Chicago Ill May 24, manuscript postmark in Red with matching "25" rate on 1833 folded letter to Collinsville, Connecticut, additional manuscript "Missent & Fwd", vertical filefold, very fine, an incredibly important piece of Chicago postal history. Only approximately a dozen manuscript postmarks are known from Chicago in the period from 1831 to 1833. Nearly all are in the handwriting of Postmaster John S.C. Hogan, who was appointed November 2, 1832. Chicago manuscript postmarks come to market less frequently than one would expect, and therefore this wonderful example represents a rare opportunity for a collector to acquire one of the key items for a comprehensive city or state collection.  
Reference: illustrated in Piszkiewicz (page 2) (Image)

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Chicago Ills. Aug 7 (A-1), red datestamp with manuscript "25" rate on 1834 folded letter to New York City, datelined "Blackstone's Grove, Aug 1st, 1834", lengthy contents about life in Chicago, very fine and early personal letter (Image)

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Chicago Ills Dec 25 (A-1), red datestamp on 1834 folded letter to Princeton, Illinois, manuscript "18¾" rate, datelined "Worcester [Illinois] Nov 8th 1834", written by C.P. Hitchcock to his sister, includes information about early life  such as "I have learnt that an opportunity offers for sending letters to Chicago...", light aging and splitting along the folds, still a fine and rare early personal letter from Chicago, Worcester (now Barry) was located on the opposite side of the state as Chicago which explains the delay in posting this letter (Image)

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Chicago Ills. Oct 28 (A-1), red datestamp with matching straight-line "Paid" and "25" rate handstamps on 1836 folded letter to Augusta, Maine, vertical filefold away from markings, very fine, this "25" handstamp was the first rate marking used in Chicago and only appears for a short time between August 1836 and March 1837 (Image)

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Chicago Ills. Nov 13 (A-1), red circular datestamp with matching "25" rate handstamp on 1836 folded letter to Albany, New York, very fine, this is the earliest rate handstamp from Chicago and was only used for a brief period from August 1836 to March 1837, the next rate handstamps (the cog wheels) would not appear until mid-1845, letter contains information about dredging machinery from William H. Davis, illustrated in Piszkiewicz (page 5) (Image)

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Chicago Ills. Sept 18 (A-1), red datestamp with four-letter month abbreviation and matching "Paid" on 1838 folded letter to Joliet, Illinois, manuscript "Paid 20" rate, two real estate contracts enclosed, letter written and signed by Gurdon S. Hubbard, one of early Chicago's most prominent residents, fine and rare with only two or three examples known of the "Sept" abbreviation (Image)

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Chicago Ills. Oct 16 (A-1), red datestamp on 1839 "courthouse" cover to Canandaigua, New York, manuscript "3¼ oz $3.25", originally contained depositions, fine cover paying 13-times the single-sheet rate of 25c, one of the highest rated covers out of early Chicago, illustrated in Piszkiewicz (page 8)

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Chicago Ills. Jun 26 (A-1), blue datestamp on 1841 folded letter to Sconondoa, New York, blue manuscript "f" (free), very fine, letter from John Calhoun, founder of the Chicago Democrat (Chicago's first newspaper) and later a city councilman (Image)

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Chicago Ills. Jul 10 (A-2), blue-green postmark on 1842 folded letter to New York City, manuscript "25" rate, very fine, letter written by William Butler Ogden who served as Chicago's first mayor from 1837 to 1838 and was referred to as the "Astor of Chicago" due to his immense wealth, a wonderful artifact written by one of Chicago's most important early citizens (Image)

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Chicago Nov 8, manuscript postmark with blue "Paid" handstamp and manuscript "12½" rate on 1842 folded letter to Koshkonong, Wisconsin Territory, vertical filefolds, very fine, illustrated in Piszkiewicz (page 3)
This cover is the only recorded Chicago manuscript postmark from 1842 and one of just two known from the 1840s. It was mailed between the latest known use of the A-2 postmark device but before A-3 entered use, suggesting the Chicago post office was without a handstamp for a short time. However, the fact that the A-2 device reappears in 1843 and 1844 seems to contradict this theory. There is also the possibility that this letter arrived at the post office shortly before closing, after the postmark had been locked away for the night. While we may never know the definitive answer, this cover remains a unique and important piece of early Chicago postal history. (Image)

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Chicago Ill. Jul 22 (A-3), red handstamp on 1845 folded cover to Philadelphia, matching "Paid" and cog "10", light wear, fine, the earliest recorded use of the cog "10" handstamp  (Image)

