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Ultimate 21-Day Golf Trip Across the Midwest Itinerary

Last updated: 2024 Jun 14

Cityscape and Culinary Delights

Morning

Start your golf journey with a delightful brunch at The Purple Pig, known for its Mediterranean-inspired dishes. Afterward, take a leisurely stroll along the iconic Magnificent Mile for some light shopping and to admire the city's architecture.

Afternoon

Head to the Art Institute of Chicago to explore one of the oldest and largest art museums in the country. For a late lunch, savor the famous deep-dish pizza at Lou Malnati's Pizzeria.

Evening

In the evening, experience the city from above at the 360 Chicago Observation Deck, followed by a sophisticated dinner at The Signature Room at the 95th, offering stunning views of the skyline.

Bedtime

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4.65
Magnificent Mile
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4.61
Art Institute of Chicago
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Architectural Wonders and River Cruises

Morning

Enjoy a classic Chicago breakfast at Wildberry Pancakes and Cafe before embarking on the Chicago Architecture Center Cruise on Chicago's First Lady to learn about the city's famous buildings.

Afternoon

For lunch, indulge in a gourmet experience on the Chicago Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise. Afterward, visit the Willis Tower Skydeck to step out onto The Ledge and take in the panoramic views.

Evening

Conclude the day with a Chicago River Guided Sunset Cocktail & Architecture Tour, where you can enjoy the city's skyline as the sun sets, followed by a dinner at Alinea, a three-Michelin-star restaurant.

Bedtime

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4.46
Chicago Architecture Center Cruise on Chicago's First Lady
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4.34
Chicago Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise
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Museums and Culinary Exploration

Morning

Start your day with a visit to the Field Museum to explore natural history and culture. For lunch, try the famous pastrami sandwich at Manny's Cafeteria & Delicatessen.

Afternoon

Spend the afternoon at the Museum of Science and Industry, a family-friendly museum with interactive exhibits. Afterward, enjoy a coffee at Intelligentsia Coffee.

Evening

In the evening, have a unique dining experience at The Aviary, known for its innovative cocktails and food pairings.

Bedtime

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4.56
Field Museum
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4.31
Museum of Science and Industry
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Cultural Gems and Local Eats

Morning

Explore the Chicago Cultural Center, known for its stunning architecture and free art exhibitions. For a mid-morning pick-me-up, stop by Do-Rite Donuts for a sweet treat.

Afternoon

Have a leisurely lunch at Rick Bayless' Frontera Grill, a renowned Mexican restaurant. Afterward, visit the American Writers Museum to learn about the country's literary history.

Evening

Enjoy a casual dinner at Pequod's Pizza, famous for its caramelized crust, followed by a walk around the vibrant neighborhood of Wicker Park.

Bedtime

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4.71
Chicago Cultural Center
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Neighborhood Exploration and Local Brews

Morning

Start your day with a hearty breakfast at Yolk, known for its creative egg dishes. Explore the trendy neighborhood of Logan Square, with its street art and unique shops.

Afternoon

For lunch, try the artisanal sausages at Hot "G" Dog. Visit the 606 Trail for a leisurely walk or bike ride through the city.

Evening

In the evening, enjoy a beer at Revolution Brewing Company, one of the city's most famous craft breweries, followed by a casual dinner at Parson's Chicken & Fish.

Bedtime

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