of layers and don’t forget your hat and gloves! Below I have highlighted my favorite things to see, do and (most importantly) EAT in Chicago!

  • Stan’s Donuts (this is the best donut shop I’ve ever been to! They have an amazing selection of donuts and the actual donut shop is very Instagram worthy)
  • LondonHouse (sometimes you just need to get breakfast in bed. We stayed at the LondonHouse Hotel and their traditional breakfast was delish)
  • Baptiste & Bottle (I was on the hunt for the best cinnamon rolls in Chicago and through my research I found this restaurant which is in the Conrad Hotel. The cinnamon rolls lived up to my expectations)

LUNCH + DINNER (and dessert)
  • Sweetgreen (best salads ever! You can also create your own salad which is what I did)
  • Giordano’s (there is truly nothing better than Chicago deep dish pizza. Visiting here is an absolute must for me!)
  • RPM Italian (holy moly I’ve found my new favorite restaurant. We went here twice for dinner because it is truly THAT good. Make a reservation!)
  • Molly’s Cupcakes (just thinking about these cupcakes is making my mouth water! Make sure to get the Cake Batter and Cookie Dough cupcakes)
  • Ghirardelli (the brownie sundae is fantastic- make sure to add the salted caramel sauce to it)

  • Michigan Avenue (this is like the Rodeo Drive of Chicago)
  • Shedd Aquarium (always a must for me when I visit. I love visiting the Shedd and seeing all of the beautiful marine life)
  • Lucky Strike (if you are looking for a bowling alley with a fun atmosphere, go here)

Gucci Card Holder

If you are planning on visiting any of these places/restaurants, I would definitely call ahead and make a reservation. Chicago is always busy (no matter what day it is), so make sure to secure your place at these hot spots.

I hope you enjoyed my Chicago weekend recap. I can’t wait to go back and visit again when it’s a little warmer outside 🙂 If you have any questions for me about my trip or any of the places that I visited, please leave me a comment down below and I will be sure to answer them!


19 thoughts on “What to Do in Chicago (Travel Diary + Vlog)”

    • I had such a great time and definitely ate WAY too much food- but it was so worth it!! Thanks for the comment, Samantha!! xo, Kimmie

  1. i always love visiting chicago! looks like you got to see a lot in just a weekend 🙂 hope your hubby had a lovely birthday darling! xo, sharon

  2. Never been to Chicago, but if i ever go – i will keep the London hotel at the top of my list of places to stay

  3. I seriously can’t believe I haven’t been to Chicago! It’s definitely on my list! Looks like you guys had a blast!


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