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10-Day Road Trip from San Jose to Chicago Itinerary
Last updated: 2024 Jun 14Exploring San Jose's Wonders
Morning
Start your day with a hearty breakfast at Bill's Cafe - Willow Glen. Known for its delicious breakfast options, this cafe will fuel you up for the day ahead.
After breakfast, head to The Tech Interactive. This hands-on technology and science museum is perfect for all ages and offers a variety of interactive exhibits that make learning fun. Spend around 2-3 hours here exploring the different exhibits and participating in the activities.
Afternoon
For lunch, visit Original Joe's San Jose, a local favorite known for its classic Italian-American dishes.
In the afternoon, take a tour of the famous San Jose Winchester Mystery House Tour. This architectural wonder is filled with mysterious hallways and rooms, making it a fascinating place to explore. The tour lasts about 1.5-2 hours.
Evening
End your day with dinner at Adega, a Michelin-starred restaurant offering exquisite Portuguese cuisine.
After dinner, if you're up for some evening entertainment, catch a game at the SAP Center with San Jose San Jose Sharks Ice Hockey Game Ticket if there's a game scheduled.
Bedtime
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Nature and Adventure in San Jose
Morning
Begin your morning with breakfast at Falafel Drive-In, known for its delicious falafel sandwiches and smoothies.
Then, embark on an adventure to Yosemite National Park with the San Jose Yosemite National Park and Giant Sequoias Trip. This full-day trip will take you through some of California's most stunning natural landscapes. Expect to spend around 8-10 hours on this excursion.
Afternoon
Evening
Return to San Jose in the evening and enjoy dinner at Henry's Hi-Life, famous for its mouth-watering BBQ dishes.
Bedtime
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Cultural Immersion in San Jose
Morning
Start your day with breakfast at Aqui Cal-Mex, which offers unique Cal-Mex cuisine.
Afterward, take part in the engaging San Jose Unveiled A Private Walking Tour. This tour will give you insights into the city's history and culture. The tour lasts about 2-3 hours.
Afternoon
For lunch, head over to The Table, known for its farm-to-table dining experience.
Post-lunch, visit the LEGOLAND® Discovery Center Bay Area with tickets from LEGOLAND® Discovery Center Bay Area. Spend around 2-3 hours exploring this fun-filled attraction.
Evening
Have dinner at La Foret, which offers French cuisine in a beautiful setting.
Conclude your day by solving puzzles at The Escape Game located in Valley Fair as part of your experience from The Escape Game at Valley Fair in San Jose.
Bedtime
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Wineries and Scenic Views
Morning
Enjoy breakfast at Bill's Cafe - Willow Glen once again; their menu is extensive enough to try something new each time.
Next, embark on a wine-tasting journey with the tour from Los Gatos South Bay Wineries via From Los Gatos South Bay Wineries Tour. This half-day tour allows you to sample some of the best wines from local wineries while enjoying scenic views. Expect this activity to last around 4-5 hours.
Afternoon
Evening
Return to San Jose for dinner at Le Papillon, an upscale restaurant known for its gourmet French cuisine.
Bedtime
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Journey to Chicago
Morning
Start your day early with a hearty breakfast at Smoking Pig BBQ Company in San Jose before beginning your road trip to Chicago. Enjoy the scenic drive and make stops along the way to stretch your legs and take in the sights.
Afternoon
Stop for lunch at a local diner or cafe along your route. Continue your journey, enjoying the changing landscapes as you head towards Chicago.
Evening
Arrive in Chicago and check into your hotel. For dinner, visit Portillo's Hot Dogs, famous for its Chicago-style hot dogs and Italian beef sandwiches.
Bedtime
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Discovering Downtown Chicago
Morning
Begin your day with breakfast at Au Cheval, known for its delicious breakfast options and famous burgers.
After breakfast, explore Millennium Park and visit Millennium Park. Spend around 1-2 hours here enjoying the art installations, gardens, and architecture.
Afternoon
For lunch, head to Girl & the Goat, a popular restaurant offering innovative dishes.
In the afternoon, take a stroll along the Chicago Riverwalk. This scenic walkway offers beautiful views of the city skyline and is perfect for a leisurely walk. Spend about 1-2 hours here.
Evening
Have dinner at The Purple Pig, known for its Mediterranean-inspired dishes.
After dinner, catch a show at the iconic Chicago Theatre, if there's a performance scheduled.
Bedtime
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Cultural Gems of Chicago
Morning
Start your day with breakfast at Lou Malnati's Pizzeria, where you can try their famous deep-dish pizza.
Then, visit the renowned Art Institute of Chicago. Spend around 2-3 hours exploring its vast collection of artworks from different periods and cultures.
Afternoon
For lunch, dine at Frontera Grill, which offers delicious Mexican cuisine.
In the afternoon, explore Grant Park by visiting Grant Park. This large urban park is home to several attractions including Buckingham Fountain. Spend about 1-2 hours here.
Evening
Enjoy dinner at Gibsons Bar & Steakhouse, known for its prime steaks and seafood.
End your evening with a visit to Skydeck Chicago at Willis Tower using tickets from Skydeck Chicago at Willis Tower (Sears Tower). Take in breathtaking views of the city from one of its tallest buildings.
Bedtime
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Architectural Marvels
Morning
Begin with breakfast at Joe's Seafood, Prime Steak & Stone Crab, offering an array of delicious morning options.
Afterward, take an architectural boat tour along the Chicago River using tickets from Chicago River. This tour will give you insights into Chicago's iconic skyline and architectural history. Expect this activity to last around 1.5-2 hours.
Afternoon
For lunch, visit The Purple Pig again; their menu is diverse enough to try new dishes each time.
Post-lunch, explore The Magnificent Mile by visiting shops and landmarks such as Water Tower Place using tickets from both activities: 360 CHICAGO Observation Deck (Formerly John Hancock Observatory) via tickets from360 CHICAGO Observation Deck (Formerly John Hancock Observatory)and Water Tower Place via tickets fromWater Tower Place . Spend around 3-4 hours shopping and sightseeing.
Evening
Dine at{ R-Alinea }, one of Chicago's most acclaimed restaurants offering an unforgettable dining experience. Conclude your day by catching some live music or entertainment at House of Blues via tickets from{ A-House of Blues[6906]}
Bedtime
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Chicago's Historic and Natural Wonders
Morning
Start your day with breakfast at Smoque BBQ, known for its mouth-watering barbecue dishes.
After breakfast, visit the Field Museum. This renowned natural history museum offers a vast array of exhibits, including Sue the T. rex and ancient Egyptian artifacts. Spend around 2-3 hours exploring the museum.
Afternoon
For lunch, head to The Purple Pig, which offers a variety of Mediterranean-inspired dishes.
In the afternoon, take a trip to the Adler Planetarium. This planetarium provides fascinating exhibits about space and astronomy. Spend about 1-2 hours here.
Evening
Enjoy dinner at Gibsons Bar & Steakhouse, famous for its prime steaks and seafood.
End your evening with a visit to the iconic Navy Pier. Stroll along the pier, enjoy the views of Lake Michigan, and perhaps catch a ride on the Ferris wheel. Spend around 1-2 hours here.
Bedtime
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Final Day in Chicago
Morning
Evening
Henry's Hi-Life
Bedtime
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