Summer Family Vacation in the Windy City

Named "The People's Pier" for a reason, Navy Pier offers a variety of free public attractions and experiences from cultural arts performances, kids' activities, lake cruises, and so much more.

The Art Institute of Chicago boasts ongoing exhibitions to intrigue any age. The Deering Family Galleries of Medieval and Renaissance Art, Arms, and Armor is particularly cool for big kids and tweens.

What trip to Chicago would be complete without an up close and personal view of Cloud Gate (a.k.a. "The Bean)? Millennium Park is the perfect all-day activity zone, especially during Summer when it hosts both a Music and Film series, dance performances, crafts and farmer's markets, and more. If you're a lover of The Blues, consider a special interest trip complete with tickets to the Chicago Blues Festival June 6-9, 2024.

Littles, grandparents, and every age between will love the Shedd Aquarium and the Lincoln Park Zoo where care, conservation and community are taught in the midst of active fun!

Sports fans in the family will enjoy a game at the historic and famed Wrigley Field. Popcorn, hot dogs and the iconic experience of just being there will create memories to last a lifetime.

Enjoy a walk along the Magnificent Mile as you experience the hustle and bustle of Chicago's commercial district, fine dining, shopping, and posh hotels.

Foodie, art and architecture tours are plenty. Spectacular views and a guided architecture tour aboard one of Chicago's river cruises will illuminate the Windy City's rich history and artistic culture.

Chicago's food scene is notorious in a good way! Food halls, swanky cocktail bars, street food, steakhouses, gastropubs, and last, but not least, deep dish pizza! There is no shortage of memorable options.

Pequod's Pizza for the iconic deep dish win! Visit and plan to eat slooooowwwwllly. You'll need a little extra time to digest what is likely the best deep dish pizza you've ever had. This one is so good, it has a cult following.

Your kids probably won't know what a carhop is, but when they get to experience the service and taste a Superdawg at the Superdawg Drive-In, they'll be asking you why drive-ins aren't everywhere!

For those who have a sitter or are traveling sans kiddos, the bucket list, 3-Michelin star Alinea is the epitome of fine dining and noted as one of the best restaurants in the world. The price tag reflects at just about $1,000 on dinner for 2.

No longer a hidden gem, but a selfish foodie's dream nonetheless, Kasama is one of the hottest restaurants in town. Known for its unique Filipino dinner tasting menu and amazing pastries for breakfast and lunch, it's on the "do not miss" list.

Craving Italian? Try the chicken parm at Monteverde - your upscale Italian kitchen. The restaurant also has a robust gluten-free menu as well as vegetarian options to meet the family's dietary needs.

Family-friendly and open all day, Daisies has a menu to please all ages. It's packed for dinner so be sure to reserve. You will not be disappointed, nor will the kiddos with the decadent cheesesteak sandwich at lunch, fresh-made pasta at dinner, and topped off with desserts to dream about, including the homemade gelato. Be sure to check the service fee policy ahead so you're not surprised with the bill, but know the fee supports equal and livable wages for Daisies' dedicated servers.

Do not leave Chicago without having had the rib tips at Soul & Smoke. Brisket, short ribs, and unforgettable smoked links are made fresh every day, so be sure to pre-order. Take a seat on the patio for fantastic river views.