The Wee Windy City with Blogger Caitlin Giles

Wee Windy City and Co-Founder of 2 Moms Media, LLC

All-American Adventurer

Although I was born in Chicago, it wasn't until I had kids that I realized what an amazing place this is to live. When you see a toddler stare up at the Willis Tower in awe or marvel at the sailboats on Lake Michigan on a summer day, it gives you the opportunity to really see the city in a whole new light.

My favorite Chicago memories involve partaking in some of the iconic aspects of the city. That includes sitting in the bleachers for a Cubs game, spending a summer afternoon at North Avenue Beach, strolling the Art Institute, or skating at Millennium Park against the backdrop of the city skyline. For dinner, the Wicker Park neighborhood is home to a myriad of amazing dinner options. Piece Pizza, Prasino, and Coast Sushi are my favorites. Post-dinner we love a twilight bike ride or trip to a local park.

The Wee Windy City with Blogger Caitlin Giles

My favorite places to eat

  1. Lou Malnati's is the best deep dish pizza in the city.
  2. Frontera Grill - chef Rick Bayless' delicious style of Mexican food is great for a special dinner out.
  3. We love Roots Pizza for a night out with other families. Ask to be seated in the back room where the kids can watch the cooks make the pizzas.
  4. Mon Ami Gabi - this Lincoln Park French bistro offers a fine dining experience where families are always welcome. When the weather is nice, request an outdoor table on the quaint patio.

My favorite family-friendly activities

  1. Navy Pier - home to the fabulous Chicago Children's Museum and a ferris wheel with a world-class view.
  2. The Lincoln Park Zoo and Nature Boardwalk offer a serene natural oasis amidst the hutle and bustle of the city.
  3. The Museum Campus - the Field Museum, Adler Planetarium, and Shedd Aquarium are all located next to one another.
  4. Glazed and Infused Donuts- the kids love them and they aren't just for breakfast!

The Wee Windy City with Blogger Caitlin Giles
The Wee Windy City with Blogger Caitlin Giles

My hidden gems

  1. The Alfred Caldwell Lily Pool is a serene space in the middle of the city - you can't hear a sound. Look for the entrance off of Fullerton near Lake Shore Drive.
  2. See the city from a whole new perspective in a Water Taxi. Avoid the traffic and treat your kids to a water taxi ride. This is a cheap thrill that the whole family will enjoy.
  3. Free museum passes from the Chicago Public Library. You can visit any major museum in the city for free - you just have to snag one of the complimentary passes for families of four available at all chicago Public Library branches.

My travel tips

Stay at the Four Seasons Hotel. They offer luxury accomodations and every family-friendly amenity you can think of. Children are truly welcome here and it shows - pop-up tent for building forts, visits from the candy cart, and baking cookies with the pastry chef!

Go to a Cubs or Blackhawks game!