Cheap flights to a Chicago Cubs home game from Boston

Round trips from Boston from $181. Fly into Chicago (MDW). Cheapest dates, deal ratings and where to book.

• Chicago: $181, 2026-10-10 to 2026-10-13
• Chicago: $190, 2026-10-09 to 2026-10-13
• Chicago: $201, 2026-11-24 to 2026-11-29
• Chicago: $303, 2026-11-11 to 2026-11-15
• Chicago: $332, 2026-12-01 to 2026-12-04
• Chicago: $332, 2026-12-25 to 2027-01-02
• Chicago: $332, 2027-02-01 to 2027-02-04
• Chicago: $332, 2027-03-01 to 2027-03-04

Nearby

• Chicago White Sox
• Milwaukee Brewers
• Detroit Tigers
• Cincinnati Reds
• St. Louis Cardinals
• Cleveland Guardians
• Minnesota Twins
• Kansas City Royals