Don’t book the cheapest flight

When I think about traveling with small children, I’m often reminded of the title of a David Foster Wallace book — A Supposedly Fun Thing I’ll Never Do Again. 

Travel with kids can be tough. It can be frustrating. It can also be fun and entertaining if you approach the trip with the right mindset: “I’m open to change and I can see the humor in life’s absurdities!” 

The good news is, traveling with babies can actually be a gentle introduction to the world of traveling with your kids. Yes, she might wail during takeoff. You might have to change a diaper in your seat when the flight attendant refuses to let you in the bathroom. (The “fasten your seatbelt” light is always on when a diaper emergency arises.) You may find yourself nursing your child while waiting in the security line. 

However, babies are also magnificently portable — simply pop little Owen into your Ergo and waltz onto the plane in style. They’re highly unlikely to wrestle themselves out of your arms and go scampering off in the general direction of the moving walkway. They can’t use their words to refer to a fellow passenger as a “stupid old lady.” 

The travel habit 

Traveling with a baby, especially for first-time parents, can be a bit overwhelming as you come to realize what “shifting your priorities” really means. But I truly believe it’s good to travel with your children — whether it’s a road trip to Red Wing or a flight to the Caribbean — if only to instill the travel habit in your family. 

In an earlier column, I wrote about my suggestions for traveling with your baby (Bring earplugs! Don’t forget the sound machine!), and I still stand by those suggestions. 

But that approach is primarily focused on the baby, and how to integrate the baby into your trip. Now I’d like to offer some ideas about how you, the parent, can approach family travel to increase the odds you’ll have an enjoyable experience, too. 

Scheduling flights 

I’m not a wealthy person. In my days pre-baby, this meant I would always book the cheapest flight I could find. Eight-hour layover in Newark on the way to New Orleans? Sold! 

Once you add a baby to the mix, you might want to rethink the “cheapest flight” strategy. Do you really want to wake up your child at 3:30 a.m. to make that early-morning flight? Is a lengthy layover really worth the $100 you save?

As a parent, I’ve experienced both ends of the spectrum (cheap-but-inconvenient vs. suck-it-up-and-pay-for-a-direct-flight), and I would highly encourage you to consider sucking it up, if your finances allow. 

Calmly sauntering onto an early afternoon flight (which your baby will hopefully sleep through) is just so much better for your well-being than staggering into the airport at 4:30 a.m., irritated baby in tow. 

A room of your own 

You know what I used to hate? Those soulless, suburban hotels I had to stay in when I went on business trips. 

But like so many parents before me, I’ve compromised my principles and chosen to embrace the hotel suites on the edge of town due to their family-friendliness. 

You know those quaint, historic hotels you used to patronize when you were childfree? They don’t have a separate room with a TV, a couch and a minibar where you can hang out with the lights on while your baby sleeps in the other room. 

So when you plan your next trip, definitely prepare in a way that gives your baby the chance to succeed (bring along her “sleep associations,” like special blankets, for example), but don’t forget to make plans that support your own comfort, too. 

Because we all want to come back from a trip thinking, “That’s a totally fun thing I’d like to do again.” Right?

Shannon Keough lives in Minneapolis with her husband and two kids. Send questions or comments to