Trip Length - I've scheduled multiple games, usually three, on all my trips. If you schedule three games in three days, you save time and money. You only have to take four flights to see three games. It's even less if you schedule cities close enough to each other to drive or take the train. I took three flights to see five games last year and will do the same in April. If you saw only one game on each trip, you take six flights to see three games.
I cluster cities that are close together. This can be valuable for a few reasons. First, there are some cities that are expensive to fly to, but driving or taking the train might be a lot less expensive. Also, flights will be cheaper if you fly to Pittsburgh from a closer city. Even heavily traveled cities will be cheaper to fly to if you're flying from one nearby. Dallas to Houston is only $79 on Southwest. Minneapolis to Houston is going to cost you more if you pair those cities. Of course you cut out flights and save yourself a lot of money if you can schedule San Francisco and Oakland on back to back days. You're also killing yourself a bit less. And if you're trying to see a game a day, you will have times when you're waking up early and rushing to get to the next city.
By scheduling three games over a weekend, I miss a minimal number of work days, something vital when you work on a contractual basis as I do. Weekend trips also allow me to go to three games with only two nights in a hotel. I always schedule the first game on a Friday night and start with the furthest city, although it's usually one where there's a non-stop from Los Angeles. Sometimes it's impossible of me to get to a day game if I fly out of Los Angeles in the morning. Why fly the day before, skipping an additional day of work, just to sleep in a hotel room? I also schedule the last game of the trip on a Sunday afternoon. I'm not doing this in New York, because I'm going to a day and night game in the same day, but I am doing it in St. Louis, Houston, and Oakland. If I pick the city carefully I can find a non-stop to Los Angeles leaving after 6:30 PM. So I don't have to spend an extra night in a hotel and then miss work the next day.
Air - I've mentioned this before but choose non-stops if you can. If you fly on two planes that doubles your chance one will get delayed. If you're delayed you might miss the game. A trip with a stop over will also add 2 hours to your travel time. I'm starting my April trip in Boston. If I didn't take a non-stop there's no way I'd be able to make it into Boston and see a game the same day. Of course seeing a game every day of your trip may mean an early morning flight. You might have to do this if there's a distance between cities or because that's the only non-stop to the next city. The upside of flying that early is that you know you'll be early for the game.
Your first flight might be a long one across country. So try to get in to the city as early as you can. You can always relax in the hotel if you're that early. But you don't want to arrive so late that a small delay could cause you to miss the game. Your flight to you second game gives you a lot of leeway if it's a night game. If it's a day game, however, you could end up on a tight schedule. Sometimes the first non-stop, especially on a weekend, doesn't leave until later in the morning. I may be tight flying in from Seattle to San Francisco. It couldn't be helped.
You might not have any choices on you last flight on Sunday night, or Monday night if it's a holiday weekend. When I'll be flying from Houston to Los Angeles on Sunday, July 13, I need to choose a flight leaving after 6:30 PM so that I can see the whole game. Sometimes that flight might not exist. Fortunately, such a flight does that'll get me into LA at 9:30 PM. But there's pretty much two choices, Southwest and United. Take this flight even if it's pricey. The alternative is to spend $150 on a hotel and fly in the morning. If you do that, you'll probably spend more anyway and miss a half day/day of work.
Try to schedule the first game in an airline hub city. This is a city where the airline flies a lot of flights into and out of. You know you'll find non-stops going in and out, even to a non-hub city. So I'm starting one trip in Minneapolis, a Delta hub. Then I'm going to Kansas City. It's not a hub, but since Minneapolis is there's a non-stop. Then I finish in St. Louis. Kansas City and St. Louis are so close that Southwest flies non-stop. St. Louis isn't a hub, but there is a Sunday night non-stop to Los Angeles on American. So I'm fortunate there.
Hotel - You're not traveling to see the sites or going for the amenities. You're looking for a clean comfortable place to sleep. In some cases, you'll get to the hotel, go to bed, wake up the next morning, and then check out. You might not be there long enough to turn on the TV. So you don't need a lot if you're doing that. What's more important is the location of the hotel and if they provide airport shuttle service. There are two locations that you should likely choose, near the airport or near the ballpark.
Near the airport is good because you'll likely get a free shuttle from the airport to your hotel and back. You can spend the $40-50 you'd spend on a Super Shuttle elsewhere. If you have an early morning flight, staying by the airport means you won't be delayed getting there and you can sleep an extra half hour. When looking for an airport hotel, check to see if it's near public transportation that'll take you to the ballpark. That's key if you're not renting a car.
The advantage of staying near the ballpark is that you don't have to worry about parking at the stadium and you're not trying to get to your hotel at 11 PM at night. Most stadiums don't have hotels within walking distance, however, although those that do are very attractive. Shout out to the Hilton Baltimore. If you're going to have to take public transportation it may be best to stay near the airport if public transportation can get you to the game from there.
Getting to the game - This should actually come before you choose your hotel. How will you get to the game? In most instances you'll be arriving in the city on the day of the game. In some cases there's public transportation to the game. You can get to games in Seattle, New York, and Baltimore, among others, on public transportation easily. So map this out well. In some cities, that isn't so easy. I may be wrong, but there doesn't appear to be any public transportation from the airport to the ballpark in Houston and Kansas City.
In those cases, it may make sense to rent a car. You can probably get one for $30-$40 a day, although taxes in some cities can be prohibitive. Sure, you'll have to pay for parking at the ballpark, unless you're lucky like I was in Cleveland, but overall you might not spend more than you would on two Super Shuttle rides. And once you've taken the Super Shuttle to your hotel, how will you get to the game? There are nice advantages to renting a car. I'm looking at a trip where I'd get to St. Louis within an hour of the game. I could get caught between buses and have to wait 15 minutes for the next one. And a car ride will likely take half the time the bus will.
Your bags - Major League Baseball won't allow you to bring your suitcases to the game and really why would you want to carry around that bulky thing when you go to the concession stand? So what can you do? If you have a rental car, this is easy. You just put them in the trunk. If you don't, one option is to leave your bags at your hotel. Even if you've checked out, they should be okay with you doing that. If your hotel is near the ballpark or airport that shouldn't add too much time to your trip. If it's not, however, you might not have time to go back to the hotel after the game. Thus, scheduling arrive, go to game, stay overnight, and catch a flight is the best way to go. The problem can be your getaway day when you're going to game and then leaving. If you can't leave your suitcase at the hotel or in your car, consider checking it in at the airport before the game. That's my plan for Oakland.
