The Ultimate Chicago Trip To Wrigley Field

Chicago, Illinois

Starting at $1399

Sold Out


Our past two Chicago Baseball Trips were huge successes with our groups and we decided to run it back for a third trip!  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 6/27 – 6/29 and our trip will be from 6/28 to 7/1.  That’s right, we are headed back to Chicago to see the Phillies beat the Cubs at the historic Wrigley Field!  They were 0-6 against the Cubs last year so there will be some revenge coming into the 2023 season.

Chicago will be beautiful in June 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 one of the two games, 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 our previous Chicago trips for many of the group members.  Don’t worry, you will have plenty of time to arrive early to the ballpark for the second game and 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 using public transportation since there is no parking at the stadium and the charter bus company cannot get anywhere close to the stadium.  This has worked out well for us with our previous Chicago trips. Our group will jump on the subway next to the hotel and it’s only a short ride and an 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 Saturday to fly home to Philadelphia.  Not a bad 3 night trip for a die-hard baseball fan.  Everyone who signs up for the Chicago trip will receive a custom T-shirt to remember this once in a lifetime trip.  Let’s go Phil’s!!

Below is the pricing for the trip leaving Wednesday, June 28th and returning Saturday, July 1st.  The self-travel package includes EVERYTHING except flights and charter bus airport transfers.


  • 1 per room – $2099 per person SOLD OUT
  • 2 per room – $1599 per person SOLD OUT
  • 3 per room – $1499 per person SOLD OUT
  • 4 per room – $1399 per person SOLD OUT

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

  • 1 per room – $1599 per person
  • 2 per room – $1099 per person
  • 3 per room – $999 per person
  • 4 per room – $899 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 One Philadelphia Phillies vs. Chicago Cubs Game

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

ROOFTOP All-inclusive Wrigley Rooftop Experience for a Second Game

HOTEL Three Nights at the Royal Sonesta Chicago Riverfront

T-Shirt Custom 2023 Season T-shirt

REFUND POLICY All deposits and payments are non-refundable.

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