01 · the cities
Bridgeport
Bridgeport is the largest city in Connecticut, sitting on Long Island Sound with a working harbor and a real waterfront. P.T. Barnum lived here and the city's museum still pays tribute to his weird genius. It's a quick train ride to New York, with much cheaper housing and proper New England summers. The food scene punches above its weight, with old-school Portuguese and Brazilian spots packed every weekend.
full dispatch→Chicago
Chicago is deep-dish for tourists, thin-crust tavern style for locals, and a hot dog that absolutely will not have ketchup on it. The L rumbles overhead, the lakefront stretches for 18 unbroken miles of beach and trail, and the architecture boat tour is the single best $50 you'll spend. Summer in Chicago might be the best summer in America. The improv comedy gene pool is unmatched.
full dispatch→02 · the money
Median rent
Median rent
$2,767/mo
$2,170/mo
$597/mo less than Bridgeport (28%)
Median home price
Median home price
$768k
$365k
$403k less than Bridgeport
State income tax
State income tax
5.5%
5.0%
Gross left after rent
Gross left after rent
$5,108/mo
$5,751/mo
Chicago has $643/mo more gross after rent at $100k
Gross left after rent reflects state income tax but not federal, based on $100k salary. Enter your salary to find your ideal city.
03 · the weather
Pleasant days/yr
Pleasant days/yr
172 days
153 days
19 fewer than Bridgeport
Extreme heat days
Extreme heat days
0 days
1 days
days above 95°F per year
Extreme cold days
Extreme cold days
15 days
38 days
days below 20°F per year
Chicago drops below 20°F on 23 more days per year than Bridgeport.
04 · the life
OutdoorScore
OutdoorScore
64 / 100
70 / 100
6.0 pts ahead of Bridgeport
Nonstop flights
Nonstop flights
1 routes
217 routes
216 more direct routes than Bridgeport
Metro size
Metro size
952k metro
9.3M metro
Bridgeport has 185.0x fewer events per month than Chicago.
the verdict
2
Bridgeport
categories won
6
Chicago
categories won
Chicago wins on money and lifestyle. Bridgeport has the edge on weather.
run your numbers
How far does your Bridgeport salary go?
Enter your salary to see a full ranked list of cities where you would live better.
see your top citiesWe use a proprietary blend of data from the US Census, Zillow, Ticketmaster, and more.
Walk Score® is a trademark of Walk Score, a Redfin company. How Walk Score works