Pitch Trips - Chicago 2017


Friday Aug 18

9am - 11am - Meet at the Acme Hotel in the AM to drop your bags, collect your L Pass and Cubs tickets.

1:20pm - Tickets are General Admission in the Budweiser Bleachers, so the earlier you arrive at the game, the better the seats.

6:45pm - Head to Howells and Hood, a 7mn walk according to the Google

7pm - Meet for dinner at Howells and Hood

9pm - After dinner, we will walk across the street to the river pier to Wendella Boats for their Architecture Cruise.

The first two drinks are on us.

10:15pm - Cruise is finished and you’re on your own, but don’t stay out too late, we have an early morning tomorrow.

Saturday Aug 19

Grab a cup of coffee for the road and get on the L Train.

8:15am - Depart hotel and walk one block south to E Grant St for the Grant L train stop.

Take the Red Line north to Addison, it should take you about 15mns.

From Addison, you have a 2mn walk to Gate H, where we will meet for our Private Wrigley Field Tour.

9:00am - Gather for start of tour at Gate H

9:15am - Start of Wrigley Field Tour (Rain or Shine)

10-10:15am - Tour finished, walk north through Wrigleyville to Uncommon Ground, the walk is 5mns

10:30 - Buffet breakfast at Uncommon Ground (buffet means quick and the ability to get back to the stadium)

Head to the game whenever you want

1:20pm - Game start time

What’s Included:

  • Two nights at the hotel in the room you chose
  • Tickets to two games in the Budweiser Bleachers
  • Pitch Talks Chicago Loot Bag
  • CTA 3-day pass for the L Train
  • Dinner at Howells and Hoods
  • Architectural cruise on the river with two drinks (Soft drinks, beer or wine)
  • Private tour of Wrigley Field
  • Brunch at Uncommon Ground


Join the Jays at Wrigley Field

We've finally secured our ticket allotment for our first Pitch Trips offering "The Jays at Wrigley" - August 18-20, 2017. 
We have a limited number of tickets, so we’re taking a first come, first served approach.  

Prices in US dollars and are based on the type of room you choose. 

  • Single $1,055 / person at The Freehand Hotel
  • Twin $850/person at the Acme Hotel (located right next door)
  • Triple $750/person at The Freehand
  • Quad $695/person at The Freehand
  • Penthouse The Freehand also has two Penthouse Suites each featuring a spacious living room and two - one with a king bed, the other with quad beds. The price is $1,055/person based on five occupants. This is a pretty cool space - see pics below.

Trip includes:

  • Two nights accommodation
  • Two games (Friday and Saturday). Bleacher seats. 
  • Cruise on Friday night with beer/wine, and we're hoping to have some of your favourite beat writers join us
  • Tour of Wrigley Field
  • Brunch and a special edition of Pitch Talks
  • Three-day transit pass for the L train
  • Three hosts: Shi Davidi, Kevin Kennedy of Pitch Talks and Chris Tabbitt of Travel Impresarios
  • Services of Pitch Trips (a partnership Travel Impresarios and Homestand Sports)


The deposit to confirm your booking is US$500. It's non-refundable, but you can change the guests in your group. 
Interested? Click below to secure your spot.

Jonah Keri (right) with Len Kasper (left, play-by-play for the Chicago White Sox) and Jason Bennetti (middle, play-by-play for the Cubs) live from Pitch Talks Chicago in 2016.

Jonah Keri (right) with Len Kasper (left, play-by-play for the Chicago White Sox) and Jason Bennetti (middle, play-by-play for the Cubs) live from Pitch Talks Chicago in 2016.

Friday, August 18

  • Catch a morning flight to Chicago. We’ll leave airline arrangements up to you but recommend flying into Midway airport for easier access to the centre of the city.
  • Meet up at the Freehand Chicago. This funky hotel in the River North district is our home base for three days of ball games and exploring. Your host for the weekend, Pitch Talks founder Kevin Kennedy, will be there to set the stage.
  • Take the “ L” to Wrigley Field. The elevated train station is right across the street from the Freehand. And your package will include a three-day Chicago Transit Authority pass.
  • Take in the Jays-Cubs game. We’re planning to have a designated Pitch Talks section for this afternoon game, ideally in one of the best-situated bleachers. Bring your glove.
  • Chicago river cruise. An ideal way to take in the city sights while enjoying post-game drinks, food and conversation.
  • Pitch Talks: Chicago edition. A great evening of insider chat, blending the perspectives of both teams – and no doubt some fresh insights from that day’s post-game interviews.

Saturday, August 19

  • Private tour of Wrigley Field. An up-close look at “The Friendly Confines” (as diehard fans call it), followed by lunch at a pub in the Wrigleyville neighbourhood.
  • Our second Jays-Cubs game. (MLB is finalizing the 2017 schedule), and ideally from a different angle this time.
  • A night out in Chicago. We can give you plenty of recommendations for places to eat, imbibe and enjoy a bit of Windy City nightlife,


Sunday, August 20

  • Discover more of Chicago. After checking out of the Freehand, store your bags and head off to eat, shop and explore the many sights in this diverse and dynamic city.
  • Optional third Jays-Cubs game. We’ll help you get seats for a likely evening start.
  • Catch your flight home. Morning, afternoon or evening – you decide what works best.

Trip Package Recap

  1. Tickets to games on August 18 & 19 (optional third game August 20)
  2. Two nights at the Chicago Freehand hotel
  3. Chicago River boat cruise
  4. Pitch Talks Chicago event
  5. Wrigley Field private tour
  6. CTA three-day transit pass
  7. Airfare is not included