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Roam Around

Ultimate 10-Day Chicago Exploration Itinerary

Last updated: 2024 Jun 14

Iconic Chicago Landmarks and Skyline Views

Morning

Start your Chicago adventure with a delicious brunch at The Purple Pig, known for its Mediterranean-inspired cuisine. Afterward, head to the iconic The Magnificent Mile for some upscale shopping and to admire the city's architecture.

Afternoon

In the afternoon, visit the historic Wrigley Building and take a walk along the Chicago Riverwalk. Enjoy a late lunch at Big Star, a popular spot for tacos and margaritas.

Evening

End your day with a sunset cocktail at the Signature Room at the 95th, where you can enjoy panoramic views of the city. For dinner, savor Italian cuisine at RPM Italian.

Bedtime

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4.65
The Magnificent Mile
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4.39
Wrigley Building
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Museum Campus and Lakefront Exploration

Morning

Enjoy a leisurely breakfast at Lula Cafe, a cozy neighborhood spot. Then, spend the morning at the Field Museum and the nearby Shedd Aquarium.

Afternoon

For lunch, head to The Publican, known for its eclectic menu and vibrant atmosphere. Afterward, take a relaxing stroll through Grant Park and visit the Adler Planetarium.

Evening

In the evening, take a Lake Michigan Skyline Cruise to see the city from a different perspective. Enjoy a seafood dinner at Gibsons Bar & Steakhouse.

Bedtime

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4.56
Field Museum
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4.75
Shedd Aquarium
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Art and Architecture Day

Morning

Start your day with a hearty breakfast at Au Cheval, famous for its burgers. Then, explore the masterpieces at the Art Institute of Chicago.

Afternoon

Have a light lunch at Xoco, a popular spot for Mexican street food. Afterward, take a guided architecture tour with the Chicago Architecture Foundation.

Evening

For dinner, experience a unique dining concept at Alinea, known for its innovative and avant-garde cuisine.

Bedtime

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4.61
Art Institute of Chicago
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4.46
Chicago Architecture Foundation
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Parks and Neighborhoods

Morning

Enjoy a relaxed breakfast at Little Goat Diner, a favorite for its comfort food. Then, spend the morning exploring the greenery of Lincoln Park and visit the Lincoln Park Zoo.

Afternoon

Have a picnic lunch in the park or grab a sandwich from Lula Cafe. In the afternoon, take a guided bike tour of the Lakefront Neighborhoods.

Evening

For dinner, try the famous deep-dish pizza at Lou Malnati's Pizzeria.

Bedtime

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4.29
Lincoln Park
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4.29
Lincoln Park Zoo
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Culinary Delights and River Cruise

Morning

Start your day with a classic Chicago breakfast at Pequod's Pizza, known for its caramelized crust. Afterward, take a Chicago River Cruise to learn about the city's architecture.

Afternoon

Enjoy a food tasting tour with a twist on the Gangsters and Food Tasting Walking Tour. Sample a variety of local dishes with a side of Chicago's history.

Evening

For dinner, indulge in a gourmet experience on a Gourmet Dinner River Cruise.

Bedtime

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4.61
Chicago River Cruise
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4.67
Gangsters and Food Tasting Walking Tour
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Gangsters and Ghosts Experience

Morning

Have a late breakfast at Lula Cafe before embarking on a Chicago Gangsters and Ghosts Guided Walking Tour. Explore the city's darker history and infamous crime scenes.

Afternoon

After the tour, have a light lunch at Lula Cafe or grab a hot dog at Portillo's Hot Dogs. Spend the afternoon at leisure, perhaps visiting the Chicago Cultural Center.

Evening

For a unique dining experience, have dinner at The Publican, known for its communal dining and extensive beer selection.

Bedtime

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4.68
Chicago Gangsters and Ghosts Guided Walking Tour
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4.71
Chicago Cultural Center
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Relaxation and Retail Therapy

Morning

Start your day with a leisurely breakfast at Lula Cafe. Then, spend the morning at the Oak Street Beach relaxing by the lake.

Afternoon

For lunch, enjoy a Mediterranean feast at The Purple Pig. In the afternoon, explore the boutiques and designer stores of Oak Street.

Evening

Have a sophisticated dinner at The Signature Room at the 95th and enjoy the twinkling city lights.

Bedtime

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Rooftop Views and City Lights

Morning

Enjoy a brunch with a view at The Signature Room at the 95th. Afterward, take a 360 Chicago Observation Deck Sip and View Ticket to see the city from above.

Afternoon

Have a light lunch at The Purple Pig before spending the afternoon at Navy Pier. Take a ride on the Centennial Wheel and explore the attractions.

Evening

For dinner, savor the flavors of Spain at Cafe Ba-Ba-Reeba!, known for its tapas and lively atmosphere.

Bedtime

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4.39
360 Chicago Observation Deck Sip and View Ticket
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4.48
Navy Pier
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Final Day of Exploration

Morning

Enjoy a classic Chicago breakfast at Au Cheval, known for its indulgent dishes. Then, take a Chicago River 1.5-Hour Guided Architecture Cruise to learn about the city's famous buildings.

Afternoon

For lunch, try the award-winning burgers at Au Cheval. Spend the afternoon at Millennium Park and take a selfie at the Cloud Gate.

Evening

End your Chicago journey with a memorable dinner at Au Cheval, savoring their famous burger one last time.

Bedtime

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