2026 Compare Cities Cost of Living:
Winter Garden, FL vs Chicago, IL

Change Cities
Highlights
Is it cheaper to live in Chicago or is it cheaper to live in Winter Garden?
- Chicago is 0.3% less expensive than Winter Garden.

Which city has more affordable housing, Chicago or Winter Garden?
- Chicago housing costs are 26.1% less expensive than Winter Garden housing costs.

Is Health Care more affordable in Winter Garden or is Health Care more affordable in Chicago.
- Health related expenses are 14.9% less in Chicago.
 Winter Garden, FLChicago, ILUnited States
 Overall  Unlock105.7100
 Food & Groceries104.5  Unlock100
 Health  Unlock88.0100
 Housing135.1  Unlock100
 Median Home Cost  Unlock$284,100$338,100
 Utilities105  Unlock100
 Transportation  Unlock138.5100
 Miscellaneous107.0  Unlock100
100 = National Average (Below 100 means cheaper than the US average. Above 100 means more expensive.)
DID YOU KNOW?

In order to keep your same standard of living your salary can vary greatly - whether you buy or rent, require child care, or want to include taxes. This is why we are now offering a Premium Salary & Cost of Living Calculator.

Our Premium Calculator Includes:
- Compare Cities cost of living across 9 different categories
- Personal salary calculations can optionally include Home ownership or rental, Child care, and Taxes (with details on state and local sales, income, property and automobile taxes)
- Includes the cost of Child Care for toddlers or infants, at a day care center or home care
- Grocery prices, detailed for 29 staple items in six categories
- Difference in cost of Utilities, including electric, gas and fuel oil
- Health Care Premiums and hospital expenses for major surgeries
- Taxes, Fees and Expenses you should know about, such as local car insurance rates, automobile taxes and registration, commuting costs.
- and 100s of other items you should consider before you relocate

Upgrade to Premium | See Example

Reviews for Winter Garden    4 Reviews

Over 11 years ago

Great town  More

   |    Reply

Over 18 years ago

Winter Garden has a nice community feel although it's part of the metro Orlando area. The downtown area has several shops and restaurants with a bike trail that leads  More

   |    Reply

Central Florida's quality of life is rapidly deteriorating from what it once was. Growing crime, uncontrolled sprawl, nightmarish traffic, poor public transportation and  More

   |    Reply

Start Your Review of Winter Garden

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


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.