Whats the Best Way to Make Flight Arrangements?

There are many good suggestions here, which I won't repeat. But there are a few things I haven't seen so far.

1. Credit Cards. I have both a southwest and united Visa credit card. It ends up giving you free flights now and then. Even for low volume fliers. The other thing, which I have almost never used, is that you get some free vouchers for the executive lounge, or whatever it is called with the United Visa card. This can be important if you are going through a major hub (Chicago, New York, Atlanta, Los Angeles, etc.) and have a chunk of time to chill out.
2. TSA precheck. Again, if you are flying out of the UP, it doesn't matter, but here in Chicago, it can make a huge difference, saving you an hour not standing in line, at peak travel times. You basically don't have to wait in line, take off your shoes, etc.
3. Thinking ahead about bumps. They are getting smarter and smarter about not overbooking. But on one occasion, flying out of Fort Wayne early in the morning and connecting through Detroit to Houston the day before Thanksgiving, my wife and I took three bumps each. We each scored 3 tickets most anywhere in the continental US, which was worth it at the time. Oh, and we were delayed maybe 3 hours max. (hourly flights from DET to HOU.)
4. Legroom. 5 years ago, I was flying from Chicago to Paraguay. As it happens, there are no US carriers at all serving Paraguay. (More remote than Bolivia!) I was offered a seat upgrade for $60 in Miami that would have given me 6 inches more legroom. It would have applied to all legs of the trip. Being frugal, I declined. That was a big mistake. Being 6'3", it would have been worth $60 multiple times to have more legroom. for 8 hours of flying. Which reminds me of something else.
5. Be wise about how cheap you are trying to go. Each of us have our price point. But for me, I've realized that spending $25 - $50 more for a flight that is non-stop, or has more room, or leaves at a more convenient time of day, is definitely worth it. It is one thing to save hundreds of dollars or more. It is another to save $25 and have a lot more grief in return.
6. Dress nice. On several occasions, I have been bumped up to first class, and this isn't because I fly all the time. If you don't look like an unkempt schlub, and are polite, gate agents will sometimes put you in first. It isn't likely, but it will definitely never happen if you don't look like you belong there. On virtually every large flight, the first class seats are the last booked (because they cost so much more.) If you have a reservation for a flight, but no seat assignment, you have a better chance of being bumped up to first (since they have to put you somewhere, and those seats aren't assigned until right before flying.)
7. Be nice. I missed a flight out of Norfolk because I overslept. I called in, and they put me standby on a later flight, but I was literally the first person AFTER every seat was full. Still the gate agents were great. They flew me home business class on American about an hour later, and gave me an additional flight voucher to boot. Pays to be nice.
8. Consider checking your luggage. I hate trying to cram a suitcase in the overhead bin. It is just easier many times to check bags. Then you have much less stuff in the cabin with you. On United and Southwest, I don't pay a dime to check baqs either.

My last ace in the hole probably won't help you. But I have multiple friends and neighbors working for American and United. I have flown using one of their passes (for friends,) and ended up in first class to San Francisco, and to La Guardia. However, I'd advise against this, because you're flying with your son. If you are flying solo, and are a risk taker, can get on a flight that isn't overbooked and is expensive otherwise, using a non-rev buddy pass can be a great way to go.

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Don't ignore smaller airports.  Occasionally there are great deals in or out of them.  I've also seen people claim they were able to get better deals flying internationally flying out of Canada than the US.  Also, as at least one other poster suggested, use whatever search site, Kayak, Google, to find the best deal but purchase through the airline itself (and realize that Soutwest flights are not included in those sites) to avoid possible headaches later.

Southwest does not charge to check bags but most of the other airlines do. I genrally do not check a bag and have found often the airlines that do charge will offer to check a bag for free at the gate.  The only catch is it has to be a carry-on size to begin with, but it can still make travelling easier not having to hassle with an extra bag for connecting flights.  I always make sure my chargers, prescriptions, other essentials are in my small shoulder bag.

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Travel agents will not save you on flights alone. They can help with packages, especially if you have an "experience" like Disney, a safari, a multi-day tour in a foreign city... The one potential exception is Costco Travel (if you are a member, they sometimes give you like a $50 gift card for booking through them).

In terms of flights, use Kayak or Google Flights and then check Southwest (I think the discount airlines like Spirit and Frontier appear in Google/ Kayak's search.

