Are you attending this year’s GBTA Conference in Chicago? Or perhaps just traveling to Chicago for a business trip and want to take a little bleisure time to experience the city? We’ve gathered some tips, tricks and must-sees from TI’s travelers to provide you with the ultimate guide to experiencing Chicago:

Indulge in Chicago-Style Food

Everyone knows the city of Chicago is revered for its culinary prowess, so it’s no surprise that trying out the local fare is at the top of our to-do list. From the iconic deep dish-style pizza, to the classic Chicago hot dog, it’s nearly impossible to not get hungry thinking about this city. Our travelers’ favorite “Chicagoan” eateries include Portillos for hot dogs, and Lou Malnati’s, Gino’s East and Giordano’s for deep dish pizza. If you’d like some fresh air on a nice day, Paradise Park serves pizza and other Italian dishes on a large outdoor patio in Wicker Park. Or, if you can’t decide on just one dish, try the Chicago French Market; an indoor European-style market with anything from Italian street food to Belgian fries and beer, vegan cuisine to sushi and Hawaiian poke.

Investigate Chicago’s Art Scene

Visit the award-winning Art Institute of Chicago, which is home to over 260,000 pieces of art that originate from cultures all around the world and cover 5,000 years of history. Wander the halls of the institute for a scholarly and enlightening experience, or explore the streets to witness the authentic culture of the city. Nearly every corner you turn in Chicago harbors some type of sculpture or mural.

Take Advantage of Public Transportation

Once you’re in the city of Chicago, everything you need is easily reachable by foot or public transportation. Chicago Transit Authority (CTA) buses and trains and Metra railways make for easy transportation around the city. In addition, Amtrak railways provide transportation from Chicago Union Station all around the city and the world. Even if you aren’t taking a train, the station is well-worth a visit just to witness its grand architecture.

Admire Chicago’s Architectural Gems

Chicago has an abundance of architectural masterpieces. A few of the must-see buildings and structures include;

  • Willis Tower: A 110-story skyscraper that held the title of The World’s Tallest Building from 1973-2014.
  • Aqua Tower: An environmentally-friendly engineering feat, designed with white concrete balconies and colored glass to create the impression of water cascading down the building’s sides.
  • Chicago Water Tower: One of the few buildings to survive the Great Chicago Fire of 1871, this Gothic Revival structure was created to hide a standpipe from the city’s primary water supply in the 19th century.

At the end of the day, wrap it all up with a Sunset Architecture Cruise on the Chicago River.


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