# 1987 Volvo Tennis Chicago – Singles

Boris Becker was the defending champion, but chose to compete at Milan during the same week.
Tim Mayotte won the title by defeating David Pate 6–4, 6–2 in the final.

## Seeds

* Yannick Noah (second round)
* Jimmy Connors (quarterfinals)
* Tim Mayotte (champion)
* Brad Gilbert (second round)
* Johan Kriek (second round)
* Scott Davis (quarterfinals)
* Christo van Rensburg (second round)
* David Pate (final)

## Draw
### Key

* Q = Qualifier
* WC = Wild card
* LL = Lucky loser
* Alt = Alternate
* SE = Special exempt
* PR = Protected ranking
* ITF = ITF entry
* JE = Junior exempt
* w/o = Walkover
* r = Retired
* d = Defaulted
* SR = Special ranking

### Finals

| Semifinals | Semifinals | Semifinals | Semifinals | Semifinals | Final | Final | Final | Final |
| 8 | David Pate | 6 | 6 | | | | | |
| | Bill Scanlon | 3 | 2 | | | | | |
| | Bill Scanlon | 3 | 2 | | 8 | David Pate | 4 | 2 |
| | | | | | 3 | Tim Mayotte | 6 | 6 |
| 3 | Tim Mayotte | 3 | 7 | 6 | 3 | Tim Mayotte | 6 | 6 |
| WC | Eliot Teltscher | 6 | 5 | 2 | | | | |

### Top half

| First round | First round | First round | First round | First round | Second round | Second round | Second round | Second round | Second round | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Semifinals | Semifinals | Semifinals | Semifinals |
| 1/WC | Y Noah | 0 | 7 | 6 | | | | | | | | | | | | | |
| | P Lundgren | 6 | 5 | 4 | 1/WC | Y Noah | 4 | 2 | | | | | | | | | |
| Q | B Moir | 2 | 6 | 3 | | M Purcell | 6 | 6 | | | | | | | | | |
| | M Purcell | 6 | 3 | 6 | | | | | | | M Purcell | 5 | 4 | | | | |
| | J Grabb | 3 | 2 | | | | | | | 8 | D Pate | 7 | 6 | | | | |
| | P Annacone | 6 | 6 | | | P Annacone | 6 | 2 | | | | | | | | | |
| | B Pearce | 2 | 4 | | 8 | D Pate | 7 | 6 | | | | | | | | | |
| 8 | D Pate | 6 | 6 | | | | | | | | | | | 8 | D Pate | 6 | 6 |
| 4 | B Gilbert | 6 | 6 | | | | | | | | | | | | B Scanlon | 3 | 2 |
| Q | K Evernden | 3 | 2 | | 4 | B Gilbert | 5 | 4 | | | | | | | | | |
| WC | R Leach | 3 | 4 | | | B Scanlon | 7 | 6 | | | | | | | | | |
| | B Scanlon | 6 | 6 | | | | | | | | B Scanlon | 6 | 6 | | | | |
| Q | E Korita | 3 | 4 | | | | | | | 6 | S Davis | 3 | 3 | | | | |
| | S Giammalva Jr. | 6 | 6 | | | S Giammalva Jr. | 6 | 3 | 2 | | | | | | | | |
| | C Steyn | 3 | 2 | | 6 | S Davis | 2 | 6 | 6 | | | | | | | | |
| 6 | S Davis | 6 | 6 | | | | | | | | | | | | | | |

### Bottom half

| First round | First round | First round | First round | First round | Second round | Second round | Second round | Second round | Second round | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Semifinals | Semifinals | Semifinals | Semifinals | Semifinals |
| 5 | J Kriek | 6 | 7 | | | | | | | | | | | | | | | |
| | M Freeman | 3 | 6 | | 5 | J Kriek | 6 | 4 | | | | | | | | | | |
| Q | P Fleming | 6 | 7 | | Q | P Fleming | 7 | 6 | | | | | | | | | | |
| | E Edwards | 1 | 6 | | | | | | | Q | P Fleming | 2 | 3 | | | | | |
| | T Nelson | 6 | 6 | | | | | | | 3 | T Mayotte | 6 | 6 | | | | | |
| | G Donnelly | 1 | 4 | | | T Nelson | 4 | 7 | 3 | | | | | | | | | |
| | D Rostagno | 1 | 1 | | 3 | T Mayotte | 6 | 6 | 6 | | | | | | | | | |
| 3 | T Mayotte | 6 | 6 | | | | | | | | | | | 3 | T Mayotte | 3 | 7 | 6 |
| 7 | C van Rensburg | 6 | 7 | | | | | | | | | | | WC | E Teltscher | 6 | 5 | 2 |
| | K Jones | 3 | 5 | | 7 | C van Rensburg | 3 | 2 | | | | | | | | | | |
| WC | E Teltscher | 6 | 6 | | WC | E Teltscher | 6 | 6 | | | | | | | | | | |
| WC | S DeVries | 2 | 4 | | | | | | | WC | E Teltscher | 6 | 6 | | | | | |
| | G Layendecker | 4 | 3 | | | | | | | 2 | J Connors | 3 | 1 | | | | | |
| | D Goldie | 6 | 6 | | | D Goldie | 1 | 6 | 1 | | | | | | | | | |
| | T Witsken | 7 | 2 | 1$^r$ | 2 | J Connors | 6 | 0 | 6 | | | | | | | | | |
| 2 | J Connors | 6 | 6 | 2 | | | | | | | | | | | | | | |