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Travel AI

3-Day Oak Park and Chicago Adventure Itinerary

Last updated: 2024 Jun 14

Exploring Oak Park's Charms

Morning

Start your day with a hearty breakfast at George's Family Restaurant & Pancake House. This local favorite offers a variety of breakfast options to fuel your day. Afterward, embark on the Oak Park Hemingway District Food Tour, where you'll explore the rich literary history and culinary delights of Oak Park.

Afternoon

For lunch, head to Maya Del Sol, known for its vibrant Latin American cuisine. Post-lunch, visit the Frank Lloyd Wright Home and Studio, an architectural gem that showcases Wright's early work and design philosophy. Spend some time biking around Oak Park to admire more of Wright's iconic homes in the area.

Evening

Dine at Trattoria 225, a cozy Italian restaurant offering delicious pasta and wood-fired pizzas. End your evening with a relaxing stroll through Scoville Park or catch a local performance at the nearby Madison Street Theatre.

Bedtime

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Architectural Wonders in Chicago

Morning

Begin your day with breakfast at Girl & The Goat, renowned for its innovative dishes. Then, head to the Art Institute of Chicago, one of the oldest and largest art museums in the United States. Spend your morning exploring its vast collection of artworks.

Afternoon

For lunch, visit Lou Malnati's Pizzeria to try some classic Chicago deep-dish pizza. Afterward, take an architecture boat tour along the Chicago River to marvel at the city's stunning skyline and learn about its architectural history.

Evening

Enjoy dinner at The Purple Pig, famous for its Mediterranean-inspired small plates. Conclude your evening with a visit to Millennium Park, where you can see iconic landmarks like Cloud Gate (The Bean) and enjoy any ongoing events or concerts.

Bedtime

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Cultural Delights and Cubs Game

Morning

Start your morning with breakfast at Au Cheval, known for its decadent brunch options. Then, visit Millennium Park if you missed it yesterday or explore more of its features like Lurie Garden or Crown Fountain.

Afternoon

Have lunch at Portillo's Hot Dogs for a taste of classic Chicago-style hot dogs. In the afternoon, head over to Wrigley Field for a Cubs game (Wrigley Field). Enjoy the lively atmosphere and cheer on the home team!

Evening

After the game, dine at Giordano's for another take on deep-dish pizza or other Italian favorites. If you're up for it, end your night with drinks at one of Chicago’s rooftop bars like Cindy’s Rooftop for stunning views of the city.

Bedtime

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