LGBTQIA+ Family Weekend in Chicago

Chicago is known to be the Windy City and after visiting there is no doubt that this is true.

The city literally blew my hat off while we were strolling downtown! Famous for its Chicago-style hot dogs, deep dish pizza, architecture and jazz music, there is so much more to this amazing city, especially when you are traveling with young children. 

On a long weekend summer getaway, my wife Caitlin and our two kids, Grey and Hayes, experienced some of the top family attractions in Chicago. Our kids had such a great time that my son is already playing “let’s go to Chicago” at home in anticipation of our next hop up to Illinois’ largest metropolis. 

Come along as we eat and play through Chicago, as well as find a community where we are welcomed as an LGBTQIA+ family with open arms and hearts.

No trip to Chicago is complete without sampling all of the local restaurants, bakeries and coffee shops. While we enjoyed dinner at Doc B’s Restaurant and Bar, sampled deep-dish pizza at Giordano’s, and wandered through the Navy Pier Food Court, there were a few standout spots we think you should definitely check out on your trip to Chicago. No parent will be surprised that breakfast was our favorite meal of the day. 

Tucked away in a cute little neighborhood in Chicago, the Original Pancake House is truly passionate about their family traditions. If you want to feel like you woke up at your grandmother’s house on a Saturday morning to the smell of her delicious homemade pancakes then the Original Pancake House in Chicago is for you. I was a super fan of the waffles topped with strawberries, but my wife and kids all ordered pancakes, which they declared were 10/10. If you haven’t had enough pancakes, check out Wildberry Pancakes & Cafe too!

M. Henry was a chic brunch spot in Andersonville, a neighborhood north of downtown, that was oozing with charm. We found everything from healthy to delightfully decadent items side by side on the menu. Most impressive was the fresh fruit that met us at the table. Let me tell you, it makes taking a look at the menu a lot easier when your kids are shoving strawberries into their mouths instead of whining about how they will surely perish from hunger. If you have time for another brunch spot, hop into Patio at Cafe Brauer during your weekend away, too. 

Another Andersonville favorite for dinner was Lady Gregory’s. Our family enjoyed a meal in their adorable outdoor space, lined with the inclusive pride flags. The vibe of this spot was exceptional, making our LGBTQIA+ family feel welcome, from the servers down to the other people enjoying their dinner right next to us. If there is one must-have menu item, though, it has to be the Irish Curry Chicken Pot Pie. It was seriously what foodie dreams are made of!

If you are looking for something a bit more on the go, you have to pop into Brown Sugar Bakery: At Navy Pier. This Black-owned bakery, an official Illinois Made Maker, sums it up with their slogan “Life is A Little Sweeter With A Little Brown Sugar.” While it might not be breakfast food, the cakes and cupcakes are worth every calorie to get a morning sugar rush or afternoon pick me up.  

Thankfully, Chicago has no end of activities for kids that their parents will also love. From a world-class aquarium to plenty of parks and beaches, natural history and art museums, you will want to plan multiple trips to start to scratch the surface of all you can do.  

But where should you start first? That’s easy- the Shedd Aquarium. My 4-year-old son Grey is still in shock that there were Beluga at this Chicago aquarium. Let your curiosity run wild and step back into your childhood while engaging with all the amazing animal interactions throughout the day, including the beluga show, stingray feeding, and starfish, stingray and sturgeon touch pools. If you have a true animal lover in the family, you can book an enhanced behind-the-scenes experience to get up close with sea otters, penguins or belugas. You can even be part of a shark feeding tour! 

The critter fun doesn’t have to stop at the Shedd Aquarium either. Step back in time at the Field Museum, one of the country’s premier natural history museums. We spent hours upon hours walking around in this amazing space. To be honest, I have yet to discover a museum that keeps my son’s attention like the Field Museum. He was in awe of everything they had to offer. We shut the place down, staying until the very last minute before closing time, and we still felt like we could go back to see new things the next day.  Thankfully, Maggie Daley Park, filled with a Play Garden and Enchanted Forest, was north of the museum, so we were able to let the kids run off any leftover energy. On the way, we popped into Millennium Park to check out Cloud Gate (better known as the “The Bean”), which is always a hit with kids who love to make silly faces at their reflection.

Keeping with our animal theme, we headed to Lincoln Park, the largest park in the city and the home of Lincoln Park Zoo. In addition to the free zoo, families can take a leisurely stroll around the pond, learn all about butterflies at the Peggy Notebaert Nature Museum, enjoy an amazing view of Chicago’s skyscrapers or simply relax with a little downtime at the playground.

After so many animals, it was time to get sky high. If you are looking for breathtaking panoramic views of Chicago, 360 CHICAGO gives you the sickest views of the city from 1,000+ feet above the famed Magnificent Mile. While up on the observation deck you must check out TILT – Chicago’s highest thrill ride. You literally stand in a window and with a click of a button, you are tilted out over Chicago. Don’t worry though, you can always step back from the breathtaking views looking down into the streets below if you get freaked out. 

Speaking of crazy views, when you head to Navy Pier, you can walk 3,000 feet out over Lake Michigan, giving you an incredible view of the skyline from the water. For even more views from the water, hop on the Shoreline Sightseeing: Skyline Tour. This 40-minute sailing adventure leaves right from Navy Pier, providing a family-friendly adventure everyone can enjoy. Back on the pier, you will find more shops and snacks than you could check out in one visit. Kids will love the Centennial Wheel and our little ones never wanted to leave the Chicago Children's Museum, located right on the pier. 

I already told you about a few of our favorite restaurants in the northern neighborhood of Andersonville, but what I didn’t tell you was that I have never felt more at home or welcomed than I did when we walked down Clark Street in Chicago. The people, the shops, the restaurants, just the atmosphere was SO inviting. As a queer person, this is so important. To feel free and safe to be my true authentic self…that my friends is priceless. 

I knew that it was OK for my family to let our guards down and enjoy this incredible time together. Pride flags blowing in the wind and walking into all these amazing LGBTQIA+ owned establishments was pretty cool and an experience I will never forget. Apparently, neither will my son, as he keeps asking to go back to the Windy City, because, as he has already learned, when you find your people who accept you for you, you don’t ever want to let go.