New York to Chicago: August 18-28, 2027
Wed, Aug 18: Check In
Thu, Aug 19: Little League World Series in Williamsport, PA
Fri, Aug 20: Guided Tour of NYC and Texas Rangers at New York Yankees 7:05
Sat, Aug 21: Free Morning/Afternoon in Manhattan
Sun, Aug 22: Pittsburgh Pirates at Boston Red Sox 1:10
Mon, Aug 23: Baseball Hall of Fame in Cooperstown, NY
Tue, Aug 24: Chicago Cubs at Pittsburgh Pirates 6:35
Wed, Aug 25: Football Hall of Fame in Canton, OH
Thu, Aug 26: Houston Astros at Chicago White Sox 1:10
Fri, Aug 27: Atlanta Braves at Chicago Cubs 1:20
Sat, Aug 28: Check Out
Download Registration Form Here
Single: $4,400, Double: $3,600/person, Triple: $3,400/person, Quad: $3,200/person
Why is this tour better than others? First 3 nights are at the same hotel near the Newark Liberty International Airport. After our free morning/afternoon in Manhattan August 21, we will travel to Natick, MA (20 miles from Boston) for the first of 2 nights in the same hotel for your comfort and convenience. The final 2 nights of the tour are at a Hampton Inn near the Chicago O’Hare International Airport. Many other trips have you in and out every night but not this one. We see and do a lot of “bucket list” items, but it’s convenient, too.
Wednesday, August 18: Check in at our hotel near the Newark Liberty International Airport at your convenience. The hotel offers free shuttle service. There is a restaurant next to the hotel if you arrive early and would like an evening meal.
Thursday, August 19: We will depart this morning from two Little League World Series games (one international game and an American matchup) in Williamsport, PA and return to our hotel that evening.
Friday, August 20: A local tour guide will show off Manhattan. You will get to walk in part of Central Park, get a view of the Statue of Liberty with free time at Battery Park, and walk to the 9/11 Memorial Pools (site of Twin Towers), and more. You won’t just see the city from the bus. After the tour, we will arrive at Yankee Stadium for the Yankees/Rangers game. We will return to our hotel after.
Saturday, August 21: We will depart our hotel at 10:00 a.m. and travel to Times Square. We will drop off near Broadway and you will have a free afternoon to do whatever you would like. Want to attend a Broadway Matinee Play? No problem. Want to shop until you drop? Go for it. Want to go to the top of the Empire State Building? You can do it or anything else you’d like during this chunk of free time in Gotham City! That evening we will travel to Natick, MA for the first of two nights in the same hotel.
Sunday, August 22: We only have a 20-mile drive to Fenway Park to watch the Red Sox host the Pirates. We’ll arrive early so you can experience the atmosphere at the oldest park in baseball. After the game we will return to our hotel. There is a nice sports bar restaurant connected to the hotel for a convenient evening meal.
Monday, August 23: You will have between 4 and 4.5 hours of free time to explore the Baseball Hall of Fame and all of the quaint little baseball shops and restaurants in the Village of Cooperstown.
Tuesday, August 24: We will travel to Pittsburgh with a stop for lunch and a pair of rest breaks on the way to get to what many claim (me included) is their favorite ball park in baseball; PNC Park. The Pirates host the Cubbies this evening.
Wednesday, August 25: We’ll make the short drive from our hotel near Pittsburgh to the Pro Football Hall of Fame in Canton, OH. You will have between 3 and 3.5 hours of free time to visit the museum and have lunch at many of the restaurants next to it.
Thursday, August 26: This is the only day of the tour where our schedule isn’t already set in stone. The White Sox game is probably going to be at 1:05. If that’s the case, we will go to the game and travel to Navy Pier for free time after. If the game is at 7:05, then we will simply go to Navy Pier for lunch and have free time until it’s time to go to the game. That night we will be checking into our hotel for the first of two nights near the Chicago O’Hare International Airport.
Friday, August 27: We will depart our hotel and travel 15 miles to Wrigley Field. We will get there at least 30 minutes before the gates open so you can experience Wrigleyville prior to entering the Friendly Confines. After the game we will return 15 miles to our hotel to conclude the tour.
Saturday, August 28: Although the tour is over and it’s time to fly wherever home is – you’ll have made great memories to last a lifetime!
