The Cubs moved a season-high six games over.500 and picked up their 16th win before May 1 for only the fourth time in franchise history.
The Cubs' five-game winning streak masked the issues, but their offense has been sputtering of late.
The Cubs have won 11 of Lester's last 12 starts on Monday, are 38-17 in his last 55 home outings and have won 39 of his last 58 starts overall.
The Rockies went on top 2-1 with a pair of runs in the fifth inning.
The Cubs came right back in the bottom of the fifth to tie the score 2-2 on an Albert Almora RBI single. Colorado managed just one more run - a third solo home run. Roark (2-2) allowed two runs on six hits, struck out four and induced two double-play grounders for his first win since April 2.
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Both benches were warned in the first inning by plate umpire Jeff Nelson when Colorado's Charlie Blackmon, the second batter of the game, was grazed on the elbow by a pitch from Cubs starter Jon Lester.
After Ian Desmond flied out, Charlie Blackmon blooped an RBI single into center and Arenado hit a tiebreaking double. The left-hander allowed five hits and three walks while striking out five. Yu Darvish will start game three and is 0-2 with a 5.26 ERA and 29 strikeouts this season. He makes his third career start against the Rockies seeking his first win against them.
During the team's five-game win streak, no one talked about how quiet the offense had been. Why? With Colorado's inability to do much at the plate lately, take the Cubs to win this one and take the series.
It was their seventh consecutive game scoring three or fewer runs - the first time in the last six of those that it cost them a game. Chicago's starting pitching is heating up as the rotation has been dominant the last week or so: the rotation hasn't allowed an earned run in the last 33.2 innings of work, the longest stretch by a rotation since the Nationals spun 47.1 frames in 2015. "I said the other day, too, when we were close to.500, I said I'd rather have the record we had but with the growth and certain guys facing some hard stretches and coming out of it and making adjustments that I think will serve them well for the rest of the season. He was missing barrels and making good pitches and that lazy flyball was tough to come by".
Colorado is 1-4 in their last 5 road games and 2-5 in Anderson's last 7 starts against a team with a winning record while the under is 6-0 in their last 6 games overall. With the way Colorado is not hitting at the moment and the way Chicago's pitchers have been throwing, this one seems poised to stay under the total.