With the COVID19 pandemic going on year two, so many of us have been hoarding our travel points on our credit cards. If you’re on the East Coast like I am, Chicago Illinois is a GREAT place to go using those points! It’s a quick two hour flight from New York City and flights are often dirt cheap. The only rub is often finding an inexpensive hotel. However, even if you’re only going for a short weekend trip, you can fit SO MUCH into your time in the Windy City. We did the following things below, and I thought you might like to as well.
#1 – Visit “The Bean” (Cloud Gate).
The image of this outdoor art piece is usually what most people imagine when they think of Chicago. It truly is an object of wonder and beauty, and it really brings people together as everyone makes funny faces, laughs at their kind of distorted reflection, and ask strangers to take their photo. The outdoor sculpture which has gained so much popularity was created by Indian born Brit, Sir Anish Kapoor. The majority of the sculpture reflects the sky and thus the original name of Cloud Gate makes sense.
#2 – Have a Bloody Mary at Happy Camper.
An alcoholic beverage is a wonderful way to start your day in a new city. Chicago does savory flavors really well (I mean, you’ve heard about their pizza right?) A great place to marry both of those facts is to visit the Happy Camper in the morning and order a bloody Mary WITH a slice of pizza on top — that’s what makes it really special.
#3 – Take an Architecture Cruise.
I’m not really an architecture nerd. Like, I appreciate the work that goes into it, and I’m happy that cool buildings exist, but I’m not particularly interested in the subject. Well, that is, until I went to Chicago. I returned from the weekend in the Windy City with a migraine, as my neck and head were craned up looking towards the buildings my entire time there. Rather than slamming into other folks around you as you stare upward, take a relaxing river cruise. You can sip a [relatively] cold beer and listen to the history of some of the more famous buildings from your tour guide. If you want to be cool like me, you can even spill some of that beer on your pants and look like you had an accident.
#4 – Eat a ‘Chicago Style Hotdog’ at Portillo’s.
Portillo’s can be a little intimidating for a first timer. You better know what you want, and you better be OK with people screaming into microphones. BUT, if you can survive all of that you’ll get one of the best hot dogs of your life — a Chicago style dog! It includes a poppy seed bun, relish, mustard, celery seed salt, chopped onions, tomatoes, and pickle spears (to stab your spouse when they ask for a bite.) There’s other options for hot dogs and food too, but you kind of can’t say you went to Chicago without trying the Chicago dog at Portillo’s.
#5 – Walk Along the Magnificent Mile.
I hate in-life shopping…a lot. I would rather go to the dentist than go shopping. However, even I, the jaded, lazy, woman that I am enjoyed strolling down the Magnificent Mile. It was especially cool once I realized that not every store on the strip is a clothing store. We had a blast wandering around the Disney store, a place that I haven’t been to since childhood.
It doesn’t hurt that Godiva has a shop nearby with gigantic sundaes and free squares of chocolate. Pro tip, once you leave Godiva, affix a false mustache to your face and go in again for a second free square of chocolate. OH WAIT – you also need to get cheesy popcorn from Garrett Popcorn Shops, they’re a Chicago institution. I know that because I’ve been to Chicago one time. But really, it’s the best cheesy popcorn in the world. Typically popcorn sold in shops can taste bland and stale, but not this. It’s oozing with flavor and very soft…like a pillow.
#6- Grab a Beer and Burger at Billy Goat Tavern.
This is my kind of bar…NO frills, NO dress code, and NO shouting. Well, unless you’re the guy in the back telling patrons that their cheeseburger is ready. In fact, the Billy Goat Tavern has ties to New York City because of that. Saturday Night Live once did a skit based on the way that the ‘burger slingers’ pronounced and yelled, ‘cheezborger.’ The staff is humorous, the burger are OK (not great) but they work as a marvelous and welcome accompaniment to a few too many beers in the afternoon.
#7 – Marvel at the Works of the Art Institute of Chicago.
I first became seriously interested in art after visiting this place on my weekend trip. It was one of the first times that I realized that art wasn’t only the Western greats, but that seemingly unheard of artists could do great things too. There always seems to be at least a few surreal, trippy, far out pieces and I really appreciate that. During my visit, I was mesmerized by the work of Ivan Albright. Each of his pieces was dark and the people looked diseased and as if their skin was being torn from their bones.
He was a medical draftsman during the first World War and so wanted to portray the “body’s vulnerability to age, disease, and death.” But that’s the thing about the art museum, it has something for everyone. It’s collection has such a range of work that people (like me) who thought art simply wasn’t ‘for people like them’ walk away eventually feeling the opposite. This museum’s praises are song from friends of mine and also heroes, like Anthony Bourdain.
#8 – Learn About Lincoln and Lincoln Logs at the Chicago History Museum.
