Fit all of your Luggage in a Carry-On


When flying, we rarely check luggage.  This not only saves us money, but time.  Fitting all your travel items into a carry-on bag can be challenging but once you get the hang of it, you’ll never want to wait for your checked luggage at the airport again.

When we went to Europe for 3 weeks in July 2016 , we both only brought carry-on bags. Since then, we’ve continued to master the art of fitting all of our travel items in a carry-on bag.  On that trip alone, not checking bags saved us approximately $240 in baggage fees (due to flying between cities numerous times).  Moreover, only having carry-on bags makes us much more mobile and reduces the time we spend in the airport. 

Furthermore, we have both previously had luggage ruined and/or lost by different airlines and find we prefer to be in control of our luggage as well.  Trust us–it’s not fun to arrive at your destination or come home to all of your luggage items ruined or lost. 

Disclosure: This article contains affiliate links. That means that, at no cost to you, we may get a small commission if you purchase through these links. This helps us keep providing travel resources for you!


Here are our top 7 tips on how to fit all of your luggage in a carry on:

1. Pick versatile clothing pieces

We recommend sticking to mainly neutral colors so you are able to make numerous outfits out of the same pieces.  Natalie typically packs one or two colorful pieces that serve as an outfit on their own (usually a colorful dress or two) but she tries to really minimize these to maximize space. Try to pack jackets and sweaters that can be used with numerous outfits as well since these tend to be more bulky items. 


2. Set out everything you plan to bring, plan out potential outfits and eliminate excess

Put together all of your potential outfits.  Natalie tries on her clothes with each potential outfit in mind, usually having at least 2 extra options for the total trip.  Natalie will take pictures in each outfit and then eliminate outfits and clothing pieces through this process.  This also makes it easier to pick out outfits on your trip when you already have in mind what you were going to wear.  Sam is not nearly as calculated in his clothing choices while packing but keeps a similar mindset of minimalism. 


3. Use packing squares and roll your clothes

Packing squares will really help you organize your luggage and fit more in your bag.  We typically have 2 or 3 packing squares per bag and find them really helpful for both space maximization and organization.  It is much easier to find items when you have them separated out in different packing squares versus just thrown into your suitcase. We also recommend you roll your clothing (i.e roll all your t-shirts together) to really maximize space. You’ll be surprised by how much more you can fit in your bag when you roll your clothes.  

Use this link for the packing cubes we use: Compression Packing Cubes for Travel, Packing Cube Set (Grey, 5 Piece Set)

Use this link for the compact hanging toiletries bag we use: HaloVa Toiletry Bag. It’s great for space maximization saving you vital extra bathroom space by being able to hang on the door (or elsewhere).


4. Get a bag that will maximize/allow you the most space

We have one bag that maximizes space–an EBag–as well as a normal sized but high quality normal sized–SwissGear– backpack.  Natalie uses the Ebag that is the maximum carry-on size because she always has more items. Sam always does just fine with the smaller normal sized carry on bag. 

EBag and SwissGear Backpack we use

For a heavy packer, we would recommend getting the EBag or another backpack that is the maximum carry on size.  Natalie never flies without her EBag and considers it a game changer when packing.  Beware though, from our experience, the EBag is perfectly sized but not as comfortable wearing for extended periods of time.

Use this link to get your own EBag: eBags Mother Lode Travel Backpack (Solid Black)

Otherwise, if you are a concise packer, using a normal sized comfortable backpack is your best bet.  One with a lot of different compartments may be helpful for organization too, especially if you are doing a lot of moving around on your trip. The one Sam uses even has a USB charging port.

Use this link to get your own SwissGear Backpack: SWISSGEAR 5358 ScanSmart Laptop Backpack |BONUS TSA Lock Included| Fits Most 15 Inch Laptops| USB Charging Port


5. Wear your largest items

On the plane, if you are trying to maximize carry-on space, plan to wear your largest coat and hiking boots (or bulkiest shoes).  You can always take your bulky coat off when you get on the plane. Bonus–it’s nice to have your coat on the plane if you are cold or want to use it as a blanket. 


6. Remember, you get one personal item in addition to your carry on.  Maximize this! 

It still needs to fit under the seat in front of you but you can essentially bring another small backpack, duffel bag or large purse.  Sam typically brings a small duffel bag that can be collapsed down if not being used and Natalie brings a large purse.   We have learned how to fit a lot into these bags as well and it is nice to have the extra space if you buy something.  

Use this link to get the bag Natalie uses: Tom Clovers Crossbody Bag. This purse is a Mary Poppins bag with how much you can fit in it!

If you are looking for a smaller versatile purse, this is the one Natalie uses: Travelon Anti-theft Heritage Crossbody Bag, Pewter. This bag is great for traveling as it has built-in security with it’s locking zippers and anti-slash technology.


7. Don’t forget to weigh your carry on

Check maximal weight for carry ons on each airline you will be flying with. Many airlines will not weigh carry ons. However, if they do, you do not want to be stuck checking a bag because it is overweight. The easiest way to check the bag’s weight is to step on your scale with/without the carry-on and do a little math.

