chicago: the windy city
I really do miss Chicago. Home for three years of my life (alright, Evanston, but still) and one of my favorite places to fly back to, Chicago has embedded itself into my identity and has shaped a good number of my views. In the spirit of the forgotten posts I’ve been trying to publish on my blog, I decided to dig up old photos and put together a recollection of some of the best things to do in Chicago, especially as a first timer. There’s lots of nostalgia involved but that’s what happens when you love a city.
What is the Statue of Liberty to New York is likely the Cloud Gate to Chicago. More informally known as The Bean, this reflective sculpture is one giant selfie attraction. Grab your iconic photo here and then explore every corner of this structure created by Anish Kapoor, a unique artist in this day and age. The Bean is found in Millennium Park, which is in itself a good space to explore. If you’re there at the right time, you could catch a free event or concert at the Jay Pritzker Pavilion, which could be a lot of fun. This entire park district runs for a while and it’s one of my favorite parts of Chicago in how they prioritize recreational spaces with the arts integrated into it.
One of my favorite things to do in Chicago is to just walk around the city. From Millennium Park, you can walk westward on either Washington or Monroe, stopping by sights such as the Chicago Theater and the City Hall. Head north and cross the DuSable Bridge (one of my favorite bridges in Chicago) to see the Wrigley Building, Tribune Tower and the historic Water Tower. It’s also from this bridge that you can take the famous Chicago Architecture Boat Tour along the Chicago River. There’s a lot of sights I wish I took photos of (and will do so when I go back) but you can check them out for yourself. Do both day and evening walks and see how this city is truly alive – there’s often something new in each walk.
One of the things people definitely like to do in Chicago is to get a good view of the whole city. You normally have two choices, either the Willis Tower (formally known as the Sears Tower) or the former Hancock Building. We did the Willis Tower which had a skydeck that was simultaneously anxiety-inducing but also spectacular. You’ll get a 360-view of the city, and an appreciation of exactly how big Chicagoland actually is.
The City of Chicago sits on Lake Michigan which leads to some of the best scenic spots on the city Spend some time at some of the beaches in the summer (Oak Street Beach is a near one) or at Navy Pier all-year round, enjoying the lake up close. My personal favorite way to enjoy the lake is to go the museum conclave at Museum Campus. Here you can go to the Shedd Aquarium, Adler Planetarium and Field Museum all within proximity to each other. The Field Museum, a Natural History museum, is home to Sue, one of the largest dinosaur bone statues out there and a legend in museum circles. Insider secret: you get a pretty good view of the city from the stretch between the Planetarium and the Aquarium.
Slightly away from the Museum Campus is also the Art Institute of Chicago, part school and part famous museum. As far as art museums go, this is one of the most impressive ones I’ve been to, having a collection spanning works across time including famous pieces such as A Sunday Afternoon on the Island of La Grande Jatte by Georges Seurat. I’ve never been able to explore the whole museum despite going at least five times when I was in Chicago, and I’ll still want to go back the next opportunity I get.
A common question I get is “What’s the difference between New York and Chicago?”. Besides some of the more obvious comparisons (e.g. Chicago isn’t as pretentious), if you define Chicago to include the wider Chicagoland area, you open yourself up to a rich and diverse population. Each ethnic diaspora tends to command a specific neighborhood which leads to unique architecture and communities melded into the broader Chicago narrative. Everything is Chicago, but everything is also incredibly unique. Head to Cermak for Chinatown, Pilsen for a bit of Mexico, Avondale for Polish treats and Devon for Indian snacks. There’s also the Ukrainian Village, Greektown, Little Italy and a number of major communities that all contribute to the Chicago story. You’ll know you’ve lived well in Chicago when you get to participate in all of the neighborhoods. For something more generic but uniquely quirky, check out Wicker Park as well – I consider this one of my favorite spots in Chicago.
Finally, Chicago loves its sports teams. From the Cubs at Wrigley Field to both the Bulls and Blackhawks at the United Center, I count myself lucky to have seen some pretty crazy games at these arenas. I’d highly recommend planning ahead to book tickets for one of these games. You also have Soldier Field for the Bears and Cellular Stadium for the White Sox if you’re interested in those teams. If you happen to go to Wrigley Field, spend some time in Wrigleyville which is the drinking area centered around the stadium.
When it comes to food, there’s lots of recommendations, but I always used to follow the Eater 38 list which introduced me to Chicago darlings, Stephanie Izard and Grant Achatz. Here are some of my favorite digs in Chicago:
- Portillo’s for the Chicago Dog and their Italian Beef sandwich. Both of these are Chicago classic bites. The Chicago Dog has the pickle and tomato slice added onto it. The Italian Beef (get it with giardinera) is a soggy but delicious mess of a meal
- Giordano’s or Pequod’s for Deep Dish Pizza (you can also do Lou Malnati’s if you want). Deep Dish is basically a heavy crust pizza with lots of cheese at the base. Sinful but worth a try.
- Au Cheval for their famous burgers (must do, probably one of the best burgers I’ve had)
- Big Star for their fish tacos
- Alinea for a fine dining treat (you can also check out NEXT, Aviary and Roister)
- Little Goat for comfort food
- Hopleaf for brewpubs
In terms of bars and nightlife, check out
- Kingston Mines or Green Mill for Jazz (must must do this!)
- Anywhere in Logan Square including Revolution Brewing
- Moneygun
- The Violet Hour
- Cubby Bear (for a party)
In retrospect, I realize that a lot of my imbibing in Chicago was as a thrifty college student so it tended to center around which was the loudest party in either Wrigleyville or Boystown. I’m going to have to make my way back and discover new spots.
If you’re a Chicagoan reading this, you’re probably realizing I missed out a lot of stuff and you’re probably right. When you live in a city, you don’t force yourself to take as many pictures as you would if you were a tourist who was unsure if he’d ever make his way back. I wish I took more pictures and wrote more descriptions so that I could share them with you here. I can tell you, however, that Chicago is a city that has a soul like no other. The people there made it their own, and when they chose to stay in Chicago, they chose so wholeheartedly. There’s lots of that that I can’t say the same for some of the other cities I’ve lived in and it’s something I miss deeply.
If you’re wondering if you should add Chicago to your US itinerary, think no further – do it and have one of the best times of your life.
