First time in Chicago? This guide’s for you. Chicago is a harmonious blend of opposites — bustling big city steeped in Midwestern charm, towering skyscrapers framed by miles of tranquil beaches, a city in a garden (Chicago’s motto, in fact). In other words, everybody feels right at home in Chicago. To make the most of your inaugural visit, add these attractions, experiences, and events to your itinerary.
One of the best things you can do in Chicago is enjoy over 130 years of amazing architecture on a famous river architecture tour. Darth & Taylie love to go anytime a friend visits Chicago for the first time! Now I know what you're thinking - March, River, Chicago..... But yes, there are two companies who can tour during the winter! Wendella Cruises and The Chicago Architectural Brunch Cruise led by City Experiences run year-round.
You can find Chicago Deep Dish Pizza all over the city, but if you want to go where the locals go, skip Lou's and Giordano's and get to Pequod's instead. If you want to go extremely local, the pizza of real Chicagoans is tavern style - a thin crust grid-sliced pizza that goes down perfectly with your beer to hold you over until you head home for dinner. Interested? Check out Pat's Pizza & Ristorante on Lincoln. Darth and Tay love their neighborhood Pizza Lobo on Fullerton and deep dish from My Pi Pizza on Damen.