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Guide to Chicago Must-dos

Gorge on Chicago-style Deep Dish

Some are partial to Lou Malnatti’s, others swear by Uno’s, and there are partisans to Gino’s East and Giordano’s. But let’s be honest, if you’ve never had deep dish before, any of these pies is going to be an experience for you, and an awesome one. We do, however, really love the pie at Pequod’s. For more on our pizza faves, click here>>

Visit the Bean

Is it a tourist icon. Yes. That doesn’t make it any less cool in our book. Its real name is Cloudgate, and it’s pretty damn fantastic, and once you see it, you’re going to want a picture in front of it to send to all your friends.

Second City

Let’s just list some names:  Chris Farley, Tina Fey, John Belushi, Alan Alda, Dan Aykroyd, Steve Carell, Stephen Colbert, Rachel Dratch, Bill Murray, Mike Myers, Bob Odenkirk, Amy Poehler.

They’ve all graced the Chicago Second City stage, and many more big stars have as well. For less than $30, this is one of the best deals in the city. Our advice - catch the late show, which often features a 3rd act that sometimes include a returning alumnus.

Stroll the Magnificent Mile

Don’t worry, you don’t HAVE to spend a dime (and believe us, a dime wouldn’t get you far) but it’s a great street for people watching and window-shopping, and there are very few places in the world like it.

Lincoln Park Zoo

In the center of the city you can stroll right into this free zoo and spend some time with the lions, tigers, monkeys and hundreds of other exotic animals.


Man, this place. ALL THE MEATS...and all the cheeses, and all the wines. What doesn't this place have? Chef Mario Batalli's ode to Italian culinary arts is an awe-inspiring trip into gluttony unlike any place you've ever been. A must for all foodies.

Visit a brewery...or 7

Chicago’s craft beer scene has exploded to proportions you’re unlikely to find in any other city in such close proximity to each other. Goose Island is the granddaddy of the local craft scene and offers a great tour. Half Acre has boomed since opening in Lincoln Square (one of our favorite neighborhoods) six years ago. Try the Daisy Cutter, their flagship beer, and have a seat in their taproom with a wall made from reclaimed Wisconsin wood from an old Mill.

In Logan Square you can swing into Revolution Brewing Co.’s brewpub if you can find a seat. If the crowd there is too much for you, head about 10 minutes to their taproom on Kedzie, with plenty of room, plenty of games, and ‘80s movies on the screen.

Breakroom opened this year on Montrose and features what has to be one of the coolest bars you’ll find.

Stand in the Clouds at Sears Tower and the Hancock Building

No, you shouldn’t pick one or the other. Sears Tower (we refuse to call it Willis) is the tallest in North America (we’re not buying the spire on 1 World Trade Center as part of its height, but we’re biased). You can see seven states from up here, and you can test your limits on The Ledge, a glass box that allows you to step out the window with nothing but glass between you and the ground 103 stories below.

At Hancock, you won’t be as high up, but the view is unrivaled. Sitting at the crook of Lakeshore Drive, the Hancock’s view of the lakefront is mesmerizing. While you’re there, grab dinner or a drink at the Signature Room on the 95th floor.

Navy Pier

Culturally, Navy Pier has few redeeming qualities. It’s not where we’d tell you to go eat, or “experience” Chicago. However, the Ferris Wheel is truly awe-inspiring and worth a ride, and the view of the skyline from the pier at night is worth a free stroll for anyone.

Get a Picture at the Jordan statue

If you’re a sports fan, or have kids that are, you’ll want to drive out or catch the Madison Bus to see the iconic statue of Michael Jordan that stands out front of the United Center. It’s likely the most famous sculpture of a sports figure ever created, and even in its stillness evokes awe in viewers.

Grab a bite or a drink at a classic:

You’ll never be able to hit them all, but a drink or famous bite at any of the following will give you bragging rights or a story to bring home with you:

  • A Schlitz and a cheezeburger at the Billy Goat Tavern (not at Navy Pier, under Michigan Ave, where the writers used to go)

  • An Italian Beef at a classic corner joint. Al’s Beef and Portillo’s are both great, don’t get us wrong, but you’ll get a true experience with a beef at one of Chicago’s great corner stands. Joe Boston’s, way out west on Grand Ave., is a classic. Bari on Grand, Fiore’s on Oakley, Carm’s on Polk.

