I spent last week at a work conference in Chicago, which is one of my favorite cities. Chicago, to me, is like a cleaner, more friendly version of New York City. There’s an incredible food scene, tons of cultural sights, great shopping, and a really beautiful skyline (especially if you’re looking at it from Lake Michigan). I’m not going to bore you with the details of the lawyer conference, but I will share with you a compilation of my favorite activities, places to go, and places to eat.

Like most big cities, Chicago is pretty easy to navigate thanks to the robust public transportation system. The train system is referred to as the “El” because, as opposed to most East Coast public transit trains, the Chicago system is predominantly on elevated tracks. There are also plentiful bikeshare bikes scattered about if you don’t want to walk, but you also don’t want to spend money on an Uber. It’s also worth noting that taxis to and from the airport or generally less expensive than rideshares.

Take a Chicago River Cruise

There are about 5,000 different options when it comes to river tours or cruises in Chicago. They have more traditional architecture tours, relaxed sunset cruises that take you out into Lake Michigan, party boats, and everything in between. I don’t care which option you choose, but you should get yourself on a boat at some point during your trip. I have been to Chicago a few times now, and have taken to the water each time. I definitely recommend both the Chicago Architecture Foundation River Cruise and the Wendella Sunset Cruise. The CAF architectural boat tour is a wealth of information about the history of Chicago, it’s river, and the buildings that flank it — I promise it’s not boring!! The sunset cruise is a little different in that you actually get to go out to Lake Michigan. To get to the lake, your boat has to use the Chicago Harbor Lock, thanks to the difference in water level between the lake and the river, which in and of itself is kind of a cool experience. Fun fact about the lock: you won’t see any seagulls sitting on the grassy patches of the lock because the lock employs a very good boy Collie to patrol the land and keep the birds away!

Eat Some Deep Dish Pizza

You have to get deep dish pizza while you’re in town. Don’t skip out because you went to an Uno Pizzeria once and think you know what deep dish is. You do not. The most famous options are Giordano’s or Lou Malnati’s. Those of you from the Philadelphia area are probably familiar with the Pat’s versus Geno’s cheesesteak rivalry. Well, Giordano’s versus Lou Malnati’s is the same type of divide. They both offer a similar product (deep dish pizza), have similar (long) wait times, and leave you similarly full of cheese and red sauce. But there are lots of very nuances differences that result in people being die-hard disciples of one or the other. Which do I prefer? I’ll never tell…

Watch a Baseball Game

Chicago is home to two MLB teams, in case you were unaware. The White Sox are located on the South Side, and the Cubbies are up in Wrigleyville. Sort of like the deep dish pizza debate, Chicagoans are either Sox fans or Cubs fans and ne’er the two shall overlap. If you’re headed to Wrigley, the Budweiser Bleacher seats are the way to go — they’re general admission so you can move around and get a number of unique viewpoints, including standing at the bar underneath the historic scoreboard. The bleachers can get a little bit rowdy, but, especially on the Right Field side, you feel like you’re directly on the field. Get there early for batting practice for the best chance of catching a homerun ball.

If you can’t catch a game, try to take a tour of Wrigley Field, which is one of the oldest ballparks in America. I took the tour with my Dad several years ago, and can will personally vouch for the experience. You’ll get VIP access all over the ballpark, including in the dugout and on the field. Plus, the tours are only $30.

Get Yourself a Little Culture

If you know me, then you know that Jurassic Park is one of my favorite movies and film scores (John Williams is a genius). Thanks to Jurassic Park and also having an older brother into archaeology, I got BIG into dinosaurs as a kid. Like, giant stuffed dilophosaurus in my room big into dinosaurs. That love of the prehistoric never quite left me, so, naturally, I booked tickets to the Field Museum of Natural History to visit Sue the T-Rex, who happens to be the largest and most complete Tyrannosaurus Rex skeleton ever discovered. If dinosaurs aren’t your thing, first of all, what’s wrong with you? Fortunately, the Field Museum still has plenty of other interesting exhibits, including one featuring mummies and relics from Ancient Egypt and another showing off glittering gemstones. Plus, for those of you that enjoy adult beverages, the Field Museum distills its own gin with the flora from their eponymous Gin Garden.

I have it on good authority (AKA from my fiancé) that Shedd Aquarium is awesome. Whilst I learned about DNA testing and organizing complex case files, he was enjoying dolphins and sea lion performances and watching penguins meander about. I got about 3,000 Snapchat videos of brightly colored fish. He had the best day, and highly recommends that you visit.

