This time of year you really can’t go wrong with hanging out at any of the beaches or spending time in Lincoln Park. Get as much sunshine as possible!
Hard to give just a few food recs but my faves now probably are Rose Mary, Mama Delia, and Armitage Ale House. For something quicker get tacos at La Pasadita or a hot dog or a burger at Red Hot Ranch.
A lot of good thrifting/antiques on Grand Avenue in West Town if you’re into that, and then some awesome bookstores too are Myopic Books in Wicker Park and Open Books in Logan Square.
The Robey Hotel is also an amazing place to grab drinks, now that it’s summer their pool bar will be open too! If that’s not your speed and you just want a good ol dive bar and cheap cans of beer, Rainbo Club is right down the road from there! Enjoy!