Birds Ultimate Chicago Trip

Chicago, Illinois

$125 VIP Tailgate

We are SOLD OUT for the full trip, but you can still join us at the tailgate with former Philadelphia Eagle, Hollis Thomas!

VIP Tailgate Party (and World Cup Final Viewing Party) 8:00AM-11:00AM
Our indoor rooftop tailgate has 3 bars, 2 patios, sweeping city views, and amazing food and drinks.  We will be showing the World Cup Final on the TVs and have a great DJ to host the party.
The tailgate party is at VU Rooftop bar and the address is 133 E Cermak Rd, Chicago, IL 60616.
Drinks include:
  • Mimosas
  • Bloodies
  • Miller Lite
  • Blue Moon
  • Goose Island
  • White Claw
  • Well Products
  • Ketel One

Menu includes:

  • Breakfast Sliders
  • Waffles
  • Chicken Sliders
  • Burger Slider Bar
  • Mini Chicago Dogs
  • Roasted Corn
  • Mac & Cheese
  • Roasted Potatoes

*The walk from our tailgate to the stadium is about 15-20 minutes.  Your tailgate pass also includes an optional one-way shuttle from the tailgate to an area close to the stadium.


Week 15 in Chicago!  Could this be the last time that the Eagles play a game at Soldier Field!?

The Philadelphia Eagles play the Chicago Bears on Sunday, December 18th at 1PM which means a noon kickoff!  We have a warm tailgate spot so we can eat, drink, and prepare ourselves for one of those legendary cold days on the South Side of Chicago.  Chicago is one of our favorite cities (maybe #1) to visit and this will be our 4th trip to the Windy City for a sporting event.

This package includes direct flights from PHI with great times, charter bus airport transfers, 3 night stay at a the Hyatt Regency Chicago, upper level game tickets, a Saturday happy hour event, and an all-inclusive tailgate party on game day.  The Hyatt Regency Chicago is a 4-star hotel in one of the best parts of Chicago and is in close proximity to all of the best nightlife.  We will be providing transportation to our tailgate on Sunday morning as well as transport everyone back to the airport on Monday morning.  As usual, we will have multiple onsite Trip Coordinators to make this cold weather weekend a blast for everyone on the trip.


We have great direct flights leaving PHI on Friday afternoon and departing from Chicago on Monday morning.  Book now to guarantee your seat on the best flights available!

Here is the pricing for the trip.  We were inspired by many Eagles fans from outside the Philly area to also add a Self-travel package. The self-travel package includes EVERYTHING except flights and charter bus airport transfers.


  • 1 per room – $1599 per person SOLD OUT
  • 2 per room – $1399 per person SOLD OUT
  • 3 per room – $1299 per person SOLD OUT
  • 4 per room – $1199 per person SOLD OUT


  • 1 per room – $1049 per person SOLD OUT
  • 2 per room – $849 per person SOLD OUT
  • 3 per room – $749 per person SOLD OUT
  • 4 per room – $649 per person SOLD OUT

Why travel with Philly Sports Trips?

We are an IATA accredited travel agency and our trips and events are planned by professionals with a VIP mindset.  Every detail of each trip is carefully planned in advance so you have a stress-free and worry-free experience.  We stay at 4 & 5 star Resorts and Hotels and try to keep the group together as much as possible with Group Flights and Charter Flights.  We have multiple onsite Trip Coordinators for every trip and add as many local experiences to the package as we can.  For the past five years, we have organized and executed dozens of incredible trips in the United States as well as in Mexico and England and hosted unforgettable events such as our 2019 Miami yacht party and our 2021 Magic Show in Las Vegas with former Philadelphia Eagle, Jon Dorenbos.  Our partnership with 97.5 The Fanatic and other local Philadelphia companies helps us to continue to add more value to the customer.

We believe in treating people the right way and exceeding expectations.  We strive to provide premium experiences and are always making small improvements so that the dedicated Philadelphia fans will choose Philly Sports Trips for their next away trip.  Hope to see you on a road trip in 2022.  Go Birds!

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:

TRANSPORTATION Round Trip Flights from Philadelphia to Chicago

HOTEL Three Night Stay at the Hyatt Regency Chicago

TAILGATE All-inclusive Tailgate Party and Welcome Party

TICKET Upper Level Ticket to Philadelphia Eagles vs. Chicago Bears

REFUND POLICY All deposits and payments are non-refundable.

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