Most people know Chicago from the ground. You drive down Lake Shore Drive, you walk through Millennium Park, you sit at a rooftop bar and take in the skyline. It’s all impressive. But here’s the truth: the city looks completely different when you’re a few hundred feet above it.

That’s what we get to see every day at Delta Fox, and honestly? It never gets old.

We’re not a big company with a fleet of planes. We’re a small, family-run outfit. We fly because we love it, and we invite people along because it’s just too good not to share. For us, it’s less about “tours” and more about moments, the way someone’s face lights up the second the city comes into view, or the quiet pause when the lake catches the sunset. Those are the things that stay with you.

What It’s Like Up There

The first thing you notice isn’t even the skyline; it’s the layout. Chicago from above is this perfect grid, stitched together by the river and framed by the lake. If you’re from here, you’ll start recognizing pieces of your own story: “That’s my neighborhood,” “That’s where I went to school,” “That’s the pizza place we always went to after games.”

And then, of course, the skyline takes over. The Willis Tower doesn’t just look tall, it looks like it belongs to the whole city. Navy Pier stretches out like a welcome mat. Millennium Park looks designed on purpose, like someone painted it with a giant brush.

Our pilots don’t recite scripts. They just point things out the way you would if you were showing a friend your city: “Over there’s the Hancock. That’s Soldier Field. If you look to the left, you’ll see the Ferris wheel turning.”

The Seasons Tell Different Stories

Chicago doesn’t give you the same view twice.

  • In spring, everything softens. Parks start to glow green again. The city feels like it’s stretching awake.

  • In summer, the lake is alive with boats and the whole shoreline buzzes with festivals. From above, you can almost hear the music drifting up.

  • In fall, the trees steal the show. Streets turn orange and gold, and the contrast with the lake is unreal.

  • In winter, the rooftops wear snow, the lake freezes, and the city slows down. With the holiday lights twinkling, it’s pure magic.

We’ve had people come back just to see Chicago in a different season, because each one feels like a brand-new city.

The People We Fly With

The city is the star of the show, but our favorite part is the people who climb aboard.

Like the father who surprised his teenage daughter with her first flight, she screamed with delight when the wheels lifted off and then went quiet, just staring out the window in awe.

Or the group of friends who laughed the entire time, taking selfies, pointing at their office buildings, and shouting “there it is!” every five minutes.

Or the couple who sat in silence the whole flight, holding hands as the sun went down. When we landed, they said, “That’s exactly what we needed.”

These are the memories we carry long after the plane is parked.

Why Fly With Us

We know there are other ways to see Chicago. Helicopter tours, big sightseeing companies, they all have their place. But that’s not us.

We’re small. We’re personal. We keep it private, every time. It’s just you, your people, and your pilot. No strangers, no crowded groups.

We care about safety like we care about family. Our planes are maintained with obsessive attention. Our pilots? They’re not just skilled, they’re storytellers.

And the details matter. Want to circle your neighborhood? Want to time it for sunset? Want to pop the question mid-flight? We’ll help make it happen.

That’s what makes us different: you’re not just buying a tour, you’re sharing a flight with people who love flying as much as you’ll love experiencing it.

Simple to Plan, Easy to Love

Booking a flight isn’t complicated. Pick a time that works, tell us what you’d like to see, and show up ready. We’ll handle the rest.

Some people book for birthdays. Others just because they had a free Saturday. Some make it part of a bigger Chicago day out. However you choose to do it, we promise it’s going to feel different from anything else.

Chicago, Rediscovered

Here’s the truth: even if you’ve lived here your whole life, Chicago from the air is going to surprise you. It makes the city feel new again.

For our middle-aged guests who want something refined and memorable, it’s a quiet, elegant way to celebrate. For our younger guests, it’s fun, adventurous, and totally Instagram-worthy.

But no matter who you are, when you land, you’ll walk away with a memory that sticks.

Ready to See It for Yourself?

We’d love to take you up and show you the Chicago we see every day.

Reach out at info@flydeltafox.com and let’s plan your flight. No gimmicks, no fluff — just the city you love, from the sky, with people who care about making it special.

Because Chicago is a city worth rediscovering, and sometimes, the best way to rediscover it is from the clouds.