Love your headshots or get your money back 
AI headshots in Chicago, from your phone
The Loop's trading firms, law and consulting offices and the city's large hospital systems keep Chicago's LinkedIn profiles busy. Get a professional headshot from your phone in about 15 minutes, no trip downtown in January.
- Free preview before you pay
- Ready in about 15 minutes
- Full refund within 7 days, no questions
- No subscription
What a studio headshot costs in Chicago
Local studio session, one person
$100–$750
From about $100 for a budget headshot (express options from $70) to $750 for an individual shoot; a 30-minute session with one retouched image is about $200.
Proud Look
from $25
Starter plan: 54 headshots in 4K, 9 styles and a commercial licence, made from your phone photos. Money back within 7 days if you don't love them.
Based on the published price lists of Chicago-area studios and photographers we checked in October 2026. Prices change and packages differ, so check with the studio.
When a local photographer is the better choice
- You want professional hair and makeup on the day.
- You need acting or modelling headshots for casting, which should be real, unaltered photos.
- You need an official photo: passport, ID, badge or military photo.
Headshots for Chicago's biggest industries
Trading and finance
Exchanges, trading firms and banks: a conservative suit headshot for the firm site and LinkedIn.
Headshots for accountants and finance professionals →Law and consulting
Large firms want matching bios; consultants need a photo for every proposal deck.
Lawyer headshots →Healthcare
Academic medical centers and hospital networks list every provider online.
Headshots for doctors and nurses →
Style tip for Chicago: Glass meeting room and Bright office backgrounds look right for Loop offices; a Charcoal suit or Black blazer keeps it formal.
En español: Chicago has one of the largest Mexican-American communities in the country, from Pilsen to Little Village. Order in Spanish whenever you like. Ver esta página en español
Real phone photos, real results
Each pair is one person's own phone photo next to a headshot we made from their upload, shown with their permission.
Selfie
Proud Look
Nina, 30sCustomer Selfie
Proud Look
Nohemy, 30sCustomer Selfie
Proud Look
Lise, 60+Compensated tester Selfie
Proud Look
Maria, 60+Compensated tester
See yourself first. Pay only if you like it.
- 1Upload 4–10 phone photosRecent photos of just you, taken on different days (6+ is best). No account needed.
- 2See your free previewWe make one headshot of you first. Pay only if you like it.
- 3Pick a plan from $25Full set in 4K in about 15 minutes. Refund within 7 days if you don't love them.
Money-back guarantee, no fine print
Not one headshot you'd use? Email us within 7 days for a full refund, even after you download. No questions, no form.
See my free previewPay only if you like it · from $25
Questions
Can I see a result before I pay?
Yes. After you upload your photos and pick your styles, we make one headshot of you for free (small, with a watermark) before you choose a plan. If you like it, your plan makes the full set in 4K without the watermark. If not, you pay nothing.
My phone photos are all from winter, indoors. Is that OK?
Yes. Indoor photos by a window work well. What matters is 4–10 recent photos of just you, taken on different days, with your face clearly visible.
Does it work in Evanston, Naperville and the rest of the Chicago area?
Yes. Proud Look is online, so it works the same anywhere in the area, including Evanston, Naperville, Schaumburg, Oak Park and Cicero: upload phone photos from home or work, and your headshots arrive by email.
Do you have a studio or office in Chicago?
No. Proud Look is an online service with no local studio or office. You upload phone photos from anywhere in Chicago, and download your headshots online.
How does the price compare with a Chicago studio?
Studio price lists we checked in Chicago in October 2026 came to about $100–$750, usually for a handful of retouched photos. Proud Look starts at $25 for 54 headshots in 4K, and you get your money back within 7 days if you don't love them.
Can I order in Spanish?
Yes. The whole flow, from upload to download, plus emails and support, is available in Spanish. Switch language at the bottom of any page.
Your new headshot is 15 minutes away
Free preview first · from $25 · full refund within 7 days