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

Monthly Cost of Living

A single person spends $3,051 per month in Chicago, IL vs $3,129 in Windsor, CT, rent included.

A couple spends around $4,638 per month in Chicago, IL vs $4,408 in Windsor, CT, rent included.

A family of three spends $6,224 per month in Chicago, IL vs $5,688 in Windsor, CT, rent included.

Chicago, IL is about 2% cheaper than Windsor, CT, driven mainly by Clothing & Footwear.

Both Chicago, IL and Windsor, CT sit above the global median – Chicago, IL by 128%, Windsor, CT by 133%.

Meal at Budget Restaurant

$20.67 $20.67

$24.57 $24.57

-15.87%

Three-Course Dinner for Two, Mid-Range

$100 $100

$101 $101

-0.79%

Fast Food Meal (McDonalds, etc)

$11.86 $11.86

$13.57 $13.57

-12.60%

Cappuccino

$5.54 $5.54

$4.38 $4.38

26.48%

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

$3.06 $3.06

$2.81 $2.81

8.90%

Water (0.33 liter bottle)

$2.48 $2.48

$2.17 $2.17

14.29%

Local Beer (0.5 liter draught)

$6.92 $6.92

$5.88 $5.88

17.69%

Imported Beer (0.33 liter bottle)

$8.13 $8.13

$7.58 $7.58

7.26%

Milk (1 liter)

$1.04 $1.04

$1.37 $1.37

-24.09%

White Bread (500g)

$3.91 $3.91

$4.53 $4.53

-13.69%

Rice (white) (1kg)

$5.42 $5.42

$5.34 $5.34

1.50%

Eggs

$4.48 $4.48

$6.67 $6.67

-32.83%

Local Cheese (1kg)

$14.52 $14.52

$21.20 $21.20

-31.51%

Chicken Fillets (1kg)

$15.21 $15.21

$13.32 $13.32

14.19%

Beef Round Steak (1kg)

$19.25 $19.25

$19.61 $19.61

-1.84%

Apples (1kg)

$5.39 $5.39

$6.74 $6.74

-20.03%

Banana (1kg)

$1.69 $1.69

$2.15 $2.15

-21.40%

Oranges (1kg)

$4.32 $4.32

$5.49 $5.49

-21.31%

Tomato (1kg)

$4.51 $4.51

$5.93 $5.93

-23.95%

Potato (1kg)

$2.56 $2.56

$2.19 $2.19

16.89%

Onion (1kg)

$2.70 $2.70

$2.26 $2.26

19.47%

Lettuce (1 head)

$2.41 $2.41

$2.44 $2.44

-1.23%

Water (1.5 liter bottle)

$2.62 $2.62

$2.23 $2.23

17.49%

Cigarettes 20 Pack (Marlboro, Camel)

$15.02 $15.02

$13.78 $13.78

9.00%

Wine (Bottle)

$14.71 $14.71

$14.96 $14.96

-1.67%

Local Beer (0.5 liter bottle)

$2.48 $2.48

$2.15 $2.15

15.35%

Imported Beer (0.33 liter bottle)

$3.69 $3.69

$2.54 $2.54

45.28%

One-way Ticket (Public Transport)

$2.55 $2.55

$2.04 $2.04

25.00%

Public Transport Monthly Pass (Regular Price)

$75.5 $75.5

$101 $101

-24.96%

Taxi Start (Normal Tariff)

$3.29 $3.29

$3.98 $3.98

-17.34%

Taxi (Normal Tariff) (1km)

$1.43 $1.43

$2.20 $2.20

-35.00%

Taxi 1hour Waiting (Normal Tariff)

$24.72 $24.72

$19.98 $19.98

23.72%

Gasoline (1 liter)

$1.09 $1.09

$0.83 $0.83

31.33%

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

$31.8K $31.8K

$29.1K $29.1K

9.00%

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

$26.4K $26.4K

$26.3K $26.3K

0.45%

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

$183 $183

$221 $221

-16.96%

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

$61.8 $61.8

$71.9 $71.9

-14.02%

Internet (50+ Mbps, Unlimited Data)

$65.0 $65.0

$69.7 $69.7

-6.67%

Gym Membership (Monthly)

$76.1 $76.1

$43.54 $43.54

74.74%

Tennis Court (1 Hour on Weekend)

$13.04 $13.04

$19.88 $19.88

-34.41%

Cinema Ticket

$14.75 $14.75

$14.53 $14.53

1.51%

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

$2,056 $2,056

$1,261 $1,261

63.11%

International Primary School, 1 Child (Yearly)

$38.5K $38.5K

$33.6K $33.6K

14.71%

Jeans (Levis 501 Or Similar)

$63.9 $63.9

$62.3 $62.3

2.57%

Summer Dress (H&M, Zara, etc)

$51.6 $51.6

$37.25 $37.25

38.50%

Sport Shoes (Adidas, Nike)

$97.3 $97.3

$66.2 $66.2

46.85%

Men's Leather Business Shoes

$147 $147

$99.8 $99.8

47.56%

1-bedroom Apartment, City Center (Monthly)

$2,349 $2,349

$2,031 $2,031

15.69%

1-bedroom Apartment, Outside City Center (Monthly)

$1,581 $1,581

$1,596 $1,596

-0.92%

3-bedroom Apartment, City Center (Monthly)

$4,708 $4,708

$2,602 $2,602

80.97%

3-bedroom Apartment, Outside City Center (Monthly)

$2,716 $2,716

$2,185 $2,185

24.28%

Buy Apartment in City Center (m2)

$3,976 $3,976

$3,090 $3,090

28.69%

Buy Apartment Outside City Center (m2)

$2,632 $2,632

$2,445 $2,445

7.65%

Average Monthly Net Salary (After Tax)

$4,723 $4,723

$5,854 $5,854

-19.31%

20-Year Fixed Mortgage Interest Rate (Annual %)

6.6

6.38

3.45%

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

Last update for Chicago, IL: April 20, 2026

Last update for Windsor, CT: April 22, 2026

Cost Breakdown

A central one-bedroom costs $2,349 in Chicago, IL versus $2,031 in Windsor, CT. 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 24% 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 $100 in Chicago, IL versus $101 in Windsor, CT. Monthly groceries follow the same trend: $447 vs $488 – making Chicago, IL the more affordable choice for daily food spending.

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

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

Monthly costs with rent: $3,051 in Chicago, IL, $3,129 in Windsor, CT – roughly 3% apart. Windsor, CT costs more across the board, with Clothing & Footwear showing the biggest gap.

For a comfortable life, plan on about $4,577 per month in Chicago, IL and $4,693 in Windsor, CT. 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 $100 in Chicago, IL and $101 in Windsor, CT. 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 $3,051 in Chicago, IL and $3,129 in Windsor, CT. 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 $3,051 in Chicago, IL to $3,129 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.