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Exploring Wrigleyville: 5-day Trip in Chicago Itinerary

Last updated: 2024 Jun 14

Discovering Wrigleyville

Morning

Start your day with a delicious breakfast at The Chicago Diner. Afterward, take a stroll along the Chicago Riverwalk and admire the stunning architecture of the city.

Afternoon

For lunch, head to Portillo's Hot Dogs to savor their famous Chicago-style hot dogs. Afterward, embark on a Chicago River Architecture Cruise to learn about the city's rich history and architectural wonders.

Evening

Enjoy a relaxing dinner at Giordano's - Wrigleyville and indulge in their famous deep-dish pizza. End the day by catching a live music performance at The Cubby Bear, a legendary venue in Wrigleyville.

Bedtime

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Chicago Landmarks and Views

Morning

Start your day with a coffee and breakfast at Starbucks. Then, head to 360 Chicago Observation Deck for breathtaking views of the city from the 94th floor of the John Hancock Building.

Afternoon

For lunch, try the mouthwatering barbecue at Wrigley BBQ. Afterward, explore the city's iconic landmarks on a Chicago Big Bus Sightseeing Tour, hopping on and off at your preferred stops.

Evening

Enjoy a romantic sunset cruise along Lake Michigan with the Chicago 1.5-Hour Romantic Sunset Cruise. Afterward, savor a delicious dinner at Rockit Burger Bar and unwind with a drink at Sluggers World Class Sports Bar.

Bedtime

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Gangsters, Ghosts, and History

Morning

Start your day with a hearty breakfast at Rick Bayless' Frontera Grill. Then, join the Chicago Gangsters and Ghosts Walking Tour to explore the city's dark history and infamous gangster sites.

Afternoon

For lunch, head to Gilt Bar and enjoy their delectable dishes. Afterward, embark on the Chicago Mob and Crime Bus Tour to delve deeper into the city's mob history.

Evening

Indulge in a delightful dinner at Girl & the Goat, known for its innovative cuisine. End the day with a visit to Goose Island Beer Company for a taste of Chicago's craft beer scene.

Bedtime

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Cultural Immersion in Lincoln Park

Morning

Start your day with a delicious breakfast at Au Cheval. Then, explore the Lincoln Park neighborhood and visit the renowned Lincoln Park Zoo to see a variety of animals.

Afternoon

For lunch, try the mouthwatering burgers at Kuma's Corner. Afterward, immerse yourself in art and culture at the Chicago History Museum and the Lincoln Park Conservatory.

Evening

Enjoy a delightful dinner at Pequod's Pizza and savor their famous caramelized crust. End the day with a cocktail at Joe's Seafood, Prime Steak & Stone Crab.

Bedtime

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River North Exploration

Morning

Start your day with a delicious breakfast at Ditka's. Then, visit the Art Institute of Chicago to admire its impressive collection of artwork.

Afternoon

For lunch, head to The Signature Room at the 95th and enjoy panoramic views of the city while savoring a delicious meal. Afterward, explore the vibrant River North neighborhood and visit the Museum of Contemporary Art.

Evening

Indulge in a memorable dining experience at Alinea, a renowned Michelin-starred restaurant. End your trip with a visit to Longman & Eagle for a nightcap in their cozy whiskey bar.

Bedtime

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