| Date: | August 21–26 |
| Edition: | 3rd |
| Draw: | 32S / 8D |
| Surface: | Hard, outdoor |
| Prize Money: | $115,000 |
| Category: | WTA 125 |
| Location: | Chicago, United States |
| Venue: | XS Tennis Village |
| Champs: | Viktoriya Tomova |
| Champd: |  Ulrikke Eikeri /  Ingrid Neel |
| Before Year: | 2021 |
| Main Name: | Oracle Challenger Series – Chicago Chicago Challenger |
The 2023 Chicago Challenger was a professional tennis tournament played on outdoor hard courts. It was part of the 2023 WTA Challenger Tour. It was the third edition of the tournament which took place from August 21 to 26, 2023 at the XS Tennis Village in Chicago, United States.[1]
| Country | Player | Rank1 | Seed | |
|---|---|---|---|---|
| Arantxa Rus | 41 | 1 | ||
| Elina Avanesyan | 64 | 2 | ||
 Colombia | Camila Osorio | 65 | 3 | |
 France | Alizé Cornet | 66 | 4 | |
 Italy | Lucia Bronzetti | 68 | 5 | |
 Spain | Rebeka Masarova | 73 | 6 | |
| France | Diane Parry | 75 | 7 | |
| Kamilla Rakhimova | 80 | 8 |
The following players received wildcards into the singles main draw:
The following players received entry using protected rankings:
The following players received entry from the qualifying draw:
The following player received entry as a lucky loser:
Adesuwa Osabuohien
Maryna Zanevska → replaced by Adesuwa Osabuohien| Country | Player | Country | Player | Rank1 | Seed | |
|---|---|---|---|---|---|---|
| Norway | Ulrikke Eikeri | Estonia | Ingrid Neel | 107 | 1 | |
| Yana Sizikova | Belgium | Kimberley Zimmermann | 109 | 2 |
The following pair received a wildcard into the doubles main draw:
Kolie Allen / Ashley MatzSee main article: article and 2023 Chicago Challenger – Singles.
Claire Liu 6–1, 6–4See main article: article and 2023 Chicago Challenger – Doubles.
Ulrikke Eikeri / Ingrid Neel def. Cristina Bucșa / Alexandra Panova, walkover