Best flights to Chicago

One of my best friends lives in Chicago now. I have been promising to come visit her, but life is hectic for her and ourselves. Figured Spring would be good bc it's way to cold in winter. Also, hard to take the kids out of school.
Any good times or advise bc it seems like the flights are always so expensive. When she comes to NJ/NY area it's for work so we'll try and meet up inbetween her meetings.

Best flights to Chicago

We always like to travel either the first flight of the day, around 6 am, or very late, like a flight that leaves between 10-11 pm. IME, the security lines, and the airport in general, are far less crowded at the very beginning and very end of the day. DH has been to Chicago several times for business. He always takes Jet Blue 905 from JFK to OHare. It is an early flight- I believe it leaves at around 6:15 AM. But he has never had a problem- he always makes sure his company books him on that flight.
Coming home he takes Flt 106. He lands at JFK at noon. The flight is 2.5 hours. I can't help with the pricing, as his company pays for the flights. However, from our experience when we book flights for family vacations, we get way better rates on sites such as Expedia, as opposed to going on the airline website directly.

Re: Best flights to Chicago

Stick with Jet Blue.
I took Delta to Chicago for work and it sucked.
The seats are insanely small. You have to pay to upgrade to "comfort select" to get a regular tight airline seat. Otherwise you are in a seat that is even tight for a child.
And the terminal at JFK if a nightmare. Its about a mile walk to the gates for Delta, no exaggeration.
I took a shuttle that drove us over the tarmac and had to stop for taxiing planes.
Mess
I hate Delta.

Re: Best flights to Chicago

We went for a day to visit a college. Flew out on an early flight southwest and back that night. We went from LAG. It was really reasonably priced