Bonus tip: Be mindful of items that are allowed in a carry on versus require checking a bag. Pay special attention to liquid sizes. This mindfulness should apply to souvenirs you may purchase to bring back with you. Avoid getting stuck checking a bag or having to throw out a purchased item.


We hope this post helps you fit all of your items into your carry on luggage.  Any tips you’d add to our list?  We’d love to hear your feedback or questions.  Please leave us a comment!

And remember, Always Have A Trip Planned!

5 Ways to Save on Flights


Who wouldn’t want to know how to save money on flights? Throughout our travels, we have really learned how to save on airfare.  We have particularly gotten good at saving money on international flights.  Typically, we pay less than $500 per person round trip to any major city in Europe but that wasn’t always the case. Here are our top five airfare savings tricks.

Fun Fact: We met on this very puddle jumper plane in 2013 and have never stopped traveling together since.

Disclosure: This article contains affiliate links. That means that, at no cost to you, we may get a small commission if you purchase through these links. This helps us keep providing travel resources for you!


1. Be Flexible with Location and Time 

Be flexible on your location and timeframe to save on airfare for flights.  For our first Europe trip, we grossly overpaid for our flights because we could only go on certain dates and we had specific locations picked out.  We do not regret that we bought these tickets for this timeframe (because it was an amazing once-in-a-lifetime trip) but if we had more flexibility, we would have saved a lot on our flights. 


Make a List of 3-5 Potential Trip Locations

Now, instead of picking out certain dates and locations, we pick a handful of places we want to go and determine what location is most cost effective during the time we plan to travel.  There are so many cool places to explore in this world that you always have options.  For example, we planned to go to Hawaii in March of 2019 but flights were $900+ roundtrip per person so we decided to go to Spain and Portugal instead when we found flights for $450 roundtrip per person.  We also try to be flexible with the days we travel.  For example, leaving on a Tuesday instead of a Thursday might save you $100+ per person. 


Use Google Flights to Compare Different Dates/Locations

We typically use Google Flights to search for airfare and then use the links provided on there to book flights.  Google flights is the most user friendly and straightforward platform we have used, making it easy to compare airfare costs on different days of the week. We would not recommend other websites such as SkyScanner and Mumondo to search for flights as we find them quite frustrating to use. Although these websites may show airfares that are about $50+ less per person than Google Flights, there is usually a catch to these prices, such as extra fees that are not shown until checkout. Also search in private browsers at first to avoid any “perceived” price adjustments that occur after the internet knows you are searching.


2. Subscribe to Scott’s Cheap Flights

This is a service you can subscribe to for free that will send you alerts about flights that are on-sale and mistake low fares.  The emails will list general flight patterns from different cities that are on sale and general dates.  You then have to go on Google Flights and see what dates the sales actually apply to. We always get the emails and then do Google Flight searches for days we know we are off/could potentially use the airfare. Flights deals typically only last for 48 hours or less and you need to be ready to book ASAP with these alerts because the deals can go away at any time.

We have used this free service to book 3 trips to Europe for $400-$500 per person round trip from Chicago (typically flights $850 + per person round trip).  We have found the free version alone to be very helpful but there is also a paid option for the premium version of Scott’s Cheap Flights that gives you access to exclusive flight deals not offered to free subscribers, particularly on domestic deals. The premium version is definitely worth the money if you are doing a lot of traveling in one year as you will typically save over $100/flight.

Use this link for a FREE 2 week trial of Premium Scott’s Cheap Flights


3. Don’t Check a Bag (if it’s not included)

 Not checking a bag will not only save you money, it can cost upwards of $60 per bag (if it is not included in your fare), but it will also save you time at the airport and we all know the saying, “time is money”.  We have had some terrible experiences with our luggage getting damaged and/or lost and try to avoid checking a bag as often as possible.  It costs more and is more of a hassle. See post on How to Fit all your Luggage in a Carry-On. (Coming soon!) 


4. Don’t Upgrade

Are those couple of extra inches or centimeters really worth hundreds of dollars in upgrade costs?  Chances are, you are still going to feel cramped.  We have never flown anything other than economy and we have survived.  Some people tell us they “have to” upgrade but this is a preference, not a need.  We could plan another overseas trip with just the money we have saved not upgrading our flights.  


5. Check Numerous Airports

If you are close to numerous airports, it makes sense to check several airports.  For example, we live in Milwaukee but typically fly out of Chicago O’Hare because it is less expensive due to it being a much bigger flight hub.  However, we always check flight options/costs out of Chicago O’Hare, Chicago Midway and Milwaukee Mitchell International. 

On our Trip to Morocco, it was actually less expensive and took the same amount of time to leave from Milwaukee Mitchell International when comparing it to Chicago O’Hare.  Also, check different arrival airports. When we went to London, flights were $400+ less per person flying into the less frequented Gatwick than the more popular Heathrow airport.  Both airports are located relatively equidistant from the city center so it made more sense to fly into Gatwick rather than Heathrow. 


We hope this post helps you save on flights and start your next adventure.  Another great way to save while flying is to not check a bag. Please see How to Fit all your Luggage in a Carry-On for more savings tricks.

Do you have any other tips on how to save on flights? We’d love to hear your feedback or questions.  Please leave us a comment!

And remember, Always Have A Trip Planned!