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Bavettes and Pequods for sure
Rising Star
Without knowing what you've done and where you're going it is hard to give good advice. Have you done an architecture boat tour? That's probably my favorite touristy thing in the city. Chicago has world class improv and plays. If you've never made it to Second City or Steppenwolf I'd put those on the list. My restaurant list is too long and what is exciting is often personal. Alinea is the most famous of the top end restaurants and is quite the experience if you can stomach the price and get tickets. Oriole has the best food of that bunch from my experience. Honestly, go check out Eater's top 38 and pick some that interest you - it's a pretty diverse list and they are great curators. I'm a Logan Square guy, so I'd add Osteria Langhe (get the plin) and Longman & Eagle to the list. Anyway, sorry for you that you're leaving the best city to live in, but you can always come visit :)
Johnnie’s Beef. Gene and Jude’s. Real ones know.
Pitchfork down
Brandon Johnson's g(r)ift room and McD's.
Chef's Special, Lula Cafe, Rico Benne's, Vito & Nick's, your fav pizza joint(s)
Chef’s Special is one of my favorite places! Order dry chili chicken, green beans and smashed cucumbers for sure.
Birria Zaragoza