OT Travel Itinerary: 3 Days In Chicago

Chicago is known for awe-inspiring architecture, great food, beautiful parks, vibrant theatres, and captivating lakefront spaces
OT Travel Itinerary: 3 Days In Chicago
Crowds of tourists in downtown Chicago by The Bean, Cloud Gate on a summer dayKK Stock/Shutterstock
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Chicago has undergone a remarkable transformation from its origins as a small trading post at the mouth of the Chicago River. Said to be one of the great cities of USA, Chicago is known for awe-inspiring architecture, great food, beautiful parks, vibrant theatres, and captivating lakefront views. As the birthplace of skyscrapers, Chicago offers diverse and exciting experiences for everyone. Here is a three-day itinerary for an unforgettable adventure in the 'Windy City'.

DAY 1

Morning

Start your day with a quick breakfast, then head to Millennium Park bright and early to beat the crowds. Located within Chicago’s Loop, Millennium Park offers the iconic Cloud Gate statue (aka “The Bean”), unveiled in 2005 and known as an iconic city symbol. The park also features interactive fountains, tranquil gardens, free events, public art, skating rinks, rock climbing, and plenty of green space, making it a must-visit destination in downtown Chicago.

OT Travel Itinerary: 3 Days In Chicago
The iconic Chicago TheatreMarcus Finn Saunders/Shutterstock

Afternoon

Head to the Chicago Theatre, situated at the northern edge of the Loop. The prominent city landmark was built in the French Baroque style and originally opened in the 1920s as a grand movie palace. The theatre boasts a miniature Paris' Arc de Triomphe replica above its State Street marquee. With a seating capacity 3,600, it hosts various events such as stage plays, magic shows, comedy, and music concerts. Throughout history, renowned stars like Frank Sinatra, Aretha Franklin, and Robin Williams have graced its stage. Designated as a historic place on June 6, 1979, the Chicago Theatre marquee is unofficially considered an emblem of the city and has appeared in numerous films, TV shows, artworks, and photographs. Visitors can admire its elegant lobby, majestic staircase, and a beautiful auditorium adorned with murals.

OT Travel Itinerary: 3 Days In Chicago
View of the Chicago Riverwalk and the Merchandise Martquiggyt4/Shutterstock

Evening

Take a leisurely stroll along the Chicago Riverwalk after a snack break. This route is easy and typically takes about 47 minutes to complete. The area is popular for running and walking, so you'll likely encounter other people. The award-winning Chicago Riverwalk is located on the south bank of the Chicago River and spans 1.25 miles from Lake Michigan to Lake Street. Along the way, you'll find cosy cafes, wineries, bars, public art, monuments, museums, and various water excursions.

DAY 2

OT Travel Itinerary: 3 Days In Chicago
Buckingham Fountain is a Chicago Landmark in the center of Grant Park, between Queen's Landing and the end of Ida B. Wells Drive.meunierd/Shutterstock

Morning

Start your day by exploring Grant Park's beauty. Whether you love nature, architecture, or public art, there's something for everyone. The magnificent Buckingham Fountain is at the park's centre, inspired by the ornate fountains of the Palace of Versailles in France. This grand fountain, twice the size of the original, is one of the largest in the world.

Afternoon

Immerse yourself in the awe-inspiring wonders of the natural world at the Field Museum, an esteemed Chicago institution and a world-renowned natural history museum. Explore captivating exhibits that showcase ancient cultures and the latest scientific discoveries through an incredible collection of over 24 million objects. From Egyptian mummies to the man-eating lions of Tsavo and the iconic SUE, the largest and most complete Tyrannosaurus rex ever discovered, the museum’s world-renowned items will leave you spellbound.

OT Travel Itinerary: 3 Days In Chicago
Navy Pier on the shoreline of Lake MichiganUmut Tolga Pehlivan/Shutterstock

Evening

Next, prepare for an exceptional experience at Navy Pier, one of Chicago's most iconic landmarks. Here, you will discover various dining options and engaging activities. Take in the breathtaking views as you engage in people-watching, or gaze out across the vast expanse of Lake Michigan. Serving as Chicago's equivalent to some of the renowned eastern boardwalks, Navy Pier welcomes visitors free of charge throughout the year. You can also sivarious Chicago boat tours and captivating evening cruises offered at the pier.

DAY 3

Morning

Explore the city's iconic architecture from the prime vantage point of the river. Led by the Chicago Architecture Center's knowledgeable docent volunteers, the 90-minute Chicago Architecture River Tour unveils captivating stories behind the city's magnificent buildings in a unique and unparalleled way.

OT Travel Itinerary: 3 Days In Chicago
Sign up for a cruise to see the citySergii Figurnyi/Shutterstock

Afternoon

After the river tour, continue the marine theme. Step into Shedd Aquarium and discover a world where early 20th-century charm meets 21st-century innovation. With a collection of 32,600 sea life species, surrounded by breathtaking architecture, Shedd promises unforgettable experiences, including up-close shark feedings and captivating penguin encounters.

OT Travel Itinerary: 3 Days In Chicago
See the city from aboveAlex Cimbal/Shutterstock

Evening

After your tryst with water, look towards the sky. Visit the Windy City's extraordinary 360 Chicago, where you can experience the most exhilarating views of Chicago and Lake Michigan. Located on the 94th floor, this one-of-a-kind observation deck offers breathtaking sights of the city. Sunset is the best time to visit, but the views in full sunlight and at night are equally captivating. Adult tickets start at $30, and it's free entry for children under 3. Keep an eye out for special offers and different admission options that may be available.

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