You can’t beat a bit of local insight when it comes to making the most of a trip to Chicago, so we decided to ask around and find out what’s fun in this Midwestern powerhouse. After all, whether you’re visiting on a sales trip or a shoot, you want to make the most of your time in the home of Al Capone and Alicia Florrick. Here’s a list of the top places to eat, visit and interesting things to do in Chicago to get you fired up about your next trip.

“JJ’s Thai Street Food serves some of the best real Chiang Mai style food (no Pad Thai on this menu!) and Breakfast House has the best chiladquiles in the city.” Mikinzie Stuart, Copywriter, R/GA.

“Check out Pilsen and Little Village for authentic Mexican food.  Chinese restaurant is Potsticker House in Bridgeport. Their dumplings are a must have. Also Lawrence’s Fisheries and Rainbow Cone.” Jennifer Chiang, SVP Strategic Planning, Customer Experience, FCB Chicago.

“Hit up Thalia Hall in Pilsen – it’s an historic venue, and the attached restaurant, Dusek’s is incredible. Anywhere on Randolph Street is good (Au Cheval, Little Goat Diner). 

“My personal favourites are Mindy’s Hot Chocolate, Osteria Langhe, and Table Stick Donkey, which are all on the west side in between Bucktown and Logan Square.  Obviously, there are the glitzy places downtown and in River North but the real hidden gems are west of the loop.” Annie Sandford, Junior Copywriter, Leo Burnett.

“If you’re looking for high-end, culinary theatrics there’s Grant Achatz’s Alinea or Next. Eat Italian beef from Portillo's.” Manny Fernandez, Creative Director, R/GA 

“Spending a Saturday drinking frozen Negroni's with friends is perfect. Also Big Star, Avec, Mott St., and Maude’s.” Derek Heinze, ACD, R/GA

“The Green Mill in uptown is cool – live music and the venue was a favourite haunt of Al Capone. Or for cocktails hit up the Aviary.” Annie Sandford, Junior Copywriter, Leo Burnett.

“Chicago’s street fests are where it’s at. When Chicago summer hits, the city comes alive. You can feel the energy in the air. I guess months of hibernating during our cold winters does that to people.” Derek Heinze, ACD, R/GA

Check Do Division and the Renegade Craft Fair.

“I highly recommend seeing a show at Steppenwolf or Lookingglass, or one of the smaller local theatres--our theatre scene is really unique.” Deb Schimmel, Editor, Whitehouse Post

“There’s a really small local theatre group called Trap Door that puts on avant-garde productions from European playwrights. Don’t forget the massive music scene in Chicago! There’s always a show going on at one of the many amazing concert venues and music festivals here. Mikinzie Stuart, Copywriter, R/GA.

“Go on the Architectural Boat Tour … And ruin other people’s selfies at 'The Bean' in Millennium Park.  If you’ve got plans, The Signature Lounge at the Hancock. If you don’t, get a last minute ticket to a Second City Show.” Matt Mortimer, ACD & Writer, R/GA

“I would personally avoid the touristy areas, but honestly they are great. This city has so much history - going to all the monuments, Magnificent Mile, Architectural Boat Tours, Navy Pier, etc. They are all amazing if you are visiting, but most people I know have gone once and have never gone back. I guess it would be the equivalent to going to Times Square in NY."  Derek Heinze, ACD, R/GA

“One thing not as commonly known is Chicagoans’ love for vintage design and antiques. As a collector of mid-century modern furniture and vintage jewellery, Try to hit up flea market events like Vintage Garage and Randolph Street Market. Even if you don’t end up buying anything, it’s fun to just walk around and appreciate vintage design.” Mikinzie Stuart, Copywriter, R/GA.

“There’s a boom of art galleries in West Town right now that support street art (and original traditional art pieces from those artists), like Chicago Truborn, Vertical Gallery, and Western Exhibitions. What’s really cool is that these galleries help the artists (legally) find walls in West Town and commission street art murals that keep the neighbourhood vibrant and beautiful.” Mikinzie Stuart, Copywriter, R/GA.