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A Weekend in Chicago
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items Recommendations based on what I did during my weekend trip in October of 2024 and December 2025!
Map
You have to go on the ferris wheel!! Tickets are $22 but the experience is priceless. I went with people who were afraid of heights and even they would recommend it!!
Navy Pier
I had the avocado toast and a caramel marshmellow iced latte and LOVED it! The store was located right by the river and had a great view. We sat outside and chatted for an hour. It was a perfect spot with great options.
Goddess And The Baker | Cafe in Chicago & WI
Breathtaking. It is located on the Magnificent Mile and is worth a trip. The lines are long but they move fast. I tried a drink exclusively at the Reserve and even bought merch!
Starbucks Reserve Roastery
A must when in Chicago! We only spent about 10 minutes here, but its a must for tourists!
Cloud Gate (The Bean!)
Tried my first deep dish pizza at Giordano’s! It was fantastic and they served it for us! I went with a big group so we had to wait a while for a table, but we were able to order before we were seated. Food and service was fantastic, but I would reco...
Giordano's Pizza: Authentic Chicago Deep Dish Pizza
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Such fantastic coffee! They have the canned options for sale but also have the option to make it for you. I got mine to go, but they also have an option to dine in with adorable glass cups! Such a cute place!
La Colombe
Literally magical. Myself my all of my friends (each in our 20s) spent an hour in here! Must try the butter beer too
Harry Potter Shop Chicago
The perfect spot right on the river walk! Our group ended the night here with drinks and apps, the vibes couldn’t be better!!
Tiny Tapp & Tiny Café
For anyone in the area in December, this is an adorable German market with the most amazing vendors. Each booth is built like a log cabin and many offer handmade foods and crafts. Of course I got one of the mugs!
Christkindlmarket | Holiday Market 2025 | Chicago
A comedy show you'll never forget. Many of these incredible improv comedians end up making it to SNL, so be sure to check out the walls fulll of comedians who have performed there.
The Second City | A Legendary Comedy Institution, Second To None
Incredible ambiance, entertainment for any age (21+).
Redhead Piano Bar
One of the most iconic fields in all of MLB. An incredible venue and it would be fantastic to catch a game. Tickets are a bit expensive, so I went to Wrigleyville to hang out instead. Before/after the game, definitely check out Wrigleyville! Always p...
Wrigley Field: Home of the Cubs - Chicago - MLB.com
