Extended Layovers: One Ticket, Two Destinations

Double the Fun

by Portia O'Laughlin
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Portia O'Laughlin, extended layovers


I typically dread extended layovers and purposely avoid them. Who wants to sit in an airport for hours with restless kids? I prefer a simple direct flight, especially when traveling with children. But recently, I noticed an opportunity and put an extended layover to the test. The right length extended layovers can add tremendous value to your short trip by providing an opportunity to explore two destinations for the price of one. Wander with me and discover how to turn layovers into mini-vacations and realize a little more out of your travel budget.

extended layovers

(Photo by Portia O’Laughlin)

My Experience: Chicago to New Orleans via Denver

Initial Plan:  During my routine visit to Chicago, I was on the hunt for an extended experience on my way back to Orlando. Initially, nothing looked quite right until I found a flight to New Orleans with an 18+ hour layover in Denver. This was the perfect opportunity to finally return to Denver after 28 years, to say I was excited was an understatement.

(Photo by Portia O’Laughlin)

Execution: The timing was perfect. Our plan was off to an amazingly synced adventure with an early morning stop in Chicago and right back out in the evening to get into Denver by midnight. I picked a hotel that was about 25 minutes from the airport but also 45 minutes from where we were headed in the morning so we could enjoy a good night’s rest and a short day of exploration before continuing to New Orleans the next afternoon. This short stopover allowed us to experience a tiny slice of Denver, making the most of our travel time and budget.

Flexibility is Key

Everything doesn’t always go according to plan so it’s highly important to have a plan and a contingency plan just in case.  For instance, I did not anticipate two huge delays that evening.  The first was the wait for an airport shuttle.  We arrived on time and made it to the shuttle for a Budget rental car pickup but waited almost an hour for one to finally arrive.  You can imagine how tense things had become in that time as many people were standing around waiting and everyone wanted on that shuttle when it came.

The second delay was that we didn’t actually get out of the airport until about 2:15 AM as they were short staffed and the line of people to service was very long.  Normally, being a Budget member would’ve saved me as I should’ve been able to use FastBreak and just go get my rental but they weren’t prepared. I knew this delay would offset our morning departure since the kids would be very tired now. There are only so many things within our control so we simply adjust the plan and keep moving forward.

(Photo by Portia O’Laughlin)

Benefits of Extended Layovers

Budget-Friendly

This approach stretches travel budgets, allowing you to experience more without the extra cost of separate trips. By strategically choosing flights with long layovers, you secure two destinations for the price of one.

Adventure and Excitement

It’s like your own segment of The Amazing Race, the thrill of a new destination without the pressure of extreme challenges. Each layover becomes an exciting mini-adventure, adding layers of fun to your journey.

Breaking Up Long Journeys

Long flights can be exhausting, especially with kids. Extended layovers provide the break you need, giving everyone a chance to see something new, explore, and recharge before the next leg of the journey.

extended layovers

(Photo by Portia O’Laughlin)

Planning an Extended Layover Trip

Finding the Right Flights

Look for flights you’ve been skipping due to long layovers—they often have the best prices. Ensure the layover duration allows for meaningful exploration, not just a night in a hotel room.

Logistics and Accommodation

Before committing, research potential accommodations, transportation options, and proximity to key attractions. Prioritize one main activity to maximize your time and lessen stress. Check for hotels offering late check-in and free parking to streamline your stay.

(Photo by Portia O’Laughlin)

Tips for Family Travel During Layovers

Family Needs

Consider how manageable an extended stopover will be for your family. For solo travel with my 9- and 11-year-olds, who are seasoned travelers, it was fairly easy. We packed light and they handled airport transitions well. Remember to travel as light as possible, less things mean less to carry and less to lose. Do not forget the necessities though: snacks, collapsible/reusable water bottles, and books/electronic devices for the children’s entertainment.

extended layovers

(Photo by Portia O’Laughlin)

Extended Layovers: Itinerary Example

Steal my itinerary if you’re flying from Chicago to New Orleans and want to explore something near Denver for a morning:

  • Arrival in Denver: A midnight arrival could be a bit tiring, especially if there are any delays with picking up your car rental so an earlier flight would be a good idea. The rental cars are pretty spread out and require their own individual shuttles to each rental company’s location.  If heading to the Garden of the Gods, you could consider heading down I-25 to a hotel that makes it easier for an early morning start.
  • We opted for Hilton Garden Inn Denver South Park Meadows but Homewood Suites by Hilton Denver Airport would be a good alternative when coming into the airport in the late evening.
  • A rental car is recommended and a hotel with free parking to keep costs minimal and options flexible without relying on public transportation or ridesharing.
  • Time management is highly important to keep the experience both enjoyable and on track.
  • Explore Garden of the Gods: Try to start with an early morning and head towards Colorado Springs with a brief stop at a popular eatery. Allow at least 2 hours to really take advantage of this stop.
    • The Donut House in Castle Rock is known for some truly yummy croissant donut holes. Rest assured though that there is no shortage of quaint donut shops to try along the route.
    • If you’d like to stay closer to the Denver area, there are plenty of other family-friendly options to look into, such as the Denver Art Museum, Denver Botanic Gardens, or a visit to Red Rocks Park & Amphitheatre.
  • Depart for New Orleans: By mid-afternoon, head back to Denver in time to return the car rental and make it to your flight to New Orleans. Allow ample time for any unforeseen delays. You don’t want to miss your connecting flight, the point is to save money NOT potentially spend more.

(Photo by Portia O’Laughlin)

Start Planning Your Own Mini-Vacations

(Photo by Portia O’Laughlin)

Extended layovers can turn into budget-friendly mini-vacations with a bit of planning and the right mindset. Whether it’s revisiting to eat at your favorite restaurant or seeing the one thing you missed, your layover could be just the adventure you didn’t know you needed.

Make the Most of Extended Layovers

  • Research the best attractions near the airport and plan your itinerary around those for extended layovers.
  • Check Visa Requirements: Be sure you don’t need a visa for a layover country if trying this method for your international travels.
  • Pack Smart by keeping essentials in your carry-on. Avoid unnecessary baggage delays.
  • Stay Flexible when things don’t go as planned. Always have a backup plan.
  • Enjoy the Journey. It’s just as important as the destination. Make every moment count!

Layovers don’t have to be dreaded downtime. With a little creativity and planning, they can become the highlight of your trip. So, next time you book a flight, look for opportunities to double your fun and explore new destinations along the way.

Suite at theNOLA Hilton (Photo by Portia O’Laughlin)

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