I would traveling from BOS to ORD for 2 consecutive weeks, leaving BOS on MOnday and coming back on Friday. I was thinking of buying a ticket from BOS-ORD R/T 2/21 returning on 3/4 and ORD-BOS R/T 2/25 returning on 2/28.

Is this doable if I buy tickets from the same airline ? Or should I use different airlines ?

I am doing this since, the price of two BOS-ORD R/Ts are coming out more expensive than the nested trips.

Thanks

From 1999-2002, I worked out of my home in NJ for a consulting firm near DFW. I did this every month, but I used separate airlines. I was fortunate; at the time, both Continental and AA had convenient flights between DFW and EWR.

I'll defer to others as to whether you could do this on the same airline without penalty, but one possible way to accomplish that would be to use FF numbers from 2 different airlines in the alliance for each trip.

A few years ago, I spent three months in NYC. I flew out on DL on at RT for the duration, and during my stay, made four or five trips back home, all on DL (used the same FF# on all tickets). I had no problems, but YMMV.

If you're going to it just once, the airline won't care. If you make a habit of it they may notice.

Book two separate carriers if possible - BOS-ORD should be easy.

It's technically a violation of the conditions of carriage (the contract between you and the airline).

You should change the second leg of your original Mon - 2nd Fri ticket to the 1st Friday and purchase a new Mon - Fri ticket for the second week.

If you do it regularly to take advantage of the lower fares, and they catch you, they can bill you for the difference. Buying the tickets at the same time is a bad idea as it shows intent.

If you do it very rarely and for demonstratable reasons, it's unlikely to cause problems. For example, I had a Tue - 2nd Thu purchased 12 weeks out. Last minute I had to return for the middle weekend to take a sick animal to the vet, so I flew home Friday's red-eye, vet Sat AM, crashed, flew back Sun PM. Other than asking if I was OK, nobody said anything (and the out-station is a smaller one, I'm well known there).