Millions were told to evacuate or shelter in place, and both airports in Orlando and Fort Myers stopped operations Wednesday morning. Tampa Bay closed its airport on Tuesday.
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"So last night I drove out ahead of the storm. I was in evacuation Zone A. So I don't know what's going on," said Mike Cauler, who fled from Tampa Bay. "I'm glad to be out of that. I have reached out to several people and most of the people I know have heeded the advice and gotten out. In my area, there wasn't anybody there."
Natalie Ruzgis' father, a former Chicagoan himself, refused to leave his condo high rise in Cape Coral, which has been clobbered by the storm all afternoon.
"Honestly the structure seems OK," she said. "It's everything that's beneath them. You can see the houses in that video - water is up to the garage. Restaurants are under water. It's wild to look at!"
Her mom, on the other hand, had no interest in riding out the storm in Sarasota.
"She decided to evacuate. My mom went across to the east coast of Florida where my sister lives in Boca. So she's safe. She has no idea what her house looks like. They tried their best to prepare," Ruzgis said.
Winds at 115 mph lashed areas around Fort Myers, Naples and Sarasota all afternoon. Now the storm is heading north and east toward Orlando, where Luis Martinez and his wife located from Chicago.
"This is our sixth hurricane," Martinez said. "We're a little bit more prepared and wiser this time around."
And that's how they know the torrential rain is only the beginning.
The passengers who deplaned from the last flights to land in Chicago this morning were thankful to escape in time.
"They had one more flight left at 7 a.m. so I hurried up and packed up," said Ariel Pryor, Chicagoan. "I went outside it was like pitch black dark. My ride took a long time because the streets were flooded but I made my flight like 30 to 45 minutes before."
Pat McGibbon left his home in Jacksonsville for a speaking engagement in Chicago. His wife and their dog are hoping to get out later this week. They have never experienced a hurricane.
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"I just moved there in July, so this is our first one, but she's got a car, and her and the dog will leave if it gets too tough, as long as they don't shut down the bridge," he said.
Another group was from Panama. They have meetings in the Midwest this week. Their flights out of Florida kept getting canceled, so they headed to Miami.
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"It was horrible. We didn't sleep at all. We woke up at 3 in the morning. There was a ton of wind and rain. We were supposed to leave Miami through Fort Lauderdale flight. That was canceled. At 3 a.m. I found out it was canceled. We went to the airport to find out what we can do -- found out I was able to get into this flight," said Gabriela Harrara, who traveled from Florida.
Phil Herr is from Indiana, and owns a home on Captiva Island. He's very concerned.
"Now they are saying a 16-foot storm surge. Our place is right on the ocean. I mean, it would be gone. It's on stilts, but, with 16 feet, everything would be gone," he said.
Chicagoans stranded in Florida as Hurricane Ian hits
By Wednesday morning it was too late to leave, and scrambling to higher ground was the only route to safety. That's what one couple vacationing from Yorkville did; they boarded up their house and evacuated to a friend that lives inland about 15 miles away in a no flood area.
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Some Chicagoans now find themselves bracing for the worst after recently moving to the Sunshine State.
"This is all new to us. I've lived in Chicago my whole life," said Patrick Trapp who recently moved from Naperville to Naples. "We bought a house here a week ago."
Patrick Trapp, who also lives near Naples, said he's lived through chaotic winds in Chicago, but nothing like what he's seen in the last few hours.
"I feel really bad for anyone, which is a lot of people, who don't have as structurally sound of a place as we have," he said. "I feel extremely fortunate that we feel relatively safe, even though this is a wicked storm."
"As of Sunday all the water was sold out up here," said Ken Cherry, who moved to Florida from Chicago Heights. "We're right next to North Tampa. All the water was sold out down there. People were in gas lines the other day I saw that."
He said he loaded up his bathtub Wednesday morning so that in the event he loses power he can flush the toilets and have drinking water.
"Just did everything I can and I got a lot of booze, as Chicago people tend to," he said.
In Des Plaines, Yasmin Clinton packed up all her Red Cross relief supplies.
"So you just pack for everything that you hope. That you might need for yourself," she said. "I also pack a first aid kit which I tend to leave at the shelter if I don't use it when I got. You just have to pack for the unknowns."
When the worst of Ian passes, she'll head somewhere in Florida where millions of people will be in need of whatever the Red Cross has to offer.
The Associated Press contributed to this report.