VanguardTarget Retirement 2015 Fund

1 VanguardTarget Retirement 2015 FundSupplement Dated January 10, 2022, to the Prospectusand Summary ProspectusReorganization of vanguard Target Retirement 2015 Fund into VanguardTarget Retirement Income Fund (collectively, the Funds)The Board ofTrustees of vanguard Chester Funds (theTrust) has approved anagreement and plan of reorganization (the Agreement) whereby VanguardTargetRetirement 2015 Fund (the 2015 Fund), a series of theTrust, will be reorganizedwith and into VanguardTarget Retirement Income Fund (the Income Fund),another series of theTrust. In accordance with the disclosure in the prospectus ,the asset allocation for each VanguardTarget Retirement Fund ( other than theIncome Fund) changes over time as the date indicated in the Fund s name drawscloser.

2 As the 2015 Fund s asset allocation has become similar to that of theIncome Fund, the Board ofTrustees has determined combining it with theIncome Fund to be in the best interest of reorganization does not require shareholder approval and is expected toclose on or about July 8, 2022. Prior to the closing, shareholders of the 2015 Fund will be issued a combined Information Statement/ prospectus , which willdescribe the reorganization, provide a description of the Income Fund, andinclude a comparison of the the Agreement and after the closing, shareholders of the 2015 Fund willreceive Investor Shares of the Income Fund in exchange for their Investor Sharesof the 2015 Fund, and the 2015 Fund will cease operations.

3 We anticipate thatthe reorganization will qualify as a tax-free reorganization under the InternalRevenue Code of 1986, as amended. 2022 The vanguard Group, Inc. All rights Marketing Corporation, 308C 012022 VanguardTarget Retirement FundsSupplement Dated September 28, 2021, to theProspectus and Summary Prospectuses DatedJanuary 31, 2021 Reorganization of vanguard Institutional Target Retirement Funds intoVanguard Target Retirement FundsThe Board ofTrustees of vanguard Chester Funds (theTrust) has approved anagreement and plan of reorganization whereby each vanguard InstitutionalTargetRetirement Fund listed in the table below, each a series of theTrust, would bereorganized with and into each corresponding VanguardTarget Retirement Fundlisted in the table below.

4 Each also a series of FundAcquiring FundVanguard InstitutionalTarget Retirement IncomeFundVanguardTarget Retirement IncomeFundVanguard InstitutionalTarget Retirement 2015 Fund VanguardTarget Retirement 2015 FundVanguard InstitutionalTarget Retirement 2020 Fund VanguardTarget Retirement 2020 FundVanguard InstitutionalTarget Retirement 2025 Fund VanguardTarget Retirement 2025 FundVanguard InstitutionalTarget Retirement 2030 Fund VanguardTarget Retirement 2030 FundVanguard InstitutionalTarget Retirement 2035 Fund VanguardTarget Retirement 2035 FundVanguard InstitutionalTarget Retirement 2040 Fund VanguardTarget Retirement 2040 FundVanguard InstitutionalTarget Retirement 2045 Fund VanguardTarget Retirement 2045 FundVanguard InstitutionalTarget Retirement 2050 Fund VanguardTarget Retirement 2050 FundVanguard InstitutionalTarget Retirement 2055 Fund VanguardTarget Retirement 2055 FundVanguard InstitutionalTarget Retirement 2060 Fund VanguardTarget Retirement 2060 FundVanguard InstitutionalTarget Retirement 2065 Fund VanguardTarget Retirement 2065 FundThe reorganization does not require shareholder approval and is expected

5 Toclose on or about February 11, 2022. Following each reorganization, it isexpected that the expense ratio for eachTarget Retirement Fund will be reducedto 2021 The vanguard Group, Inc. All rights Marketing Corporation, 308B 092021 vanguard Target Retirement FundsSupplement Dated February 17, 2021, to the Prospectusand Summary Prospectuses Dated January 31, 2021 Addition of New Underlying FundThe board of trustees of each vanguard Target Retirement Fund approved theaddition of vanguard Total International Bond II Index Fund as a new underlyingfund for each vanguard Target Retirement Fund.

6 The addition of vanguard TotalInternational Bond II Index Fund is not expected to change the expense ratio forany vanguard Target Retirement Fund. Furthermore, the addition of VanguardTotal International Bond II Index Fund will not alter the glide path, asset class andsub-asset class exposures, investment methodology, or advisory structure of anyVanguard Target Retirement Total International Bond II Index Fund mirrors the investment strategyof vanguard Total International Bond Index Fund, is subject to substantially similarrisks, and seeks to track the same benchmark index as vanguard TotalInternational Bond Index Fund, the Bloomberg Barclays Global Aggregate ex-USDF loat Adjusted RIC Capped Index (USD Hedged).

7 Therefore, each risk applicableto vanguard Total International Bond Index Fund is also applicable to VanguardTotal International Bond II Index Total International Bond II Index Fund will receive the fixedincome allocation of new cash flows into each vanguard Target Retirement vanguard Target Retirement Fund s existing allocations to bondswill be moved from vanguard Total International Bond Index Fund to VanguardTotal International Bond II Index Fund over time. During this period, a VanguardTarget Retirement Fund may be invested in both vanguard Total InternationalBond Index Fund and vanguard Total International Bond II Index Fund to achieveits target allocation to bonds.

8 2021 The vanguard Group, Inc. All rights Marketing Corporation, 308A 022021 vanguard Target Retirement FundsProspectusJanuary 31, 2021 Investor SharesVanguard Target Retirement Income Fund Investor Shares (VTINX) vanguard Target Retirement 2015 Fund Investor Shares (VTXVX) vanguard Target Retirement 2020 Fund Investor Shares (VTWNX) vanguard Target Retirement 2025 Fund Investor Shares (VTTVX) vanguard Target Retirement 2030 Fund Investor Shares (VTHRX) vanguard Target Retirement 2035 Fund Investor Shares (VTTHX) vanguard Target Retirement 2040 Fund Investor Shares (VFORX) vanguard Target Retirement 2045 Fund Investor Shares (VTIVX) vanguard Target Retirement 2050 Fund Investor Shares (VFIFX) vanguard Target Retirement 2055 Fund Investor Shares (VFFVX) vanguard Target Retirement 2060 Fund Investor Shares (VTTSX) vanguard Target Retirement 2065 Fund Investor Shares (VLXVX)See the inside front cover for important information about access to yourfund s annual and semiannual shareholder prospectus contains financial data for the Funds through the fiscal year endedSeptember 30, Securities and Exchange Commission (SEC)

9 Has not approved or disapproved thesesecurities or passed upon the adequacy of this prospectus . Any representation to the contrary information about access to shareholder reportsBeginning on January 1, 2021, as permitted by regulations adopted by theSEC, paper copies of your fund s annual and semiannual shareholder reportswill no longer be sent to you by mail, unless you specifically request , you will be notified by mail each time a report is posted on thewebsite and will be provided with a link to access the you have already elected to receive shareholder reports electronically.

10 Youwill not be affected by this change and do not need to take any action. You mayelect to receive shareholder reports and other communications from the fundelectronically by contacting your financial intermediary (such as a broker-dealeror bank) or, if you invest directly with the fund, by calling vanguard at one ofthe phone numbers on the back cover of this prospectus or by logging on may elect to receive paper copies of all future shareholder reports free ofcharge. If you invest through a financial intermediary, you can contact theintermediary to request that you continue to receive paper copies.