Apple Watch tap to pay not working with transit debit card in Chicago

For weeks, I’ve been paying for transit in NYC with a pre-tax debit card using Apple Watch and tap to pay.

I am in Chicago currently. For some reason, this tap to pay using Watch doesn’t work. Tap to pay on Watch does work with another card, so the problem is not the watch. Chicago transit is an eligible expense as I’ve used my phone previously. The problem now is that I don’t have the transit debit card in my iPhone wallet, since I wanted only the Watch to have the express transit setting.

Has anyone else experienced something like this? Any suggestions? Unfortunately, the physical card is at home so I can’t remove and then reload the card into Wallet.

Posted on Oct 30, 2026 6:19 AM

8 replies

RKNYC Author

Level 1 (102 points)

Oct 30, 2026 3:38 PM in response to RKNYC

I have a new data point. I just tapped in manually by double pressing the side button on the Watch and it worked! So it’s only the express tap to pay that doesn’t work with this debit card on my watch for some reason.

Chattanoogan

Level 8 (43,489 points)

Oct 30, 2026 10:20 AM in response to RKNYC

See if anything in this article might help:

https://www.ventrachicago.com/mobile/applepay-faq/

FWIW, I’ve never had issues in Chicago w/ my Ventra Card + iPhone Wallet. (Ack’d that this isn’t your configuration)

… and as Jeff has already pointed out, Metra (commuter rail) requires using the Metra app.

Jeff Donald

Level 9 (64,078 points)

Oct 30, 2026 12:12 PM in response to RKNYC

That eliminates hardware issues. I’d contact Ventra support and see if they’ve had any other reports of issues. I’m sure you’re not the first experiencing issues. Good luck.

Jeff Donald

Level 9 (64,078 points)

Oct 30, 2026 8:56 AM in response to RKNYC

You are using the Ventra card, correct?

RKNYC Author

Level 1 (102 points)

Oct 30, 2026 9:55 AM in response to Jeff Donald

No, you can pay per ride with a device without the Ventra card. It worked last month when the card was in my iPhone wallet. Now it's in my Watch wallet only.

Jeff Donald

Level 9 (64,078 points)

Oct 30, 2026 10:06 AM in response to RKNYC

There may have been changes by either or both parties. I also see that Ventra is not accepted for Metra trains.

Is it working with a credit card?

RKNYC Author

Level 1 (102 points)

Oct 30, 2026 11:23 AM in response to Jeff Donald

Yes, it works with a normal credit card.

Chattanoogan

Level 8 (43,489 points)

Oct 30, 2026 3:42 PM in response to RKNYC

Interesting …

If the behavior you’ve encountered isn’t intentional, glad you’ve at least found a workaround.

Thanks for the follow-up.

Originally posted at discussions.apple.com/thread/256385891