VanguardTarget Retirement Funds - Vanguard Advisors

Vanguard Target Retirement 2015 Fund

Supplement Dated February 14, 2022, to the Prospectus and Summary Prospectus

Closed to New Accounts

As previously announced, the Board of Trustees of Vanguard Chester Funds (the Trust) has approved an agreement and plan of reorganization whereby Vanguard Target Retirement 2015 Fund (the 2015 Fund), a series of the Trust, will be reorganized with and into Vanguard Target Retirement Income Fund, another series of the Trust. The reorganization is expected to close on or about July 8, 2022.

Effective immediately, the 2015 Fund is closed to new accounts, and it will stop accepting purchase requests from existing accounts shortly before the reorganization is scheduled to occur.

? 2022 The Vanguard Group, Inc. All rights reserved. Vanguard Marketing Corporation, Distributor.

PS 308F 022022

Vanguard Target Retirement Funds

Supplement Dated February 14, 2022, to the Prospectus and Summary Prospectuses Dated January 31, 2022

Reorganization of Vanguard Institutional Target Retirement Funds into Vanguard Target Retirement Funds

Effective as of the close of business on February 11, 2022, the previously announced reorganization of each Vanguard Institutional Target Retirement Fund listed in the table below with and into each corresponding Vanguard Target Retirement Fund listed in the table below is complete.

Acquired Fund Vanguard Institutional Target Retirement Income Fund Vanguard Institutional Target Retirement 2015 Fund Vanguard Institutional Target Retirement 2020 Fund Vanguard Institutional Target Retirement 2025 Fund Vanguard Institutional Target Retirement 2030 Fund Vanguard Institutional Target Retirement 2035 Fund Vanguard Institutional Target Retirement 2040 Fund Vanguard Institutional Target Retirement 2045 Fund Vanguard Institutional Target Retirement 2050 Fund Vanguard Institutional Target Retirement 2055 Fund Vanguard Institutional Target Retirement 2060 Fund Vanguard Institutional Target Retirement 2065 Fund

Acquiring Fund Vanguard Target Retirement Income Fund Vanguard Target Retirement 2015 Fund Vanguard Target Retirement 2020 Fund Vanguard Target Retirement 2025 Fund Vanguard Target Retirement 2030 Fund Vanguard Target Retirement 2035 Fund Vanguard Target Retirement 2040 Fund Vanguard Target Retirement 2045 Fund Vanguard Target Retirement 2050 Fund Vanguard Target Retirement 2055 Fund Vanguard Target Retirement 2060 Fund Vanguard Target Retirement 2065 Fund

Any references to the Vanguard Institutional Target Retirement Funds in the Prospectus are hereby deleted.

Prospectus and Summary Prospectus Text Changes The Annual Fund Operating Expenses table is restated as follows for each Vanguard Target Retirement Fund (each, a Fund):

Annual Fund Operating Expenses (Expenses that you pay each year as a percentage of the value of your investment)

Management Fees 12b-1 Distribution Fee Other Expenses Acquired Fund Fees and Expenses1 Total Annual Fund Operating Expenses

0.00% None 0.00% 0.08% 0.08%

1 The Acquired Fund Fees and Expenses in this table have been restated to reflect current investments in the underlying funds following the reorganization of each Vanguard Institutional Target Retirement Fund into its corresponding Fund and, therefore, will not correlate to the Acquired Fund Fees and Expenses shown in the Financial Highlights table.

In addition, the hypothetical expenses example is restated as follows for each Fund:

Example

The following example is intended to help you compare the cost of investing in the Fund (based on the fees and expenses of the acquired funds) with the cost of investing in other mutual funds. It illustrates the hypothetical expenses that you would incur over various periods if you were to invest $10,000 in the Fund's shares. This example assumes that the Fund provides a return of 5% each year and that total annual fund operating expenses (of the Fund and its underlying funds) remain as stated in the preceding table. You would incur these hypothetical expenses whether or not you were to redeem your investment at the end of the given period. Although your actual costs may be higher or lower, based on these assumptions your costs would be:

1 Year $8

3 Years $26

5 Years $45

10 Years $103

? 2022 The Vanguard Group, Inc. All rights reserved. Vanguard Marketing Corporation, Distributor.

PS 308D 022022

Vanguard Target Retirement 2015 Fund

Supplement Dated January 10, 2022, to the Prospectus and Summary Prospectus

Reorganization of Vanguard Target Retirement 2015 Fund into Vanguard Target Retirement Income Fund (collectively, the Funds)

The Board of Trustees of Vanguard Chester Funds (the Trust) has approved an agreement and plan of reorganization (the Agreement) whereby Vanguard Target Retirement 2015 Fund (the 2015 Fund), a series of the Trust, will be reorganized with and into Vanguard Target Retirement Income Fund (the Income Fund), another series of the Trust. In accordance with the disclosure in the prospectus, the asset allocation for each Vanguard Target Retirement Fund (other than the Income Fund) changes over time as the date indicated in the Fund's name draws closer. As the 2015 Fund's asset allocation has become similar to that of the Income Fund, the Board of Trustees has determined combining it with the Income Fund to be in the best interest of shareholders.

