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Chicago Father's Day Fun: Deep Dish, Cubs & Cloud Gate Await!

By Shay Trotter In Woman's World

Updated June 12, 2026 7:38 PM

Celebrate Father’s Day in the Windy City! Nestled along Lake Michigan in Illinois, this walkable destination has much to offer this time of year. Enjoy activities like lakefront biking, river kayaking and farmers market shopping, then catch an outdoor concert or a Cubs game at Wrigley Field.

Savor a famous food staple at Gino’s East

Start your visit at one of the city’s many fantastic museums, like the Field Museum. Wander its exhibits to see more than 40 million stunning specimens, including SUE, the world’s most complete Tyrannosaurus rex fossil. Afterward, stop by Gino’s East of Chicago for a taste of delicious deep-dish pizza.

Enjoy a night of laughs at Second City

As dusk approaches, treat yourself to a night of entertainment at Second City in Old Town, home to renowned sketch and improv comedy. This six-decade-old spot is where comedy actors like Tina Fey, 56, and Steve Carell, 63, got their start and today continues to entertain and delight both locals and tourists.

Catch a game at Wrigley Field

This famous MLB park is the second-oldest in the country, and has long been known as “The Friendly Confines.” It boasts a hand-turned scoreboard and ivy-covered outfield walls. Plus, unlike many other stadiums, it’s located in a residential neighborhood. Mary DeCicco / Stringer/Getty

Admire the Cloud Gate sculpture

Locals have given the impressive art piece, located in Millennium Park, the nickname The Bean. As one of the largest permanent outdoor art installations in the world, it continues to attract visitors from all over!

Bonus: Experience the Windy City at home!

Get whisked away to Chicago with a cocktail inspired by the beloved Irish tavern The Dearborn and a classic romance story set in the city.

Maple Old Fashioned

Ingredients:

1 1/2 cups bourbon
⅓ cup maple syrup
1/4 cup orange juice
2 tsp. orange bitters

Combine all ingredients in a large pitcher. Chill until ready to serve. Pour over ice and garnish each with an orange slice and a cherry. Makes 6 drinks.

**Read a Chicago-based book: The Time Traveler’s Wife by Audrey Niffenegger**

In this Chicago-based love story, Henry and his wife, Clare, must navigate their new normal when a genetic disorder causes him to time-travel unpredictably.

This story first appeared in the June 22, 2026, issue of Woman’s World magazine.

This story was originally published June 12, 2026 at 7:00 PM.