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Best chicken tenders and fries in Chicago?
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https://www.timeout.com/chicago/news/you-can-watch-free-movie-screenings-beside-wrigley-field-this-summer-060921
https://www.groupon.com/deals/pizzeria-uno-deep-dish-pizza-cooking-class-chicago
Time Out Market
I think you could do Cindy’s rooftop for a meal and the view without a drink? Also look to see if there are any movies or concerts at pritzker in millenium park. I also love the chicago architecture center walking tours, small boat or kayak rental on the river, and seeing if there are any good exhibits at the chicago cultural center (it’s free!) And a beach day is always an unexpected and fun activity in the summer
Farmers market and then zoo/beach walk at Clark and north on sat morning, or depending on weekend a good street fest
Museums , Navy pier, good restaurants in and around downtown.
You should buy a Groupon for the unos deep dish pizza making class!!! Super fun and inexpensive
Conversation Starter
Lollapalooza
Lakefront
Could probably find an 18+ concert