Chicago City GuideWelcome to Chicago!

Brian O’Neill, Conversion Copywriter

The Chicago Cultural Center has exhibitions, music, and more in a building that is in and of itself an architectural gem (with a brilliant Tiffany dome). If it’s weird you want, check out the Museum of Surgical Science. It’s both stranger and more beautiful than you’d think.

For a taste of 1960s Chicago, when the Loop was run-down, and swanky was not-quite-swanky, go to Miller’s Pub. Great food and an old-school atmosphere. Monk’s Pub has great beer, good food, and an atmosphere unlike anything else in the Loop. It’s the kind of place where you drop peanut shells on the floor.

Laurel Miltner, Director of Digital Strategy

Wanna play some games? Check out Emporium (West Loop), Headquarters (River North), or the Game Room at the Chicago Athletic Association (Loop).

Bonus: The CAA is also where you’ll find Cindy’s rooftop bar with tasty cocktails overlooking Millennium Park, Michigan Ave and Lake Michigan.

For the foodies: Toni Patisserie on E. Washington (Loop) is a cute little spot for a breakfast bite or French pastry (approved by my French former colleague). And if you’re feeling extra adventurous, here’s something for the 90’s action movie fans.

Kayla Johnson, Content Coordinator

“Before it gets too chilly to enjoy, take a stroll down the Chicago River Walk to take in beautiful sights of the windy city while being steps away from the river. Another thing I love to do is hang out in and around the Fulton Market. I love the many restaurant choices, there is something for everybody!

Both the River Walk and the Fulton Market have great views of gorgeous Chicago sunsets.”  

Kurt Cruse, Creative Director

Call ‘em classics, staples, or even cliché — I just call ‘em delicious. Lou Malnati’s for a pepperoni and spinach deep dish pizza (mmmm garlic). Head over to Portillo’s and get yourself a Chicago dog and an Italian beef with cheese and sweet peps (ask for it dipped). Grab some Chicago Mix at Garrett’s Popcorn. Boxes checked.

If you’re looking for something a bit more local, I recommend taking the blue line up to Logan Square. Get off at California, walk into the Boiler Room, and ask for a PB&J — a slice of pizza, a PBR tall boy, and a shot of Jamo (ask for Malort instead) for 10 bucks! Now you’re a real Chicagoan.

From there, walk up Milwaukee Ave and pop into any shops or bars that grab ya. If I were you, I’d be sure to hit Estereo to pet all the dogs and drink all the Mezcal Breezys.

Dan Moran, Content Coordinator

To get a full sense of where Chicago has been and where it’s going, you’ve got to go to the West Loop. Tech giant headquarters intermingle with century-old family-run businesses.

For dinner, check out Randolph Row. You’ll find a smattering of dining options, from beer and tacos at Rick Bayless’ Cruz Blanca, to the crown jewel of Randolph Row (IMHO), The Publican, whose motto is “oysters, pork, and beer”. They were, and still are, ground zero for the slow food, farm-to-table movement in Chicago.

For after dinner libations, check out the nearly adjacent Chicago Brewing District, featuring 6 different breweries all within a few blocks of each other and Kaiser Tiger, one of the biggest beer gardens in the city of Chicago.

Trudy Hobfoll, Finance

For a hoot of a good time go to Teatro Zanzani, check out Andy’s Jazz on Hubbard, grab drinks at The Signature Room on the 96th floor of The Hancock. They have the best views of the city. You can see for miles.

Swing by the Art Institute, one of the best museums in the world and then grab a water taxi at Michigan and the river over to Chinatown for some of the best Dim Sum in the city!

Amanda Gant, Marketing Director

Go grab a pic at the world famous “Bean” downtown and then head across the street to Cindy’s rooftop for a cocktail (see above).

Head over to Fulton Market to High Five Ramen. It’s the best ramen in the city! There are only 18 seats and it’s in the basement of Green Street Meats. Get there right when it opens, put your name in, then hang out in Green Street and have a drink while you wait for your table. They make a mean Manhattan. Highly recommended. 

You have to head out on an Architecture Cruise. Sit back with a cocktail or a cheeky pint and hear all about the history of Chicago while cruising down the Chicago River. The boat launches right off of Michigan and the River. 

If you need a good laugh, I recommend catching a show at Second City, Zanie’s or IO Theatre.