Destination · Chicago, Illinois

Chicago in May 2027: What's Already on the Calendar

Baseball, the symphony and the river tours: what is already scheduled for the weekend of May 7 to 9, 2027, and what to book first.

Facts checked November 14, 2026

Chicago in May 2027: What's Already on the Calendar
Photo: Sightseeing Boat, DuSable Bridge and Chicago River (49713551202).jpg by Matt Kieffer from London, United Kingdom, CC BY-SA 2.0, via Wikimedia Commons. Resized.

Chicago in early May is a city waking up for summer: the river tours are running, the ballpark is open and the concert season is still going. If you are looking at the weekend of Friday, May 7 to Sunday, May 9, 2027, a surprising amount is already on the calendar.

What is already scheduled

Date What Status when checked
Fri May 7 to Sun May 9 Cubs vs. Seattle Mariners at Wrigley Field Dates announced; game times not yet set
Thu May 6 to Sat May 8 Chicago Symphony Orchestra: Honeck conducts Mahler and Bruckner 9 Listed, from $39 including fees
Sun May 9, 3:00 PM Piotr Anderszewski piano recital, Symphony Center Listed, from $39 including fees
Sun May 9 Mother's Day in the US Plan around busy brunch tables and a busy ballpark

What to book first

  • The river cruise. The Chicago Architecture Center's 90-minute cruise aboard First Lady explains the buildings you will see all weekend. Its tickets have no refunds or exchanges, so book once your flight is firm.
  • Sunday brunch. With Mother's Day on May 9, book the day reservations open.
  • A rainy-day backup. Garfield Park Conservatory strongly recommends advance reservations.

Getting around

  • The CTA Blue Line runs from O'Hare to downtown in about 40 to 45 minutes.
  • A CTA 3-Day Pass costs $15 and covers 72 hours from your first ride, including the train from O'Hare.
  • Millennium Park is open 6 a.m. to 11 p.m. daily. Its Crown Fountain usually starts running in May; the exact 2027 date was not posted when we checked.

Book the boat and the brunch first, and let the rest of the weekend fall into place.

Sources

Read on November 14, 2026. Dates, times and prices can change; check the source before you buy.

  1. Chicago Cubs 2027 schedule announcement (Cubs Media Relations, Jul 16, 2026)
  2. Chicago Symphony Orchestra: Honeck Conducts Mahler & Bruckner 9
  3. Chicago Symphony Orchestra: Piotr Anderszewski, May 9, 2027
  4. Chicago Architecture Center: River Cruise aboard First Lady
  5. City of Chicago: Millennium Park, Plan Your Visit
  6. Garfield Park Conservatory: Visit
  7. CTA: Fares
  8. CTA: Airports (O'Hare and Midway)

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