Chicago has so many amazing places to explore that it could take weeks or months to fully experience everything that this amazing city has to offer. Here is a list of fun things to do in Chicago in one adventure-filled day.

Chicago, Illinois is the largest city in the Midwestern United States and borders the shore of beautiful blue Lake Michigan. Chicago is filled with some of the best architecture in the world, in addition to delicious hot dogs and pizza. Chicago is a destination for solo travelers as well as families with kids. Around every corner is something new and we were excited to share the magic of my Mom’s hometown with our kids.

One Day in Chicago

We set off on our adventure early in the morning, aiming to squeeze in as many sights, sounds, and tastes as possible during a single day in downtown Chicago. Without a car and five kids under the age of ten, we selected a route that minimized the number of steps our trackers would accrue and as a result, expanded the transportation options from our usual roads to include railways and rivers. At the end of the day, we accumulated over 16,000 steps and captured many memories and numerous pictures in our minds and cameras.12 Things to do in Chicago

12 Things to do in Chicago

Take the Train

One way to start your adventure is by taking a commuter train into Union Station just outside the Loop in downtown Chicago. We enjoyed the double-decker railway ride and avoided traffic and parking. Buying both outbound and return tickets made things simpler on the way back and we had the unexpected bonus that kids ride for free.

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Ride the Water Taxi

Views from the water taxi in Chicago

Coming out of Union Station, take a right, cross the river, and board the Shoreline Sightseeing Water Taxi for an unforgettable journey through the architectural wonderland riverside. We hopped on the top deck and sat up front to get the best view as we passed under bridges and went around bends in the Chicago River.

View the ArchitectureChicago Architecture

Chicago is known for amazing architecture and it was almost too much to absorb on the short trip to Navy Pier. We wound our way through the curves in the river admiring the crisp, tall buildings rising around us on every side. We felt the wind in our hair and appreciated the opportunity to look around while relaxing. Before we felt ready to stop our visual feast, we arrived at Navy Pier and disembarked for our continued adventure.

Explore Navy Pier

The 1.5-mile-long pier has served freight and commercial interests and was a military training center for the Navy pilots during WWII. My grandfather rode take the train to his job on Navy Pier when my Mom was growing up. Now it is the top Midwestern destination attracting more than nine million visitors annually containing entertainment, food and shopping.

Ride the Centennial WheelCentennial Wheel the Ferris wheel at Navy Pier in Chicago

Even those with a fear of heights can safely enjoy the beautiful scenery from a completely enclosed seat on the Centennial Wheel. We enjoyed 360-degree views of Lake Michigan and the Chicago skyline while circling smoothly on the giant white Ferris wheel. Briefly distracted from the spectacular view by our family making goofy faces through the windows in the next car, we appreciated the unexpected moment of levity.

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Eat pizza

A day experiencing Chicago is not complete without a slice (or two) of Chicago-style pizza. The thick crusted cheesy, saucy pizza at Giordano’s is our favorite way to fully appreciate the savory, buttery local food. Just make sure you order enough to save a slice for breakfast.

Take the Navy Pier Free Trolley

Navy Pier in ChicagoTraveling with 11 people, we tried to maximize our time and minimize our walking. Luckily for us, the seasonal trolley was available to take us from Navy Pier to the Art Institute of Chicago, where we could walk to our next destinations at Millennium Park. The best part was the cost – free!

Immerse yourself in Millennium ParkMillennium Park in Chicago

An art filled architectural meeting spot sits in the heart of this beautiful city. Sculptures like Cloud Gate and the Jay Pritzker Pavilion provide metal features nestled amid the lawn and Lurie Gardens with the striking skyline as a backdrop. There is something for everyone to appreciate in the midst of an urban setting.

See Cloud Gate (also known as “The Bean”)The Bean in Chicago

Take a peek in this unique reflective sculpture made from welded stainless-steel plates. Amazing craftsmanship displays no visible seams on the highly polished exterior. Try walking underneath for a different perspective or grab a selfie with the skyline “bending” across the shiny surface.

Listen to MusicJay Pritzker Pavilion in Chicago

Appreciate Frank Gehry’s architectural design at Jay Pritzker Pavilion. We stumbled upon an orchestra warming up for their performance and listened in awe in the open air bandshell auditorium. It has a state-of-the art acoustic system that distributes the sound across the lawn area. We did not have the chance to attend ourselves, but the free Millennium Park Summer Music Series looked like an amazing lineup of musical artists.

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Play in Crown Fountain

Crown Fountain in Chicago

Crown Fountain in Chicago

We had beautiful weather as we sat back and watched the water cascade down the walls, creating a mist that kept us cool. The intermittent spouts spraying from the pursed mouths of projected faces created pandemonium with the kids impatiently waiting for the next round. The happy squeals were continued as they jumped and splashed each other even when the spouts took a break.                              

Adventure in Maggie Daley

Maggie Daly Park in Chicago

Maggie Daly Park in Chicago

Park Nearing the end of our adventure, we took the winding pathway to Maggie Daly Park showcasing a collection of recreational options for ages 1-100. From climbing walls to roller-skating/scootering surfaces to actual playgrounds, plentiful choices are available to be active. For those looking for a more relaxing time, benches, picnic groves and concessions are sprinkled around the area.

We ended our day back on the train along with many commuters heading home. Tired and happy, we settled into the express train leaving downtown.

Chicago has many places to explore and discover. We enjoyed our single day adventure into the city and would recommend a day visit to downtown Chicago exploring via water taxis, free trolleys and walking whether you are a native or a visitor. We are already planning to go back!

Save 51% on Chicago’s 5 best attractions with CityPASS – Shop Now!image 3447064 10763415

Chicago Travel discounts and deals

More things to do in Chicago

Where to Stay in Chicago

Hotel Julian is the hotel we recommend. 

Should You Get Travel Insurance?

Don’t forget travel insurance! I’m a fan of Travelex insurance, because of the variety of options. Protect yourself from possible injury & theft abroad. I have gotten extremely sick twice now out of the country and Noah has had seizures in other countries, so I always recommend getting some sort of coverage. Noah’s last ambulance ride in America cost me $1800. Read more about why you should always carry travel insurance here.

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