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Chicago Amtrak Adventure 6 Days Itinerary

Last updated: 2024 Jun 14

Welcome to the Windy City

Morning

Start your day with a visit to Millennium Park. This iconic park is home to the famous Cloud Gate sculpture (also known as "The Bean"), Crown Fountain, and Lurie Garden. It's a great spot for a morning stroll and some fantastic photo opportunities.

Afternoon

Head over to The Magnificent Mile for some afternoon shopping and sightseeing. This bustling stretch of Michigan Avenue is lined with high-end shops, restaurants, and historic landmarks. Don't forget to grab lunch at Girl & The Goat, known for its innovative small plates and vibrant atmosphere.

Evening

In the evening, enjoy a relaxing walk along Chicago Riverwalk. This scenic waterfront path offers stunning views of the city's architecture and is perfect for an evening stroll. For dinner, head to Joe's Seafood, Prime Steak & Stone Crab for some of the best seafood in Chicago.

Bedtime

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Millennium Park
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4.65
The Magnificent Mile
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Cultural Gems and Classic Eats

Morning

Begin your day with a visit to the renowned Art Institute of Chicago. Spend your morning exploring its vast collection of art from around the world. Afterward, grab breakfast at The Purple Pig, which offers delicious Mediterranean-inspired dishes.

Afternoon

In the afternoon, take a trip to Skydeck Chicago at Willis Tower (Sears Tower). Experience breathtaking views from one of the tallest buildings in the Western Hemisphere. For lunch, try out some deep-dish pizza at Lou Malnati's Pizzeria, a Chicago classic.

Evening

Spend your evening enjoying live music at House of Blues. This iconic venue hosts an array of musical performances that will make your night unforgettable. Before heading there, have dinner at Portillo's Hot Dogs for a taste of Chicago's famous hot dogs.

Bedtime

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Art Institute of Chicago
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4.27
Skydeck Chicago at Willis Tower (Sears Tower)
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History and Entertainment Extravaganza

Morning

Kick off your day with a visit to the historic Field Museum. Explore fascinating exhibits on natural history and ancient civilizations. For breakfast or brunch afterward, head over to Au Cheval, known for its mouthwatering burgers.

Afternoon

Afterward, make your way to Navy Pier for an afternoon filled with entertainment options like rides, games, shops, and restaurants. Enjoy lunch at one of Navy Pier's many eateries or try out some BBQ at nearby Smoque BBQ.

Evening

Conclude your day with an exciting game or concert at the legendary United Center, home to both the Chicago Bulls and Blackhawks. Beforehand enjoy dinner at nearby steakhouse favorite Gibsons Bar & Steakhouse.

Bedtime

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Field Museum
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Navy Pier
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Architectural Wonders and Local Flavors

Morning

Start your morning by exploring architectural marvels on an informative tour through downtown Chicago including stops like 360 Chicago Observation Deck (Formerly John Hancock Observatory) offering panoramic city views.

Afternoon

Continue discovering architectural wonders by visiting places such as Tribune Tower & Wrigley Building while stopping by popular lunch spot Avec Restaurant serving Mediterranean-inspired cuisine paired perfectly alongside local flavors!

Evening

'End another amazing day within this incredible city attending comedy show Second City where numerous famous comedians got their start! Dinner beforehand should be enjoyed Bavette’s Bar Boeuf providing upscale dining experience featuring French cuisine.'

Bedtime

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Science and Serenity

Morning

Begin your day with a visit to the Museum of Science and Industry. This massive museum offers interactive exhibits that cover everything from space exploration to the human body. It's a great way to spend a few hours learning and having fun.

Afternoon

After your museum visit, head over to Grant Park for a relaxing afternoon. This large urban park is perfect for a leisurely walk or picnic. For lunch, stop by The Publican, known for its hearty dishes and communal dining experience.

Evening

In the evening, enjoy some live theater at the historic Chicago Theatre. This iconic venue hosts a variety of performances from plays to concerts. Before the show, have dinner at RPM Italian, which offers delicious Italian cuisine in an elegant setting.

Bedtime

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Museum of Science and Industry
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Grant Park
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Final Day Fun

Morning

Lincoln Park & Zoo is the perfect spot to start your final day in Chicago. This free zoo is home to a wide variety of animals and is located within the beautiful Lincoln Park.

Afternoon

Chicago Pedway offers an interesting way to explore the city from below ground. This network of underground tunnels connects many of Chicago's buildings and provides a unique perspective on the city. For lunch, try out some classic Chicago-style pizza at Pequod's Pizza.

Evening

360 Chicago Observation Deck (Formerly John Hancock Observatory) provides stunning views of the city skyline and Lake Michigan. It's a great way to end your trip on a high note. For your final dinner in Chicago, head over to Giordano's for another taste of deep-dish pizza.

Bedtime

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