Chicago City Experiences Itinerary for 2 Days

Day 1: Chicago Landmarks

Chicago, USA

8:00AM

Breakfast at Lou Mitchell's

Start your day at Lou Mitchell's, a cherished Chicago diner known for its breakfast classics and homemade pastries that provide the perfect fuel for a day of exploring.
Head northeast on W Jackson Blvd towards S Halsted St, approximately 0.5 miles.
USD20, 1 hour

9:30AM

Willis Tower Skydeck

Experience breathtaking views of Chicago from the Skydeck at Willis Tower, where you can step out onto the iconic glass ledge for a thrilling perspective of the city.
Walk 0.3 miles southeast to the Willis Tower.
USD30, 1.5 hours

11:30AM

Millennium Park Visit

Stroll through Millennium Park to admire sculptures like the famous 'Cloud Gate' and lush green spaces perfect for iconic Chicago selfies.
Take the Green Line from Clark/Lake to State/Lake; a short walk from there, approximately 1.3 miles.
Free, 1 hour

12:30PM

Lunch at The Art Institute Café

Enjoy a delightful lunch at The Art Institute's café, serving seasonal dishes that reflect local flavors inside a beautifully designed space.
Walking distance within the Art Institute at Michigan Ave & Adams St.
USD25, 1 hour

1:30PM

Art Institute of Chicago

Explore the extensive collection of the Art Institute, featuring works by renowned artists like Monet, Grant Wood, and many more in a historic setting.
Inside the same building from lunch.
USD25, 2.5 hours

4:00PM

Navy Pier Walk

Head to Navy Pier for a scenic walk along the waterfront, where you will find entertainment options, shops, and stunning views of Lake Michigan.
Take the 29 State bus or rideshare for approximately 2 miles.
Free, 1.5 hours

6:00PM

Dinner at Giordano's

Indulge in Chicago's famous deep-dish pizza at Giordano's, a local favorite that's been satisfying diners for generations.
A short walk from Navy Pier, approximately 0.5 miles.
USD35, 1.5 hours

8:00PM

Chicago Riverwalk

End your day with a serene walk along the Chicago Riverwalk, where you can enjoy the city illuminated at night, a relaxing way to reflect on your first day.
Just off from Giordano's, a short stroll to the river.
Free, 1 hour
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Day 2: Cultural Depths

Chicago, USA

9:00AM

Breakfast at Wildberry Pancakes and Cafe

Fuel up with a delicious breakfast of fluffy pancakes and fresh fruit at Wildberry, known for its delicious take on brunch staples.
Take the Red Line from State/Lake to Harold Washington Library Station, roughly 1 mile.
USD20, 1 hour

10:30AM

Chicago History Museum

Discover the rich history of the Windy City at the Chicago History Museum, offering engaging exhibits and local artifacts that capture the essence of the city.
Take the #151 bus towards the museum, approximately 2 miles.
USD20, 2 hours

12:30PM

Lunch at Portillo's

Savor Chicago's famous Italian beef sandwiches and hot dogs at Portillo's, a casual eatery with a lively atmosphere.
Take the bus back to Downtown Chicago, approximately 2 miles.
USD15, 1 hour

1:30PM

Shedd Aquarium

Visit the Shedd Aquarium, one of the largest indoor aquariums in the world, where you can explore aquatic wonders and attend engaging shows.
Take the #146 bus from State St., approximately 2 miles.
USD40, 2.5 hours

4:00PM

Museum of Science and Industry

Delve into science and technology with interactive exhibits at the Museum of Science and Industry, hailed as a must-see attraction in Chicago.
Take the #10 bus, which goes directly to the museum, around 2 miles.
USD22, 2 hours

6:00PM

Dinner at The Cheesecake Factory

Wrap up your culinary journey with dinner at The Cheesecake Factory, often enjoyed for its vast menu and, of course, delicious cheesecake.
Take the #55 bus from the museum back to downtown, approximately 3 miles.
USD30, 1.5 hours

8:00PM

Evening Architecture Boat Tour

End your Chicago adventure with a relaxing evening architecture boat tour on the Chicago River, where you can marvel at the city's stunning skyline from the water as the sun sets.
Walk to the Chicago Riverwalk from The Cheesecake Factory, about a 0.5-mile stroll.
USD50, 1.5 hours
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