Cost of Living Comparison Between Chicago, IL and Annapolis, MD
For one person, living is cheaper in Chicago, IL: $3,037 a month against $3,513 in Annapolis, MD, rent and utilities included – about $5,700 less a year. Rent and utilities account for most of the difference.
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Chicago, IL Living Index147Cost of Living Index in Chicago, ILLearn more -
Annapolis, MD Living Index170Cost of Living Index in Annapolis, MDLearn more
How much you'll spend in Chicago, IL and in Annapolis, MD
Real prices from locals and on-the-ground checks – rent, groceries, transit and the daily extras. Here's what a month in Chicago, IL and in Annapolis, MD actually costs, broken down by who's living it.
Monthly costs for one person with rent: $3,037 in Chicago, IL versus $3,513 in Annapolis, MD.
- Chicago, IL $3,037
- Annapolis, MD $3,513
Estimated couple costs with rent: $4,518 in Chicago, IL versus $4,964 in Annapolis, MD.
- Chicago, IL $4,518
- Annapolis, MD $4,964
Monthly costs for a family of three with rent: $5,999 in Chicago, IL versus $6,415 in Annapolis, MD.
- Chicago, IL $5,999
- Annapolis, MD $6,415
Living in Chicago, IL costs roughly 14% less than in Annapolis, MD, and outside of rent the biggest gap is in eating out.
Both cities are pricier than the global median: Chicago, IL 123% above, Annapolis, MD 158% above.
CityCost data is based on AI and user input – minor inaccuracies may occur.
Last update for Chicago, IL: October 25, 2026
Last update for Annapolis, MD: October 26, 2026
Categories marked with * are only partly priced – their share counts the items that do have prices.
Cost Breakdown
A one-bedroom apartment in the center runs $2,526 in Chicago, IL and $1,706 in Annapolis, MD. Housing cost is often the main lever when comparing two cities.
Annapolis, MD pays 11% more on average. The extra income cushions the higher costs, though housing choices and lifestyle decide how much of the gap is truly closed.
Dining out: $89 in Chicago, IL vs $79 in Annapolis, MD for a mid-range dinner for two. Groceries echo the gap at $447 vs $394 per month, with Annapolis, MD cheaper across the board.
- Chicago, IL Annapolis, MD 990 km ≈ 1 h 45 min nonstop flight
- Chicago, IL
- Annapolis, MD
Distances are measured in a straight line. Your location is detected approximately.
City Median Internet Speeds Comparison (Updated April 2026)
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