There’s a LOT to learn here, particularly about former President Lincoln. One of the Lincoln exhibits shows you what Chicago looked like during his lifetime. The other traces his legacy from his campaign, through the Civil War, and to the end of his life by assassination. When we visited, we were able to see the actual bed in which he passed away after being shot.
He was so tall, that he had to be laid horizontally which I found fascinating. In other exhibitions you can climb aboard a railway car, see the toys and scientific inventions created in Chicago, see an antique store front, and visit a jazz club. The City on Fire: Chicago 1871 is set to open soon and will deliver the truth about the event which destroyed and devastated so much of the city.
#9 – Hate Yourself After Eating a Deep Dish Pizza.
First you eat the deep dish pizza…then the deep dish pizza eats YOU. Deep dish pizza is like a wedding cake…but full of pizza. It’s decadent as hell, and SO heavy. I don’t think anyone really warns you about just how much food even a single slice of deep dish pizza can be. If you eat too much, just lay down on the floor and the servers anywhere will just roll you out.
#10 – Pee Your Pants at the Sky Deck.
See Chicago from a different view entirely. Sky Deck allows you to step out onto an entirely glass platform to look down over the Windy City. Sky Deck is a part of the Willis Tower which means you’re so high up that you can see for fifty miles in each direction (on a fair weathered day.)
#11 – Search for Artifacts on the Chicago Tribune Tower.
If you’re a travel enthusiast, then you’ll probably enjoy this free activity. The history on exactly how this happened is a little hazy, but evidently foreign correspondents for the Chicago Tribune would return to the city with all sorts of artifacts from Paris and Giza and beyond. As the tower was being built, these artifacts were embedded into the outside of it. So, today, you can walk around the building and see about 150 different artifacts from around the world with descriptions to match each one.
#12 – Drink with Al Capone’s Ghost.
During the Prohibition era, the Green Mill Cocktail lounge hosted Chicago’s best jazz performers and also its most powerful criminals. Not much has changed in terms of decor, and you can still enjoy jazz performances each and every evening. The Green Mill served as a speakeasy back in the day, and in the event of a raid had a door that led directly outside. Al Capone sat in a particular booth (always the same one) when he visited that allowed him to have a clear view of the doors to the place. You can still sit at his booth today.
#13 – Tour the Chicago Theater.
Back in the day, the Chicago Theater showed movies (in the 1920’s) Today, it hosts a plethora of important live shows. Even without catching a performance, you can still tour the building and even go backstage. There’s an autographed ‘wall of stars’ in the dressing room and depending on the tour you see the lobby and orchestra area too. You’ll learn not only about the operations and people who perform/have performed there, but also the architectural history.
#14 – Listen to Live Blues Music.
Whether you’re not sure if you’ve ever heard blues, or if you’re a blue aficionado, you’ll love hearing it live in Chicago. Artists like Muddy Waters gave rise to the soulful way of playing and singing and it’s still very much enjoyed in the city today. Places like Rosa’s Lounge, Kingston Mines, and Blue Chicago, and Buddy Guy’s Legends (a touch touristy) are popular haunts. Don’t forget to order a glass of wine and some food as you get lost in truly awesome sounds.
#15 – Take a Crime Tour.
If you’re an American, you probably know their names…Al Capone, Bugs Moran, John Torrio, Big Jim Colosimo, Hymie Weiss, John Dillinger, Dean O’Banion, there’s quite a few notorious mobsters who have Chicago roots. Learn all about their criminal legacies and enterprises with a walking tour. On most tours you’ll get a glimpse at Dean O’Banion’s flower shop and the site of the St Valentine’s Day Massacre.
#16 – Hang Out at Navy Pier.
Sure it’s touristy, but it’s also really fun, and newsflash — you are a de facto tourist when you visit anywhere. Ride the Centennial Wheel, grab an ice cream, try some sunset yoga, shop at a pop up market, listen to tunes from an outdoor performance, and of course — smile as you watch the fireworks burst in the area, marking the end of a great day in a new city.
#17 – Have a Drink at the Chicago River Walk.
Sure it’s likely to be a very expensive drink and meal, but THAT VIEW of the river kind of makes it all worth it. From Chicago Brew House with locally made brews and food inspired by ‘global’ neighborhoods, to City Winery with climate controlled igloo domes, to Island Party Hut which serves delicious tropical drinks and has lots of games to entertain your group, you’ll love hanging out here.
#18 – Explore ‘Oz Park.’
This small park pays tribute to the creator of Wizard of Oz, Frank L. Baum. Statues of Dorothy, Toto, Lion, Scarecrow and the Tin Man stand tall and proud in the park and you can download an app that tells you more about each one. There’s also a playground on site that is perfect for really little ones (like toddlers.)
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