2025 Compare Cities Rankings:
Highland Park, IL vs Cheshire, CT

#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 Sperlings Skincare Wrinkle Ranking

#7 Sleep in the City Study

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

#7 Best Block Party Places

#8 Best and Worst Airports to make a Connection List

#8 Most Energetic Cities

#8 America’s Least Manly Cities

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

#9 Gloomiest Places in America

#10 Best States for LGBTQ Rights

#10 Best Cities for Seniors 2005

#13 Best Airports to Make a Connection

#13 Sleepless Cities 2011

#14 Best Baseball Cities

#14 Cities on the Edge of Greatness

#16 Stressful Cities 2012

#16 America's Most Playful Cities

#16 Most and Least Risky Places for Identity Theft

#17 Most Irritation Prone Cities

#19 The Most Single Cities

#19 America's Best Cities for a Healthy Retirement

#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 Comfortable Summer Cities

#27 Most Competitive Private Colleges

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

#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 America's Riskiest Online Cities

#35 Failure To Lunch

#36 The Most (and Least) Gender Imbalanced Cities

#36 Hypertension Hot Spots

#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 Most Competitive Private Colleges

#6 Best Cities for Teleworking - Medium Metro Areas

#17 Fiscally Fit Cities Report

#17 2005 High Gas Prices

#20 Most Secure Places to Live in the U.S. (Large Metro Areas)

#20 The Most Single Cities

#22 The Most (and Least) Gender Imbalanced Cities

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

#31 Most Comfortable Summer Cities

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

#48 America's Best and Worst Cities for Crime (Mid-Size Metro Areas)

#62 Drought-Riskiest Cities

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

#109 America's Migraine Hot Spots

#149 2005 Best Places to Live

#207 Best Green Cities

#312 2005 Best Places to Live

You can sail on Lake Michigan, and your culture differences are welcomed. look up "North Shore Yacht Club" for sailing and kayaking  More

Highland Park (and the village of Highwood, which it surrounds) is a great place to live, offering a unique combination of benefits. First, it is on the shore of Lake  More

A wonderful place to rasie a family, but quite expensive. Great schools, but the "wealth culture" of this tony Chicago suburb causes a lot of anxiety among the kids.   More

Overall excellent town for raising kids. When comparing towns look at the numbers, they take out any biases. You get the most for your family in  More

I love Cheshire because the people there are friendly,mind their own business and the town is so pretty! I live in Meriden and I go to Cheshire often just to relax.  More