Chicago and Boston – Wrigley and Fenway

Chicago and Boston

Starting at $999

6 Day Trip SOLD OUT.  3 Day Trip Deadline extended to Sunday, May 9th or until all spots are filled!

The 2021 Phillies’s season is underway and we have an incredible trip planned to see the Phillies play in the two oldest baseball stadiums in America in the same week.  The Phillies play Chicago 7/5-7/8 and Boston 7/9-7/11.  Check out all of the details below.  You can choose the Chicago trip, the Boston trip, or a combined once in a lifetime trip to spend time in both of these great cities.  All details and pricing are listed below!


We are headed back to Chicago in July 2021 after staying there and traveling to Green Bay to watch the Eagles beat the Packers on Thursday Night Football in 2019!  This time we are going for the Phillies to see them beat the Cubs at the historic Wrigley Field.

Chicago will be beautiful in July and there is so much to do in this city.  The Phillies play the Cubs in a four 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.  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.

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 is a similar situation to Boston in 2019.  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 Thursday and either travel back to Philadelphia or on to Boston to extend the trip!!!


The Philadelphia Phillies are headed back to Boston this summer and so are we!  In 2019, we traveled with 100 fans to Fenway and we plan to bring an even larger group in 2021.  July is a great time to be in Boston with weather in the 70s. Perfect Baseball weather.

The Phillies play the Red Sox for a three game series and we have group tickets to the first two games (lower level one night and roof box tickets the next).  We leave on direct flights from PHI (or Chicago if you are extending the trip) on Thursday and check into the beautiful Hyatt Regency Boston in the early afternoon.  We will have plenty of time to check out the Boston Back Bay area and to explore the rest of Boston on Thursday and Friday morning before heading to Fenway Park for Friday night’s matchup.  On Friday, we will also host an all-inclusive Phillies happy-hour party at a great local pub that the group loved in 2019.  We will then head back to the stadium for Game 2 of the series on Saturday afternoon.  Our group will travel to the airport on Sunday and arrive back in Philadelphia by Sunday afternoon.  Not a bad week for a die-hard baseball fan.  Everyone who signs up for the Chicago or Boston package will receive a custom T-shirt and those who sign up for the combined trip will receive an additional gift from Philly Sports Trips to remember this once in a lifetime trip.  Let’s go Phil’s!!


  • 3 Nights 1 per room – $1449 per person
  • 3 Nights 2 per room – $1199 per person
  • 3 Nights 3 per room – $1099 per person
  • 3 Nights 4 per room – $999 per person


  • 6 Nights 1 per room – $2499 per person SOLD OUT
  • 6 Nights 2 per room – $1999 per person SOLD OUT
  • 6 Nights 3 per room – $1849 per person SOLD OUT
  • 6 Nights 4 per room – $1699 per person SOLD OUT

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

Package Includes:

TICKET Group Tickets to Philadelphia Phillies vs. Chicago Cubs Games and vs. Boston Red Sox

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

TAILGATE Two all-inclusive Tailgate/Viewing Parties (One in each City)

HOTEL Three Nights at the Royal Sonesta Chicago Riverfront and Three Nights at the Hyatt Regency Boston

T-Shirt Custom T-shirt and Additional Gift for Combined Trip Attendees

REFUND POLICY All deposits and payments are non-refundable, but due to COVID-19 and the current uncertainty in the world, all payments can be applied to any other future trip. Some partial cash refunds may also be possible depending on the circumstances. We are extremely flexible and have been treating our customers like Family since 2017.

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