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6-Day Downtown 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 popular spot is known for its mouth-watering pancakes and fresh coffee, providing the perfect start to your Chicago adventure. After breakfast, head over to Millennium Park, where you can admire the iconic Cloud Gate sculpture (also known as 'The Bean') and take a leisurely stroll through the beautiful gardens.

Afternoon

For lunch, visit Portillo's Hot Dogs to try one of Chicago's famous hot dogs. Afterward, explore The Magnificent Mile, a bustling shopping district filled with high-end stores, restaurants, and historic landmarks. Don't forget to check out the historic Water Tower Place while you're there.

Evening

In the evening, enjoy dinner at Girl & the Goat, one of Chicago's most acclaimed restaurants. After dinner, catch a live show at Chicago Theatre, an iconic venue known for its stunning architecture and world-class performances.

Bedtime

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Cultural Gems and Culinary Delights

Morning

Begin your day with breakfast at Lou Mitchell's Restaurant, a classic Chicago diner that's been serving up hearty breakfasts since 1923. Then head over to the Art Institute of Chicago, home to an impressive collection of art from around the world.

Afternoon

For lunch, stop by The Purple Pig, known for its 'cheese, swine & wine' theme. Spend your afternoon exploring Grant Park, often referred to as 'Chicago's front yard,' which offers beautiful green spaces and stunning views of Lake Michigan.

Evening

Dine at Alinea, one of only 14 Michelin three-star restaurants in the United States. After dinner, take a stroll along the Chicago Riverwalk where you can enjoy breathtaking views of the city skyline.

Bedtime

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History and Architecture Extravaganza

Morning

Start your morning with breakfast at Eataly Chicago - La Pizza & La Pasta, where you can enjoy Italian pastries and coffee. Then visit the iconic Skydeck Chicago at Willis Tower (Sears Tower) for panoramic views of the city from one of its tallest buildings.

Afternoon

For lunch, try some deep-dish pizza at Lou Malnati's Pizzeria. Afterward, explore more architectural wonders by visiting the historic Rookery Building and taking a guided tour through its beautifully designed interiors.

Evening

Have dinner at Bavette's Bar & Boeuf, known for its excellent steaks and vintage ambiance. Conclude your day with some live music at the famous blues club, House of Blues.

Bedtime

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Science Wonders and Scenic Views

Morning

Enjoy breakfast at Giordano's Pizzeria before heading over to explore marine life at the renowned Shedd Aquarium. This aquarium is home to thousands of aquatic animals from around the world.

Afternoon

Lunch will be at Shaw's Crab House, where you can indulge in fresh seafood dishes. Post-lunch visit Adler Planetarium to delve into astronomy exhibits while enjoying scenic views of Lake Michigan.

Evening

Dine in style atop The Signature Room at the 95th for an unforgettable meal paired with panoramic city views. End your evening with a relaxing walk along Navy Pier.

Bedtime

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Sports and Skyline Views

Morning

Start your day with a hearty breakfast at Lou Mitchell's Restaurant, a Chicago institution known for its generous portions and freshly baked goods. After breakfast, head to Wrigley Field, one of the oldest baseball stadiums in the country. Take a guided tour to learn about its rich history and maybe even catch a game if the Cubs are playing.

Afternoon

For lunch, visit RPM Italian, where you can enjoy delicious Italian cuisine in a chic setting. Afterward, explore Lincoln Park & Zoo, one of the oldest zoos in North America that offers free admission and houses a wide variety of animals.

Evening

In the evening, dine at Gibsons Bar & Steakhouse, renowned for its prime steaks and lively atmosphere. After dinner, make your way to 360 Chicago Observation Deck (Formerly John Hancock Observatory) for breathtaking views of the city skyline from 1,000 feet above.

Bedtime

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Cultural Finale and Farewell

Morning

Begin your final day with breakfast at Wildberry Pancakes and Cafe, where you can savor their famous pancakes one last time. Then visit the Field Museum, home to Sue, the largest and most complete T. rex ever discovered.

Afternoon

For lunch, head to The Purple Pig for a delightful meal featuring Mediterranean-inspired dishes. Spend your afternoon exploring Museum of Science and Industry, which offers fascinating exhibits on everything from space exploration to historical artifacts.

Evening

Conclude your trip with dinner at Au Cheval, known for its legendary burgers. End your evening with a visit to Navy Pier where you can enjoy rides, games, and perhaps even catch some fireworks if you're lucky.

Bedtime

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