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This Chicago trip itinerary highlights three days of must see attractions. Chicago is one of my favorite cities to visit in the US. It’s got so much history and remnants from the 1920s and 1930s – an iconic time in American history. As a result, in my quintessential Chicago trip, you’ll see many legendary destinations from the prohibition and depression eras.
This itinerary is organized by region so you can easily make it to a few spots in one day. You’ll want to book a hotel in the area roughly around the Chicago Riverwalk. That will ensure easy access to these things to do along the shoreline.
Day 1: Take a boat tour from Navy Pier
Navy Pier
Before the boat ride, you can walk around Navy Pier. This vibrant hub was originally built in 1916 as a shipping and recreation facility. Navy Pier is one of Chicago’s most iconic destinations, stretching 3,300 feet along the shoreline of Lake Michigan.
You can ride the Centennial Wheel, a 200-foot-tall Ferris wheel to see breathtaking views of the city skyline. The pier hosts the Chicago Children’s Museum and Chicago Shakespeare Theater. It also offers a variety of restaurants, shops, and seasonal events.
If you’re planning a trip, keep in mind that parking can be pricey, so public transportation might be a better option.
Lake Michigan Boat Tour
You can’t miss this opportunity to see Chicago’s skyline from out on Lake Michigan.
Take a boat tour from navy pier – you can book it here through Viator. It only cost me about $35 per person and it lasted about 45 minutes.
From the boat , you’ll see beautiful views of the Chicago shoreline.
Day 2
For day two, your Chicago trip itinerary brings you on tours of Soldier Field and the Shedd Aquarium. Both are located on what’s called the Museum Campus. This is a dedicated area in the lakefront that houses many of Chicago’s premier cultural institutions
Soldier Field
Take a tour of Soldier Field, the historic stadium home of the Chicago Bears (NFL) and Chicago Fire FC (MLS).
First opened in 1924, it was given the name Soldier Field in honor of American soldiers who died in wars. Over the years, it’s hosted legendary events like boxing matches, political speeches and the first Special Olympics Games in 1968.
Shedd Aquarium
Don’t miss one of the largest aquariums in the world. Shedd Aquarium houses over 32,000 animals across 1,500 species and was opened in 1930.
You can explore marine life from places like the Amazon, Caribbean Reef, Polar Caps and more. The aquarium offers interactive experiences, including encounters with penguins, stingrays, sea otters, and sharks.
Shedd Aquarium is a National Historic Landmark, recognized for its architectural beauty and conservation efforts.
Day 3
On Day 3 of your Chicago trip itinerary, you’ll spend some time in the Riverwalk and Loop area.
Chicago Theater
If you plan ahead, you might be able to catch a great show the Chicago Theater. Think comedy shows like Nikki Glaser and music acts like Barenaked Ladies.
This historic building was built in 1921 with opulent French-inspired architecture and a bright marquee.
Millennium Park
Make your way over to “The Bean” and take a photo with this massive, mirrored sculpture. It’s in Millennium Park which is famous for public art, gardens, and outdoor spaces.
While at Millennium Park, you can also see the Crown Fountain is one of my other favorite things to see in Millennium Park. It’s an interactive fountain featuring LED screens displaying faces of Chicago residents.
London House
See the city from the rooftop bar at the LondonHouse Chicago hotel. Above you’ll see the beautiful view I saw on my last visit.
This is a hidden gem in Chicago that I don’t think gets talked about. Its the perfect place to end the trip with stunning views of this metropolitan paradise.
Love visiting big cities? Check out this guide on visiting San Francisco!
