Top things to do in Chicago
Only 36 hours in Chicago? No problem. Yes, it’s absolutely possible to soak up the best of the Windy City in a day and a half. Think deep-dish pizza, world-class museums, jaw-dropping architecture, and some seriously good shopping — all packed into one unforgettable stop in Illinois.
My Chicago Story
I flew from San Francisco to Chicago on a Monday morning — a quick 4-hour flight. After arriving, I hopped on the train into the city, grabbed lunch at Vapiano, and jumped on a Hop-on Hop-off tour to see as much as possible in little time. In the evening, I took a train to stay with my host mum’s cousin — a super kind real estate broker who welcomed me warmly despite the rain. We chatted for hours about her job and life in Chicago. The next morning, I had breakfast with her kids and their Au Pair from Costa Rica before heading back into the city.
TOP 10:
- Millenium Park
- Navy Pier
- Art Institute
- The Field Museum
- Museum of science and industry
- Skydeck Chicago
- Lincoln Park Zoo
- University of Chicago
- Lake Michigan
- Deep Dish Pizza
From the iconic Millennium Park and Navy Pier to the world-class Art Institute and Field Museum, Chicago offers endless adventures — whether you’re exploring the Museum of Science and Industry, taking in the views from Skydeck, visiting the Lincoln Park Zoo, or soaking up the academic vibe at the University of Chicago. Don’t forget to relax by the shores of Lake Michigan and indulge in a slice of the legendary Deep Dish Pizza.
Another must-see on your U.S. city checklist? San Francisco. From cable cars and colorful Victorian houses to Golden Gate views and techy vibes — this city has its own unique energy. Whether you’re strolling through the Mission, snapping pics in front of the Painted Ladies, or catching the sunset at Ocean Beach, San Francisco is the kind of place you don’t want to skip. Trust me — this city’s got style, soul, and just the right amount of weird.