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Roam Around

23-Day Grand Chicago Exploration

23-Day Grand Chicago Exploration Itinerary

Last updated: 2024 Jun 14

Sky-High Views and Iconic Streets

Morning

Begin your Chicago adventure with a hearty breakfast at Lula Cafe. Afterward, ascend to the Skydeck Chicago at Willis Tower (Sears Tower) for breathtaking views of the city. The Ledge's glass boxes will give you a unique perspective from 1,353 feet in the air.

Afternoon

After coming down from the heights, enjoy a classic Chicago lunch at Giordano's for some deep-dish pizza. Spend your afternoon shopping and exploring The Magnificent Mile, a premier commercial district that is home to upscale shops and posh boutiques.

Evening

Conclude your day with a sophisticated dinner at Gibsons Bar & Steakhouse. Post-dinner, take a leisurely stroll to the nearby Chicago Riverwalk, a scenic promenade along the Chicago River.

Bedtime

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4.27
Skydeck Chicago at Willis Tower (Sears Tower)
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4.65
The Magnificent Mile
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Cultural Pursuits and Park Pleasures

Morning

Start with breakfast at Xoco, Chef Rick Bayless's casual eatery. Then, immerse yourself in the world of art at the Art Institute of Chicago, known for its impressive collection of Impressionist and Post-Impressionist works.

Afternoon

For lunch, head to The Purple Pig for Mediterranean-inspired dishes. Post-lunch, wander through Millennium Park and see the famous Cloud Gate sculpture, also known as "The Bean." Continue to the serene Grant Park for a relaxing afternoon.

Evening

Dine at Girl & the Goat for an eclectic meal. In the evening, catch a show or a concert at the historic Chicago Theatre, an iconic landmark of the city's rich cultural scene.

Bedtime

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4.61
Art Institute of Chicago
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4.69
Millennium Park
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Aquatic Wonders and Starry Skies

Morning

Enjoy breakfast at Little Goat Diner before heading to the Shedd Aquarium, where you can explore the wonders of aquatic life from around the globe.

Afternoon

Have a delightful lunch at Au Cheval and then visit the Field Museum to discover natural history exhibits, including the famous Tyrannosaurus rex skeleton named Sue.

Evening

End your day with dinner at Frontera Grill, another of Chef Bayless's acclaimed restaurants. Afterward, explore the universe at the Adler Planetarium, which offers spectacular nighttime sky shows.

Bedtime

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4.75
Shedd Aquarium
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4.56
Field Museum
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Historic Landmarks and Culinary Delights

Morning

Grab a coffee and a pastry at Eataly Chicago before embarking on an architectural tour featuring the Wrigley Building, Marina City, and the Tribune Tower.

Afternoon

Savor a mouthwatering lunch at Big Star known for its tacos and whiskey. Post-lunch, continue your architectural journey with visits to the Rookery Building and the Palmer House Hilton, both steeped in history.

Evening

For dinner, indulge in the innovative cuisine at Alinea, one of Chicago's most renowned fine dining experiences. Cap off the evening with a casual walk through the Chicago Loop, the city's bustling central business district.

Bedtime

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4.39
Wrigley Building
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4.84
Marina City
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Green Spaces and Sporting Places

Morning

Begin with breakfast at Lou Malnati's Pizzeria for a taste of their legendary Chicago-style pizza. Then, head to Lincoln Park & Zoo to enjoy one of the oldest zoos in North America, set against the backdrop of Chicago's skyline.

Afternoon

For lunch, visit Smoque BBQ for some of the best barbecue in the city. Spend your afternoon exploring Wrigley Field, the historic home of the Chicago Cubs. Even if there's no game, the behind-the-scenes tours are a hit.

Evening

Dine at The Publican, an homage to beer, pork, and seafood. In the evening, take a leisurely stroll through United Center, home to the Chicago Bulls and Blackhawks, and perhaps catch an exciting game or event if the timing is right.

Bedtime

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4.29
Lincoln Park & Zoo
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4.86
Wrigley Field
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Innovative Science and Iconic Design

Morning

Start your day with a creative breakfast at Revolution Brewing, which offers a unique brunch menu. Afterwards, head to the Museum of Science and Industry, where you can engage with hands-on exhibits and marvel at the museum's innovation.

Afternoon

Enjoy a laid-back lunch at Portillo's Hot Dogs for a classic Chicago-style hot dog. Post-lunch, visit the Frederick C. Robie House, a masterpiece of the Prairie School of architecture designed by Frank Lloyd Wright.

Evening

For dinner, experience the flavors of Longman & Eagle, a Michelin-starred gastropub. End your day with a visit to the Biograph Theater, known for its storied past and as the site of John Dillinger's infamous last stand.

Bedtime

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4.31
Museum of Science and Industry
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3.51
Frederick C. Robie House
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Pier Walks and Theater Talks

Morning

Have breakfast at Kuma's Corner, famous for its gourmet burgers. Then, make your way to Navy Pier, a Chicago landmark offering entertainment, shopping, and more, with beautiful views of Lake Michigan.

