I am going to be commuting mon-fri from new york city to chicago. Any recommendations on how to find the cheapest flights?

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If it's less expensive to stay over a weekend (not sure that is the case that often now on that route) consider getting a ticket on one airline for monday from NY to Chicago with the return the second Friday after, and another on another airline for chicago to NY on the Friday and Monday in between.

Mike,

Thanks for the tips. With regards to booking flights over the weekend, why is it necessary to book with different airlines? I had planned on trying to stick to one airline as that would be the best way to reach frequent flyer status.

He was saying that if you want to go home on the weekends and if there are significantly cheaper tickets for trips that include Saturday night stays, you can buy staggered tickets that allow you to go home each weekend, but get fares with Saturday night stays.

I don't see why you couldn't still do this with the same airline.

Example.

Making up dates

Book a trip from New York to Chicago on Airline ABC

Monday Feb 18 fly New York to Chicago on ABC
Friday Feb 29 fly Chicago to New York on ABC

That includes a Saturday night stay

Book Chicago to New York on Airline XYZ
Friday Feb 22 fly Chicago to New York on XYZ
Monday Feb 25 fly New York to Chicago on XYZ

Then you will use them this way

On the 18th fly out on the first half of the Airline ABC Ticket
and return on the 22nd with the first half of the XYZ ticket

On Monday the 25th fly out with the second half of the XYZ ticket, and return on Friday the 29th on the second half of the ABC ticket

You need to use two separate airlines, as you are combining tickets to not have to meet the saturday night stay requirement, and the airlines contract of carriage prevents you from doing that. You have to use up your tickets before using part of a next one to keep you from doing this.

I don't know the bump probabilities on that route (for some reason I hardly ever fly it during heavy times anymore), but that's another way to keep the costs down overall, if you can predict the good chance of getting a bump flight, and use the vouchers for a later trip. When I was getting bumped a lot on that route, there were always later flights that evening to get me home (Boston at the time), so it was like being paid cash, and it was cash at the time and a free ticket) to sit in a lounge for a couple hours.

Thanks, Mike. A cursury look at flighs seems to show no decrease in price for booking over a saturday. I'll keep looking around.

Your 2 main choices here are UA and AA - look at the stickies at the top of each forum to get an idea of what benefits each program has and then go for the one best suited to your needs.

I strongly suggest you pick 1 and stick to it AND that you consider throwing in a few w/e mileage runs to get you to top tier (1K on UA/Exp on AA) as this commute will easily bring you to mid-tier, but only tantalizingly close to top tier unless you throw in some addtional flying.

Be warned that you are picking a particularly problem prone city pair - snow in winter (eg today) and both cities prone to thunder/lightening in the summer.

Happy flying!

Sorry for being misleading before and thinking you could do the overlapping ticket strategy with the same carrier. I would think it would still be possible (if cost-effective, also) to book on two carriers in the same alliance, like United one week and US Airways the next, if you credited the miles to the same program.

Many airlines now got rid of Saturday requirement so this might not be needed

Another way I've done it in the past is to buy a one-way ticket for the first Monday from NYC, then buy Friday-Monday roundtrip tix ORD-NYC-ORD, then buy either a one-way (or a roundtrip and throw away the return) for the last Friday.

actually there was something online last week or 2 weeks ago that some had brought them back...but can be avoided with a 3day trip or more

This is exactly what I was encouraged to do when I was consulting (back and forth between ORD and NYC, actually), but I found that it wasn't any cheaper to book tickets like this vs. without the Saturday night stay (as the OP himself has discovered).

Book as early as possible, and make sure you consider EWR as a start-/ end-point, unless it is ridiculously inconvenient to get there, as oftentimes the ORD-EWR tickets were a little cheaper than ORD-LGA.

As other posters have indicated, stick with one airline. UA flies direct from EWR and LGA, CO from EWR, Jetblue from JFK, and AA from all three NYC airports. Since that route gets impacted a lot by weather, being at least in a mid tier status becomes important. Can't tell you the number of times I have seen paxs sleeping on the floors at ORD trying to get out after a snow or thunderstorm.

With Jetblue on that route, fares have actually become fairly competitive.

Note that of course the frequency on ORD-LGA is hourly or better whereas ORD-EWR is only every 2-3 hours so the capacity and ability to make changes is a bit more restricted.

Sorry for the naive questions, but what is the significance of mid tier status with regards to weather problems. Does it give you leverage getting on later flights?