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![5 Days Exploring Chicago](https://storage.googleapis.com/bd-app-dev-375714.appspot.com/itineraries/018fb3c9-c064-79fa-a0de-c1b3a479f411/location44.jpg)
5 Days Exploring Chicago Itinerary
Last updated: 2024 Jun 14Welcome to the Windy City
Morning
Start your day with a delicious breakfast at Wildberry Pancakes and Cafe, known for its mouth-watering pancakes and vibrant atmosphere. After breakfast, head over to Millennium Park to see the iconic Cloud Gate sculpture (The Bean) and enjoy a leisurely stroll through the park.
Afternoon
For lunch, indulge in some deep-dish pizza at Lou Malnati's Pizzeria. Afterward, visit the Art Institute of Chicago, one of the oldest and largest art museums in the United States. Spend a few hours exploring its extensive collection of artworks.
Evening
In the evening, dine at The Purple Pig, which offers a variety of Mediterranean-inspired dishes. After dinner, take a scenic walk along the Chicago Riverwalk and enjoy the beautiful city lights reflecting on the water.
Bedtime
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![Visit Millennium Park in Chicago, Illinois](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/5c/00.jpg)
4.69Millennium Park
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![Visit Millennium Park in Chicago, Illinois](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/5c/00.jpg)
Millennium Park
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![Visit Art Institute of Chicago in Chicago, Illinois](https://media.tacdn.com/media/attractions-content--1x-1/12/33/15/da.jpg)
4.61Art Institute of Chicago
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Art Institute of Chicago
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![Visit Chicago Riverwalk in Chicago, Illinois](https://media.tacdn.com/media/attractions-content--1x-1/12/3f/5c/d3.jpg)
4.72Chicago Riverwalk
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![Visit Chicago Riverwalk in Chicago, Illinois](https://media.tacdn.com/media/attractions-content--1x-1/12/3f/5c/d3.jpg)
Chicago Riverwalk
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Cultural and Historical Gems
Morning
Begin your day with breakfast at Girl & The Goat, known for its innovative dishes. Then head to Field Museum, where you can explore fascinating exhibits on natural history.
Afternoon
For lunch, try some classic Chicago-style hot dogs at Portillo's Hot Dogs. Afterward, visit the nearby Shedd Aquarium to see an impressive array of marine life from around the world.
Evening
Enjoy dinner at Bavette's Bar & Boeuf, famous for its steaks and elegant ambiance. End your day with a visit to the historic Chicago Theatre, where you can catch a live performance or simply admire its stunning architecture.
Bedtime
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![Visit Field Museum in Chicago, Illinois](https://media.tacdn.com/media/attractions-content--1x-1/12/33/16/53.jpg)
4.56Field Museum
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![Visit Field Museum in Chicago, Illinois](https://media.tacdn.com/media/attractions-content--1x-1/12/33/16/53.jpg)
Field Museum
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![Visit Shedd Aquarium in Chicago, Illinois](https://media.tacdn.com/media/attractions-content--1x-1/12/2e/46/94.jpg)
4.75Shedd Aquarium
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![Visit Shedd Aquarium in Chicago, Illinois](https://media.tacdn.com/media/attractions-content--1x-1/12/2e/46/94.jpg)
Shedd Aquarium
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![Visit Chicago Theatre in Chicago, Illinois](https://media.tacdn.com/media/attractions-content--1x-1/0b/39/80/84.jpg)
4.71Chicago Theatre
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![Visit Chicago Theatre in Chicago, Illinois](https://media.tacdn.com/media/attractions-content--1x-1/0b/39/80/84.jpg)
Chicago Theatre
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Architectural Wonders
Morning
Have breakfast at The Publican, known for its hearty brunch options. Then take an architectural boat tour along the Chicago River to learn about Chicago's iconic skyscrapers and architectural history.
Afternoon
For lunch, savor some Italian beef sandwiches at Al's Beef. Afterward, visit the impressive observation deck at 360 Chicago Observation Deck (Formerly John Hancock Observatory) for panoramic views of the city.
Evening
Dine at Au Cheval, renowned for its burgers. In the evening, explore Navy Pier with its many attractions including rides, shops, and entertainment options.
Bedtime
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![Visit Chicago River in Chicago, Illinois](https://media.tacdn.com/media/attractions-content--1x-1/12/33/9a/fa.jpg)
4.61Chicago River
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![Visit Chicago River in Chicago, Illinois](https://media.tacdn.com/media/attractions-content--1x-1/12/33/9a/fa.jpg)
Chicago River
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![Visit 360 Chicago Observation Deck (Formerly John Hancock Observatory) in Chicago, Illinois](https://media.tacdn.com/media/attractions-content--1x-1/0b/a7/0e/e7.jpg)
4.17360 Chicago Observation Deck (Formerly John Hancock Observatory)
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![Visit 360 Chicago Observation Deck (Formerly John Hancock Observatory) in Chicago, Illinois](https://media.tacdn.com/media/attractions-content--1x-1/0b/a7/0e/e7.jpg)
360 Chicago Observation Deck (Formerly John Hancock Observatory)
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Parks and Museums Day
Morning
Start your day with breakfast at Smoque BBQ before heading over to Lincoln Park Zoo for an enjoyable morning with wildlife in one of America's oldest zoos.
Afternoon
For lunch enjoy delicious Mexican cuisine from Rick Bayless' restaurant: Frontera Grill. Then make your way towards Adler Planetarium which offers incredible exhibits about space exploration as well as breathtaking views across Lake Michigan.
Evening
Have dinner reservations set up ahead-of-time so that you can experience fine dining French cuisine paired perfectly alongside wines from Everest Restaurant located high above downtown providing stunning vistas while enjoying gourmet meals prepared by world-class chefs.
Bedtime
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Final Day Fun
Morning
Kick off your last day by having breakfast/brunch served up fresh daily over Parson’s Chicken & Fish followed closely behind visiting Skydeck located atop Willis Tower offering unparalleled vantage points stretching outwards far beyond city limits.
Afternoon
Grab quick bites midday via Pequod’s Pizza featuring caramelized crusts unlike any other pie around town then venture forth towards Museum Science Industry where countless interactive displays await discovery
Evening
Cap off trip indulging yourself gastronomically speaking @ Alinea Michelin-starred establishment showcasing avant-garde culinary techniques guaranteed leave lasting impressions long after returning home.
Bedtime
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