Cost of Living Comparison Between Windsor, CT and Chicago, IL Cost of Living Comparison Between Windsor, CT and Chicago, IL

Monthly Cost of Living

A single person spends $3,170 per month in Windsor, CT vs $3,077 in Chicago, IL, rent included.

A couple spends around $4,429 per month in Windsor, CT vs $4,628 in Chicago, IL, rent included.

A family of three spends $5,689 per month in Windsor, CT vs $6,179 in Chicago, IL, rent included.

Windsor, CT costs about 3% more than Chicago, IL, driven mainly by Clothing & Footwear.

Both Windsor, CT and Chicago, IL sit above the global median – Windsor, CT by 137%, Chicago, IL by 130%.

Meal at Budget Restaurant

$25.45 $25.45

$20.91 $20.91

21.71%

Three-Course Dinner for Two, Mid-Range

$98.2 $98.2

$98.1 $98.1

0.05%

Fast Food Meal (McDonalds, etc)

$13.54 $13.54

$11.86 $11.86

14.17%

Cappuccino

$4.61 $4.61

$5.60 $5.60

-17.68%

Coke/Pepsi/Fanta/Sprite (0.33 liter bottle)

$2.72 $2.72

$3.07 $3.07

-11.40%

Water (0.33 liter bottle)

$2.17 $2.17

$2.47 $2.47

-12.15%

Local Beer (0.5 liter draught)

$5.87 $5.87

$7.14 $7.14

-17.79%

Imported Beer (0.33 liter bottle)

$7.70 $7.70

$8.08 $8.08

-4.70%

Milk (1 liter)

$1.40 $1.40

$1.05 $1.05

33.33%

White Bread (500g)

$4.51 $4.51

$4.11 $4.11

9.73%

Rice (white) (1kg)

$5.48 $5.48

$5.61 $5.61

-2.32%

Eggs

$6.61 $6.61

$4.51 $4.51

46.56%

Local Cheese (1kg)

$21.33 $21.33

$14.27 $14.27

49.47%

Chicken Fillets (1kg)

$13.30 $13.30

$14.89 $14.89

-10.68%

Beef Round Steak (1kg)

$20.04 $20.04

$19.19 $19.19

4.43%

Apples (1kg)

$6.92 $6.92

$5.14 $5.14

34.63%

Banana (1kg)

$2.21 $2.21

$1.77 $1.77

24.86%

Oranges (1kg)

$5.48 $5.48

$4.39 $4.39

24.83%

Tomato (1kg)

$5.98 $5.98

$4.56 $4.56

31.14%

Potato (1kg)

$2.24 $2.24

$2.54 $2.54

-11.81%

Onion (1kg)

$2.23 $2.23

$2.75 $2.75

-18.91%

Lettuce (1 head)

$2.37 $2.37

$2.42 $2.42

-2.07%

Water (1.5 liter bottle)

$2.12 $2.12

$2.62 $2.62

-19.08%

Cigarettes 20 Pack (Marlboro, Camel)

$13.78 $13.78

$14.92 $14.92

-7.64%

Wine (Bottle)

$15.05 $15.05

$14.80 $14.80

1.69%

Local Beer (0.5 liter bottle)

$2.11 $2.11

$2.46 $2.46

-14.23%

Imported Beer (0.33 liter bottle)

$2.47 $2.47

$3.73 $3.73

-33.78%

One-way Ticket (Public Transport)

$1.98 $1.98

$2.48 $2.48

-20.16%

Public Transport Monthly Pass (Regular Price)

$102 $102

$75.4 $75.4

35.08%

Taxi Start (Normal Tariff)

$3.88 $3.88

$3.18 $3.18

22.01%

Taxi (Normal Tariff) (1km)

$2.15 $2.15

$1.42 $1.42

51.41%

Taxi 1hour Waiting (Normal Tariff)

$20.37 $20.37

$24.94 $24.94

-18.32%

Gasoline (1 liter)

$0.88 $0.88

$1.06 $1.06

-16.98%

Midsize Hatchback 1.4l (Volkswagen Golf, Toyota Prius, Honda Civic, etc)

$29.3K $29.3K

$31.9K $31.9K

-8.32%

Compact Sedan 1.6l (Toyota Corolla, Mazda3, Kia K4, Hyundai Elantra, etc)

$26.4K $26.4K

$26.0K $26.0K

1.22%

Utilities for 2 People in 2-bedroom Apartment (Heating, Electricity, Gas, Water, Garbage) (85m2)

$223 $223

$185 $185

20.81%

SIM Card Monthly Plan (Calls and 10GB+ Data)

$72.3 $72.3

$61.7 $61.7

17.17%

Internet (50+ Mbps, Unlimited Data)

