Vision Critical

The customer insight platform
for customer-centric companies

Request a Live Demo


Renowned for its bold architecture and speciality food, the infamous ‘windy city’ of Chicago is also host to this year’s Customer Intelligence Summit. Join us this September 20-21 to learn from some of the world’s leading brands about the latest trends in customer experience, innovation and marketing.

While you’re in Chicago for the Summit, here are 21 unforgettable experiences to knock off your bucket list.

  1. Take a selfie in Millennium Park

Known for its photogenic sculpture Cloud Gate (also known as ‘the bean’) by artist Anish Kapoor, nothing says you’re in Chicago like a selfie and a stroll through Millennium Park.

  1. Ride the Ferris wheel at Navy Pier

Navy Pier Park has it all. From parks, gardens and shops to a 150-foot-high Ferris wheel, this tourist hot spot (it draws nine million annual visitors) is worth checking out—if not for the people watching.

  1. Take in culture at the Art Institute of Chicago

Home to more than 300,000 artworks, the Art Institute of Chicago is a great opportunity to view iconic modern masterpieces by Picasso, Matisse, Andy Warhol and Roy Lichtenstein.


    Wrigley Field, Flickr image by Justin Mier


    Catch a game at Wrigley Field

Built in 1914, Wrigley Field is an iconic baseball field, legendary stadium and home to the beloved Chicago Cubs. Even if you can’t catch a game, take a tour of the building.

  1. Gawk at dinosaurs in the Field Museum

Two decades after the entire city burned to the ground, Chicago rebuilt and hosted the 1893 World’s Fair. The Field Museum was assembled for the exposition and still houses biological and anthropological collections such as dinosaurs and Egyptian tombs.

  1. Get dizzy at 360 Chicago

Previously known as the John Hancock Observatory, 360 Chicago is located on the 94th floor of the historic John Hancock Center in downtown Chicago. If you can handle heights, the observatory deck offers awe-inspiring 360 degree views of Chicago.

  1. Walk the 606

This former Bloomingdale train line was converted into an elevated community park and trail system that connects four ethnically diverse Chicago neighborhoods: Wicker Park, Bucktown, Humboldt Park and Logan Square. Bring walking shoes or rent a bike and breathe in some fresh air.

  1. Not for the faint at heart: Willis Tower Skydeck

Willis Tower is the second-tallest building in America, stretching 1,454 feet high and taking up two city blocks. This landmark also has observatory, which is aptly named ‘the ledge’ for its glass cube structure precariously suspended 1,353 feet off the ground.

  1. Stroll through Lincoln Park

Lincoln Park is named after the 16th president for good reason. It houses a famous statue of Abraham Lincoln himself, as well as the Lincoln Park Zoo, a conservatory, a rowing canal, the Chicago History Museum, an outdoor theatre, a beach and a sanctuary, among many other attractions.

  1. Tour Chicago Riverwalk

The Chicago Riverwalk scene is one to behold. This meandering public walkway follows the Chicago River, offering breathtaking views of Chicago’s bold and iconic architecture, boat and walking tours and waterfront eateries.

  1. Blend with the locals at Wicker Park

Called the ‘hipster center of Chicago,’ Wicker Park is home to many of the best restaurants, nightlife, bars, music spots and galleries in the city. Vintage stores, boutiques and artisan donut shops compete for space within this neighborhood’s many flatiron buildings.

  1. Get cheesy at Pequod’s

Pequod’s near Lincoln Park has some of the best pizza in town with its caramelized cheese crusts. Need I say more?

  1. Order takeout from Big & Little’s

Chicago has no shortage of good eats, and Big & Little’s tops everyone’s must-eat burger list. This burger joint is more like an institution, bringing in celebrities and locals for its burgers, pork belly po’boys, tacos and burritos. They’ve got it all.

  1. Mellow out at The Broken Shaker

If you’re looking for a cozy spot to sip on a late-night cocktail, then The Broken Shaker is your jam. This spot made it to number 22 on the world’s best bars list for a reason.


    The Original Rainbow Cone, Flickr image by Eric Allix Rogers The Original Rainbow Cone, Flickr image by Eric Allix Rogers


    Go nuts at The Original Rainbow Cone

Chicago’s oldest ice cream shop is The Original Rainbow Cone, in the heart of Beverly neighborhood. Established in 1926, the rainbow cone layers chocolate, strawberry and Palmer House (NY vanilla with cherries and walnuts) with pistachio and orange sherbet on top.

  1. Bring home treats from Garrett Popcorn

If you don’t do anything else on this list, try Garrett Popcorn. These shops have been popping up across Chicago since 1949, and are famous for a sweet and savory mix of caramel and cheese popcorn. Play it safe and get the bigger bag.

  1. Try a Chicago-style dog at Portillo’s

To top off your food tour of the city, make sure you get an original Chicago-style hot dog at Portillo’s italian meat shop. Beyond the dog and steamed poppy seed bun, they’ll load you up with onions, tomato, relish, mustard, sport peppers and a kosher pickle.

  1. Discover budding artists at the West Loop Art Festival

If you’re in town before the Customer Intelligence Summit, don’t miss the West Loop Art Festival, which showcases the work of more than 150 juried national artists, on September 17-19, along six blocks of Washington Boulevard.

  1. View art from more than 140 galleries at EXPO Chicago

If you’re staying in town after Summit, check out EXPO Chicago at the historic Navy Pier on September 22-25. The fifth international exposition of modern and contemporary art features more than 140 galleries, including EXPOSURE, a section for young galleries to participate in international art fairs.

  1. Bring in autumn at Oktoberfest Chicago

Nothing says fall quite like Oktoberfest. If you’re into Bavarian music, beer, pretzels and lederhosen, check out Oktoberfest in Chicago this September 23-25 at the St. Alphonsus Roman Catholic Church

  1. Free jazz at Hyde Park

Hyde Park Jazz Festival is a two-day festival on September 24-25 that features the finest jazz from local and international artists, as well as food vendors, an open dance floor and picnic areas. It’s also free.

Looking forward to seeing you in Chicago this September. Learn more about our upcoming Customer Intelligence Summit today.

New call-to-action

Text Size

- +

Subscribe & Stay Informed

Can't get enough? Want to be notified as we continue to publish new content? Subscribe now and get insights straight to your inbox.