  • A drink at Old Town Social

  • A burger at Au Cheval, Owen and Engine, or Kuma’s, Lockdown or Bad Apple. All will change your idea of what a good burger ought to be.

  • A taco at Antique Taco or Big Star.

  • A cocktail at Aviary (you’ll need a ticket to get one, and room on your credit card, but it will be an experience)


Summer Musts

A Concert in the Park

Take in a free show at the Frank Gehry-designed Pritzker Pavilion in Millennium Park. While not quite the icon that the Bean has become, this explosion of steel is more architecturally significant than its sculptural neighbor is to the art world, and a show here in summer, with the skyline as your backdrop, is mesmerizing.

Riverboat Architecture Tour

It’s on every list for a reason. If you’re here in summer, and you have one day in the city, this should be on your list. It lives up to its billing every time. Enjoy a drink as you spend 90 minutes learning more about Chicago, it’s architecture, its mistakes, and it’s growth than you will from any book or museum. If you’re a photo buff, this is your dream.  Get tickets>>

Kayak the Chicago River

Like the architecture tour, a trip down the river on kayak will give you a view of the skyline few ever see, with a great angle for photos. Tip:  Search sites like Groupon or Living Social for a great deal on these, as you can often find a discount here. Makes a great date too!

Festival Hop

A lot of cities have festivals, but Chicago, well, in Chciago these are more like gigantic block parties, and come summertime you can often find three or four in different neighborhoods each summer. You’ll get to sample the food from the neighborhood done street-style, hear great local bands, and drink in the street, which for some reason is always more fun.

Wrigley Field

The first time I walked into Wrigley Field it felt like I’d stepped into a movie, with the crumbling grandstand showing its century of age, the ivy creeping up the outfield walls, and a vendor hawking peanuts. Wrigley is where baseball still feels like it looks in the movies, even with the recent upgrades. Cubs fan or hater, if you’re in Chicago and the Cubs are home, the experience is more than worth the price of admission.

Run or bike the Lakefront Path

If another city offers an outdoor experience to rival Chicago’s Lakefront Path, we haven’t seen it. Run uninterrupted from the northern edge of the city in Rogers Park to the far South Side and you’ll experience an urban panorama of people, sports, tourist attractions. You’ll pass Soldier Field, Navy Pier, the Adler Planetarium, the Shedd Aquarium, the Field Museum, Grant Park, Millenium Park, the Museum of Science and Industry. You’ll wind through the lakefront beaches, each with their own vibe and culture - the reserved Foster Beach with room to sprawl, the volleyball crowd at Montrose, the swarms at North Ave. and the bros at Oak Street Beach.

You’ll experience this all with the world’s most beautiful skyline unfolding to your right, the shape twisting and re-emerging anew around each bend. Lace up your shoes, grab your bike, or rent a divvy and cruise the path to get a glimpse of what Chicagoans remember to get them through the cold of winter.

See Icons at the Art Institute

It’s hard not to be spellbound when roaming the halls of the Art Institute of Chicago. You’ll stnad  face-to-face with world-renowned works like Van Gogh’s “The Bedroom,” Grant Wood’s “American Gothic” or George Seurat’s “A Sunday Afternoon on the Island of La Grande Jatte.”

Ride the El

The El (short for Elevated Train) is as much a part of the character of Chicago as the buildings, the river, and the Bears. The rumble of the El lurks ever in the background, whisking people from far-flung city’s and suburbs, through neighborhoods, under the streets, and eventually around the downtown loop through the caverns of skyscrapers. Even if you have nowhere to go on it, do yourself a favor and take a ride and see the city in a new way.

Take the Kids to Maggie Daley Park

A massive climbing wall, a play garden featuring slides, and come wintertime, an ice ribbon that weaves its way through the park like a river in the woods.


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