Ready-made itinerary
Chicago & San Francisco & Miami, USA 14-day travel plan covering Top attractions and Shopping
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This comprehensive 14-day Chicago, IL adventure covers everything from must-see landmarks to off-the-beaten-path discoveries. Perfect for 2026 travelers who want an immersive experience in USA, including top attractions and shopping experiences.
Day 1 starts at Millennium Park at 9 AM - allow 2 hours to enjoy the gardens and Cloud Gate. Travel 10 minutes via taxi (~$10) to The Art Institute of Chicago by 11:30 AM; allow 3 hours to explore the collections. Conclude with a 10-minute taxi ride (~$10) to Navy Pier at 3 PM, where you can unwind for 3 hours with attractions and views of Lake Michigan.
1Millennium Park
2 hr
2
3Navy Pier
3 hr
Start Day 2 at Skydeck Chicago at 9 AM - allow 90 minutes for breathtaking views. Then, take a 10-minute walk to the Chicago Riverwalk at 11 AM for a relaxing 2-hour stroll along the river. Finally, grab a 15-minute taxi (around $10) to the Field Museum at 1:30 PM, spending 3 hours exploring fascinating exhibits. This balanced itinerary ensures leisure while enjoying Chicago's best attractions.
1
2Chicago Riverwalk
2 hr
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