Hey there! I don’t know about you, but every time I catch a glimpse of the Chicago skyline, it’s like seeing it for the first time. There’s just something about the way the buildings rise up against the sky, especially when the sun sets or the lights start twinkling at night. So, I figured I’d share my favorite places to soak in that unbeatable view. Whether you’re new to the city or have been here forever, these are my personal top 5 spots to see the Chicago skyline in all its glory.
1. Skydeck at Willis Tower – one of the best Spots to See the Chicago Skyline
Let’s start with the classic: Skydeck at Willis Tower. I know it might seem like the obvious choice, but for good reason! You’re literally standing 1,353 feet above the ground on the 103rd floor, with views that stretch out as far as Indiana and Wisconsin on a clear day. But the real kicker? The Ledge. It’s this glass box that extends out from the side of the building, so when you step onto it, you’re basically floating above Chicago. Yeah, it’s a little scary at first, but that view is so worth it.
Pro Tip: If you can, go at sunset. You’ll catch the city bathed in golden light and, as night falls, you’ll get to see the city lights sparkle like a blanket of stars. It’s the best of both worlds!
2. See the Chicago Skyline at 360 Chicago at the John Hancock Building
If you’re not into the glass box at Skydeck, then head to 360 Chicago in the John Hancock Building. You get a totally different, but just as stunning, view of the city and Lake Michigan. It’s 1,000 feet above the ground on the 94th floor, and they’ve got something called TILT—an enclosed moving platform that literally tilts you out over the edge of the building. Talk about an adrenaline rush! I personally love how calm and peaceful the views are from up here, especially when looking out over the lake.
Pro Tip: Check out their bar! You can grab a drink and just relax while taking in the skyline from this incredible height. I mean, who wouldn’t want to enjoy a cocktail while gazing out at the city?
3. Cindy’s Rooftop (Chicago Athletic Association)
For a more down-to-earth but equally stunning view, Cindy’s Rooftop is one of my absolute favorite spots. Located above the Chicago Athletic Association Hotel, this rooftop bar and restaurant offers sweeping views of Millennium Park, Lake Michigan, and, of course, the skyline. There’s something about the vibe here—super cozy, with a greenhouse-like setting—that makes it the perfect place for an evening with friends. Plus, who doesn’t love the combo of skyline views and great food?
Pro Tip: Make a reservation if you’re planning to dine here—it can get packed. But if you’re just popping by for a drink, the bar area is a little easier to get into. Either way, it’s worth it for those views!
4. ROOF on theWit
If you’re looking for a spot that’s more chic and lively, ROOF on theWit is your place. It’s a rooftop lounge located on the 27th floor of theWit Hotel, and the view of the skyline is stunning, especially at night when the city lights really pop. I love coming here for a night out—the music, the drinks, the atmosphere—it’s all top-notch. Plus, the vibe here is more on the trendy side, so if you’re looking for a mix of good beats and great views, this is the place to be.
Pro Tip: Go during the summer when they have their outdoor terrace open. It’s the perfect spot for a sunset cocktail or a night under the stars with the city lit up around you.
5. Terrace 16 (Trump International Hotel & Tower)
Last but not least, Terrace 16 offers a more upscale option for skyline views. The terrace here overlooks the Chicago River, giving you this breathtaking view of the skyline, with some of the city’s most iconic buildings right in front of you. The food and drinks are amazing, but honestly, the views steal the show. It’s a great spot for a special occasion or even just a fancy night out.
Pro Tip: Try to grab a seat outside on the terrace—it’s the best way to really soak in that view. And if you can, come for brunch or dinner—the lighting during these times makes the skyline look even more spectacular.
So, there you have it—my top 5 favorite spots to see the Chicago skyline! Whether you’re looking for a heart-pounding view from way up high or a relaxed rooftop vibe, these places have got you covered. Honestly, you can’t go wrong with any of them. So next time we hang out, let’s hit one of these spots and just take in the beauty of the city we love! 😄
