Chicago travel view

A Verdict itinerary

Chicago for a first trip

Start with the landmarks, neighbourhoods and meals that make the city clear. This is a first-trip shortlist, not a race to tick everything off.

Independent, never pay-to-rankGraded for your kind of tripHow we decide
The plan

9 places worth your time

Open any place for the full call, the tradeoffs and the practical details.

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  1. Chicago Architecture River Cruise01experienceChicago Architecture River CruiseThe single best orientation to the city; do this early in your trip.Read the verdict
  2. Millennium Park & Cloud Gate (The Bean)02attractionMillennium Park & Cloud Gate (The Bean)An unmissable, low-effort first stop that orients you in the heart of downtown.Read the verdict
  3. Museum Campus03attractionMuseum CampusAn efficient way to bag a marquee museum plus the postcard skyline view.Read the verdict
  4. Willis Tower Skydeck04attractionWillis Tower SkydeckThe definitive top-of-Chicago moment if you only do one observation deck.Read the verdict
  5. Chicago Cultural Center05attractionChicago Cultural CenterA high-value free landmark right across from Millennium Park.Read the verdict
  6. The Loop & the 'L'06neighborhoodThe Loop & the 'L'The essential downtown core; riding the 'L' loop is a rite of passage.Read the verdict
  7. Lou Malnati's Pizzeria07restaurantLou Malnati's PizzeriaIf you only try one deep-dish, this is the canonical version to measure others against.Read the verdict
  8. Deep-Dish Pizza Crawl08experienceDeep-Dish Pizza CrawlWorth doing once for the experience, even if locals favor thin crust.Read the verdict
  9. Buckingham Fountain09attractionBuckingham FountainAn easy landmark tick, just don't expect to linger.Read the verdict