My boyfriend S and I began our relationship long distance – he currently lives in Chicago, while I’m out east in New Jersey. Needless to say, I’m in Chicago quite frequently visiting him.
I compiled a list of our favorite places to go around the city; we’re big into breweries, cheese plates, and eating food we shouldn’t. I hope you enjoy this list!
Lagunitas

The Lagunitas Brewing Co was one of the very first places S took me before we began dating. The large facility, which hosts free brewery tours each day, is perfect for not only dates, but families as well. We have a cheese plate tradition – and Lagunitas has kept the #1 spot! Website
Location: 2907 W 17th Street, Chicago Illinois 60608
Headquarters Beercade
I don’t know anyone who doesn’t love old-school arcade games. At Headquarters, the two-floor facility is filled (and I mean filled) with vintage arcade game favorites. Anything you can think of, it’s there. And the best part? 99% of them are free to play as many times as you want. My favorite are the pinball machines and skeeball! Website
Location: 950 W Wolfram St, Chicago, IL 60657
Oak Park Brewing Co

About a mile from where my boyfriend lives is the Oak Park Brewing Co. A small-time brewery that packs big-time quality brews, and we absolutely love it. If you’ve ever wanted to make a beer cap table, take notes on theirs. The furniture style is also incredible! Website
Location: 155 S Oak Park Ave, Oak Park, IL 60302
Half Acre Brewing

You’re never supposed to judge a book by it’s cover, but talk about artwork! Half Acre Brewing has one of the coolest logos I’ve ever seen. Not to mention every brew I’ve had from them is absolutely off-the-charts. If you’re looking for a bargain, their brewery tours are amazing. For $10, you get three of their amazing beers, and a pint glass (bonus that they don’t sell them in the shop!). Website
Location: 4257 N Lincoln Ave, Chicago, IL 60618
Tiny Tapp
Located right on the Chicago river, Tiny Tapp is a great place to sit and watch the boats after a long day of exploring the city. (Please excuse my manicure, I need a new one!) Website
Location: 55 W Riverwalk S, Chicago, IL 60602
Citrine
Another great spot in Oak Park that deserves a mention. They have a fabulous selection of craft cocktails and interesting menu choices to keep you adventurous. However, it’s extremely pricey. On Tuesday’s, they boast half-off their bar menu, which is when S and I went to try it out. The food is good, but they try a bit hard to be “unique” if you know what I mean. Nonetheless, it’s a great local spot. We tried the cheese plate and the Korean short rib tacos! Website
Location: 100 S Oak Park Ave, Oak Park, IL 60302
I hope you enjoy our recommendations, if you’ve been to any of these places before or happen to visit, leave me a comment! x
