I lived in the Lincoln Park and Lakeview areas and spent 2 years at the infamous "Snacc Shacc."
BRUNCH
Ann Sather - Swedish Brunch restaurant that is always packed but moves people quickly. Cinnamon Buns are a SIDE! (Lakeview)
Barcocina - the most basic place in Chicago, great vibes and IG photo ops (Lakeview)
Fremont - never actually went but heard it's a staple (River North)
ACTIVITIES
Biking by Lake Michigan - spring for the electric Divvy and CRUISE. This is seriously my favorite thing in Chicago (Docks all along lake)
Lake Michigan (seriously warm or cold just go)
Shedd Aquarium, Museum of Science and Industry - well-done museums if you're into that kind of thing, very scenic location and reachable by Divvy! (Downtown/The Loop)
The Riverwalk - re-done in the 2010's. A beautiful place for an evening stroll or a mid-afternoon work call (Downtown)
HAPPY HOUR
The Signature Room - on the 97th floor of the Hancock Tower. Buy a drink instead of spending $30+ to get to the top of the Willis Tower! (River North)
Cubby Bear - a must if you're going to a Cubs game, a suggestion if you're in the area (Wrigleyville/Lakeview)
Kirkwood - the best patio and chicken tenders in Chicago. Great for a game or an inebriated afternoon. (Lakeview)
DINNER
DEEP DISH
Pequods - the BEST deep dish in town, pepperoni is loaded and the crust is perfect (Lincoln Park)
Lou Malnati's, Giordanos - the next best 3 (locations everywhere)
The Vig - surprisngly good food for a surprisingly fun club (Old Town)
NIGHTLIFE
Celeste - go to the third floor and dance on the spotlights and tell me you didn't have fun (River North)
The Bassment - underground speakeasy-type with fun live music (River North)
Bub City - country music and good vibes (River North)
Matilda's - frankly a weird place, but with a lot of character. Go downstairs after a cocktail upstairs (Lakeview)
Karaoke at Trader Todd's - this is the best karaoke in Chi, and the host usually puts on an incredible show making every other participant seem terrible in an endearing way (Lincoln Park)
Parrot's - another weird, uniquely Chicago spot. There are always a few people here but not a lot, and they're either playing pool or darts or making you uncomfortable (Lakeview)
TOURIST TRAPS
Three Dots and a Dash - overpriced, crowded, and still somehow worth a visit (River North)
The Bean - I mean it's free and outside so you might as well get your picture (Downtown)
Willis Tower - read the happy hour section on the Signature Room! I never actually have been up... (Downtown)
OTHER NOTES
Take the L - the "el" is the elevated train. It's cheap, convenient, and runs on time. Good views crossing into downtown!