In the past few years, when I've needed to travel for work (yes, I have a "real" job too!), I either arrive early or stay later to explore. That's what I did in July in Chicago: I needed to be in the suburbs for work but also wanted to see the city and lakefront. I went to college about 3 hours away from Chicago, have spent many weekends there with friends, and I've been back for a couple of concerts. But those visits were a hot minute ago, and any time in Chicago between then and now had mostly been spent in its airports. So, I was excited to reacquaint myself with the city.

 

I only had 1.75 days for myself, so I opted to purchase a Chicago CityPASS. This tourist ticket allows access to five of the city’s top attractions and lets you skip most lines, making it easy to focus a short visit on the top things you want to see and do. The CityPASS includes admission to Shedd Aquarium and Skydeck Chicago, plus your choice of three more from these options: Art Institute of Chicago, Field Museum, 360 CHICAGO Observation Deck, Griffin Museum of Science and Industry, Shoreline Sightseeing Architecture Boat Tour, and Adler Planetarium.

 

The CityPASS cost $142 for an adult (July 2025). That may sound high, but if you obtained individual tickets to each attraction, the cost would be much higher. It's really quite a bargain. My only wish is that it included parking. I drove on this trip, and stayed at the hotel in the burbs, closer to my work commitments. But since I had my car, it seemed easier to just drive downtown than to drive to a train station and spend 2 hours one way on the train. Yes, it would have been less expensive, but I was short on time. One day of downtown parking and one day of parking at Soldier Field cost a total of $80, so don't forget to factor that into your budget if you decide to drive to Chicago.

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Day 1: Art, Parks, and Skyline Views

I started my day at the Art Institute of Chicago, one of the most renowned art museums in the world and probably my favorite attraction in the city. From Impressionists and Post-Impressionists such as Renoir, Monet, Van Gogh, and Seurat to Postmodern works from Pollock and Pop Art pieces from Warhol, the museum’s collection spans continents and centuries. You can view heavy armor and weapons alongside delicate lace and jewels, plus ancient Egyptian sarcophagi and Asian ceramics. The serene Modern Wing features some of the architectural history of Chicago and home design pieces from a century ago that still seem space-age.

 

Note that the CityPASS does not include entrance to any limited-time exhibits happening at the time of your visit, and that the Art Institute is closed on Tuesdays.

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Once I'd refilled my eyes and soul with art, I headed outside and northbound into Millennium Park, one of the city’s most beloved gathering spaces. This is where you'll find "Cloud Gate" — better known as "The Bean" — a gleaming, reflective sculpture that mirrors the city’s skyline in surreal, dreamlike distortion. I couldn't help but hear the commotion going on at the Pritzker Pavilion, an outdoor amphitheater designed by architect Frank Gehry, and quickly learned it was a sound-check session in preparation for Lalapalooza. It wouldn't be uncommon to catch a live concert, yoga class, or even a symphony rehearsal, all coming from the stage beneath the iconic swooping ribbons of steel.

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Next up: Navy Pier. Though it’s not part of the CityPASS lineup, this lakefront hotspot is a great place to grab lunch, shop for souvenirs, take a spin on the Centennial Wheel or, if you have kids with you, check out the Children's Museum (both ticketed separately). The pier offers unbeatable views of Lake Michigan and the skyline, and is one of the boarding points for the Shoreline Sightseeing Architecture Boat Tour.

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I arrived at the pier around 5 p.m., and the heat made me wish I had waited a bit longer. — It. Was. Hot. — I thought being near (and then on) the water would be cooler, but no luck. I joked with other boat-tour passengers: "Where's all the wind this city keeps braggin' about?" Anyway, the speed of the boat created a nice breeze and I decided I'd survive. This 75-minute boat ride along the Chicago River is a true highlight. The guide explains the history behind the city’s iconic skyline — from remnants of the Great Chicago Fire to Art Deco buildings to sleek modern towers — all while gliding beneath bridges adorned with greenery and overflowing flowers. It was an informative, scenic, and entertaining close to the day.

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Day 2: Dinosaurs, Dolphins, and Discovery

I began my second day with a deep dive into history at the Field Museum, home to “Sue,” the largest and most complete Tyrannosaurus rex fossil ever discovered. But dinosaurs are just the beginning — this vast museum also houses human migration exhibits, sparkling gems, Indigenous artifacts, and rotating special exhibitions (also included with your CityPASS). I enjoyed special exhibits of real-life reptiles and types of trees. It’s easy to spend hours getting lost in the wonders of natural history.

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Just a short walk away is the Shedd Aquarium, another must-see included with a CityPASS ticket. This world-class aquarium offers colorful creatures of the Caribbean plus octopus, stingrays, and coral. Don't miss the Oceanarium, where beluga whales and dolphins steal the show. In the lower levels of the building, you can watch the dolphin show from below the surface through several glass panes with seating, which is pretty cool. There are also areas for playful sea otters and curious Magellanic penguins. A word of caution: This spot is filled with children, of course, and the likelihood of having your ankles bitten by a stroller is high. The mesmerized looks on the kids' faces make it OK, though. The Shedd is both entertaining and educational, making it a hit for all ages.

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I wanted to also visit the Adler Planetarium, but ran out of time before my work events began. ​If you find yourself with extra time on the Museum Campus, I suggest the planetarium, a walk along the lakefront trail, or grabbing a bite to eat from a food cart and relaxing on the grassy lawn to view the water and skyline.

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So yes, it is possible to experience the city’s most iconic sites with ease and value in just a few short days. Whether you're a first-time visitor or a return traveler looking to make the most of a short stay, this type of itinerary offers a nice blend of culture, nature, and architectural wonder — for a reasonable price and in just 48 hours.

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A FEW OF MY PHOTOS: