Despite the troubled relations between the Norman earls and the princes of Gwynedd, the Cestrians' need was such that the Welsh were encouraged to trade in the city's market, supplying especially cattle and meat. They were not, however, accorded equal status with the English and French. The less generous treatment which they received when their goods were stolen shows their inferior status at the end of the 12th century. So too does the disdainful attitude of the Cestrian monk Lucian: 'The native [Cestrian] knows how savagely our neighbour often approaches, and stimulated by hunger and cold haunts the place, and then cannot help but compare the difference in supplies. Yet he returns, but with hostile glance and evil thoughts envies the citizen within the walls.'
The trade with Ireland was perhaps crucial to Chester's economy. Besides food, the city imported animal pelts, especially marten. Its exports are much less certain. As earlier, they presumably included salt, needed for Dublin's trade in hides and fish, and some at least of the English pottery which in the absence of home-based manufactures Dublin continued to use in considerable quantities before 1200. That such trading remained significant after the English conquest of Dublin and the grant of the city to the men of Bristol is clear from the city charters, all of which post-date those events. Evidently Henry II's predilection for loyalist Bristol did not have as much effect on Chester as has sometimes been suggested, and there was no sudden rupture of Chester's relations with Dublin in the late 12th century.
Ireland was not Chester's only international link. In the late 12th century, for example, ships from Aquitaine, Spain, and Germany brought cargoes of wine into the harbour on the south side of the city. Wine was clearly a valuable import, for in 1238 it formed the basis of the rent which the burgesses paid the new royal earl for one of the Dee Mills. All that activity was reflected in the city's markets and fairs. There was undoubtedly a market in Chester well before it was first documented c. 1080, in the city centre immediately south of St. Peter's church. A focal point, it was fronted in the 1120s by important buildings, including the sheriff's house and a 'great shop' (magna sopa). In the 1090s Gruffudd ap Cynan was supposedly exhibited there in chains and released by a young Welshman visiting 'to buy necessities'. A second market place was established in front of St. Werburgh's abbey gate by Earl Ranulph II. Commodities on sale there were mainly provisions, both local and imported, including cereals, cattle and meat, and fish from the Dee and Ireland.
The city also had two annual fairs, at Midsummer and Michaelmas. Their origins are uncertain. From an early period the monks of St. Werburgh's claimed that Earl Hugh I (d. 1101) had granted them the right to hold a fair on the three days around the feast of St. Werburg's translation on 21 June. Although the grant was not mentioned in Earl Richard's confirmation of Hugh's charter to the abbey, on balance the claim is likely to have been correct. Almost certainly, however, the fair was reorganized in the 1120s by Ranulph I, who provided new regulations governing its hours of opening. Further regulation took place under Ranulph II (1129-53), who permitted stalls and a market to be set up before the abbey gate, and prohibited trading elsewhere in the city while the fair lasted. Ranulph later pledged his peace to all attending the fair and extended responsibility for its policing to the barons of Cheshire. By the early 13th century the fair was associated with the feast of St. John the Baptist, Midsummer Day (24 June), and had evidently been extended to probably at least a week. The origins of the Michaelmas fair are even more obscure. It was certainly held in the early 13th century, and may have been much older. It was never, however, as important or long-lasting as the Midsummer fair.
The city did not depend simply upon trade. In the 12th century industrial workers included leatherdressers and artisans, and probably potters making wares for local use and export to Dublin. Provisioning the city and its environs was especially important. Brewing, recorded in 1086, was regulated by a charter of Earl John (1232-7) which limited the levy (capcio) on beer to himself and his justiciar while they were present in the city, and restricted the amount taken from each brewing to 4 sesters (24 gallons). Milling was of prime importance. The Dee Mills, located at the bridge, seem to have existed by the late 11th century.By 1238 there were six mills there, farmed separately from the city for the very large sum of £100. From an early date all citizens, except the monks of St. Werburgh's and their tenants, were required to grind their corn there and pay the earl a toll for the service. Though the customs governing the monopoly, apparently systematized by Ranulph III, were later regarded as benefiting the city, among contemporaries they seem to have occasioned resentment, and after the death of Earl John in 1237 the mills were destroyed by the inhabitants.
Another important activity was fishing, especially the taking of salmon from the Dee, where they abounded. The earls had a fishery by the Dee Bridge, and by the 1140s they had assigned the monks of St. Werburgh's a tithe of the fish taken there and in other fisheries. Throughout the later 12th century they continued to grant boats on the Dee to various ecclesiastical establishments, including in the 1150s the newly established nuns of Chester and the monks of Much Wenlock (Salop.).
In the 1160s Hugh II's similar grant to Trentham priory (Staffs.) expressly allowed for fishing 'above and below the bridge', evidently that at Chester. Hugh clearly valued his fisheries highly, and he and his predecessors perhaps had a monopoly. His successor Ranulph III, however, was apparently much more prodigal of his rights on the Dee, and from c. 1200 increasing numbers of citizens held stalls, nets, or boats on the river.