The Windy City’s pizzazz—like its pizza—is no secret. You can’t possibly see and taste everything on one trip (or even fit every must-do into a bucket list … ahem, Navy Pier, the Riverwalk, the Mag Mile and The Bean). And that’s exactly why we love it.
Canoeing on Lake Michigan overlooking Chicago
Credit: David Nevala

Bucket List

A Museum

OK, we're cheating and listing a few: Join the fun at The Art Institute of Chicago, Adler Planetarium, Shedd Aquarium or Field Museum, or discover a gem like the DuSable Museum of African American History. 

A Boat Ride

Chicago has two waterfronts—Lake Michigan and the Chicago River. Explore with Kayak Chicago tours and rentals. Or hop aboard Chicago's First Lady for a Chicago Architecture Foundation Center cruise.

A Ball Game

Even America's pastime can't be narrowed to one pick!  The CTA Red Line train takes Cubs fans north to Wrigley Field—and also carries White Sox fans south to Guaranteed Rate Field

A Show

A few hot tickets: Catch Broadway in Chicago in the Theater District. LOL at The Second City comedy club. See the Joffrey Ballet at the Lyric Opera House

It's a Date!

Warm weather in Chicago means time on the water and oh-so-many outdoor concerts. The Millennium Park Music Series puts on 10 shows of various genres­. For a classy time, Grant Park Music Festival entertains with the Grant Park Orchestra. The best news: They are free!

Lardon in Logan Square reuben sandwich
Credit: Kevin J. Miyazaki

Where to Eat

New Classic

If it's not broke, don't fix it—but a little upgrade never hurts. At Lardon in Logan Square, the Reuben is enriched with Gouda, house sauerkraut and "fancy sauce" (garlic aioli with ketchup and cornichons).

Delish Deals

Chinatown can overwhelm (and excite!) with its restaurant options, but trust us when we say to order Pork Soup Dumplings at Hing Kee Restaurant. Laid-back vibes rule at Parson's Chicken and Fish in Logan Square. Enjoy a huge plate of crispy chicken and waffles while slurping down a Negroni Slushy on the patio picnic tables.  

Worth the Splurge

At Mi Tocaya Antojeria in Logan Square, chef and owner Diana Dávila creates elevated dishes inspired by her Mexican ancestors, including the popular Peanut Butter Lengua.

The Aviary in the West Loop serves artistic cocktails that almost double as fun science experiments. Let your server help guide you through a three-course cocktail progression before it's time to take an Uber home.   

Free and Fab

At the site of the 1893 World's Fair on Jackson Park Island, stroll through the Japanese Garden of the Phoenix. Bonus:  cherry blossoms in the springtime.

Family Hits


Start the day with a brioche French toast flight at Lincoln Park's Batter and Berries. Most kids love a dog (a hot dog, that is). A quick stop at Fatso's Last Stand will set you up with the famous Chicago Char dog. Dinner is meant for deep dish. Options abound, but Giordano's and Lou Malnati's are a couple of the classics.


Cool off in the big lake at one of the city's beaches. Monroe Harbor is near Navy Pier; North Avenue Beach has snack vendors and rentals for the water, plus bikes for the 18.5-mile Lakefront Trail.  

Budget Pick

Always free and always fun, Lincoln Park Zoo is a wildlife oasis sandwiched between Lake Michigan and skyscrapers. Don't miss the red pandas and polar bears. 

Buckingham Fountain at Grant Park
Credit: Caroline Naif

Photo Op

If you didn't 'gram Grant Park's Buckingham Fountain, were you really here?

Publishing House Bed and Breakfast
Credit: Bob Stefko

Where to Stay

Guests of Publishing House Bed and Breakfast in the West Loop stay in one of 11 luxe rooms, but curling up with a book in a nook of the 1909 historic building is encouraged. The Robey in Wicker Park  has a posh rooftop pool and bar with perfect skyline views.