Matchbox Bar (770 N Milwaukee Ave) - Sam and Michelle are more than regulars at this neighborhood corner bar. We will usually be holding court, dominating the front corner of the narrow bar. Pro tip: The cocktails might be small, but they pack a punch—just like this cozy spot.

Chip Inn (832 N Greenview Ave) - Cash-only, no-frills, and 100% Chicago. If you’re looking for authenticity, this dive has is it—plus a pool table for settling any wedding weekend grudges. Bonus points if you can beat Sam off the table so that he'll hang out with me.

Star Bar (853 N Western Ave) - This is where Michelle takes over the TouchTunes like it’s her personal DJ booth, and Sam becomes one with the pool table. Come at your own risk with us, I will not apologize for playing Creed.

Aberdeen Tap (440 N Aberdeen St) - This bar is a staple for when Sam and Michelle want pub food, sports, and good vibes all in one place. Beware of mixing mimosas and vegas bombs.

Brasero (1709 W Chicago Ave) - The perfect place for sharing South American-inspired tapas with friends and family. Pro tip: if going in smaller numbers (or just have commitment issues), you can order half portions of just about everything.

NADC Burgers (415 N Milwaukee Ave) - This smash burger is so good it practically derailed our fitness routine. Seriously. We had to change our route home from the gym to avoid temptation, and even then, we still found excuses to “accidentally” end up here. Is it worth it? Oh, 100%.

Pie Eyed Pizza (1111 W Chicago Ave) - When your local pizza spot knows your name, your order, and your late-night secrets, you know you’ve found something special. Perfect for 2 a.m. cravings, post-bar adventures, or when “one more slice” turns into the whole pie.

Publican Quality Bread (1759 W Grand Ave) - We’d do just about anything to get our hands on their flaky pastries and sourdough loaves—seriously, anything. It's the ultimate “treat yourself” moment. Warning: you’ll have dreams about these pastries later.

Kingston Mines (2548 N Halsted St) - Tear up the dance floor at this historic blues nightclub in Lincoln Park. There’s usually a cover charge, but trust us—it’s worth every penny for the authentic blues experience!

Phyllis' Musical Inn (1800 W Division St) - Step back in time to 1954 at this classic Chicago cash only establishment. Phyllis' Musical Inn has been serving up high-quality vibes and excellent service for decades.

Midwest Coast Brewery (2137 W Walnut St) - Adjacent to the Walden, this brewery has got high quality beers on tap, a love for dogs, and a recently remodeled roof. We highly recommend stopping in for one to wet the whistle before heading up to the ceremony (it can only make it more fun).

Bungalow by Middle Brow (2840 W Armitage Ave) - This adorable spot typically offers live acoustic music, high quality pizza, and crushable brews. We found that this is the perfect spot to wander into after a day of sailing.

and of course...

Guinness Open Gate (901 W Kinzie St) - the closest you'll come to tasting The Black Stuff on US soil. We went straight to the source on the Durkin family vacation and have no problem bragging to you that we can taste the difference and that we won't drink a Guinness that has been improperly served. We have never turned down the challenge to "split the G".