The Skydeck Chicago: Go Out on a Ledge to Share a Memorable & Romantic Moment With Your Special Someone

Women's Dating

The Skydeck Chicago: Go Out on a Ledge to Share a Memorable & Romantic Moment With Your Special Someone

Amber Brooks Amber Brooks
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The Short Version: On the 103rd floor of the Willis Tower, formerly known as the Sears Tower, people enjoy a breathtaking and heart-stopping view of Chicago and its surrounding area. The Skydeck Chicago observation deck invites brave visitors to step out on the Ledge, an all-glass balcony that extends four feet outside the skyscraper. Standing 1,353 feet in the air, individuals, couples, and families can look down at the city streets below and come away with a fantastic story to tell. Couples can take advantage of this spectacular venue to plan a romantic proposal, a one-of-a-kind wedding, or a private dinner in the sky. Throughout the year, the Skydeck provides incomparable views of the skyline and makes any special occasion truly unforgettable.

When Lyndsey M. started planning her wedding, she hoped to find a venue close to Chicago’s Willis Tower. Then she found out the Willis Tower itself could be her wedding venue, and she jumped at the chance to say her vows in the second tallest building in the US.

Photo of the Willis Tower in Chicago

The Willis Tower is the second tallest building in the US.

On New Year’s Eve in 2014, her wedding party watched fireworks go off below them as they celebrated at a private venue on the 99th floor of the tower. After dinner, the wedding party ascended to the 103rd floor, known as the Skydeck, where they could take turns standing on the Ledge: a glass box extending four feet beyond the Willis Tower.

“It was incredible!” Lyndsey gushed. “The lights of the city illuminate for miles and truly give this venue a magical, one-of-a-kind experience.”

At the end of the night, the staff took professional photos of the newlyweds and their guests standing on the Ledge on the 103rd floor. “I cannot say more wonderful things about the Skydeck,” Lyndsey said. “From the kind staff going above and beyond to help us to the views speaking for the majesty of the venue itself, it was a night that I will never forget for all the right reasons.”

Of course, you don’t have to get married here to appreciate the Skydeck’s romantic atmosphere. Couples of all ages plan dates, proposals, and anniversaries at the observation deck and take their relationships to new heights in an iconic setting. You can make your time together more memorable by visiting the Skydeck with your significant other.

“We’re in the memory business,” said General Manager Randy Stancik. “If you spend an hour with us, you’ll never forget it, and we stand behind that.”

Since the ‘70s, This Iconic Destination Has Welcomed Visitors

As with many native Chicagoans around at the time, Randy watched in awe as the Sears Tower was being built from 1970 to 1973. He told us that, as far as the people in his neighborhood were concerned, the construction workers on that project were the best in the world. “They were building something we could be proud of,” he said. “Something that had never been done before.”

The Sears Tower was the tallest building in the world from 1973 to 1998. Although it changed its name to the Willis Tower in 2009, it has remained a towering paradigm of what makes Chicago a world-class city. Today, it’s the second tallest building in the US, and one of the most Instagrammed destinations in Chicago. Its sweeping views from the 103rd floor aren’t something you can find anywhere else. At 1,353 feet high, the Skydeck is the highest observation deck in the US.

“I love the fact that we can share what we have up here with visitors from all over the world,” Randy said. “It’s a really cool experience to share.”

Over 1.7 million people a year visit the Willis Tower. It may not be the tallest building in the world anymore, but it’s still a local treasure and a must-see for tourists in the area.

From early morning to late evening, visitors line up for as much as three hours for a chance to stand on the Ledge where only 1.5 inches of glass separate them from the Chicago streets below. Many couples capture gorgeous engagement photos from these heights and take their wedding announcements up a notch. Around sunset, the views become even more impressive as the sky becomes filled with color. Just be sure to get there early — or call ahead and see if you can get in before or after the official hours — so you can beat the crowds.

Whether you’re looking to ask your girlfriend to prom or take a family photo for your Christmas cards, the Skydeck serves as a stunning platform for all of life’s milestones.

