The Windy City, the Second City, Chitown, whatever you want to call it, there’s no debate that Chicago is such a fun city with so much to do. Even if you’re only there for a weekend, you can still see a lot of what the city has to offer (then realize how much more there is to see and start planning your next trip).
Lou Malnati’s
It wouldn’t be a trip to Chicago without having deep dish pizza, and there’s no better place to try it than the iconic Lou Malnati’s. As a New Yorker, I wouldn’t necessarily call it pizza, but it wasn’t bad either. We got the Malnati Chicago classic, which has sausage, extra mozzarella, and tomato sauce, and one slice was definitely enough.
The Bean
Another item on everyone’s Chicago to-do list is seeing The Bean. You really don’t need more than five minutes in Millenium Park to see the sculpture and take some pictures, but it’s worth the photo op.
Monk’s Pub
Chitown is home to an abundance of great restaurants, and Monk’s Pub is one of them. Located in The Loop, they serve bar food, salads, wraps, and dozens of beers. Some of the standout dishes are the loaded tater tots, the chicken avocado wrap, the BLT, and the steak sandwich.
Tilt
At the top of the John Hancock Tower, Tilt is a “ride” on the 360 Chicago Observation Deck. If you haven’t already seen videos online, you’re in a glass enclosed room that “tilts” outside of the building. While Tilt is cool (read: terrifying), it doesn’t give you any better views than the rest of the 94th floor observation deck. If anything, it allows you to see straight down to the street, but the real views are out across the horizon to Lake Michigan, the Willis (formerly Sears) Tower, and the Chicago skyline. My advice is to skip the ride and just buy a pass to the observation deck. But if you are going to do Tilt, get the all access pass, which includes a cocktail from the bar up there.
Piece Pizzeria
When you’ve had your fill of deep dish, head to Piece in for some New York-style pizza. They have some amazing pies like pepperoni and white pizza. But my favorite was hands-down the honey butter fried chicken, topped with juicy fried chicken, scallions, buffalo sauce, and blue cheese. They’re also a brewery and have a lot of great beers on tap.
Welcome Back Lounge
Welcome Back Lounge is a ’70s and ’80s-themed bar in Logan Square. Inside, there’s a bar (duh), tables, and a DJ booth. Outside, the theme really comes to life with a bar inside of an old Volkswagen bus. There’s even bar seating and the original driver’s seat in the front of the bus. The outdoor area was tented in the cold, but this would be a great hang out spot in the summertime.
Recess
Located in West Loop, Recess is a Sunday brunch hotspot. The menu is stacked with innovative food items like the chicken and waffle fries: juicy fried chicken and waffle fries drizzled with Nashville hot honey. I’m a sucker for breakfast burritos and theirs did not disappoint, stuffed with scrambled eggs, chicken chorizo, queso fresco, black bean salsa, avocado mayo, and served with a side of home fries. And of course they offer what everyone comes to brunch for: bottomless mimosas.
Galway Bay
Located in Lincoln Park, Galway Bay is a casual basement bar. The space is pretty large and they have multiple bars, a pool table, and darts. It’s a good Irish pub to hang out in even when it’s not St. Patty’s weekend.
See the Green Chicago River
Though this is only an option one weekend a year, visiting Chicago for St. Patrick’s Day weekend is definitely a bucket list item. They dye it early in the morning and it usually takes around 30 minutes. Or if you want to avoid the crowds (and standing out in single-digit temperatures), you can walk along the river at any time over the weekend, as the neon green color lasts for days.
Coffee and Countries 