How to Send a Check with Wintrust Bank N.A. - Digital Banking
Learn how to easily send physical checks using Wintrust Bank N.A. - Digital Banking with Check Supply. Follow this simple step-by-step guide.
Wintrust Bank N.A. - Digital Banking
Trusted financial institution
Wintrust Bank N.A. - Digital Banking is supported by Check Supply, enabling you to send secure, convenient check mailing services directly from your mobile device.
Visit Wintrust Bank N.A. - Digital Banking WebsiteWintrust Bank N.A. - Digital Banking Bill Pay vs Check Supply
See how Check Supply compares to Wintrust Bank N.A. - Digital Banking's traditional bill pay system
Wintrust Financial Bill Pay allows customers to make one-time or recurring payments to businesses or individuals directly from their Wintrust checking accounts. The service supports electronic payments when the biller accepts them, with same-day or next-business-day processing for eligible payments. For recipients who cannot accept electronic payments, Wintrust mails a paper check on the customer's behalf. Electronic payments are typically debited on the scheduled payment date, while paper checks are debited when the recipient deposits the check. Wintrust provides features like eBills, payment reminders, and the ability to view payment history online. The service is available through Wintrust Online Banking and the Wintrust Mobile app, with no monthly service fees for most accounts.
Compared with Wintrust's built-in bill pay, Check Supply offers superior speed, visibility, and control for mailed checks. We process payments in one business day with same-day print-and-mail capability when queued by 3 PM ET (including Saturdays), provide granular status tracking (queued → printed → mailed), and clearly confirm when the check is deposited. Funds remain in your Wintrust account until the recipient deposits the check—we do not place pre-debit holds. The experience is a modern, simple flow similar to Cash App or Venmo for sending checks, and you can connect multiple bank accounts and choose which one to pay from. USPS transit times are not guaranteed by either service.
| Feature | Wintrust Financial Bill Pay | Check Supply |
|---|---|---|
| Physical checks | Yes — mails a check if the biller cannot accept electronic payments | Yes — we print & mail on your behalf |
| Average processing time | Electronic: same-day or next business day; Mailed check: schedule ≥5-7 business days | 1 business day; same-day print & mail if queued by 3 PM ET (Sat included) |
| When funds are withdrawn | Electronic: on the scheduled date; Check: when recipient deposits the check | Only when recipient deposits the check; no pre-debit holds |
| User experience | Traditional bill-pay interface inside Wintrust Online/Mobile Banking | Modern, simple flow (Cash App/Venmo-like) for sending checks |
| Account flexibility | Use accounts at Wintrust only | Connect multiple banks; choose which account to pay from |
| Delivery time (mail transit) | Typically 5–7 business days for mailed checks (not guaranteed) | Typically 1–5 business days (USPS not guaranteed) |
| Tracking | Basic scheduled/sent status; limited visibility for mailed checks | Granular: queued → printed → mailed + deposit confirmation |
Note: Values verified against general Wintrust bill pay practices and industry standards. USPS delivery not guaranteed.
Save money and time with Check Supply's superior features and pricing compared to Wintrust Bank N.A. - Digital Banking's bill pay system.
💡 Why Choose Check Supply?
No hidden fees, faster delivery, and a seamless mobile experience designed specifically for check mailing.
Step 1: Download Check Supply from the App Store
Download the Check Supply app from the Apple App Store.
Step 2: Enter the Payment Amount
Open the app and navigate to the Pay tab. Type in the amount you want to send and tap Mail My Check.
Step 3: Add Recipient's Details
Input the name and address of the person you wish to send the check to. You can also import this information from your iPhone's contact list for added convenience.
Step 4: Connect Your Wintrust Bank N.A. - Digital Banking Account
Connect your Wintrust Bank N.A. - Digital Banking account securely using Plaid. Your financial information is encrypted and stored only with Plaid; Check Supply never accesses or stores your sensitive data.
Step 5: Optional Memo or Note
Add a memo or note to be printed on the bottom left corner of the check. This step is optional. When you're ready, tap Pay.
Step 6: Review and Confirm
You'll see a confirmation page to review all the details. Confirm and pay for the service. If completed before 3 PM EST on a business day, your check will be printed and mailed the same day.
Step 7: Track Your Check
Under the Payments tab, you can track your checks. Most are delivered within 1-5 USPS business days, including Saturdays.
Conclusion
Sending a physical check with Wintrust Bank N.A. - Digital Banking has never been easier. With Check Supply, you handle everything from your iPhone—quickly, securely, and without any hassle. Download the app today and simplify your payments.
Wintrust Bank N.A. - Digital Banking
Trusted financial institution supported by Check Supply
Frequently Asked Questions
How does Wintrust Financial deliver bill payments?
Wintrust sends payments electronically when possible, with same-day or next-business-day processing. For recipients who cannot accept electronic payments, Wintrust mails a paper check on your behalf.
When does Wintrust Financial debit my account for Bill Pay?
For electronic payments, funds are withdrawn on the scheduled payment date. For paper checks, funds are withdrawn when the recipient deposits the check.
How does Check Supply reduce uncertainty compared with Wintrust bill pay?
Check Supply provides step-by-step tracking (queued → printed → mailed) and confirms when the check is deposited, eliminating guesswork about mail timing and delivery status.
Does Check Supply hold my money before delivery?
No. With Check Supply, funds stay in your account until your recipient deposits the check. We do not place pre-debit holds.
What if my payee cannot accept electronic payments?
Check Supply specializes in mailed checks with same-day processing if queued by 3 PM ET (Saturdays included) and provides granular status updates through deposit confirmation.
How fast will my payment arrive?
Wintrust electronic payments can be same-day or next business day. Wintrust-mailed checks typically require 5-7 business days. Check Supply processes in 1 business day with same-day print-and-mail cutoff at 3 PM ET; USPS transit times are not guaranteed.
Do I need to keep using Wintrust's bill pay if I use Check Supply?
No. You can use Check Supply independently to generate and mail checks from your Wintrust account while still seeing deposit confirmation.
Are there fees for Wintrust Bill Pay?
Wintrust Bill Pay is typically free for most checking accounts. Check Supply charges a transparent per-check fee for printing and mailing, with tracking included.
Routing Numbers
Send checks securely with Wintrust Bank N.A. - Digital Banking through the Check Supply mobile app