Chicago: A Travel Guide

Chicago might be the most underrated big city in America: jaw-dropping architecture, a gorgeous lakefront, world-class food, and genuine Midwestern warmth. Here is how I would plan it.

Architecture and the skyline

This is the birthplace of the skyscraper, and the architecture river cruise is the single best thing you can do here, hands down. Add the views from Willis Tower or 360 Chicago, and a stroll through Millennium Park to see “The Bean” (Cloud Gate).

The lakefront and the neighborhoods

Walk or bike the Lakefront Trail along Lake Michigan, wander Navy Pier, and explore the distinct neighborhoods, from Wicker Park to Pilsen to Hyde Park. The Art Institute of Chicago is one of the great museums in the country.

The food

Come hungry. Deep-dish pizza and a classic Chicago hot dog are musts, but the city is also a serious fine-dining town with a deep bench of celebrated and Michelin-starred restaurants. Tell me how you like to eat and I will build the list.

Here is what people get wrong. The river cruise only runs the warm months and the best sailings sell out, the celebrated tables release reservations on a fixed window weeks ahead, and picking the wrong neighborhood to stay in can add a long ride to everything you want to do. It all works beautifully in the right order, and getting that order right is my job.

When to go, and why plan with me

Summer and early fall are glorious on the lake; winters are famously cold. Chicago rewards the right neighborhood to stay in and reservations at the tables that book up. I plan it all, with VIP recognition where available, in English or Español.