Chicago
The Best of the Windy City
May 15 - May 20, 2028Chicago is bursting with world-class, big city culture. But at its heart, it's a Midwestern city — which means a warm welcome and genuine hospitality. Come with WTT as we explore the Windy City. We'll walk the Loop, Chicago's downtown area which has the largest concentrations of skyscrapers in the city; and visit Millennium Park, the green space that's become the heart and soul of the waterfront. We'll board a boat to learn more about the city's iconic architecture designed by legendary architects. We'll taste our way through some of Chicago's finest deep-dish pizza and stop by the legendary Wrigley Field. If you've always wanted to see this Midwestern hub, now's your chance.
Chicago
May 15 - May 20, 2028MAKE A PRE-RESERVATION
Here is an easy way, with no obligation whatsoever, to have WTT notify you when this tour is finalized, with all the details including pricing, hotels, firm dates, etc. You can select up to 5 tours per calendar year and can rank your choices.
Our small-group tours often fill up quickly, but your pre-reservation will ensure you are the first to know** when this tour is accepting reservations -and- you will be eligible for the pre-reservation discount.
You are under no obligation once contacted. Just delete the email we send you.
** When a tour is open for reservations, we notify WTT members first, followed by non-members four days later.
You have selected the dates of for your prereservation. Once confirmed, we will add this request to your list of prereservations for the year .
Our Promise to You
It doesn’t matter which tour you choose.
You’ll find your people and make memories that last a lifetime.