Chicago Baseball Trip: Wrigley Field

Tuesday, September 27, 2022

Chicago, Illinois

Starting at $1199

Sold Out


The 2022 Phillies’s season is underway and we have an incredible trip planned to see the Phillies play in the second oldest baseball stadium in America.  The Phillies play the Chicago Cubs 9/27 – 9/29 and our trip will be from 9/27 to 9/30.  That’s right, we are headed back to Chicago to see the Phillies beat the Cubs at the historic Wrigley Field in the second to last week of the 2022 season (Playoff push time!).  Last summer’s trip to Chicago with over 100 Phillies fans was a big hit so we decided to go back this season!

Chicago will be beautiful in September and there is so much to do in this city.  The Phillies play the Cubs in a three game series and we will have excellent group tickets to two games.  This package includes direct flights from Philadelphia to Chicago, charter bus airport transfers, a 3 night stay at the Royal Sonesta Chicago Riverfront, and your group tickets to both games.  For the first game, we will be renting out one of the best rooftops right outside the stadium with all-inclusive food and drinks!  Watching baseball from the rooftops surrounding Wrigley Field has been a tradition since the ballpark opened in 1914.  This was the highlight of the 2021 Chicago trip for many of the group members.  Don’t worry, you will have plenty of time to arrive early to the ballpark on night two to walk around and check out the stadium. Our on-site coordinators will also assist with anything you need during the trip.

The Cubs highly recommend to use public transportation since there is no parking at the stadium and the charter bus company cannot get anywhere close to the stadium.  This worked out well for the group that went to Chicago in 2021.  Our group will jump on the subway next to the hotel and it’s only a short ride and additional 5 minute walk.  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.

After our three full days in Chicago, our group will travel back to the airport on Friday to fly home to Philadelphia.  Not a bad week for a die-hard baseball fan.  Everyone who signs up for the Chicago trip will receive a custom T-shirt and an additional gift from Philly Sports Trips to remember this once in a lifetime trip.  Let’s go Phil’s!!

Below is the pricing for the trip leaving Tuesday, September 27th and returning Friday, September 30th.  The self-travel package includes EVERYTHING except flights and charter bus airport transfers.


  • 1 per room – $1799 per person
  • 2 per room – $1399 per person
  • 3 per room – $1299 per person
  • 4 per room – $1199 per person

3 NIGHT SELF-TRAVEL PACKAGE (without flight and airport transfers)

  • 1 per room – $1399 per person
  • 2 per room – $999 per person
  • 3 per room – $899 per person
  • 4 per room – $799 per person

Reserve your spot now! E-mail us with any questions.  Event will take place rain or shine.  Trip details and pricing are subject to change.

Package Includes:

TICKET Group Tickets to Two Philadelphia Phillies vs. Chicago Cubs Games

TRANSPORTATION Round Trip Non-stop Flights from Philadelphia to Chicago and Airport Transfers

TAILGATE All-inclusive Tailgate Party near Wrigley Field

HOTEL Three Nights at the Royal Sonesta Chicago Riverfront

T-Shirt Custom 2022 Season Phillies T-shirt

REFUND POLICY All deposits and payments are non-refundable.

Philly Sports Trips is the Official Fan Travel Partner of the Philadelphia Union