Question 1

Is Chicago or Portland cheaper to live in?

Accepted Answer

Chicago, IL is cheaper. Estimated essentials for a single person run about $148/month less than in Portland, covering rent plus everyday costs. Typical rent is $1,781/mo in Chicago versus $1,922/mo in Portland.

Question 2

What salary do you need in Chicago vs Portland?

Accepted Answer

Living comfortably takes roughly $81,000/year before tax in Chicago, IL and $89,000/year in Portland, OR — a difference of about $8,000. Both figures are after state and local income taxes are accounted for.

Question 3

Is Chicago or Portland cheaper for a family?

Accepted Answer

Chicago, the same answer as for a single person. Two adults with a pre-schooler and a school-age child run about $9,545/month in Chicago and $10,916/month in Portland, including county-median childcare.

Question 4

Should I move to Chicago or Portland?

Accepted Answer

It depends on what you weight. Chicago costs less month to month, but cost is one of six factors — jobs, safety, climate, housing and amenities all differ too. Compare them against your own income and priorities rather than a single ranking.

Metric	Chicago61	Portland59
Est. monthly cost (single)	$4,293	$4,441
Est. monthly cost (family of 4, incl. childcare)	$9,545	$10,916
Salary for comfort	$81,000/yr	$89,000/yr
Typical rent	$1,781	$1,922
Median home value	$315,200	$557,600
Median household income	$75,134	$88,792
Unemployment	5.9%	5.2%
Housing score	52	36
Jobs score	7	30
Safety score	66	53
Climate score	89	93
Amenities score	73	79
Population	2.7M	642.7K
Summer high / winter low	85° / 21°	81° / 36°

Chicago, IL vs Portland, OR