City comparison
Brookline, MA is about 850 miles (1,400 km) from Chicago, IL in a straight line. By road, the drive is roughly 1,100 miles, or about 18 hours behind the wheel at highway speeds.
Driving distance is a rough estimate (great-circle × 1.25); driving time assumes a 60 mph blended average. Real trips run 10–20% longer with stops.
A direct flight from Brookline, MA to Chicago, IL takes about 1 h 42 min, covering roughly 850 miles in a straight line. Connecting itineraries with a layover typically add 1–3 hours.
Block-to-block estimate at ~500 mph cruise, including taxi, climb, and descent — what an airline would publish, not pure airborne time.
Brookline, MA is on Eastern Time and Chicago, IL is on Central Time — a 1-hour difference. When it's noon in Brookline, it's 11 a.m. in Chicago, which puts Brookline 1 hours ahead.
Standard-time offsets. Daylight saving applies in both cities for most of the year (exceptions: Hawaii and most of Arizona), and the gap between the two stays the same.
Chicago has a population of 2,721,914, vs 62,698 in Brookline — about 43.4× larger by population. By land area, Chicago covers about 230 sq mi vs 6.8 sq mi for Brookline.
Population from US Census ACS. Land area from the Census Gazetteer (city proper, excluding inland water).
Cost indices by category, with the US city average (100) marked.
Index: 100 = US city average. Lower is more affordable.
Side-by-side costs, salaries, and sub-category indices.
| Metric | Brookline | Chicago | Difference |
|---|---|---|---|
| Median rent | $2,702/mo | $1,314/mo | 105.6% higher in Brookline |
| Median home value | $1,181,200 | $304,500 | 287.9% higher in Brookline |
| Median household income | $130,600 | $71,673 | 82.2% higher in Brookline |
| Groceries index | 99.8 | 106.4 | 6.6% higher in Chicago |
| Utilities index | 144.3 | 84.4 | 71.1% higher in Brookline |
| Transportation index | 102.9 | 100.3 | 2.6% higher in Brookline |
| Healthcare index | 103.7 | 100.2 | 3.5% higher in Brookline |
How much you'd need to earn in the other city to keep the same standard of living.
If you earn $100,000 in Brookline, you'd need $81,712 in Chicago to maintain your standard of living.
Climate, safety, and demographics side by side.
Chicago, IL is about 18.3% cheaper overall than Brookline, MA, based on our cost-of-living index. Housing costs are roughly 39% higher in Brookline than in Chicago. If you earn $80,000 in Brookline, you'd need about $65,370 in Chicago to keep the same standard of living.