Collected by Melanie Pellegrino
Chicago, IL 60601, USA
Visitors take their best Chicago photographs in front of the iconic Millennium Park sculpture called Cloud Gate (known colloquially as the Bean, for its shape). Conceived by British artist Anish Kapoor and constructed from 168 stainless steel...
233 S Wacker Dr, Chicago, IL 60606, USA
Willis Tower—originally known as the Sears Tower—was the world's tallest building for 23 years until it was unseated in 1996 by the Petronas Twin Towers in Kuala Lumpur. The 110-story skyscraper is still mighty impressive. Its "bundled...
1616 N Wells St, Chicago, IL 60614, USA
The Second City has come a long way since the small cabaret theater that launched in 1959. As a sketch comedy and improvisational performance theater, the venue has been keeping people laughing for over 50 years. Situated in the historic Old Town...
6836 N Sheridan Rd, Chicago, IL 60626, USA
Ask any local where to try your first real deep-dish pizza and they'll say "Giordanos." It's obviously the best in town. Chicago-style pizza is unique and totally different than what you'll find in Italy. More like a pie, the crust is tall and...
5507 N Clark St, Chicago, IL 60640, USA
The goods at Arrin Williams’s year-old Andersonville shop, Haymaker, are mostly handmade by local artisans. Powder-coated-steel side tables by David Greene, hanging plant holders made from reclaimed wood, and coveted leather bags by Chicago-based...
900 Michigan Avenue, Chicago, IL 60611, USA
I thought New York was a good shopping city but Chicago has pretty much the same big name shops and they're spaced out. The 900 Shops was probably my favorite space in terms of cleanliness, space and quality of shops. The best J. Crew is here and...
3535 N Clark St, Chicago, IL 60657, USA
One of the first craft beer breweries in Chicago, Goose Island is now owned by Anheuser Busch but I’d still recommend checking it out as part of your Chicago experience. The Goose Island Brewpub in Wrigleyville is smack in the middle of a...
3250, 4900B S Lake Shore Dr, Chicago, IL 60615, USA
Love biking along Chicago's gorgeous lake front but are intimidated by insane traffic? Check out the bike trails south of Northerly Island. There you will find quiet Burnham Harbor with a casual cafes and die for views. You'll find quiet and clean...