A couple weeks ago I took a spontaneous weekend trip to Chicago, the windy city. Lucky for me, I went in the Summer when it was beautiful, and everyone came out to play at all times of the day. This was very relieving, since last time I was in Chicago it was so cold I couldn’t help but constantly think, ‘why am I here, why am I here, why am I here.’
After being there for about 4 days and traveling up and down the city for the best meal and beer, I have no realized why Chicago is a great place to visit, and live.
And besides Kanye West, there are a lot of awesome, and crazy things that come from Chicago.
Here are 10 things you MUST do if you ever visit Chicago, and they aren’t the typical “tourist” spots:
1) Go to a Cubs Game. Wrigley Field is not to be missed, especially since it’s one of the oldest baseball fields next to Fenway Park.. Granted, since it was built so long ago, you don’t have much leg room when you sit down in your seats. There are bars leading up to the ballpark all along the street so it’s the perfect place to skip the $12 beers before going in. Most importantly, you cannot leave Wrigley Field without getting a Chicago Dog! And load it up, don’t cut yourself short.
2) Head to Parsons for A Negroni Slushy: With a huge outdoor space, fried chicken and fish that are top notch, Parsons is a great go-to for anyone above 21. But what they’re best known for is their Negroni Slushy – it’s tasty, and they don’t mess around when it comes to the amount of Negroni.
3) Grandma J’s for Breakfast: I went to brunch almost every day for 4 days, and I went to all of the “preferred spots,” but nothing sold me more than Grandma J’s. A quaint, comfort-food brunch spot run by a family that genuinely cares about your experience and tastebuds. Everything is homemade in-house, organic and locally grown. Everything from their homemade Kombucha to the infamous Chicken + Waffle fritters are absurd! I will never go to Chicago without making a stop to Grandma J’s.
4) Big Star for Tacos and Whiskey: If you’re between the ages of 21 and well…. 45, you will enjoy Big Star. A Paul Kahan restaurant that’s a great place to party with unique whiskey and delicious tacos. Come here with a group and take a seat outside in their huge patio or a meet a friend at the bar, but come early (seriously early).. place gets packed.
5) Ride Bikes along the Shoreway: The fact that Chicago sits on Lake Michigan with the city behind gives you every reason to rent a bike and ride along the shore-way. Check out Bobby’s Bike Hike, located right at the beginning of the bike trail downtown.
6) Go to the beach: Lake Michigan, sand, volleyball nets, babes, and the city skyline right behind you. Need I say more? PS: There is a dog beach over at Montrose Beach solely for dogs to swim in a gated area – absolutely awesome.
7) Get fancy and get cocktails at Violet Hour: Right across from Big Star is a place called The Violet Hour (also owned by Paul Kahan). Violet Hour is very tough to get into, another place you have to get in early, but the cocktails are amazing and it’s definitely a great place to take a date (if you have a fat wallet for the night). High chairs and a dark ambiance makes for a great night-cap. Heads up: There isn’t a sign and the door discreetly blends into the city-walls, but you’ll see people waiting in line.
8) Danny’s to Dance + Sweat: Sweaty times, good music. Danny’s is the spot to dance and not be so classy for a night.
9) Be Trendy in West Loop: West Loop was very trendy, kind of reminds you of the East Village in New York. There is no shortage of restaurants and places to drink. Be sure to dress up, everyone seemed all dolled up around here.
10) Get a Burger from Au Cheval: Apparently this was voted the best burger in the nation, but I don’t totally agree. Don’t get me wrong, the burger was juicy and amazing, but I have had better (Sorry guys, still love ya). I can say the thick-cut bacon on top of the burger was unlike any other. We waited 2 hours (average wait for this place) for this burger, and then I fell into a food coma and my night was ended shortly after. They just opened up a Small Cheval for a more “to-go” type place with the same burger. Get the egg and bacon on it, or you’re doing it wrong.
Of course, there’s deep dish pizza, the Bean in Millennial Park, and the Sears tower, but these are all suggestions for the person who doesn’t want the typical touristy weekend.
Please do let me know if you take any of my recommendations + as always, happy travels!