The couples won the second annual "Love on the Edge" contest ahead of Valentine's Day for the rare opportunity.
"I feel like I'm on top of the world," said newly married Lara Robinson.
Her husband added: "Very surreal, it feels like a dream."
Each couple submitted video entries that showed why they should win a wedding atop Chicago's most iconic landmark.
For groom David Castillo, wedding jitters were turned up because he is also afraid of heights.
"I made the mistake of looking down when I first stepped out," Castillo said.
At 103 floors up, Castillo said he was comforted by the sight of his lovely bride.
Kathy and Denis Kendall renewed their vows to celebrate 26 years of marriage.
"We didn't have a big wedding, we just got married in the courthouse 26 years ago. I saw this opportunity and it was just beautiful," Kathy Kendall said.
Red roses decorated the white runner for the couples' private ceremony for close family and friends.
"It's like a storybook wedding it's a dream come true," said bride Jennifer Canales. null