Outside of Activate: Things to Do in Chicago

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Activate will be a great opportunity to hear great speakers, network with like-minded folks, and learn some tips to keep your business growing.
But as is the case with any conference you attend, it’s not all about the conference. If you’re coming to the Second City, chances are you’ll want a little break to let your hair down.
With that in mind, we’ve compiled a list of some things to do if you’re visiting Chicago. Let’s take a look.

Food & Drink

Chicago has one of the best food scenes in the country, so if you’re visiting the Windy City, make sure to partake. We can’t even come close to listing all the great places to grab a bite to eat or cocktail to drink, but here’s a shortlist of some of the best spots.

Duck Duck Goat

The creation of Top Chef winner, Stephanie Izard, Duck Duck Goat’s aesthetic is inspired by American Chinatowns with an “upscale twist.” You’ll find delightful Chinese dishes and a full bar with some great cocktails.
“it may seem like they took the best of every Chinatown in America and squeezed it into a few rooms on the corner of Fulton Market.” – UrbanDaddy


This rooftop restaurant is situated right across from Millenium Park, which means awesome views of not just the park, but also the lake. This is an ideal spot to stop into on a warm Chicago night for a bite to eat.
“Cindy’s is one giant greenhouse with communal seating, a large over-crowded bar, and the crown jewel – the patio. When you step out on that magnificent overhang, it’s suddenly [worth the wait] as you take in the sun setting over Millennium Park.” – The Infatuation


If you’re looking for something a little more casual and—umm—hearty, Portillo’s is the place to go. This chain of Chicago-style, quick, cheap eats will leave you satisfied for the next meal. Or two. They’re known for their Italian Beef sandwiches, but might I recommend the chili-cheese dog.
“Portillo’s has locations all over Illinois, plus Indiana, Arizona, and California, but the River North location is the focus here. If you’re ever in need of a fast food-esque meal, specifically for a classic Chicago style hot dog or Italian beef, this is your spot.” – The Infatuation

Pequod’s Pizza

You’ve probably heard of Lou Malnati’s or Giordano’s, but here’s a little secret: Pequod’s is better. They have a deep dish that rivals any other and, unlike many deep dish pizzerias, they have incredible thin crust as well. If you’re in Chicago and are looking for a pie, this is the place.
“Ditch your diet, grab your fellow Blackhawks fans, and head to this Lincoln Park stalwart for some of the best pies in town.” – Michelin Guide

Green Mill

If you’re staying downtown, this won’t be the most convenient option, but if you’re willing to hop on the “L”, it’s right off the Lawrence Red Line stop. The Green Mill is an old-school jazz club with a ton of history—guest lists of days past featured names like Frank Sinatra and Al Capone.
“History drips from every note and the music swings with cool precision at this not-to-be-missed Uptown jazz club hosting the best in the business and maybe even the ghost of Al Capone.” – Zagat

The Signature Room

The Signature Room sits atop the 95th floor of the John Hancock building on Michigan Ave. It’s got an upscale bar and restaurant, but if you go to this place, the thing you’ll be talking about are the panoramic views of the city and lake, and while I’ve never seen it, the rumor is the best view is from the women’s restroom.
Some people like to drink. Other people like to drink in the sky overlooking a sprawling metropolis. Drinks are expensive. Also, it’s 96 floors in the air!” – Chicago Reader

City Winery

City Winery has two locations, both great options for an after-conference drink. The main location is close to Activate’s venue and has a music hall as well as some nice food options. The second location is situated right on the riverwalk downtown.
“City Winery’s Chicago location (the original is in New York) occupies a lovely West Loop space with lots of wood and exposed brick. Barrels of wine behind glass constitute part of one wall and empty wine bottles decorate another; lamps, candles, and a fireplace make the place feel almost cozy despite its cavernous size.” – Chicago Reader

Extend your Stay?

If you’re arriving Monday morning and leaving Tuesday evening, you may only have time for a bite to eat, but if you’ve managed to take an extra day to see some of the city, you won’t be short on options.

Millenium Park

Just on the other side of Michigan Avenue, Millenium Park is filled with plenty of open space, interesting architecture, and landscape design. Make a stop and take your picture in front of The Bean for a quintessential Chicago tourist experience.

Hit the Beach

We may not have an ocean, but there’s no shortage of beaches. All along the city are beaches on the “closest thing to an ocean that’s not actually and ocean” Lake (also known as Lake Michigan). Here are some options: 12th Street Beach, Ohio Street Beach, North Ave. Beach, Montrose Beach.

Lincoln Park Zoo

Lincoln Park Zoo is one of the oldest zoos in America. Snow leopards, hippopotamuses, lions, gorillas. Would you like to look at any of these? Well, you can. For free. That’s right, we have one of the few free zoos in the country, and there’s no shortage of awesome animals to take a look at.

The Museums

I didn’t want to list one because there are plenty worth going to. If you’re the type that likes to take in some culture or science, we have you covered. Here’s a quick list:

There are plenty of other options, but these are big ones that surely won’t disappoint.

Architecture River Tour

Chicago has one of the richest architectural histories in America. If you don’t believe me, give Devil in the White City a read. The river tour is a great way to spend an afternoon. The boat will take you along the Chicago River while a charismatic guide will fill you in on what makes our skyline unique.

Navy Pier

This is another tourist staple. Navy Pier offers a wide-array of things to do from shopping to eating to seeing a live show. Check out their “things to do” page to find out what activity best suits you.

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