Chicago Summer Bucket List

best view of chicago skyline

I asked you guys on Instagram if you’d be interested in seeing my Chicago summer bucket list and wow. The results were hugely in favor! So here is a list of the things I want to do this summer! I’m also writing this as a way to keep myself honest and actually do them all! 

If you’re coming to Chicago for the first time, this travel guide has an amazing weekend itinerary in it! I recommend it for anyone that is a first time visitor or relatively new to the city! There are some items you just can’t miss in there which aren’t on my bucket list because I’ve already done them! If you’re looking for places to eat, here is a list of my favorite restaurants in Chicago too!

1. Go to at least one outdoor concert at Ravinia and sit on the lawn. DONE!

2. Happy hour at Cindy’s and Londonhouse!

3. Have a glass of wine at City Winery on the Riverwalk. DONE!

4. Kayak the Chicago river (this is going to take some serious convincing of Matt).

5. Go to at least 2 food festivals. There is something almost every weekend and they’re usually free with a suggested donation for entry! Taste of Randolph and Chicago Gourmet were my favorites last year.

6. Rent a boat or yacht and go out on the lake for a day. You can rent from this website and you can fit up to 16 people!

7. Have a girls day by the pool. DONE!

8. Go to North Avenue beach or Oak St. beach.

9. Take a romantic walk along the Riverwalk at night. DONE!

10. Try at least 2 new restaurants. Here are my favorites so far! DONE! We tried The Publican and Chicago Cut. 

11. Go to one of the free concerts in Millennium Park.

12. Watch the fireworks on Navy Pier. They go off on Wednesdays and Saturdays!

13. Boozy brunch cruise with Mystic Blue.

14. Lollapalooza! DONE!

15. Date night at one of the museums after hours! They serve drinks and it’s a fun twist on a museum!

Is there anything I missed on my Chicago summer bucket list? What are you looking forward to this summer?

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