The reorganization does not require shareholder approval and is expected to close on or about July 8, 2022. Prior to the closing, shareholders of the 2015 Fund will be issued a combined Information Statement/Prospectus, which will describe the reorganization, provide a description of the Income Fund, and include a comparison of the Funds.

Under the Agreement and after the closing, shareholders of the 2015 Fund will receive Investor Shares of the Income Fund in exchange for their Investor Shares of the 2015 Fund, and the 2015 Fund will cease operations. We anticipate that the reorganization will qualify as a tax-free reorganization under the Internal Revenue Code of 1986, as amended.

? 2022 The Vanguard Group, Inc. All rights reserved. Vanguard Marketing Corporation, Distributor.

PS 308C 012022

Vanguard Target Retirement Funds Prospectus

January 31, 2022

Investor Shares Vanguard 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)

This prospectus contains financial data for the Funds through the fiscal year ended September 30, 2021. The Securities and Exchange Commission (SEC) has not approved or disapproved these securities or passed upon the adequacy of this prospectus. Any representation to the contrary is a criminal offense.

Contents

Fund Summaries

More on the Funds

76

Vanguard Target Retirement Income Fund

1 The Funds and Vanguard

87

Vanguard Target Retirement 2015 Fund

7 Investment Advisor

88

Vanguard Target Retirement 2020 Fund

13 Dividends, Capital Gains, and Taxes

89

Vanguard Target Retirement 2025 Fund

19 Share Price

92

Vanguard Target Retirement 2030 Fund

25 Financial Highlights

93

Vanguard Target Retirement 2035 Fund

31 Investing With Vanguard

105

Vanguard Target Retirement 2040 Fund

37 Purchasing Shares

105

Vanguard Target Retirement 2045 Fund

43 Redeeming Shares

108

Vanguard Target Retirement 2050 Fund

49 Exchanging Shares

112

Vanguard Target Retirement 2055 Fund

55 Frequent-Trading Limitations

112

Vanguard Target Retirement 2060 Fund

61 Other Rules You Should Know

115

Vanguard Target Retirement 2065 Fund

68 Fund and Account Updates

119

Investing in Vanguard Target Retirement Funds 74 Employer-Sponsored Plans

120

Contacting Vanguard

122

Additional Information

122

Glossary of Investment Terms

126

Vanguard Target Retirement Income Fund

Investment Objective The Fund seeks to provide current income and some capital appreciation.

Fees and Expenses The following table describes the fees and expenses you may pay if you buy, hold, and sell shares of the Fund. You may pay other fees, such as brokerage commissions and other fees to financial intermediaries, which are not reflected in the table and example below.

Shareholder Fees (Fees paid directly from your investment)

Sales Charge (Load) Imposed on Purchases Purchase Fee Sales Charge (Load) Imposed on Reinvested Dividends Redemption Fee Account Service Fee Per Year (for certain fund account balances below $10,000)

None None None None

$20

Annual Fund Operating Expenses (Expenses that you pay each year as a percentage of the value of your investment)

Management Fees 12b-1 Distribution Fee Other Expenses Acquired Fund Fees and Expenses Total Annual Fund Operating Expenses

0.00% None 0.00% 0.12% 0.12%

1

Example

The following example is intended to help you compare the cost of investing in the Fund (based on the fees and expenses of the acquired funds) with the cost of investing in other mutual funds. It illustrates the hypothetical expenses that you would incur over various periods if you were to invest $10,000 in the Fund's shares. This example assumes that the Fund provides a return of 5% each year and that total annual fund operating expenses (of the Fund and its underlying funds) remain as stated in the preceding table. You would incur these hypothetical expenses whether or not you were to redeem your investment at the end of the given period. Although your actual costs may be higher or lower, based on these assumptions your costs would be:

1 Year $12

3 Years $39

5 Years $68

10 Years $154

Portfolio Turnover

The Fund may pay transaction costs, such as purchase fees, when it buys and sells securities (or "turns over" its portfolio). A higher portfolio turnover rate may indicate higher transaction costs and may result in more taxes when Fund shares are held in a taxable account. These costs, which are not reflected in annual fund operating expenses or in the previous expense example, reduce the Fund's performance. During the most recent fiscal year, the Fund's portfolio turnover rate was 6% of the average value of its portfolio.

Principal Investment Strategies

The Fund invests in a mix of Vanguard mutual funds (underlying funds) according to an asset allocation strategy designed for investors currently in retirement. As of September 30, 2021, the Fund's allocation among the underlying asset classes was as follows:

? U.S. fixed-income securities ? U.S. stocks ? Inflation-indexed securities ? Foreign fixed-income securities ? Foreign stocks

37.4% 17.3% 17.1% 16.3% 11.9%

At any given time, the Fund's asset allocation may be affected by a variety of factors, such as whether the underlying funds are accepting additional investments.

The Fund's indirect fixed-income holdings are a diversified mix of short-, intermediate-, and long-term U.S. government, U.S. agency, and investment-grade U.S. corporate bonds; inflation-protected public obligations

2

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