If you’re more of an artsy type, check out the Art Institute of Chicago, which houses one of the finest art collections in the world. If I’m being honest, art museums are not my first museum choice. It’s not that I don’t appreciate the art and its history, I just don’t know what I’m looking at, and it all gets a bit overwhelming. I’ve found that picking up an audio guide device super helpful in actually getting something meaningful out of art museum visits, and AIC has an excellent one. Pick one up to take in the highlights here because the collection is MASSIVE and somewhat intimidating without a game plan.

Enjoy the Great Outdoors in Millennium Park and Grant Park

MIllennium Park and Grant Park are Chicago’s answer to Central Park, in that they come together to create a large green space in the center of the city. However, unlike their East Coast friend, these Parks are right on the banks of Lake Michigan, giving them the feeling of being far more vast.

There are a couple of notable landmarks within the parks to check out, but first and foremost is The Bean. While it is technically named “Cloud Gate,” this sculpture got its nickname thanks to it’s resemblance to a giant, silver bean. It’s a fun piece of art to take picture of and with, as the curvature of the structure leads to distorted images of that which it reflects. So go take a picture with the Bean.

Check the calendar of events for when your trip is planned because there are a lot of free (and no free) concerts in the park, especially over the summer. There are splash pads and fountains for you and any little ones to cool off in. Grab some charcuterie essentials from Eataly, rent a bike or a scooter, and meander through the parks on a sunny afternoon.

Speaking of Food…

You do have a multitude of options outside of deepdish pizza or Chicago dogs at a Cubs game. For example, the steakhouse scene in Chicago is hard to beat. If you’re looking for a very worthwhile splurge, make a reservation at Gibson’s Steak House.

For breakfast, I highly recommend a trip to Stan’s Donuts. There are numerous locations scattered throughout Chicagoland, so no matter where you’re staying, you should be able to get some fresh donuts to start your day. They have other pastries as well and rotating seasonal donuts, so make sure to peruse the menu online.

If you’re in the market for something quick and cheap for lunch, the Billy Goat Tavern is a Chicago landmark. Hidden underneath an overpass near the DuSable Bridge, the Billy Goat is not going to win any awards for ambiance, but the burgers are fresh and cheap. The walls are also lined with photos of famous patrons over the years, so you have plenty to look at while you nosh on your burger.

Another lunch or happy hour option is the Chicago Brewhouse, which is located right on the Riverwalk. It’s only open seasonally, so you’re out of luck in the winter, but this spot provides a nice selection of local craft beers, seasonal cocktails, frose, and giant pretzels. The added benefit is excellent people watching both of pedestrians on the Riverwalk and passengers on the many boats that will pass you by.

Finally, if you want a little nightcap with a view, the Londonhouse Rooftop Bar comes highly recommended. Located at the top of the old London Insurance building right off Michigan Avenue, you get sweeping city views and delicious cocktails. Apparently you can also rent the cupola on top of the building to get down on one knee, if you’re looking for somewhere to do something like that, but it will set you back around $1,000.

Chicago has so much to offer that I have merely scratched the surface here. There is also a robust theater scene, gangster tours, beaches on Lake Shore Drive, and quirky shopping out in Bucktown. It’s an easy 90ish minute flight from the East Coast, and there are tons of flights ever day. Do yourself a favor and book one and then tell me whether you prefer Giordano’s or Lou Malnati’s.

3 responses to “Chicagoland”

  1. My daughter and I used to sing in Chicago from time to time. Try Ann Sather next time for a spectacular breakfast (although you will probably have to wait for it.)
    We had a favorite Mexican restaurant as well, and if I remember it I’ll send it. Used to stay in a small guest suite on the near North Side. Shedd Aquarium rocks, and so does the Museum of Science and Industry. It’s all good.
    Thanks for the memories!


    1. I’ll have to check that restaurant out next time! Thanks for the recommendation!

      Liked by 1 person

  2. I loved Chicago! I really would like to visit again soon! Last time I went was in like 2019 for like a day and I half to support my aunt that was running the marathon and didnt get to do much. My first time I did a bit exploring but that was like back in 2015. So I am due to a new trip to be able to do more stuff! The Architecture Boat Tour has been probably one of my favorite things to do!!


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