Hi, can regular fliers between nyc and Chicago give me an opinion on which airlines offer best experience and which airports you prefer. Thanks.

If you're flying non-stop, it really doesn't matter which airport you fly to. Midway is a little closer to downtown, but both are easily accessible by public transportation (if that's your plan -- the El is the best way to get from either airport to downtown IMHO, because traffic in Chicago can be awful). O'Hare is huge, so it's a difficult airport to change planes at, but again, you'll be flying non-stop and that's your end point, so that's not an issue.

Thanks, are there any airlines that are better for this route?
Thanks.

Jetblue is my airline of choice, and leaves from JFK (subway or LIRR to Airtrain is cheap and reliable) to ORD (train to Loop is cheap and reliable). Also, more legroom than other carriers.

The cab ride from LaGuardia is cheaper and shorter than JFK.

Avoid American at all costs - there service people were trained by the Spanish Inquisiiton.

I recently flew Jet Blue for the first time and loved the extra room (I'm 5'9" and have long legs and if I'm stuck in coach can;t bear the person in front leaning back on my knees the whole flight.)

For a 2-hour flight, it really does not matter which airline you choose. However, I would definitely fly into LGA over JFK.

Wouldn't choose anything other than SWA to MDW. Best prices and services. MDW is much easier to manage as well.

I used to do that a couple of times a month not long ago, and my suggestion is do it on price. Both airports are convenient if you are going downtown by public transit.

I'd also have to agree that flying JetBlue is the best airline out there these days. More comfortable, more room and TVs available at each seat.

Have fun.