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Roam Around

4-Day Chicago Adventure Itinerary

Last updated: 2024 Jun 14

Welcome to the Windy City

Morning

Start your day with a delicious breakfast at Wildberry Pancakes and Cafe. This highly-rated spot is known for its extensive menu of pancakes, omelets, and other breakfast favorites. It's the perfect way to fuel up for a day of exploration.

Afternoon

Head over to Millennium Park where you can marvel at the iconic Cloud Gate sculpture (also known as "The Bean") and take a leisurely stroll through the beautiful gardens. For lunch, enjoy some classic Chicago-style deep-dish pizza at Lou Malnati's Pizzeria. This famous pizzeria is a must-visit for any pizza lover.

Evening

In the evening, catch a show at Chicago Theatre. This historic venue offers a variety of performances from concerts to comedy shows. For dinner, dine at Girl & The Goat, one of Chicago's most popular restaurants known for its innovative dishes and vibrant atmosphere.

Bedtime

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4.69
Millennium Park
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Chicago Theatre
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Cultural Gems and Culinary Delights

Morning

Begin your day with a visit to the renowned Art Institute of Chicago. Spend your morning exploring its vast collection of artworks from around the world. For brunch or lunch, head to The Purple Pig, which offers an array of Mediterranean-inspired small plates.

Afternoon

After lunch, take a walk along the scenic Chicago Riverwalk. Enjoy the views of the city skyline and perhaps even take a boat tour. In the afternoon, visit Skydeck Chicago at Willis Tower (Sears Tower) for breathtaking views from one of the tallest buildings in the Western Hemisphere.

Evening

For dinner, make reservations at Alinea, one of Chicago's most acclaimed fine dining establishments offering an unforgettable culinary experience. End your evening with some live music at House of Blues, where you can enjoy performances by talented musicians in an intimate setting.

Bedtime

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Art Institute of Chicago
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Chicago Riverwalk
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History and Entertainment Extravaganza

Morning

Kick off your day with breakfast at Portillo's Hot Dogs, famous for its classic Chicago-style hot dogs and Italian beef sandwiches. Then head over to explore the fascinating exhibits at Field Museum, one of the largest natural history museums in the world.

Afternoon

In the afternoon, visit Adler Planetarium where you can learn about astronomy and space exploration through interactive exhibits and stunning planetarium shows. For lunch nearby, try out some mouthwatering BBQ at Smoque BBQ.

Evening

Spend your evening enjoying America's favorite pastime with a visit to historic Wrigley Field for a Cubs game if they're playing. If not available or preferred otherwise enjoy dinner at another iconic spot: Gibsons Bar & Steakhouse renowned for its prime steaks and lively atmosphere.

Bedtime

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4.56
Field Museum
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4.61
Adler Planetarium
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Architectural Wonders & Lakeside Leisure

Morning

Start your morning with coffee or breakfast pastries from Eataly’s cafe section before embarking on an architectural tour via boat along Lake Michigan taking in sights like Marina City & Tribune Tower ending near Navy Pier where you can grab lunch inside!

Afternoon

Afterwards spend time exploring Navy Pier itself which includes rides like Centennial Wheel plus shops & attractions galore! Visit Shedd Aquarium nearby afterwards seeing aquatic life up close!

Evening

Conclude this exciting day dining out either Avec Restaurant or Pequod’s Pizza both offering unique flavors sure satisfy cravings whether seeking Mediterranean fare or more deep dish delights!

Bedtime

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Final Day of Chicago Magic

Morning

Begin your last day in Chicago with a hearty breakfast at Wildberry Pancakes and Cafe. This beloved spot is known for its delicious pancakes, omelets, and other breakfast delights. It's the perfect way to start your day before diving into more city adventures.

Afternoon

Spend your afternoon exploring the Museum of Science and Industry. This fascinating museum offers a wide range of exhibits that cover everything from space exploration to historical artifacts. For lunch, head to Giordano's for another taste of Chicago's famous deep-dish pizza.

Evening

Conclude your trip with a visit to the iconic Navy Pier. Enjoy the beautiful views of Lake Michigan, take a ride on the Centennial Wheel, and explore the various shops and attractions. For dinner, make reservations at Bavette's Bar & Boeuf, known for its classic steakhouse fare and elegant ambiance.

Bedtime

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