The good news is that travel for the Christmas holiday is spread out for a longer period of time as opposed to Thanksgiving where airports are jammed the day before and the Sunday after.
However, airlines are encouraging anyone who can to be flexible with their plans and try to get out earlier before the storm hits.
Hopes for hassle-free travel have been dashed at O'Hare as messy weather is already causing flight delays.
"We're attempting to head to Tulsa, Oklahoma. My flight has been delayed three times so far and now it looks like we are leaving on the last flight out, and most likely it's not going to get out," said Charlie Prendiville, air traveler.
When the weather system hits Chicago Wednesday, it will take the shape of sleet and freezing rain. Airlines are determined to get in front of the storm by accommodating passengers who want to get out of town sooner.
Passengers flying Southwest out of Midway can change their itineraries without being charged a fee. Delta and United are issuing travel waivers.
"We want to get our passengers out ahead of the storm to avoid some of the delays and the backlog that can occur when flights are cancelled and weather impacts operations at the airport," said Michael Trevino, United Airlines spokesperson.
Some travelers are avoiding airports all together like the Liberski family from Wisconsin. They are undertaking the 24-hour drive to Fort Myers, Florida.
Last year the Liberskis' flight to Florida took 27 hours.
"We were going to take a different flight that took us to New York, but then the connecting flight was gone and we had to stay overnight in J.F.K. Airport. Not a good experience," said Bruce Liberski, motorist.
If you want to try for an earlier flight, specifically if you are flying United, Delta or Southwest, log on to their web sites and make arrangements there.