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Differences

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Monaco

Monaco

Closed
The '&' (ampersand) is traditional style with two enclosed loops.
Circle
The dot on the '?' (question-mark) is circular or oval.
Round
The top storey of the '3' is a smooth curve.
1-Storey
The lower-case 'a' stem stops at the top of the bowl (single storey).
Two
The 'l' (lower-case 'L') has a left-facing upper serif and right-facing lower serif or tail.
Single-bar
The upper-case 'J' has a bar to the left.
Straight
The leg of the upper-case 'R' is straight.
Tapered
The upper-case 'A' has tapered verticals.
V-shaped
The sides of the lower-case 'y' are angled (V-shaped).
Circle
The dot on the lower-case 'i' or 'j' is circular or oval.

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Note that the fonts in the icons shown above represent general examples, not necessarily the two fonts chosen for comparison.

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Chicago

Chicago

Gap top
The '&' (ampersand) looks like 'Et' with a gap at the top.
Square/rectangular
The dot on the '?' (question-mark) is square or rectangular.
Angled
The top storey of the '3' is a sharp angle.
2-Storey
The lower-case 'a' stem curves over the top of the bowl (double storey).
Plain
The 'l' (lower-case 'L') has no serifs or tail.
Plain
The upper-case 'J' has no bar.
Outwards
The leg of the upper-case 'R' is curved outwards.
Parallel
The upper-case 'A' has parallel verticals.
U-shaped
The sides of the lower-case 'y' are parallel (U-shaped).
Square/rectangle
The dot on the lower-case 'i' or 'j' is square or rectangular.