2025 Compare Cities Rankings:
Grayslake, IL vs Winter Park, FL

#4 Best Cities for Teleworking - Extra Large Metro Areas

#4 Wrinkle Ranking Cities Most at Risk for Skin Damage by 2040

#5 Best and Worst Cities for Sleep

#7 Sleep in the City Study

#7 Sperlings Skincare Wrinkle Ranking

#7 Second Annual “America’s Manliest Cities” Rankings

#7 Best Block Party Places

#8 America’s Least Manly Cities

#8 Most Energetic Cities

#8 Best and Worst Airports to make a Connection List

#9 Gloomiest Places in America

#9 America's Most (and Least) Stressful Cities (117 Smallest Metro Areas)

#10 Best Cities for Seniors 2005

#10 Best States for LGBTQ Rights

#13 Best Airports to Make a Connection

#13 Sleepless Cities 2011

#14 Best Baseball Cities

#14 Cities on the Edge of Greatness

#16 America's Most Playful Cities

#16 Stressful Cities 2012

#16 Most and Least Risky Places for Identity Theft

#17 Most Irritation Prone Cities

#19 America's Best Cities for a Healthy Retirement

#19 The Most Single Cities

#20 America's Top Hygge Cities

#21 America's Best and Worst Cities for Crime (Smallest Metro Areas)

#22 Most Romantic Cities for Boomers

#24 Americas Manliest Cites 2011

#25 Best US Cities for Seniors 2011

#26 America's Most (and Least) Stressful Cities (100 Largest Metro Areas)

#27 Most Competitive Private Colleges

#27 America’s Best (and Worst) Cities for Dating

#27 Most Comfortable Summer Cities

#29 Healthiest Cities

#29 Worst Cities for Respiratory Infections

#31 Best Cities for Board Gamers

#34 America's Best and Worst Cities for Crime (Large Metro Areas)

#35 Failure To Lunch

#35 America's Riskiest Online Cities

#36 Hypertension Hot Spots

#36 The Most (and Least) Gender Imbalanced Cities

#45 2005 High Gas Prices

#46 America’s Manliest Cities

#46 America’s Manliest Sports Cities

#49 Fiscally Fit Cities Report

#55 America’s Best (and Worst) Cities for Dating

#57 High Gas Prices - Which Cities are Hit the Hardest?

#77 Drought-Riskiest Cities

#82 Most Popular Cities for the Holidays

#90 America's Migraine Hot Spots

#155 2005 Best Places to Live

#192 Best Green Cities

#2 Failure To Lunch

#5 High Gas Prices - Which Cities are Hit the Hardest?

#5 Fiscally Fit Cities Report

#6 Stressful Cities 2012

#6 2005 High Gas Prices

#7 Sleepless Cities 2011

#8 Best Cities for Teleworking - Large Metro Areas

#9 America’s Manliest Sports Cities

#10 Sperlings Skincare Wrinkle Ranking

#11 Most Irritation Prone Cities

#14 America’s Manliest Cities

#15 Drought-Riskiest Cities

#15 Most Popular Cities for the Holidays

#15 Best Cities for Board Gamers

#15 America’s Least Manly Cities

#16 Second Annual “America’s Manliest Cities” Rankings

#18 Worst Cities for Respiratory Infections

#19 Most Romantic Cities for Boomers

#20 Most and Least Risky Places for Identity Theft

#21 America's Most (and Least) Stressful Cities (100 Largest Metro Areas)

#22 Best and Worst Airports to make a Connection List

#23 America’s Best (and Worst) Cities for Dating

#27 Best Block Party Places

#29 Hypertension Hot Spots

#30 Best Cities for Seniors 2005

#30 Americas Manliest Cites 2011

#31 Most Energetic Cities

#32 Wrinkle Ranking Cities Most at Risk for Skin Damage by 2040

#34 America's Most Playful Cities

#34 Best Airports to Make a Connection

#35 America's Best Cities for a Healthy Retirement

#36 The Most Single Cities

#37 Best and Worst Cities for Sleep

#38 Cities on the Edge of Greatness

#38 America's Top Hygge Cities

#40 Gloomiest Places in America

#44 Best Baseball Cities

#46 Healthiest Cities

#49 Metro Areas with Fastest Rising Income 2020

#76 America's Migraine Hot Spots

#96 Most Comfortable Summer Cities

#97 The Most (and Least) Gender Imbalanced Cities

#134 2005 Best Places to Live

#143 Best Green Cities

Property tax is one of the highest in the nation a $220000 home will cost you $10980 in taxes annually as of 9/2014 This information can be verified on the  More

Grayslake weather is very difficult to enjoy outdoor activities. In summer, it is SO humid and hot and full of mosquitos that you cannot enjoy a beautiful summer night.  More

3% of home value annually/ A $300,000 home will cost you 10K in annual property taxes. Where does it all  More

I think Winter Park is ideally suited for families and couples, and individuals. It is a beautiful part of Central Florida. There is almost no crime, and it is  More

I've lived in the city for 5 years and certainly, I ??it! Polite people, great schools, nice & very pacific oriented entertainment, family  More

near park  More