I have done this several times, different routings. The only “penalty” I got then was that I was not awarded the corresponding mileage for the trips. These were pre-9–11 era. Since then, I have not had the opportunity to do this again.

Would you get your luggage back?

Nice catch, @Pi @Phi!

You would have to carry on your luggage. It would be nice if you let them know you won’t be tra elling farther so they can sell your seat.

You might want to check with the airline how they handle it. Make sure they don’t try to come after you for money if the shorter flight cost more. If they do I think it is horribly obnoxious.

@robmandu Ask before you check in and check your bags that you want to get off in Chicago and see if they can pull your baggage in Chicago instead of NY or if you have more than a carry on, put as much as you can in the carry on and UPS the rest to your destination in Chicago.

@JLeslie, roughly $700 just to ORD but only $250 if continue on to JFK.

@creative1 I think the ticket would have to be rebooked to check the luggage. The plane cannot take off from Chicago to NY if his luggage is in cargo and he is not on the plane.

@robmandu Yeah, that’s what I figured. Totally annoying bullshit, right?! Make a call to the airline, anonomously, just ask their policy.

I did this recently: I had a change of plans, so instead of going to city A, with a connection in B, I had to get from B to C. It cost less to buy a new one-way ticket (with another airline) than what it cost to change my original flight (at least $250, with American Airlines).

I was not awarded the miles for the connection I paid for but did not board. I only had carry-on, so luggage was not an issue, and it was also a one-way ticket, so there were no other connections/return flights they could cancel (which I’ve heard they can do).

There’s a chance that your name would briefly visit a watch list.

This is known as “Hidden City Booking”. Some airlines specifically prohibit this practice, and can result in penalties including cancelling the return trip of a round-trip booking or being booted from their frequent flier program. Other airlines (like Southwest, I know for one) specifically allow it and don’t have any problems with it.

You also run the risk that your original flight is cancelled or delayed, and they rebook you on another flight to your booked destination, but this newly booked flight doesn’t stop where you actually wanted to end your trip. They’re only responsible for getting you to your originally booked destination.

Here’s a copy of the relevant portion of Continental’s Contract of Carriage:

J) Prohibited Practices:
Fares apply for travel only between the points for which they are published. Tickets may not be purchased and used at fare(s) from an initial departure point on the Ticket which is before the Passenger’s actual point of origin of travel, or to a more distant point(s) than the Passenger’s actual destination being traveled even when the purchase and use of such Tickets would produce a lower fare. This practice is known as “Hidden Cities Ticketing” or “Point Beyond Ticketing” and is prohibited by CO.

K) CO’s Remedies for Violation(s) of Rules – Where a Ticket is purchased and used in violation of these rules or any fare rule (including Hidden Cities Ticketing, Point Beyond Ticketing, Throwaway Ticketing, or Back-to-Back Ticketing), CO has the right in its sole discretion to take all actions permitted by law, including but not limited to, the following:
* Invalidate the Ticket(s);
* Cancel any remaining portion of the Passenger’s itinerary;
* Confiscate any unused Flight Coupons;
* Refuse to board the Passenger and to carry the Passenger’s baggage, unless the difference between the fare paid and the fare for transportation used is collected prior to boarding;
* Assess the Passenger for the actual value of the Ticket which shall be the difference between the lowest fare applicable to the Passenger’s actual itinerary and the fare actually paid;
* Delete miles in the Passenger’s frequent flyer account (CO’s “OnePass” Program), revoke the Passenger’s Elite status, if any, in the OnePass Program, terminate the Passenger’s participation in the OnePass Program, or take any other action permitted by the OnePass Program Rules in CO’s “OnePass Member’s Guide;” and
* Take legal action with respect to the Passenger.

I have done this many times over the years. The rules on this have gotten tighter, but I have yet to be denied sale. If you know you are doing this, carry-on pack appropriately.
The loss of perks from an airlines is inconsequential to me. One can always determine a “valid” reply to an airlines if they question you on it.

In the past I used to purposely miss the flight at my layover city in order to spend time with friends or family in that layover location. You are at the airlines mercy now even when flying standby. This no longer play this lengthy layover game when I almost missed my business trip at the end of the last leg.