2025 Compare Cities Housing:
Chicago, IL vs Winter Park, CO

Change Cities
Highlights
- The median age of a home in Chicago is 55.7% older than the median age of a home in Winter Park.
 Chicago, ILWinter Park, COUnited States
 Median Home Age70  Unlock42
 Median Home Cost  Unlock$814,500$338,100
 Home Appr. Last 12 months10.1%  Unlock16.6%
 Home Appr. Last 5 yrs.  Unlock69.5%57.0%
 Home Appr. Last 10 yrs.66.0%  Unlock101.1%
 Property Tax Rate  Unlock$3.7$11.0
 Homes Owned40.5%  Unlock57.4%
 Housing Vacant  Unlock87.6%11.2%
 Homes Rented48.3%  Unlock31.4%
 space
 Avg Rent For Home Or Apartment
 Chicago, ILWinter Park, COUnited States
 Average Rent  Unlock$2,460$1,840
 Studio Apartment$1,190  Unlock$1,080
 1 Bedroom Home or Apartment  Unlock$1,790$1,180
 2 Bedroom Home or Apartment$1,480  Unlock$1,430
 3 Bedroom Home or Apartment  Unlock$2,490$1,860
 4 Bedroom Home or Apartment$2,230  Unlock$2,160
 space1
 Vacant Housing
 Chicago, ILWinter Park, COUnited States
 Vacant For Rent  Unlock7.2%1.9%
 Vacant Rented0.4%  Unlock0.4%
 Vacant For Sale  Unlock0.0%0.7%
 Vacant Sold0.3%  Unlock0.4%
 Vacant Vacation  Unlock79.4%3.6%
 Vacant Other5.9%  Unlock4.1%
 space2
 Owner-Occupied Housing Value
 Chicago, ILWinter Park, COUnited States
 Less Than $20,000  Unlock4.7%2.6%
 $20,000 to $39,9990.9%  Unlock2.4%
 $40,000 to $59,999  Unlock0.0%2.8%
 $60,000 to $79,9991.8%  Unlock3.9%
 $80,000 to $99,999  Unlock0.0%4.5%
 $100,000 to $149,9998.8%  Unlock11.3%
 $150,000 to $199,999  Unlock0.0%13.0%
 $200,000 to $299,99924.5%  Unlock20.1%
 $300,000 to $399,999  Unlock34.9%13.6%
 $400,000 to $499,9999.6%  Unlock8.3%
 $500,000 to $749,999  Unlock30.6%9.7%
 $750,000 to $999,9994.0%  Unlock3.9%
 $1,000,000 to $1,499,999  Unlock11.6%2.2%
 $1,500,000 to $1,999,9990.9%  Unlock0.8%
 $2,000,000 and over  Unlock0.0%1.1%
 space3
 Housing Units By Year Built
 Chicago, ILWinter Park, COUnited States
 2015 and Newer0.0%  Unlock0.2%
 2010 to 2014  Unlock27.4%13.6%
 2000 to 20098.0%  Unlock13.6%
 1990 to 1999  Unlock21.0%13.6%
 1980 to 19894.8%  Unlock13.2%
 1970 to 1979  Unlock21.4%14.8%
 1960 to 19695.1%  Unlock13.6%
 1950 to 1959  Unlock0.7%10.0%
 1940 to 19498.8%  Unlock4.7%
 1939 or Earlier  Unlock0.0%12.2%
Reviews for Chicago    270 Reviews

I've lived in Chicago city and later moved to suburbs when family size increased. Absolutely love this city. This is the cleanest and most beautiful among the major  More

   |    Reply

Chicago is probably the best value in a major city that you can find and my personal favorite city. It will become increasingly important as climate change makes the  More

   |    Reply

I've live on north side and south side, UIC medical center. Don't move here go to the north side. No good amenities, if you get bored with one there is no other choices.  More

   |    Reply

Start Your Review of Chicago

Reviews for Winter Park    3 Reviews

Over 2 years ago

The article states this place is affordable. That is either an ignorant statement or a lie. The place is 5 stars no doubt. So much to offer. But as a place to live,  More

   |    Reply

Over 15 years ago

It's  More

   |    Reply

Over 16 years ago

How can you bat an eye at the ability to go outside and play in the Mountains everyday of the year? In the winter you can ski, board, snowmobile, snowbike, snowshoe,  More

   |    Reply

Start Your Review of Winter Park


Premium Subscription
Includes Cost of Living compares for child care, utilities, transportation, health, taxes, housing for home owners vs renters, weather, insurance premiums and so much more.


The premier source for comprehensive city data for over 30 years.

© Best Places. All rights reserved.