Summer is my favorite season in Chicago. I love it when it’s warm outside during the day, but it’s even better when the weather is warm enough in the evening to sit out on a restaurant’s patio and enjoy a pizza, a beer, and the company of a friend.
Chicago is perfect for this. It’s amazing how the whole city seems to open up when it finally stops feeling like your legs are going to fall off from cold every time you walk outside. Every new restaurant seems to have a whole wall that opens up onto the street, but it’s really the patios you need to find. The summer is only getting hotter and more humid, which means that patios at night are really the best way to spend an evening out. Who wants to go anywhere during the daytime anyway? Here are a few patios to check out in the sunny Windy City
1415 W. Randolph Street
Kaiser Tiger is so far out in the West Loop that I often forget it’s there, but that’s really a shame. Though they don’t have many food or drink specials, their prices are fair and their patio is worth it. Due to its location in the often-unoccupied West Loop, the patio is huge. Filled with picnic tables and games, such as bocce ball and giant Jenga, this place is just screaming for a summer birthday party or a huge group hangout. One tip: I would only drink and play games here. The food is so-so and the service on the patio could use some work. Order from the bar if you can.
Phyllis’ Musical Inn
1800 W. Division Street
This place is truly weird and is really hard to describe. I usually read Yelp reviews before going somewhere, but the reviews for this dive bar just confuse me. Either Phyliss’ is the “mecca of cool dive bars in Wicker Park,” as Evil B. from San Diego California claims; or, as Ashley C. from the Ukranian Village here in Chicago writes, “There is no good time or sanitary time to be had here.” Per my own experience, I agree that the inside of this place is downright nasty, but the outside area is okay and there is a basketball hoop. My companions and I played HORSE and “Shoot Out” for over two hours there. We ended the night sweaty and happy.
Ten Cat Tavern
3931 N. Ashland Avenue
Ten Cats Tavern is by far my favorite patio spot on this list. Located on Ashland by the Irving Park Brown Line stop, it looks like an ordinary storefront from the outside and is easy to simply walk right past. I happened upon this place by accident, but have been back several times since. Come in, grab a drink at the bar (which has very plush, leather bucket chairs), and make your way through this dive-y space (that looks just like the first floor of your grandmother’s house) to the back patio. The patio, located under a huge, leafy tree, feels like a friend’s backyard. Last time I was there, two very nice ladies informed me that the bar has been in the neighborhood for at least 15 years. It was named after the owner’s ten cats that used to roam around the bar. Unfortunately, that was some kind of a health hazard, so the cats are no longer there, but the name and memory remain.
This cafeteria-style barbecue joint/ cocktail bar/ coffee shop is a weird concept, but it totally works. As it is in the West Loop it is a little bit on the pricey side, but it’s a location that you should check out at least once. I would suggest you splurge for the $11 pulled pork sandwich if you are a carnivore; everyone I’ve taken to this spot will attest to how completely delicious it is. While the cafe doesn’t necessarily have a patio, there is a little alley off of the restaurant with picnic tables that is cute beyond words. Go in the evening when the hanging lights are on and you will feel like you stepped into a cute little European city. It’s nice to get away for a little while.
2034 W Irving Park
A Bierstube in Germany could be compared to the American dive bar. Bierstube are typically tiny, hole-in-the-wall places where you will only find locals who come consistently after work or live close by. Rosie’s Bierstube holds true to this concept, but, in my opinion, is much cleaner than a typical dive bar. Also, their Biergarten/ patio is surprisingly great. You wouldn’t even know walking into this place that they have one. Stepping onto the back patio is like stepping into a secret fairy garden. It is small, but very nice. I highly recommend coming to enjoy great, authentic German food or to sip on a good German beer.