Philly Sports Trips: Chicago 2020

Thursday, April 23, 2020

Chicago, IL

Starting at $599


We are headed back to Chicago in April 2020 only 7 months after staying there and traveling to Green Bay to watch the Eagles beat the Packers on Thursday Night Football!  This time we are going for the Phillies and to see them beat the Cubs at the historic Wrigley Field.

Chicago will be beautiful in late April and there is so much to do in this city.  The Phillies play the Cubs in two 2:20PM day games on Friday, April 24th and Saturday, April 25th and we have group tickets to both games.  This package includes direct flights from Philadelphia to Chicago, charter bus airport transfers, a 3 night stay at the Wyndham Grand Chicago Riverfront, your group tickets to both games, and two all-inclusive tailgates.

After our three full days in Chicago, our group will travel back to the airport on Sunday and arrive in Philadelphia on Sunday afternoon.  Wrigley Field is one of those stadiums that every baseball fan must see for themselves.  This is truly an unforgettable trip for Phillies’s fans of all ages.

Below is the pricing for the trip.  The self-travel package includes EVERYTHING except flights and charter bus airport transfers.

Direct Flights (Thursday 4/23 to Sunday 4/26)

American Airlines PHI to ORD – Leave Thursday morning,  Return Sunday morning


  • 1 per room – $1199 per person
  • 2 per room – $799 per person
  • 3 per room – $699 per person
  • 4 per room – $599 per person


  • 1 per room – $1549 per person
  • 2 per room – $1149 per person
  • 3 per room – $1049 per person
  • 4 per room – $949 per person

Reserve your spot now! E-mail us with any questions.

Trip Includes:

TICKET Group Tickets to Friday and Saturday Philadelphia Phillies vs. Chicago Cubs Games

TRANSPORTATION Round Trip Non-stop Flights from Philadelphia to Chicago

TAILGATE Two all-inclusive Tailgate Parties

HOTEL Three Nights at the Wyndham Grand Chicago Riverfront