“Pie in the Sky” Private Dining Makes a Perfect Date Night

Willis Tower’s observation deck on the 103rd floor is a popular tourist attraction — for obvious reasons. There’s something inherently romantic about being so high up that you see the world from a new perspective. The Skydeck’s retractable glass boxes, known as the Ledge, often give people goosebumps and provide a remarkable backdrop for a photo. This tourist destination is open until 8 p.m. October through February and until 10 p.m. March through September 365 days a year. The last entry is 30 minutes until closing time. If you go late at night, the Skydeck usually won’t be too crowded, so it’s an intimate place to cap off a date night.

Photo of the Skydeck's Pie in the Sky

The Skydeck arranges exclusive dinners in the sky to make date nights extra romantic.

Couples can also enjoy a romantic private meal at the Skydeck. The observation deck extends its hours for nine to 14 couples and other small parties throughout the week. Breakfast in the Sky is served at 7 a.m. or 8 a.m Monday through Friday. Lunch in the Sky is available at noon on Saturday and Sunday only.

Finally, Dinner in the Sky is a slam dunk for couples hoping to raise the caliber of their date nights. For $100 per person, you’ll enjoy a three-course meal catered by Giordano’s Pizza across the street. You can sit on the Ledge and take in the Chicago skyline with your partner. That’s something you’ll never forget.

These private meals offer a once-in-a-lifetime experience for people in Chicago. You can book a table perched 1,353 feet in the sky and enjoy the VIP treatment at the Skydeck. While you dine together and watch the city lights sparkle below, you have the perfect opportunity to tell that special someone how you feel or pop the question.

“We’re always thinking about what we can do to make guys look like heroes to their dates,'” Randy said. “And what we can do to make ladies feel special and like it’s their day.”

A Distinctive Place for a Proposal, Rehearsal Dinner, or Wedding

On a clear day, you can see the city of Chicago and the surrounding area for 50 miles from the Skydeck. You can gaze out at the hustle and bustle of the streets and then look beyond the city limits to quiet neighborhoods and rural towns in Illinois, Indiana, Michigan, and Wisconsin. The glass walls provide spectacular views, and it’s not uncommon to see people get down on one knee here. Randy said they have a 100% success rate — they’ve yet to see someone say no to a proposal from the observation deck.

Photo of a married couple on the Ledge

The Skydeck offers couples a private photo session on the Ledge as part of their wedding package.

Since 1974, the Skydeck has opened its doors to couples looking to elevate their date nights, and some have even chosen this venue for their rehearsal dinners, wedding ceremonies, and wedding receptions.

The 99th floor of the Willis Tower can accommodate private parties of 50 to 300 people, and it offers a distinctive location complete with a dance floor and professional photo shoot. You and your significant other can enjoy a panoramic view of Chicago as you enter the next chapter of your lives together. You can schedule an appointment online and start planning an extraordinary wedding.

“It was very easy working with the event planners,” said Amy F., who got married on the Willis Tower’s 99th floor. “The day could not have been more perfect, and the location played a huge role in that!”

You can always count on the Skydeck team to do everything they can to facilitate your romantic celebrations and surprises. They’ve admitted professional violinists up to the 103rd floor for a proposal. They’ve put romantic messages on their 60-character welcome board on the ground floor. They’ll do whatever it takes to help couples have that wow moment together.

“If someone has a romantic idea, we’re always open to it,” Randy said. “We tell people to challenge us and let us know what we can do to create a special moment.”

At the Skydeck, Enjoy an Experience You Won’t Soon Forget

Thousands of sightseers come and go from the Willis Tower every day and enjoy picture-perfect moments on the 103rd floor. The Skydeck provides a beautiful observation deck where couples can linger for hours, take crazy photos, and create special memories that will last a lifetime.

“I would make this your first attraction to see if you are planning to go sightseeing in Chicago. The tower has 103 floors with incredible 360-degree views.” — A TripAdvisor review of the Willis Tower

From first dates to wedding ceremonies, the Skydeck has hosted countless romantic moments for couples. If you want to feel on top of the world on your next date, you can make a reservation for breakfast, lunch, or dinner at the Skydeck and enjoy a private meal for two over a thousand feet in the air. Or you can visit the Willis Tower just before sunset and hold hands with your date as you inch out onto the Ledge to take in an awesome view of the city.

“People, especially couples, are looking for an experience,” Randy said. “And, I think, the more we can do to provide that experience and that emotion, the more people will want to share their romantic moments with us.”