Time Well SPENT: Chicago Bleisure Travel

Chicago. Chi-town. The Windy City. Home of the Bulls and deep dish pizza. Did you know this city is also home to the nation’s largest convention center? We’re talking 2.6 million square feet of pure exhibition space.

For those of you headed there for your next tradeshow, I’ve included a list of cool things to do when you get tired of shmoozing on the exhibition floor. Or better yet, you could extend your stay and turn this into a bleisure trip. (Business + Leisure = Bleisure)

Be sure to book through SPENT Travel and get cash back on your hotel stay, which can be up to 25% in some cases. I’ve included a few popular names at the end of this article.


If looking at this pic gets your palms sweaty, then congrats…you’re human!  Located on the 94th floor of the world famous John Hancock building, this observatory offers you insane views of the city 1000 feet below. Kick it up a notch by stepping onto a ledge and tilting outward from the side of the building. Vertigo, anyone?

Chicago Crime Tours

Are you a fan of gangster movies? Can you hum every note of “The Godfather” theme song without breaking a sweat? Then put this one on your list. From the comfort (and safety) of a bus you’ll visit the hangouts of notorious mobsters and check out crime scenes like the St. Valentine’s Day Massacre and the courthouse where famous mob cases were tried.

Third Coast Surf Shop

“Hanging Ten” just outside of Chicago? Yep, that’s right. Turns out, you can go surfing right off the shores of Lake Michigan! Who knew? Rent a surfboard from the Third Coast Surf Shop and take a lesson or two as well. The waves of this Great Lake are calling!

Green Mill Cocktail Lounge

Not that we’re into gangsters or anything, but this one was too cool to pass up. The Green Mill Cocktail Lounge first opened its doors in 1907 and became one of Al Capone’s hangouts during Prohibition. In fact, you can sit at his regular booth, which had a direct view of the front and back entrances. You know, in case he needed to make a fast exit. Today, this is a spot to take in some jazz.

Garfield Park Conservatory

If checking out plants is your idea of fun (who are we to judge?) then you’ll definitely want to make a stop here. Described as “one of the largest and most stunning conservatories in the nation,” Garfield Park Conservatory houses 1000s of lush and tropical plants. Step inside for a welcome break from the notoriously cold winters!

Leave a comment below if you try out any of these activities on your Chicago bleisure adventure. And don’t forget…make your travel bucks go further. Book with SPENT Travel for great cash back to reinvest in seeing more of Chi-town. Here’s some additional inspiration.*

Hyatt Regency Chicago: $158.24 cash back.

PUBLIC Chicago: $129.91 cash back.

The Westin Michigan Ave.: $230.69 cash back.


*Based on a 2 night standard room from 11/13-11/15. Subject to change.


Mark Scherzer

Mark Scherzer is a writer and communications expert with over 15 years of experience. He’s worked for Fortune 500 companies, produced content for digital startups, written for television, created curricula for education companies and developed programs for non-profits. He is also the author of “Hire Me, Hollywood” published by Adams media, a division of Simon and Schuster.
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