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Family Fun in Chicago: A 5-Day Adventure Itinerary

Last updated: 2024 Jun 14

Iconic Chicago Landmarks

Morning

Start your Chicago adventure with a bird's eye view from the 360 Chicago Observation Deck (Formerly John Hancock Observatory). After taking in the cityscape, head to The Magnificent Mile for some world-class shopping and a glimpse of the Wrigley Building.

Afternoon

For lunch, savor the deep-dish pizza at Lou Malnati's Pizzeria. Afterward, take a relaxing walk at Millennium Park to see the famous Cloud Gate sculpture, also known as "The Bean."

Evening

In the evening, enjoy a delightful dinner at The Purple Pig, known for its Mediterranean small plates, followed by a leisurely stroll along the Chicago Riverwalk.

Bedtime

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4.17
360 Chicago Observation Deck (Formerly John Hancock Observatory)
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4.65
The Magnificent Mile
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Museum Campus and Navy Pier

Morning

Spend your morning exploring the natural world at the Field Museum and the Shedd Aquarium on the Museum Campus.

Afternoon

For a late lunch with a view, head to The Signature Room at the 95th in the John Hancock Center. Afterward, take a ride on the Centennial Wheel at Navy Pier and enjoy the various attractions.

Evening

Have a fun family dinner at Big Star in Wrigleyville, known for its tacos, and take a post-dinner walk around the lively neighborhood.

Bedtime

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4.56
Field Museum
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4.75
Shedd Aquarium
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Art and Architecture

Morning

Begin your day with a visit to the Art Institute of Chicago, home to a world-renowned collection of art. Take a stroll through the nearby Grant Park.

Afternoon

Enjoy a leisurely lunch at Cafe Ba-Ba-Reeba!, known for its Spanish tapas. Afterward, take an architectural boat tour on the Chicago River to learn about the city's famous buildings.

Evening

For dinner, experience the vibrant atmosphere of Girl & the Goat, a popular spot for creative cuisine, followed by a visit to the historic Chicago Theatre.

Bedtime

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4.61
Art Institute of Chicago
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4.70
Grant Park
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Family Day at the Zoo and Ballpark

Morning

Spend the morning at the Lincoln Park & Zoo, a free and family-friendly attraction. Afterward, take a walk through the scenic Lincoln Park.

Afternoon

Enjoy a classic Chicago hot dog for lunch at Portillo's Hot Dogs. In the afternoon, catch a Wrigley Field tour, even if it's not baseball season.

Evening

For dinner, indulge in the famous burgers at Au Cheval, known for their deliciousness, and take a leisurely evening walk along the Chicago River.

Bedtime

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4.29
Lincoln Park & Zoo
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4.29
Lincoln Park
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Final Taste of Chicago

Morning

On your last day, visit the United Center, home to the Chicago Bulls and Blackhawks, for a tour of the arena.

Afternoon

Have a memorable final lunch at Alinea, a three-Michelin-star restaurant known for its innovative cuisine. Afterward, explore the vibrant neighborhoods of Chicago Loop and Wicker Park.

Evening

Conclude your trip with a special dinner at Gibsons Bar & Steakhouse, a Chicago classic, and a walk along the Chicago Riverwalk to take in the city lights.

Bedtime

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