Cost of Living Comparison Between Annapolis, MD and Chicago, IL
For one person, living is cheaper in Chicago, IL: $3,185 a month against $3,458 in Annapolis, MD, rent and utilities included – about $3,300 less a year. Rent and utilities account for most of the difference.
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Annapolis, MD Living Index169Cost of Living Index in Annapolis, MDLearn more -
Chicago, IL Living Index153Cost of Living Index in Chicago, ILLearn more
How much you'll spend in Annapolis, MD and in Chicago, IL
Real prices from locals and on-the-ground checks – rent, groceries, transit and the daily extras. Here's what a month in Annapolis, MD and in Chicago, IL actually costs, broken down by who's living it.
Monthly costs for one person with rent: $3,458 in Annapolis, MD versus $3,185 in Chicago, IL.
- Annapolis, MD $3,458
- Chicago, IL $3,185
Estimated couple costs with rent: $4,748 in Annapolis, MD versus $4,631 in Chicago, IL.
- Annapolis, MD $4,748
- Chicago, IL $4,631
Monthly costs for a family of three with rent: $6,038 in Annapolis, MD versus $6,077 in Chicago, IL.
- Annapolis, MD $6,038
- Chicago, IL $6,077
Living in Annapolis, MD is roughly 9% more expensive than in Chicago, IL, and outside of rent the biggest gap is in transport.
Both cities are pricier than the global median: Annapolis, MD 156% above, Chicago, IL 136% above.
CityCost data is based on AI and user input – minor inaccuracies may occur.
Last update for Annapolis, MD: October 11, 2026
Last update for Chicago, IL: October 12, 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 $2,092 in Annapolis, MD and $2,383 in Chicago, IL. Housing cost is often the main lever when comparing two cities.
Annapolis, MD pays 14% 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: $80.0 in Annapolis, MD vs $89.0 in Chicago, IL for a mid-range dinner for two. Groceries echo the gap at $396 vs $451 per month, with Annapolis, MD cheaper across the board.
- Annapolis, MD Chicago, IL 990 km ≈ 1 h 45 min nonstop flight
- Annapolis, MD
- Chicago, IL
Distances are measured in a straight line. Your location is detected approximately.
City Median Internet Speeds Comparison (Updated April 2026)
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