Whats the Best Way to Make Flight Arrangements?

Call an airliner that offers a credit card and book directly. For example,Delta and Amex are offering an almost one for one, if you sign up for amex. Other airliners/credit cards are offering similar invectives. My take, if this is one of the few times traveling with your son, invest in it so you can do it again

driving allows for more bonding

southwest

ITA Flight Matrix. But they don’t pull from everyone so search southwest individually on their website (and spirit, frontier if you don’t care about comfort)

https://matrix.itasoftware.com

is the goal, good suggestions here thus far.  Third party sites tend to favor certain airlines though so check Travelocity, Expedia, Priceline, etc. and the airline website too.  Longtime airline employee and I have lots of irrelevant stories to tell.  Pay ahead for any upgrades you are seeking if that's important.  

skiplagged.com

Matrix ita is a great way to find flights and come up with creative itineraries. Google flights is also great bc when you select the outbound date it’ll pop up the round trip price depending on when you decide to return. I’m a frequent leisure traveler and that’s what I use mostly. Skiplagged is also great but you have to be careful and since you’re not overly experienced I would say don’t use that.

Don’t fly Spirit

Where are you flying out of? Sometimes flexibility with airports yields real price gains. I prefer flying out of Duluth, but flying out of MSP can often save me hundreds and I always check for options. Also, Spirit is fine if you accept that you get what you pay for. They're extremely up front about the fact that they nickel-and-dime you for anything beyond a very small middle seat with a personal item at your toes.

There are a few things to think about here.  First of all, what's most important to you? Price. comfort, or convenience?  There are obviously going to be trade-offs involved.

There have been lots of good suggestions on this thread, but one thing I can't emphasize enough: there is no magic bullet.  There is no single best time to buy airfare -- if there were, airlines would immediately change their pricing algorithms to eliminate it.  In general, airfare is seasonal; summer is more expensive than winter for most destinations, and Tuesday, Wednesday, and Saturday are normally the cheapest travel days.

What's far more important, though, is flexibility.  The more dates, airports, and airlines you can consider, the better.  Maybe you're thinking of going to Rocky Mountain National Park.  I'm not sure exactly where you're located, but I gather it's somewhere north of Midland in the LP.  Several of the northern Michigan airports only have Delta service, which drives the price up due to lack of competition.  If you can make the drive to Traverse City, Bay City, Grand Rapids, or Lansing, you'll get more choices.  At your destination, you might find that it's cheaper to fly into Colorado Springs than Denver, so check both.  That's one of the things that Google Flights or matrix.itasoftware.com are really good at -- letting you plug in multiple airports to see what comes up.

Southwest Airlines is not included in those search results -- they fly from Grand Rapids, Flint, and Detroit.  You'll need to search their website separately to get their fares.  They are often a good deal for families, as they include two pieces of checked luggage for free with each ticket.

The other piece of advice I'd give you is to make sure you've included all costs -- baggage, food, seat selection, parking, etc.  Some airlines will charge you extra for using a credit card to book or for failing to check in online (I'm looking at you, Allegiant).  They count on passengers being swayed by the low fare they offer and then making it up on the incidentals.  That goes beyond the flight, BTW -- if you plan to rent a car at your destination, and you have a couple of possible destination airports, it might be worth an extra $20 per ticket on the flight to save $15 per day on the rental car.

Oh, that reminds me -- if you're tall and/or wide, make sure you pay attention to the seat sizing information.  Airlines are offering less and less space between seats -- unless you're willing to cough up extra cash.  If that's important to you, make sure you include those costs in your calculation.

Hope this helps.  Have a great trip. :)

I travel at least one week a month, maybe two. I used to book with Expedia and those type sites but now I book directly with the airlines. I fly all the same routes so I always have the same schedule but when I fly somewhere I don’t go as often I still use Expedia to “shop” for the best deal, airline, schedule, etc but will always book directly with the airline. Why? Because the airlines are much easier to deal with than Expedia when there is a change or cancelation or even asking a question. If you book through one of those sites the airlines won’t even talk to you. I am now doing the same thing with hotels. Also- one other thing I picked up along the way.. airlines like united and American are now offering “basic economy” fares, which is a new bottom tier fare. Basically, you are not allowed to pick your seat or use the overhead bins. If you try to gate check, they charge you double. I always avoid these whenever possible. Hope this helps.

Others have posted about days of the week to book flights. You could also find cheaper fares if you stay over a Saturday night during a trip. It's another way the airlines sticks it to the business traveler who don't like to travel over weekends.

After you book, keep checking the fares. If the fares have dropped, the airline often will credit you the difference in fares.

Delta and Alaska have 20 minute checked baggage guarantee. As soon as the plane is deboarding, check your clock. If the checked bags don't arrive at luggage claim in 20 minutes, Alaska will give you a $25 certificate and Delta will give you 2,500 miles.

 

Seconding the reco for Skyscanner as it's a great app for searching conveniently. Matrix is probably the best but if you want to take a glance at current state of things you can easily peek at the Skyscanner app every now.

If you're just on the look out for great deals on trips (and not married to location), The Flight Deal has some specials I don't always see everywhere else. It's a bit more for the spontaneous traveler and only really useful near major airports; more of an "I want to go somewhere cool in July and I'm flexible on where/open to ideas" type service. This doesn't sound like your trip but thought I'd toss it in while we're on the topic. 

Travel agents are only useful if you just don't want to spend time looking and/or want to hang out with some Russian spies.