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I haven't traveled SW before. Traveling from Denver to Nashville in September, I'll be in a wheel chair (which I surely hope will be available at the curb; I see no way to request one before arriving at the airport). Myadult granddaughter and her husband will be with me. Can I be reasonably sure that I can arrange boarding in the first group so we can sit together? Three seats together may be unrealistic, but I will need her help when we change planes in Dallas.
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There is a place online when making the reservation to indicate that you are disabled and whether or not you need wheelchair service in the terminals upon departing and arriving. I am often put into a wheelchair right at the curb by the skycaps.
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I have arranged for one for my parents using Twitter. You can send a message to @SouthwestAir - don't include your name or confirmation number, they will ask you for a direct message where you can include that information.
The time I did this was Denver to MDW, although I believe they got the wheelchair at the ticket counter and not curbside so I'm not 100% sure how that would work, but it should be possible.