Afternoon

Grab a quick bite at Pequod's Pizza and enjoy their caramelized crust. Spend your afternoon at the Chicago River, perhaps taking a boat tour to fully appreciate the city's architecture from the water.

Evening

Conclude your day with a meal at The Purple Pig, offering a variety of Mediterranean small plates. After dinner, if you're in the mood for a laugh, catch a comedy show at one of Chicago's famous improv theaters.

Bedtime

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4.48
Navy Pier
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4.61
Chicago River
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Modern Art and Historic Parks

Morning

Enjoy breakfast at Eataly Chicago before exploring the contemporary works at the Museum of Contemporary Art. The museum showcases thought-provoking art in various mediums.

Afternoon

Have lunch at Girl & the Goat and then visit Grant Park, known as "Chicago's front yard." Take time to appreciate the Buckingham Fountain, one of the largest in the world.

Evening

Dine at Au Cheval for an upscale take on the classic diner experience. Later, enjoy the evening ambiance of the Chicago Riverwalk, with its array of public art, wine bars, and cafes.

Bedtime

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4.70
Grant Park
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4.72
Chicago Riverwalk
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Architectural Marvels and Evening Stars

Morning

Start with a breakfast sandwich from Xoco before heading out to admire the iconic Chicago Picasso (The Picasso) in Daley Plaza. Then, explore the stunning architecture of the Chicago Cultural Center, with its beautiful stained-glass domes.

Afternoon

For lunch, stop by Big Star for their acclaimed tacos. Afterward, visit the Palmer House Hilton and the Rookery Building, both of which are architectural gems with rich histories.

Evening

Enjoy an elegant dinner at Gibsons Bar & Steakhouse. Post-dinner, head to the Adler Planetarium for a night of stargazing and to learn more about the cosmos.

Bedtime

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4.64
Chicago Picasso (The Picasso)
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4.71
Chicago Cultural Center
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Lakeside Leisure and Cultural Icons

Morning

Have a classic Chicago breakfast at Lou Malnati's Pizzeria. Spend your morning at Lincoln Park & Zoo, where you can enjoy the greenery and visit the animals.

Afternoon

Indulge in a BBQ lunch at Smoque BBQ. After lunch, take a walk through Chicago Loop, the heart of the city, and marvel at the towering skyscrapers and public art installations.

Evening

For dinner, visit The Publican for a diverse selection of meats and seafood. Wrap up your evening with a performance at the Chicago Theatre, a venue known for its stunning architecture and entertainment offerings.

Bedtime

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4.29
Lincoln Park & Zoo
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4.83
Chicago Loop
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Museum Mile and Pizza Pies

Morning

Begin with breakfast at Revolution Brewing. Then, head to the Field Museum to explore its extensive natural history collections.

Afternoon

Enjoy a classic deep-dish pizza for lunch at Giordano's. Spend your afternoon at the Museum of Science and Industry, where science comes to life through interactive exhibits.

Evening

Dine at Frontera Grill for a taste of authentic Mexican cuisine. End your day with a visit to the Chicago Riverwalk, a perfect spot for an evening stroll along the water.

Bedtime

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4.56
Field Museum
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4.31
Museum of Science and Industry
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Zoo Adventures and Comedy Encounters

Morning

Enjoy a hearty breakfast at Little Goat Diner. Spend your morning at Lincoln Park & Zoo, where you can connect with nature and wildlife.

Afternoon

Have lunch at Portillo's Hot Dogs for a quick and delicious meal. In the afternoon, visit the historic Wrigley Field and take a tour of the ballpark, or if it's baseball season, catch a game.

Evening

For dinner, head to Girl & the Goat for an innovative culinary experience. Afterward, enjoy a night of laughter at one of Chicago's renowned comedy clubs, where improv and stand-up comedy are king.

Bedtime

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4.29
Lincoln Park & Zoo
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4.86
Wrigley Field
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Historic Homes and Modern Tastes

Morning

Start your day with breakfast at Kuma's Corner. Visit the Frederick C. Robie House, a stunning example of Frank Lloyd Wright's architecture.

Afternoon

Grab a bite at The Purple Pig for a selection of cheese, swine, and wine. After lunch, take a leisurely walk through Grant Park, enjoying the open spaces and beautiful gardens.

Evening

Savor dinner at Alinea, a culinary adventure that's sure to be a highlight of your trip. Later, take in the city lights along the Chicago Riverwalk, a perfect way to end the evening.

Bedtime

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3.51
Frederick C. Robie House
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4.70
Grant Park
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Theater District and River Views

Morning

Have breakfast at Eataly Chicago, offering a variety of Italian delicacies. Then, explore the theater district and visit the iconic Chicago Theatre.

