Chicago, IL
Send a real letter in Chicago.
Send a heartfelt real letter from your heart to a loved one in Chicago or send one from a Chicagoan to someone special elsewhere. Experience the warmth of a handwriting-style letter on paper.
Real letters, delivered across Chicago
SentInstantly mails your real letter to Lincoln Park (60625), River North (60611), Old Town (60610), Hyde Park (60637) or the Willis Tower in the Loop (60601).
Genuine, personal touch with handwriting-style script.
Delivery across Chicago.
Affordable: from $3 a letter, or $3 each in bulk ($2.50 at 10+, $2 at 50+).
Perfect for Chicagoans who value real connections.
Who sends in Chicago
Mail worth keeping.
Realtors’ Closing Notes
Realtors in Chicago can send closing notes to their clients with SentInstantly.
Wedding Thank-Yous
Chicago couples send their wedding thank-yous with SentInstantly to guests.
Small-Business Client Notes
Local small-business owners send personalized notes to clients with SentInstantly.
Questions
How fast is delivery to Chicago?
We print and mail your order after checkout; Certified and flat letters come with a tracking number to follow it. Delivery time depends on the carrier. Certified Mail isn’t overnight or Priority. It travels as USPS First-Class Mail with Certified tracking added, and usually arrives in about 5–7 business days. Need it faster? Choose a Certified letter sent Priority Mail.
What is the price for sending a letter from Chicago?
$3 for a letter folded and mailed USPS First-Class, $11 by Certified Mail with tracking, or from $15 flat in a rigid mailer with tracking, including paper and postage. Bulk mail merge is $3 a letter, $2.50 from 10 letters, or $2 from 50, folded and mailed USPS First-Class.
Can I send bulk letters to Chicago?
Yes. Bulk mail merge is $3 a letter, $2.50 from 10 letters, or $2 from 50, folded and mailed USPS First-Class.
Can I mail to any address in Chicago?
Absolutely, we deliver to any address in Chicago.
Does a person write the letters?
No. Every letter is printed on paper in a handwriting-style script, then mailed the way you choose: folded First-Class, Certified, or flat in a rigid mailer with a free tracking number.
Can I send a real letter from Chicago to another city?
Yes, SentInstantly sends real letters nationwide.
SentInstantly across Illinois
Write to someone today.
Say it on paper.
Write your letter from $3Postage included. Postcards from $2 · Letters $3 · Certified $11 · Flat & tracked from $15. Sales tax where it applies.