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5 Days of Great Lakes Adventure in Chicago Itinerary

Last updated: 2024 Jun 30

Welcome to the Windy City

Morning

Start your day with a visit to Millennium Park, one of Chicago's most iconic attractions. Here you can see the famous Cloud Gate sculpture (also known as 'The Bean') and enjoy the beautiful gardens and art installations. After exploring the park, head over to The Goddess and Grocer for a delightful breakfast.

Afternoon

In the afternoon, take a tour with Chicago: Art Institute of Chicago Guided Tour. This guided tour will give you an in-depth look at one of the world's greatest art museums. Afterward, grab lunch at The Gage, a highly-rated gastropub located nearby.

Evening

Spend your evening at Navy Pier, where you can enjoy various attractions including rides, shops, and restaurants. For dinner, dine at Riva Crabhouse on Navy Pier, which offers stunning views of Lake Michigan.

Bedtime

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Millennium Park
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Chicago: Art Institute of Chicago Guided Tour
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Exploring Chicago's Rich History

Morning

Begin your second day with a visit to Skydeck Chicago at Willis Tower (Sears Tower). Enjoy breathtaking views from one of the tallest buildings in the Western Hemisphere. For breakfast before or after your visit, stop by The Bongo Room for some delicious pancakes.

Afternoon

In the afternoon, explore Chicago's architectural marvels with Chicago River: 1.5-Hour Guided Architecture Riverboat Tour. This tour will take you through the heart of downtown along the Chicago River. Have lunch at Portillo's Hot Dogs, a local favorite known for its classic Chicago-style hot dogs.

Evening

End your day with a visit to The Magnificent Mile, where you can shop and dine in some of Chicago's finest establishments. For dinner, try out Gibsons Bar & Steakhouse, renowned for its steaks and vibrant atmosphere.

Bedtime

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Skydeck Chicago at Willis Tower (Sears Tower)
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Chicago River: 1.5-Hour Guided Architecture Riverboat Tour
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Cultural Gems and Scenic Views

Morning

Start your third day by visiting Field Museum, one of the largest natural history museums in the world. Enjoy breakfast at Yolk South Loop before heading into the museum.

Afternoon

In the afternoon, take part in an exciting tour with Chicago: Amazing Lakefront Segway Tour. This tour will allow you to explore Chicago’s beautiful lakefront area while riding a Segway. Have lunch afterward at Girl & The Goat, one of Chicago’s most popular restaurants.

Evening

Spend your evening enjoying some live music at House of Blues. This iconic venue offers great performances and an electric atmosphere. For dinner before or after the show, dine at Siena Tavern, known for its Italian cuisine.

Bedtime

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Field Museum
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Chicago: Amazing Lakefront Segway Tour
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Architectural Wonders and Local Flavors

Morning

Begin your fourth day with a visit to Chicago Cultural Center. This stunning building is known for its beautiful architecture and free art exhibits. Enjoy breakfast at Lou Mitchell's, a classic Chicago diner that has been serving delicious meals since 1923.

Afternoon

In the afternoon, embark on the Chicago: Food, History and Architecture Tour. This tour combines three of Chicago’s best features: its food, history, and architecture. You’ll get to sample local delicacies while learning about the city’s rich past. For lunch during the tour, you’ll stop at various iconic eateries.

Evening

End your day with a visit to 360 Chicago Observation Deck (Formerly John Hancock Observatory). Enjoy panoramic views of the city from this iconic skyscraper. For dinner, head to The Signature Room at the 95th, located in the same building, offering both exquisite cuisine and breathtaking views.

Bedtime

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Chicago Cultural Center
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Chicago: Food, History and Architecture Tour
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Final Day of Fun and Farewell

Morning

Start your final day with a visit to Adler Planetarium, where you can explore fascinating exhibits about space and astronomy. Have breakfast at Wildberry Pancakes and Cafe, known for its extensive menu of delicious pancakes and other breakfast items.

Afternoon

In the afternoon, take part in an adventurous tour with Chicago: Bikes, Bites, and Brews Biking Tour. This tour will take you through some of Chicago’s most famous neighborhoods while sampling local food and drinks. Enjoy lunch during the tour as you stop at various local spots.

Evening

Conclude your trip with a relaxing evening at Chicago Riverwalk, where you can stroll along the riverfront and enjoy beautiful views of the city skyline. For your farewell dinner, dine at RPM Steak, one of Chicago’s top steakhouses offering a luxurious dining experience.

Bedtime

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