Chicago goes by many nicknames – the Windy City, Chi-Town, the City of Big Shoulders, and the Second City are just a few – but it derives its official name from an Indigenous word meaning Stinky Onion.

Well, I personally don’t like onions – but I do love visiting Chicago.

Chicago, like its peer and frequent rival, New York, is a city that is tailor-made for tourism. With world-class restaurants, over sixty museums, and a public transit system that is both easy to use and cost-efficient, Chicago is always worth a visit.

A large, sprawling city on the edge of Lake Michigan, the city is divided up into 77 community areas – each with its own personality and more-or-less centered around The Loop. Here is where all of CTA’s rail lines (or the “L” – short for elevated trains) converge.

Chicago is so much more than its downtown core, but with just 36 hours in the city, I decided it was wise to spend our time all in one place (commuting around to different neighborhoods soaks up valuable travel time, after all!). Today I’m sharing my guide to the best things to see and do (and eat!) in The Loop, West Loop, and River North – or the areas most would consider downtown. But before we jump into the guide, here are five fun facts to get you acquainted with the city quickly:

Five Fun Facts about Chicago

  • The Chicago Fire of 1871 might just be the most well-known fire in U.S. history, but you might not know that the Chicago Fire Academy is now housed at the fire’s ignition point.
  • The famed American roadway Route 66 begins in Chicago (unless you’re starting on the other end, in L.A.!) – you can find the route marker near the main entrance to the Art Institute of Chicago.
  • The Chicago River is the only river in the world that has been reversed to run backward. Instead of running toward Lake Michigan, it now runs away from it.
  • The Centennial Wheel at Navy Pier is now an iconic part of the Chicago skyline, but its importance to the city runs deeper than just sheer thrills. When Chicago hosted the World’s Fair in 1893, the Ferris wheel was the centerpiece of the exhibition – and the very first one.
  • Commercial rent for properties along The Magnificent Mile (a 13-block portion of Michigan Avenue with hundreds of luxury retailers) is currently the third-highest in the nation – after Fifth Avenue in NYC and Rodeo Drive in Beverly Hills.


Wendella Tours & Cruises bills itself as Chicago’s Original Architecture Tour® because, well, it is. Since 1935 the tour operator has been shuttling locals and visitors alike up and down the Chicago River, offering the most incredible perspective on the city’s renowned architectural marvels. While you can get some sense of the scale and details of Chicago’s architecture from the street level, it doesn’t compare to the clear view only available from the water. And, of course, a guide provides invaluable context to what you’re currently viewing.

The 90-Minute Chicago River Architecture Tour is the perfect introduction to the city’s layout and history, and tours are typically available from morning until evening year-round. Purchase your tickets online to save time, and arrive early for the best seat selection. There’s not a bad seat onboard, but in my opinion, the front right offers the best views. After a brief introduction and safety presentation, you’ll start making your way down the Chicago River! Our guide was engaging and knowledgeable, sharing each building’s story as it came into view. Properly bundled to fight the chill, we remained outside on the top deck for the majority of the ride – but even if we decided to pop down to the bar to grab a drink or a snack from the full-service bar, speakers are mounted throughout the vessel for an uninterrupted tour experience. I won’t spoil all that we learned from our guide because I want to make sure you add this essential Chicago attraction to your list. For a quick weekend getaway, I know that it can be difficult to commit a full ninety minutes to any singular stop on your itinerary; for those extra short on time, Wendella offers a condensed 45-minute tour in the evenings.

Art Institute of Chicago

Some of the most iconic works of art can be found at the Art Institute of Chicago. Like many museums in its class, it is simply too vast to be fully appreciated in just a day – and with only 36 hours in the city, that shortens a visitor’s attempts even further. Thankfully, the museum website offers a helpful database of its collection so you can map out your favorites in advance – and there is even a “What to see in an hour” section for those who are unsure of where to start. Do make sure to linger awhile in the Miniatures collection for me (it’s my favorite!).

Buy tickets online to save time and skip the queue – although I will note that the ticket line was significantly shorter than the coat check line (a must-visit portion of the museum when the temperature hovers around the freezing mark!). It is also helpful to time your visit wisely if you can. Arriving earlier in the day will give you better chances of receiving timed tickets for any popular rotating exhibits, if necessary. This visit coincided with the display of Salvador Dalí: The Image Disappears, and obtaining the (free) tickets for the exhibit was quite competitive. Thankfully, we made it in – a great opportunity to revisit some of the artist’s works. On a cold, rainy day the museum was quite crowded (it is the perfect rainy day activity, after all!), and I should note that there was never much time to oneself with any particular work. Any hopes of recreating the iconic scenes from Ferris Bueller’s Day Off are best left in your dreams (or perhaps, on a weekday).

Cloud Gate (a.k.a. The Bean)

A stop at Cloud Gate (a.k.a. The Bean) feels like such an iconic part of the Chicago visitor experience that it’s hard to believe it was only installed in 2004. There’s no denying how mesmerizing the reflective sculpture is; the city is reflected so beautifully in the art piece, and there’s something so fascinating about studying the way your reflection moves with you as you explore the curves of it. And despite being practically made for Instagram (even before Instagram was a thing), it makes for a frustrating subject. It’s nearly impossible to photograph well, because not only will your camera always be in the reflection, but there will always be people around, too. Snap a few anyway, and enjoy a bit of people-watching in Millennium Park.


It seems I have a thing for five-letter fine dining: Pujol, Xokol, and now Tzuco. I wasn’t expecting to find some of the very best Mexican food I’ve had the pleasure to experience this side of the border in Chicago, but that’s exactly what happened. When making a reservation, the only option remaining was a seat at the Kitchen Counter; after visiting, I’d say this is the best seat in the house. Here, you get a front-row seat to the action: the reduction of the broth for the mejillones, the precision of the application of salsas, and the sizzle and snap of a gloriously-made burger (yes, a burger). Monthly, Chef Carlos Gaytán rotates regional specials in a “Back to My Roots” series, in addition to serving elevated versions of the classic dishes you love. Everything on the menu was tempting, but we landed on two appetizers and a main dish to share. Even my “I don’t like avocados” fiancé couldn’t resist the most heavenly guacamole, and the chicken tinga tetela had the perfect balance of filling and masa. The cochinita pibil fell to pieces at the mere sight of a fork, so tender and perfect paired with handmade tortillas. The portions were so generous that a third person could have easily joined us, but the team at Tzuco gilded the lily by bringing the most fetching dessert: a corn cake with popcorn and saffron ice cream. The sweetest ending, indeed.