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Chicago Ill. Aug 30 (A-3), bold red handstamp on 1845 folded letter to Milwaukee, Wisconsin Territory, matching straight-line "Paid" and cog "5", vertical file folds, fine strikes, the earliest recorded use of the cog "5" handstamp (Image)

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Chicago Ill, Feb 9 (A-3), red datestamp with matching cog "10" on 1846 folded letter to Versailles, France, red boxed "Colonies &c.Art.13" and French entry handstamp, several backstamps, fine (Image)

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Chicago. Ill. Paid 3Cts 24 Jul (AN-3), large red 36mm circular datestamp on 1851 folded letter to Westfield, New York, matching "Paid" handstamp, light wear and vertical crease away from postmark, very fine strike, the earlier of the two known examples of this postmark, which was the first employed by Chicago to incorporate the rate into the datestamp (after the rate reduction of July 1, 1851), a rare and important postmark (Image)

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Chicago Ill. Nov 15 (A-3), red datestamp with matching straight-line "Paid" and "24" in circle on 1851 cover to Thurso, Scotland, red "Paid In America Liverpool 4 De 51" tombstone,  light folds, fine and scarce, the only recorded example of this rate handstamp (Image)

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Chicago Ill. Jul 4 (A-3), clear strike of circular datestamp ties 1851 3c Dull red (11) to cover to Detroit, blue cornercard for "James H. Rees, Land Agent, No. 63 Clarke St.", extremely fine, an immaculate Independence Day cover which represents the latest known use of the A-3 device, this postmark was in use for almost 11 years and is the longest-lived postmark in Chicago history, illustrated in Piszkiewicz (page 9) (Image)

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Chicago Ill. Nov 23 (A-4a), red datestamp with letters very close to the rim on 1849 folded letter to Philadelphia, matching cog "10", small nick along top edge, very fine strikes, the earliest recorded use of postmark A-4a, this postmark was first reported by Leonard Hartmann in the 1960s and was only used for two months in late-1849 and early-1850, letter written by J.B.F. Russell of the General Land Agency (Image)

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Chicago Ill. Dec 26 (A-4a), red datestamp with matching cog "10" on 1849 folded letter to Newark, New Jersey, personal letter written on Christmas Day, fine and attractive, this scarce postmark was only in use for two months (Image)

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Chicago Ill. Jan 27 (A-4a), red datestamp on with cog "10" rate on 1850 folded letter to Whitesboro, New York, very fine, lengthy letter from B.W. Raymond datelined January 26 describes the first train from Chicago to Elgin which begins "This has been an exciting week for me, on Tuesday the first train of cars ran to Elgin...", an important piece of both Chicago and railroad history (Image)

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Chicago Ill. 17 Sep. (A-4), red datestamp with matching straight-line "Paid" and "48" in circle on 1850 folded letter to Newry, (Northern) Ireland, red "America Liverpool Paid Oc 6 50" and "38" credit handstamps applied upon arrival in England, some overall wear but fine appearance, the only example of this rate handstamp and the highest rate stamp recorded from Chicago, Reference: illustrated in Piszkiewicz (page 22) (Image)

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Chicago Ill. May 10 (A-4), red datestamp on 1852 folded letter to Edinburgh, Scotland, black "24" in circle rate handstamp, black British "19" and "1/-" one shilling due handstamps, backstamped "America Liverpool My26 52F", very fine, Reference: illustrated in Piszkiewicz (page 22) (Image)

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Chicago Ills. Feb 10 (A-6), black datestamp on 1854 cover to Sacramento, California, red straight-line "Paid" and "Paid 6" in arc, light edge wear, very fine, a rare use of the "Paid 6" handstamp which only appeared for a short time in 1854, Reference: illustrated in Piszkiewicz (page 23) (Image)

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Chicago Ills. Feb 7 (A-6), black datestamp on oversized wrapper to Rockford, Illinois, two strikes of red "Paid" and "9" in circle rate handstamp, light wrinkles, very fine, scarce for such a large piece to have survived intact (Image)

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"Free S.A. Douglas", free frank on cover to "The Salem Register, Salem, Essex County, Mass.", small tears, very fine signature, Stephen A. Douglas served as a Representative from Illinois from 1843 to 1847, a Senator from Illinois from 1847 until his death in 1861, and is best remembered for his series of debates with Abraham Lincoln between August and October 1858 (Image)

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Chicago Stampless Cover Group 1835/55, 20 covers, variety of different datestamps and rate markings, mixed quality but many strikes and covers fine or better, an interesting group (Image)

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