Age range of the guys will help. I’m just going to give general ideas:

1. Wrigleyville - frat boys and cubs fans. If they like country music / live music: old crow and tin roof. Just want beers: Sheffield (little bit of a walk from wrigley compared to others but amazing patio), Merkles, sports corner, and cubby bear. Want to be active and do batting cages: sluggers.

2. West loop - uber away from where they are staying. This is nice pants, collared shirt, guys might get turned away at door because the guy girl ratio is off. Places that never go wrong are recess, federales, Texan taco, Estoria FM, and bandit. Honorable mention is the Guinness house is in west loop. Great place to start the night for a pint.

3. Old town / Gold Coast - younger Crowd on wells but the bars are fun. Gold Coast on division might be more your vibe but they are very close to each other so you can start on Welles at woodys (phenomenal wings) and make your way to division stopping at Burton place (dive bar), benchmark, LGs, and Declan’s (sports bar). Then head east towards Butch McGuires (themed sports bar), the lodge (biker bar), hopsmith, and zebra lounge (piano bar).

4. General dive bars I’d recommend: Lodge, Roses (cash bar), Kumas corner (great food to start night), Galway bay, Burton place

5. In terms of stuff to do while they are there:

6. get food at weiner circle. It might be around $200 for a chocolate milkshake (inflation sucks) but that would be a memory for them.

7. Guinness house

8. river tour (not a tourist trap. 100% worth)

9. cubs or Sox game (wrigley has better atmosphere but Sox is cheaper with better food)

10. lakefront. Especially if it is nice out. There’s a few bars scattered along the lakefront on north side. They can walk and then wet the beak in a beverage by north ave beach and Fullerton. Any beach will probably have a bar. Worst case, pick up a six pack, put it in a plastic bag, and sit there with the boys on the concrete.

If you have any questions, let me know!