Why Are There No Direct MDW - IAD Flight?
 

My next project will be in western VA and IAD is a lot closer to fly into than DCA or BWI. However, there are no direct flights between MDW and IAD, so I would have to connect through ATL which is a 7 hour flight. I will have to fly UA from ORD instead and I am not looking forward to that.
Is there are chance that WN will introduces the flight from MDW to IAD any time soon? Did that flight exist in the past?

Southwest runs a pretty small operation at IAD. I believe only 3 gates and about 8 daily flights (On weekdays, 3x to ATL. 1x to FLL, 1x to MCO, and 3x to DEN - and less service on weekends).

To my knowledge, this flight didn't exist in the past.(edit: as per others' comments below, these flights did exist pre-DCA service) The WN schedule is set through Aug 6 2018, so even if WN introduced that flight, it wouldn't be until after that. My guess is that it's unlikely though, given the large WN presence at BWI and at DCA. My guess is also that the demand for IAD-Chicago traffic is filled by United's flights to ORD and given the limited number of slots, WN doesn't think it'd be profitable. It does look like there's a lot of capacity across different airlines between the DC/Chicago area airports - just not between MDW-IAD. Unfortunately there are limits to the numbers of gates and planes WN has access to. (A similar thing happens out here in California, for example - flying out of OAK you can go to any Southern California airport on WN, but out of SFO the Southern California airport options are a little more limited).

Pre DCA they had a few flights per day between MDW and IAD. However, MDW-Washington service was shifted from IAD to DCA after they acquired enough DCA slots to make it viable.

Yes, it did. I think we had 3 or 4 MDW-IAD non-stops a day. I assume they were dropped sometime in the last 18 months since I retired...

Yup - I flew MDW-IAD-MDW trips several times - IAD gates were right by the BA lounge for which Priority Pass afforded access...it was convenient. But, once WN got the DCA slots, the frequency dropped.

When Dulles service was originally announced and inaugurated back in 2006, WN flew MDW-IAD 7x per day. Service diminished over time and then shifted entirely over to DCA upon WN’s entry over there. Used to fly the MDW-IAD route quite a bit and miss it. It beat going to the only DC alternative at the time, BWI.

https://www.swamedia.com/releases/re...st-Destination

Your only other bet, and maybe not much better, is to build a custom connection through MCO. Not sure of your dates, but looking in early March and you can depart MDW at 5:35am and get to IAD at 12:30pm thru MCO. A little over 4.5 hours of flying time plus the 1 hour layover in MCO. Just beware of the usual caveats of a custom connection (combined fare maybe higher/lower, no protection for IRROPs, checked baggage potentially not making it all the way). Obviously, going N/S out of ORD on UA makes the most sense but this may be an option if you must go out of MDW and/or use WN.

Wow! I didn't know you're retired from WN. We have no idea! Hope you enjoy for your retirement.

If Midway is your more convenient Chicago airport, then WN to DCA is going to be by far your best bet. Worst case - your office is right by IAD - DCA is really only 45 minutes or so worse than IAD, so no connecting flight is ever going to be worth your time.

Some would argue that DCA isn't even 45 minutes worse, given that it's much easier to rent a car and easier to get in, out, and through the airport in general. I spent years commuting in/out of DCA, sometimes renting a car, sometimes using taxis or Metro, and even a year or so parking my own car. It was always easier than IAD.

Since OP's "next project will be in western VA," the 45-minute argument in DCA's favor doesn't apply.

AirTran's DCA slots were critical to WN's acquisition. Five years earlier, WN launched IAD:

The simple answer is that WN can't generate the PRASM serving both IAD and DCA and so it serves the one with the higher PRASM. That is generally DCA for O&D traffic. Not to suggest that there is not a market to the Dulles corridor, simply that it's not the same. So, I would not look to see IAD service restored.

However, OP says "Western Virginia." Thet can mean many things. Is it possible that RIC is closer? Any other airport? Why not provide the name of the specific destination and the advice could be narrowed down.

I'm just saying that DCA is, at worst, a 45-minutes-worse option than a nonstop to Dulles would be. Doesn't matter where the office is. It's not bad enough, even if you land at evening rush hour, to warrant a connection in Atlanta or Orlando.

Plus, MDW-DCA is probably my favorite way to fly CHI-WAS. Those are the two easiest-to-deal-with airports for O&D. I'd have to already be high-tier status on UA (which I'm not) to want to deal with ORD-IAD on a regular basis.

The return is not as laid back. Making a 9:30 am flight ex-Winchester I'd never count on 45-minutes from Dulles to Crystal City. But I yield to your experience. It's 3:39 MDW-DTW-IAD, but only RJs do it :(

How’s that Metro to IAD coming along?