Afternoon

For lunch, enjoy the flavors of Au Cheval. Spend your afternoon on a boat tour of the Chicago River, taking in the architectural splendor from a different perspective.

Evening

Dine at Gibsons Bar & Steakhouse for a classic Chicago steakhouse experience. Post-dinner, enjoy a leisurely walk or a scenic cruise along the Chicago Riverwalk.

Bedtime

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4.71
Chicago Theatre
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4.61
Chicago River
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Science Wonders and Architectural Feats

Morning

Begin with breakfast at Xoco. Afterwards, head to the Museum of Science and Industry to discover the marvels of science and technology.

Afternoon

Have a Chicago-style hot dog for lunch at Portillo's Hot Dogs. In the afternoon, explore the architectural landmarks of the city, including the Wrigley Building and the Marina City.

Evening

For dinner, visit The Publican for a rustic yet refined dining experience. End your day with a visit to the Chicago Cultural Center, known for its free cultural events and stunning interior design.

Bedtime

Find amazing hotels in Chicago.

4.31
Museum of Science and Industry
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4.39
Wrigley Building
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Parkland Escapes and Deep-Dish Delights

Morning

Start with a breakfast pizza at Lou Malnati's Pizzeria. Then, enjoy the greenery and art installations at Millennium Park and the adjacent Grant Park.

Afternoon

For lunch, savor the gourmet burgers at Kuma's Corner. Spend your afternoon exploring the Lincoln Park & Zoo, a perfect place to relax and enjoy nature in the city.

Evening

Enjoy an upscale dinner at Girl & the Goat. After dinner, catch a game or a concert at the United Center, depending on the schedule of events during your visit.

Bedtime

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4.69
Millennium Park
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4.70
Grant Park
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Culinary Heights and Nighttime Lights

Morning

Have breakfast at Revolution Brewing, known for its craft beers and hearty brunch menu. Then, take a walk through the Chicago Loop, admiring the hustle and bustle of the city.

Afternoon

Enjoy a lunch of deep-dish pizza at Giordano's. After lunch, visit the Art Institute of Chicago to view one of the world's most notable art collections.

Evening

Dine at Frontera Grill for a taste of award-winning Mexican cuisine. End your evening with a visit to the Chicago Riverwalk, a perfect spot for a romantic stroll or a nightcap at one of the riverside bars.

Bedtime

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4.83
Chicago Loop
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4.61
Art Institute of Chicago
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Zoological Discoveries and Comedy Nights

Morning

Enjoy a leisurely breakfast at Little Goat Diner. Spend your morning at the Lincoln Park & Zoo, where you can see a wide variety of animals and enjoy the beautiful park setting.

Afternoon

Have a quick and satisfying lunch at Portillo's Hot Dogs. In the afternoon, explore the historic and lively Wrigley Field, and if it's the season, catch a Cubs game.

Evening

For dinner, head to Girl & the Goat for a meal that's both innovative and delicious. After dinner, enjoy a night of comedy at one of Chicago's famous improv theaters, where the laughs are guaranteed.

Bedtime

Find amazing hotels in Chicago.

4.29
Lincoln Park & Zoo
Book Now

4.86
Wrigley Field
Book Now

Architectural Wonders and Gourmet Bites

Morning

Start your day with breakfast at Kuma's Corner. Then, embark on an architectural tour to see the Frederick C. Robie House and other iconic buildings designed by Frank Lloyd Wright.

Afternoon

For lunch, enjoy the Mediterranean-inspired cuisine at The Purple Pig. Afterward, take a leisurely stroll through Grant Park, admiring the open spaces and art installations.

Evening

Indulge in a fine dining experience at Alinea, where the meal is as much a work of art as it is delicious. Later, take a walk along the Chicago Riverwalk, enjoying the evening ambiance.

Bedtime

Find amazing hotels in Chicago.

3.51
Frederick C. Robie House
Book Now

4.70
Grant Park
Book Now

Theater Thrills and Riverfront Chills

Morning

Have an Italian-style breakfast at Eataly Chicago. Spend your morning exploring the theater district, including a tour of the Chicago Theatre.

Afternoon

For lunch, treat yourself to the upscale diner fare at Au Cheval. Then, take a relaxing boat tour along the Chicago River, admiring the city's architecture from the water.

Evening

Enjoy a steak dinner at Gibsons Bar & Steakhouse. After dinner, take a scenic evening walk or cruise along the Chicago Riverwalk, taking in the city lights and vibrant atmosphere.

Bedtime

Find amazing hotels in Chicago.

4.71
Chicago Theatre
Book Now

4.61
Chicago River
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Science Exploration and Architectural Impressions

Morning

Begin with a flavorful breakfast at Xoco. Then, dive into the interactive exhibits at the Museum of Science and Industry, where science comes alive.

Afternoon

Have a classic Chicago-style hot dog for lunch at Portillo's Hot Dogs. Spend your afternoon admiring the architectural feats of the

Evening

4.31
Museum of Science and Industry
Book Now

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