Getting ready to travel alone with a preschooler isn't easy, but in this post I help you think about what you need to do to get ready for a great trip!
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Preparing to travel alone with a preschooler

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My 4.5 year old daughter M and I head out to Chicago soon for a fun little daddy-daughter weekend. We plan to spend a night in the city on our own using a Hyatt credit card free night and then will meet up with some friends for the weekend. This will be our third time traveling together alone (fourth if you count my flight with the two kids). Might be the last for awhile since her brother just turned two and I can start taking him on solo trips. Now that we’ve done this a few times, I’m beginning to pinpoint what makes travel alone with kids difficult for me as a dad. So let’s a take a look at what preparations I need to make to travel alone with a preschooler!

Preparing to shoulder 100% of the “mental load”

A coworker shared a comic with me the other day about the “mental load” many moms bear. (By the way, don’t click on it expecting a funny comic like I did! It’s just a straight up essay with pictures – not even any satire 🙁 sadface). The comic introduces this concept of “mental load” in a household. I’ve found this concept very useful and I’ve been thinking about it a lot. Basically, there is a huge burden in keeping track of everything that goes on in a household and while raising children, mentally. Then you put the work of the actual tasks on top of that mental burden and those two things add up to be quite a job. It’s a good concept, in my opinion. Here’s a stay at home dad’s take on it (in response to the original comic). Lifehacker even shared some tips for how to relieve mental load from the more burdened partner

One of the many challenge traveling alone with kids is preparing to shoulder 100% of that mental load. Jess definitely carries more than 50% of the mental load in general, so when I travel alone with the kids I need to mentally psych myself up for taking on her (bigger) percentage completely. What that means for me is mentally going through the various aspects of the trip and calculating the best way to get through them. I’m rarely a planner, but I make an exception for traveling alone with the kids (and Disney World). 

Now if I could offer a word of advice to parents considering traveling alone with their kids: if you don’t know how to shoulder 100% of the mental load at home, you’re in a tough spot if you have to do it on the road. Act accordingly.

Booking flights, hotels, and transportation 

Since we don’t travel as much as we used to, I’ve found my miles and points accounts building. So I’ve quickly learned to adopt Freequent Flyer’s spend cash last mantra. Obviously, I still care about my cents per point value, but I’m always looking to redeem points first. To that end, I booked our outbound using United miles (12.5K per ticket) and our return using Jetblue miles (about 11,000 points per ticket). These are prices I can definitely live with, especially given the constraint I put on our flights. I couldn’t leave too early in the morning and didn’t want to deal with a connection since I’m traveling alone with a preschooler. 

Getting ready to travel alone with a preschooler isn't easy, but in this post I help you think about what you need to do to get ready for a great trip!
Can’t say I’m thrilled to fly the friendly skies again, but gotta do what you gotta do (Photo Credit | Pixabay)

For hotels, I booked the one night I needed at the Hyatt Place Chicago/River North using my Cat 1-4 certificate I get from the Hyatt credit card. While I could have stayed at the Hyatt Regency or even used points to book the Conrad or the Park Hyatt, I don’t need frills when traveling alone with a kid. I just need a good location and I needed to use that free night. Note, I don’t actually think of this night as “free”. I paid $75 (the annual fee) for this room, so about 50% savings. 

As for transportation, I’m not renting a car since we plan to link up with our friends after that first night. To save time, we’re going to Lyft to and from O’Hare, which costs more but M and I only have about 24 hours on our own so I want to make the most of it. I’ll be bringing along our mifold booster – no more bulky car seat huzzah!

Luggage and stroller

M and I will have to duke it out tonight. She wants to bring her Trunki, which we love but I sort of regret ever buying. Is it super cute? Yes. Is it super annoying to deal with a little kid trying to drag that through the airport? Also yes. But I don’t want to bring more than one suitcase, so we might just end up bringing that. Sigh.

Getting ready to travel alone with a preschooler isn't easy, but in this post I help you think about what you need to do to get ready for a great trip!
Teaching independence, I guess.

I also decided that since we’ll be doing a couple of miles of walking each day, I’ll still need M’s stroller. Our Uppababy G-lite has taken a beating over the years, but it’s still ticking and still our favorite stroller to travel with. Small and compact wins the day when you’re traveling.

Entertainment and snacks

Now that M’s older, I’m not super worried about keeping her entertained on the flight anymore. Chicago’s pretty close by, so I’m just running with our tablet (a Nexus 7 from like 5 years ago that I rooted), my phone, her Kidzgear kids’ headphones, some coloring books, and a couple of real books. Shouldn’t be an issue. United also has that personal device entertainment stuff so I might use that on my laptop in a pinch.