If you have a travel credit card (e.g. Chase Sapphire, Amex...) then they should give you extra points from booking through their site (which is usually a parntership with expedia...

My only other advice is that when you find a flight you like, see if you can get the same price through the carrier's website. It's usually better to book direct than through a 3rd party (e.g. Expedia).

Google Flights and then use the airlines website. What I've found is deals tend to be too good to be true (definitely hide the fees when they advertise them). 

I'm definitely warming up to the use of a travel agent for expensive trips down the road but haven't done it enough to suggest that. Highly doubt a travel agent would give you tips on how to save money though. They aren't getting paid to give people travel tips. 

I use the app Hopper to watch flights, it's a very simple interface which basically says "Wait" or "Book Now".

Additionally, I use SkyScanner.

Since I typically try to book low cost I cycle through the low cost carriers of Spirit, Southwest, and Frontier (out of Detroit) but if my flight is much more than 2 hours long I tend to favor Delta.

Compare two or more, then pick the lowest fare.

Flights of 2 hours or less.  I am 6'3" and yes I am shoehorned in, but when flying with (and paying for) more than 1 person, I am willing to put up with everything to save the money, but only for destinations that are 2 hours or less of flight time.

I encourage as many of you as possible to fly Spirit.  Bring down the demand and make it cheaper for me to fly United with all of the other normal upper middle-class people.

Almost all on business ... If you're an infrequent flyer, and don't anticipate the need for loyalty points/miles, then by all means, use the various sites (like Hopper) mentioned on this thread. However, there are definitely a few caveats:

• Know what the TOTAL cost will be for the flight; airlines (I'm looking at YOU, Spirit) have become very good at charging you for checking a bag, carrying on a bag, selecting seats, and on, and on, and on. Don't just pay attention to the base airfare - it's almost NEVER going to be what you actually pay; you're definitely going to pay more.
• Each airline has a bit of a different approach to its "classes" of service. Some aren't really just classes at all, but rather the degree to which you can make changes to your itinerary without paying steep penalties (or losing your $ altogether). Know the difference between each type of fare; it can be confusing.
• Because you don't have an elite frequent flier status (and I'm assuming that you're not booking first class tickets), you'll have to use the regular TSA security lines. That can add as much as 30 minutes (or longer, depending on the airport and time of day) to the time you need to get to your gate. Also, know the "3-1-1" rule from TSA about which liquids and gels (and how much) you can bring through the security line; bringing a bag full of snacks can also cause you delays if they need to inspect that case of Doritos and egg salad sandwiches your wife packed for you.
• If you have a smart phone, use it to check in for your flight, either with the airline's mobile website or via their mobile app; it can save you some time and prevent you from losing your boarding pass. 
• The boarding process is BY FAR the part of the flight I hate the most. People crowd the front trying to buck the system established by the airline. They're doing it because they want to grab the precious overhead storage space for their carry-ons. That, alone, is a good reason to check your bags, and put small items under the seat in front of you. It'll cost a few $ more (about $25/bag) to check luggage, but it'll give you smug satisfaction as you sneer at the idiots who pretend to "need extra time or assistance in the boarding process."

Have a great trip!

And please, no one get TSA precheck.  The fewer people in my line the better.

So I am thinking about taking my 5 year old to his first game at the big house this fall as well. Ideally I'd like to get 4 seats together.

Does anyone know when season ticketholders receive their tickets and when seats will go on sale to the general public?

Get an Aadvantage credit card, fly American. Get TSA precheck -- you will fly through the TSA lines. Virgin is a good airline, too, but only flies to limited destinations. I know everyone wants to get a cheap flight but I like to get what I pay for, and American is consistently high quality air travel. If you're only flying this one time, go first class. Sometimes it's only a few hundred bucks for the upgrade when you're making the reservation, so don't overlook those seats. Totally worth it. I book on AA.com.

FYI: I've been an American customer since the early 90's. My family of four traveled to Europe in business class a few years ago with miles. Totally worth the few extra bucks you might pay just for that. 

I use Hipmunk and Kayak and set flight alerts. 

Some people sign up for services like Scott's Cheap flights which often offer some insider tips on deeply discounted rates. And if you want to get into the points/redemptions game (beware), The Points Guy is a great resource.

This is a great thread. Lots of good info from people. I don't consider myself a novice but I've learned stuff.

for travel to Canada, it works to get you TSA pre-screening status on the airlines.  Use it all the time.