Side-by-side distribution
Boston
$151,000
median · per year, annualized USD
- Disclosing
- 68.7%
- Live roles
- 3,988
Chicago
$135,000
median · per year, annualized USD
- Disclosing
- 67.9%
- Live roles
- 4,537
Highest-paying jobs
Senior Manager, Search Marketing
Sr. Business Development Leader - S&T Market
Enterprise Account Executive
Co-Founder & CEO - AI Retail Planning Autopilot
Strategic Account Executive - Boston (Remote)
Senior Account Executive, Startups(NYC OR Boston)
Senior Account Executive, Start-ups (NYC OR Boston)
Research Engineer/Research Scientist, Pre-training
VP, Namer Strategic Sales
Head of GovTech Sales
Highest-paying jobs
Regional Health Market Leader - Great Lakes Region
Sales Leader, Quality Engineering Services
Account Manager
Outside Sales Representative
Co-Founder & CEO - AI Retail Planning Autopilot
Director / VP Sales
Senior Account Executive, Emerging Enterprise
Senior Account Executive, Emerging Enterprise
Strategic Account Executive - Chicago (Remote)
Licensed Mental Health Therapist- Illinois
Top companies hiring
| Company | Median | Roles |
|---|---|---|
Whoop
|
$163,750 | 140 |
Klaviyo
|
$177,000 | 109 |
Motional
|
$200,500 | 73 |
| AX Axon | $184,275 | 72 |
Anduril Industries
|
$193,000 | 64 |
InterSystems
|
$134,750 | 60 |
Datadog
|
$166,000 | 57 |
DIG INN Chefs-In-Training
|
$35,360 | 54 |
Top companies hiring
| Company | Median | Roles |
|---|---|---|
DoorDash USA
|
$130,200 | 107 |
Okta
|
$213,750 | 75 |
|
Braze
|
$140,000 | 69 |
| DR DRW | $177,500 | 57 |
IMC
|
$212,500 | 48 |
Insomniacookies
|
$35,412 | 42 |
Real Chemistry
|
$123,750 | 40 |
Optiver
|
$200,000 | 39 |
Highest-paying roles in Boston
| Role | Median | Roles |
|---|---|---|
| Software Engineer | $182,500 | 597 |
| DevOps | $172,500 | 125 |
| Data Scientist | $171,150 | 107 |
| UX Designer | $168,000 | 22 |
| Recruiter | $167,813 | 478 |
| Product Manager | $161,121 | 600 |
| Customer Success | $160,875 | 847 |
| Sales | $150,000 | 970 |
| Project Manager | $141,250 | 293 |
| Marketing Manager | $138,500 | 319 |
Highest-paying roles in Chicago
| Role | Median | Roles |
|---|---|---|
| Software Engineer | $170,000 | 377 |
| Data Scientist | $163,000 | 30 |
| DevOps | $160,000 | 97 |
| UX Designer | $158,750 | 20 |
| Customer Success | $145,000 | 793 |
| Product Manager | $142,500 | 609 |
| Financial Analyst | $141,250 | 200 |
| Sales | $136,000 | 1,119 |
| Recruiter | $132,900 | 410 |
| Marketing Manager | $129,000 | 425 |
Boston vs Chicago: which pays more?
The median for Boston is $151,000 per year (typically $107,500–$195,000), versus $135,000 for Chicago ($90,000–$180,000). That puts Boston about 12% ahead at the median.
Both figures are computed live from active listings on JobsRadar and normalized to annualized USD, so Boston and Chicago are compared on equal terms regardless of the currency each role was originally posted in. Only roles that publish a salary range feed the medians; numbers refresh every few hours as new roles post and older ones close, so this comparison reflects the market right now rather than a fixed survey. Use it as a directional benchmark when weighing one path against the other.