Getting ready to travel alone with a preschooler isn't easy, but in this post I help you think about what you need to do to get ready for a great trip!
These Kidzgear headphones have worked great with both our kids

In terms of snacks, I’m just grabbing two small tupperwares with goldfish and crackers – again, shouldn’t be a major issue. 3 hour flights seem like a piece of cake after Hong Kong. If you want to see other stuff I’ve used in the past to keep the kids entertained, I’ve included my favorites on my Family Travel Gear page.


I always like to empty out my wallet before a trip, though that presents some conundrums. What if I find a MS friendly location? What if something goes on sale and I need to buy it online?

My general theory is that vacation is vacation, so I don’t want to be bound by hacking or deals. Still…I don’t like missing deals. One thing I know people do (and I should get around to) is use 1Password or equivalent to store all their CC info electronically, which covers online deals. Generally, I carry whatever card I’m meeting min spend on and a couple of others just in case.

On this particular trip, I’ll probably cut down to three cards: Jetblue Plus card (working on Mosaic status), AMEX Delta Plat business (sign up bonus), and Chase Sapphire Reserve (all around card). I’ll throw my Priority Pass card in there as well for lounge access and call it a day. Hopefully I don’t miss out on any deals, but if I do, hey, I’m spending some quality time with my daughter.

Final Thoughts

I love traveling alone with my kids and can’t wait to take H on his first solo trip in the future. M and I have done this so many times, it’s old hat now. Sure, I may have to take on 100% of the mental load (for one kid, obviously Jess also takes on 100% of the load for H since he’s staying behind), but it’s well worth the experience. I can’t wait to show M “the giant mirror shaped like a bean” and the other adventures awaiting us in Chicago!

How do you prepare to travel alone with your kids? I’d love to hear everyone else’s thought processes/tips/ideas in the comments!

Getting ready to travel alone with a preschooler isn't easy, but in this post I help you think about what you need to do to get ready for a great trip!


Just an average joe trying to fly his family for less

6 thoughts on “Preparing to travel alone with a preschooler

  1. Do you have travel carseat recs? Like, the convertible variety. Only have one right now (Chicco Nextfit) and it’s just way too heavy to bring around via air travel.

    1. We use the Evenflo tribute for travel. It’s no frills but still a major PITA to bring around. We throw it in one of those Jeep car seat bags ($15 on Amazon) and call it a day but it sucks. I hate car seats so much! Boosters are life changing…

  2. That mifold booster looks like a heaven sent! I just got 2 of them. Used Ebates got 2% cash back. Shopped at Bed Bath & Beyond and used their 20% coupon. Paid for the purchase using a gift card purchased through the MileagePlusX App and received 4 United points per dollar. Paid with my SPG card and scored some more points.
    Totals for 2 boosters:
    Ebates cash back – $1.32; BB&B coupon – $16; Total spent = $62.68
    MileagePlus miles = 270
    SPG points = 80

    This is how I turbo boost my mileage/points earning. 🙂

  3. Thanks for this post. The idea of having one parent / one child short trips seem like a good bonding experience. I’ve discussed this with my wife and she likes the idea very much.

    I’d be curious to know your strategy for holding or swapping out Hotel branded Credit Cards. I have the Chase/Hyatt card (recently earning the 2 night stay bonus), but also carry the Amex/Hilton and the Chase/IHG (which I’ve recently passed the first year on and received the free/fee night for usage).

    Some travel sites recommend hanging on to these after gaining the signup bonus for the annual night award benefit (offsetting the annual fee slightly). But is there a point at which you should dump the card, wait for the time period (2 years?) so that you can do a points grab again? Is it worthwhile to do so if you are forfeiting the discounted annual night awards? (e.g. IHG has a huge sign up bonus at the moment, but I’m obviously not eligible as a cardholder). Do you only focus on one brand for loyalty and rotate out other brand cards?

    Thanks for any and all advice. 🙂

    1. I think best practice is to go one year on one year off (or two if need be) and churn the sign up bonuses, but at this point I’m too lazy to do that. But that will give you the most hotel nights not paid for by cash, because you are paying for the free night benefit via the annual fee. If you work in tandem with your spouse you can always maintain status too…but I’m at the point where I’m too tired to game like that. Maybe when the kids are older 😛

      Splitting the team for solo travel is great. Wife and I are looking forward to when we can switch kids heh

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