Here is the 1999 Chicago Fire schedule. Please note that all times are CT and that the schedule is subject to change.
| Date | Opponent | Time (CT) |
| Sat. March 20 | at San Jose | 10:00 p.m. |
| Sat. March 27 | at Kansas City | 7:30 p.m. |
| Sat. April 3 | at Miami | 6:00 p.m. |
| Sat. April 10 | Dallas | 7:00 p.m. |
| Sat. April 17 | Los Angeles | 7:00 p.m. |
| Sat. May 1 | D.C. United | 7:00 p.m. |
| Sat. May 8 | at Tampa Bay | 6:00 p.m. |
| Sun. May 16 | Colorado | 4:00 p.m. |
| Sat. May 22 | Kansas City | 7:00 p.m. |
| Sat. May 29 | at D.C. United | 6:30 p.m. |
| Sat. June 5 | at New England | 6:30 p.m. |
| Sat. June 12 | at Los Angeles | 9:30 p.m. |
| Sat. June 19 | San Jose | 7:00 p.m. |
| Sat. June 26 | at Colorado | 8:00 p.m. |
| Fri. July 2 | Dallas | 7:30 p.m. |
| Sun. July 4 | at Dallas | 7:30 p.m. |
| Sat. July 10 | MetroStars | 7:30 p.m. |
| Fri. July 23 | San Jose | 7:00 p.m. |
| Sat. July 31 | Los Angeles | 3:00 p.m. |
| Thu. Aug. 5 | at Kansas City | 7:00 p.m. |
| Sun. Aug. 8 | Colorado | 12:00 a.m. |
| Sat. Aug. 14 | Miami | 7:30 p.m. |
| Sun. Aug. 22 | at Dallas | 12:00 a.m. |
| Wed. Aug. 25 | Kansas City | 7:30 p.m. |
| Sat. Aug. 28 | New England | 7:00 p.m. |
| Sun. Sept. 5 | at MetroStars | 12:00 a.m. |
| Sat. Sept. 11 | at Los Angeles | 9:30 p.m. |
| Fri. Sept. 17 | Tampa Bay | 7:30 p.m. |
| Thu. Sept. 23 | Columbus | 7:00 p.m. |
| Sun. Sept. 26 | at San Jose | 4:00 p.m. |
| Wed. Oct. 6 | at Colorado | 8:00 p.m. |
| Sun. Oct. 10 | at Columbus | 12:00 a.m. |