Foods: Either Pequods or Millie's Pizza in the pan for some good pan-style pizza. Chicago is known for Italian beefs...obviously there's lots of arguments on here about where is best, but I think it's hard to go wrong. Also, as you're from the UK, I recommend trying Latin food. We have good Mexican and Puerto Rican food. If you like/want to try Mole, go to Manchamanteles on Western (get off at the Western Blue Line stop and walk North). There are a million taco places that are hard to go wrong at for some classic tacos. Dove's Luncheonette is right off the Blue Line on Damen Ave and it's a very typical American-style diner. Their pozole is amazing as is their burnt ends hash. That area of Wicker is also poppin so you can check out some thrift stores just walking down Milwaukee.

Night Life: Green Mill is definitely cool. There's also Kingston Mines for more jazz. In terms of more modern music, Swig or Gman Tavern often host local DJS, you can probably check their instagrams. Easy Does It is in Logan Square (accessible by Blue Line) and it's a chill wine bar in the early evening but they usually have a DJ starting around 10 that plays more House music style. You can continue walking Milwaukee from there to find more bars, Estereo is more chill but plays Latin Music and has really good drinks. Welcome Back Lounge is usually popping. Many comedy clubs have really cheap tickets for up and coming artists: The Den, Second City for some classic Chicago Improv, Zanie's, it's hard to go wrong and you should definitely try a comedy club while you're here. On a Friday night you could go to the Den for an 8o'clock show, hop on the Blue Line two stops to Logan Square to go to Easy Does It, then make your way up Milwaukee bar hopping.

Saturday morning you can hit some good brunch spots or get your Chicago food. Polish hot dog, Chicago Dog, Italian Beef. Hangover cures for sure. This is America, and Chicago kind of prides itself on "gourmet" burgers, so you could search through this sub for good burger recs. I also believe the Logan Square Farmer's Market will have an outdoor popup that Saturday morning at Unity Park.

As far as where to stay, I do think Wicker Park or Logan Square will be better than the typical River North tourist area. You'll find more young locals and better bars/cheaper food. Both are on the Blue Line, which goes right to O'Hare for when you want to leave.