Whether you’re in town for a long layover or that big conference, we understand that you may not have time to do research when it comes to what to eat, see and do in Chicago – This is where we have you covered. Our Fox Stars offer up their top tips for the windy city, saving you time while allowing you to enjoy some of the most underrated experiences.

Attractions

Shopping on the Magnificent Mile

The Magnificent Mile is a great place to visit. Just a short ride away on the Milwaukee Amtrak, there are plenty of stores to take the family shopping. I loved to get lunch with my daughter and her favorite American Girl doll when she was younger.

-Mike Heck, vice president, supplier solutions

Garrett Popcorn

I always stop and grab some Chicago style popcorn from Garrett Popcorn. It is the BEST and they even pack it to go.

-Gina Maylath, client solutions manager

Pick a District

With so many districts all offering a unique experience, pick one and adventure. There is Chinatown for great sights and even better food, Boystown for LGBTQ+ culture, Wicker park for hip cafes and galleries and plenty more to choose from.

-Natalie Heidenreich, marketing intern

Entertainment

SPIN Chicago

SPIN is a two-level ping pong bar/restaurant. The top-level has comfy seating and a large bar, and the lower level is a massive open area full of ping pong tables to play on as well as a bar. They have great food as well. Just make sure you get a reservation.

-Wade Derby, program manager

Attend a Show

With over 250 theatre companies in Chicago, there is always something going on. Attend a large national tour show or a small, local improv show. Ask your hotel concierge what is available in your area.

-Karissa Duel, marketing events coordinator

Take a River Cruise

Everyone knows about Chicago’s famous parks, you see them everywhere. I suggest mixing it up by taking a river cruise. Many offer a unique focus, depending on your interests.

-Carisa Bartelt, creative marketing supervisor

Eats

Twin Anchors Restaurant & Tavern

Twin Anchors Pub is a historic pub and a place where celebrities still frequent because it’s quirky and off the beaten path. I enjoy the ribs and pizza. It was also Frank Sinatra’s favorite in Chicago.

-Tina Bandy, global sales director

Castaways on the Lakefront

One of my favorite things to do is take a walk, jog or bike ride along Chicago’s Lakefront Trail. If you head north, you’ll pass below the Hancock building and North Beach Ave., where Castaways is located. The views of the city and Lake Michigan rival the drinks.

-Chip Juedes, chief executive officer

Roister Open Kitchen Concept Restaurant

While in Chicago why not enjoy food from one of the best chefs in the world for a reasonable price? Roister is an open kitchen concept, casual restaurant from Alinea founder, Grant Achatz that features an a la carte menu. As with any award-winning restaurant, it’s best to make a reservation well in advance.

-Andrew Tradewell, marketing communications specialist

Next time you’re in Chicago, be sure to give one of these a try. Traveling to San Diego? Give our Guide to San Diego When in Town for a Conference a read HERE.