$70.1 $70.1

$66.9 $66.9

4.68%

Gym Membership (Monthly)

$42.90 $42.90

$75.2 $75.2

-42.93%

Tennis Court (1 Hour on Weekend)

$20.06 $20.06

$13.08 $13.08

53.36%

Cinema Ticket

$14.97 $14.97

$14.71 $14.71

1.77%

Preschool or Kindergarten, Full Day, Private, 1 Child (Monthly)

$1,269 $1,269

$2,020 $2,020

-37.17%

International Primary School, 1 Child (Yearly)

$33.4K $33.4K

$39.4K $39.4K

-15.11%

Jeans (Levis 501 Or Similar)

$63.7 $63.7

$64.6 $64.6

-1.47%

Summer Dress (H&M, Zara, etc)

$37.73 $37.73

$52.5 $52.5

-28.06%

Sport Shoes (Adidas, Nike)

$65.5 $65.5

$97.8 $97.8

-33.04%

Men's Leather Business Shoes

$101 $101

$148 $148

-31.44%

1-bedroom Apartment, City Center (Monthly)

$2,027 $2,027

$2,313 $2,313

-12.34%

1-bedroom Apartment, Outside City Center (Monthly)

$1,599 $1,599

$1,590 $1,590

0.58%

3-bedroom Apartment, City Center (Monthly)

$2,651 $2,651

$4,608 $4,608

-42.47%

3-bedroom Apartment, Outside City Center (Monthly)

$2,226 $2,226

$2,779 $2,779

-19.89%

Buy Apartment in City Center (m2)

$2,813 $2,813

$3,922 $3,922

-28.26%

Buy Apartment Outside City Center (m2)

$2,051 $2,051

$2,613 $2,613

-21.51%

Average Monthly Net Salary (After Tax)

$5,749 $5,749

$5,217 $5,217

10.20%

20-Year Fixed Mortgage Interest Rate (Annual %)

6.38

6.6

-3.33%

CityCost data is based on AI and user input – minor inaccuracies may occur.

Last update for Windsor, CT: May 31, 2026

Last update for Chicago, IL: May 30, 2026

Cost Breakdown

A central one-bedroom costs $2,027 in Windsor, CT versus $2,313 in Chicago, IL. Rent is usually the largest line item in a monthly budget, so the gap here sets the tone for the overall comparison.

Salaries run about 10% higher in Windsor, CT, which partly offsets the higher cost of living there. Purchasing power depends on which expenses matter most to you.

A mid-range dinner for two costs $98.0 in Windsor, CT versus $98.0 in Chicago, IL. Groceries tell a different story – $489 in Windsor, CT vs $447 in Chicago, IL – so Chicago, IL wins on supermarket bills even if dining out costs more.

City Median Internet Speeds Comparison (Updated April 2026)

The chart highlights the Precision Threshold for mobile and fixed broadband internet speeds, updated quarterly.

Digital Nomad Cost of Living Index

Windsor, CT vs Chicago, IL: Cost of Living - Frequently Asked Questions

Monthly costs with rent: $3,170 in Windsor, CT, $3,077 in Chicago, IL – roughly 3% apart. Windsor, CT costs more across the board, with Clothing & Footwear showing the biggest gap.

For a comfortable life, plan on about $4,755 per month in Windsor, CT and $4,616 in Chicago, IL. That covers rent, food, utilities, transport, and enough left over to feel settled – not just surviving.

Rent is clearly cheaper in Chicago, IL, especially for central apartments. Housing is actually the single biggest factor behind the overall cost gap between these two cities.

Groceries cost about 9% more in Windsor, CT, though it depends on what you buy. Local produce may be comparable; imported and premium items show the biggest price gap.

A mid-range dinner for two costs $98.0 in Windsor, CT and $98.0 in Chicago, IL. That's a good indicator of the overall restaurant and café pricing gap between the two cities.

$3,000 is a stretch for both – monthly costs hit $3,170 in Windsor, CT and $3,077 in Chicago, IL. You'll need shared housing and careful budgeting no matter which city you pick.

It depends on your priorities. Chicago, IL has an edge in some lifestyle areas, with costs from $3,077 in Chicago, IL to $3,170 in Windsor, CT. Climate, culture, job market, and personal taste all factor in.

Both have safer and rougher neighborhoods, but overall safety is comparable to other large cities. Neighborhood choice matters more than the city-level comparison – central, well-trafficked areas feel secure in both.

If budget matters most, go with Chicago, IL. If higher salaries, better infrastructure, or specific career opportunities are the priority, Windsor, CT makes more sense. Both are solid long-term options with distinct trade-offs.