Multi City Trips Made Easy: Save More, See More

Table of Contents

How to Book a Multi-Leg Flight and Maximize Your Travel Value

Sometimes, you want to travel somewhere but can’t find a good flight. So how do you maximize the value of your time and money? In this post, I’m going to share how I’m planning a multi city trip that solves that exact problem. My wife and I are traveling to Guam, and while we’re on that side of the world, we’d like to visit some friends in Sydney. I’ll show you how I plan to book better flights for less money while also taking advantage of the opportunity to visit more exotic destinations.

Using Google Flights to Find the Best Options

We have already lined up our flights to Guam, so I’m not going to discuss that here. So, to book our trip from Guam to Sydney, my first stop is Google Flights, where I check availability. I also use the Points Path browser plug-in to compare points prices alongside cash fares. The standard option for this trip takes 26 hours and costs $1,328 for two tickets. The downside? A 13-hour layover isn’t enough time to explore another country, and that makes for a long travel day. Since there are no direct flights, let’s see what alternatives we can find.

google flight calander showing prices to Sydney. It is to show how to look for award flight availably. How to Book Multi City Trips

Using Flight Connections to Find Alternative Routes

Flight Connections is my preferred website for finding routing options. You can enter a destination and see every available flight from the selected airport. If you click on a route, it also shows which airlines operate that route.

In my search on Flight Connections, I’m going to enter Guam (GUM) and see where I can fly from there, and then I’ll open another browser and enter Sydney (SYD). Since I have multiple monitors, I set up two screens side by side for easy comparison. A printer would work just as well for those who prefer a physical reference.

All airports that fly direct to Sydney, Use to Find Multi City Trips and Optimal Flight Routing

All Airports you can fly to from Guam. Use flight connections to help plan a multi city trip!

Finding Overlapping Destinations for Better Flight Routing the Key for a Multi City Trip

Next, I look for overlapping destinations. I found Manila (MNL), Taipei (TPE), Tokyo (NRT), Osaka (KIX), and Seoul (ICN). From here, you can choose the destination you’re most interested in and start searching for flights. However, I typically search all the options to ensure I know what’s available.

Now, I’m going back to step one—Google Flights. I’ll run a search from GUM to MNL. Be sure to select “nonstop only,” as those are the only flights we’re considering.

Multi City Trip - How to Master Flight Routing

Comparing Cash vs. Points Pricing

On United’s flight portal, cardholders can access special rates, sometimes. They are offering me 67% off the standard price of 60,000 points from GUM to MNL, making it 20,000 points. That’s a decent deal. However, 60,000 points would be a poor redemption, as it values each point at less than half a cent. ($275.00 / 60,000 = $0.004583.)

Below are all the flights I found departing GUM. Points Path doesn’t always display every available award. For example, the United flight from GUM to TPE didn’t show a mileage price, so I logged into my United account to check—it was 20,000 points, which gives your points a value of over two cents per point.

Airport & Time	Airline	Cash Price	Points Price
GUM -> MNL 3 hr 55 min	Philippine Air	$242
GUM -> MNL 3 hr 55 min	United	$275	60,000 Miles + $6
GUM -> TPE 4 hr 10 min	United	$404	20,000 Miles + $6
GUM -> NRT 3 hr 55 min	United	$371	30,000 Miles + $6
GUM -> NRT 4 hr 5 min	United	$371	17,400 Miles + $6
GUM -> KIX 3 hr 55 min	United	$371	30,000 Miles +$6
GUM -> ICN 4 hr 50min	Jeju Air	$127
GUM -> ICN 4 hr 40 min	Jin Air	$189
GUM -> ICN 4 hr 45 min	Korea Air	$351	17,500 Miles + $7

I selected the highlighted flights as possible choices. United miles are typically valued at 1.2 cents per mile, which makes the United flight for 17,400 miles a very strong redemption at 2.1 cents per mile.

Researching Airlines and Hidden Fees

If you’re not familiar with overseas airlines, be sure to research them to ensure they meet your standards. In this instance, I will look up all three airlines. The searches I use are:

Airline name + Reddit
Airline name + fees
Airline name + baggage policy

These searches provide a good starting point. My research on Philippine Air, Jeju Air, and Jin Air yielded some complaints, nothing serious. I also found Cebu Pacific charges 200 PHP per kilo of baggage (approximately $3.44 at the time of this writing), depending on fair class. Jeju Air and Jin Air have similar pay per kilo systems.

Planning Your Stopover for a Multi City Trip

Now, we need to check flights from Tokyo, Seoul, and Manila. When planning a multi city trip, I strongly advise against booking flights that arrive and depart on the same day. If you experience delays and miss your next flight while traveling on two separate tickets, neither the arrival nor departing airline will assist you. You may be able to use credit card insurance or trip insurance if you purchased it, but it’s best to avoid the risk. I aim to book my flights one to three days after arrival. This gives me enough time to explore extra destinations and ensures a smoother travel experience. Obviously, this means we’ll spend one to two nights in a hotel.

Airport & Time	Airline	Cash Price	Points Price
MNL -> SYD 8 hr 40 min	Cebu Pacific	$205
MNL -> SYD 8 hr 45 min	Philippine Airlines	$416
ICN -> SYD 10 hr 15min	Jetstar	$293
ICN -> SYD 10 hr 15min	Korean Air	$591

I found no direct flights from Tokyo to Sydney, so, for this trip, Tokyo is not an option.

My research led me to the following questions. Do we want to fly to the Philippines for $447 with a total flight time of 12 hours and 35 minutes, or to South Korea for $420 with a total flight time of 15 hours and 5 minutes? We’re leaning toward the Philippines because of the shorter flight time.

Finding Affordable Hotels and Accommodation

Before making a final decision, it’s important to consider hotel and other expenses at the stopover destination—especially when planning a multi city trip. In this case, economy lodging with easy access to the airport in Manila is quite affordable, ranging from $12 to $80 per night, while high-end resorts start at $300 or more. I found acceptable hotels and vacation rentals for $42 per night.

If you’re looking for something a bit nicer and have points to redeem, Hyatt offers two Category 3 properties in Manila that range from 12,000 to 18,000 points per night. You’ll need to check your destination to see what’s available. Hyatt offers some of the best redemptions for points, check out my review of the Andaz Papagayo, one of my favorite hotels.

The Final Cost Comparison – Is a Multi City Trip Worth It?

As you may recall, the benchmark cost for traveling from GUM to SYD was $1,328 for two with a total travel time of 26 hours. Instead, we’re opting for a three-day stopover in the Philippines with under 13 hours of flight time. Let’s estimate the cost of this detour:

Flights: $894
Hotel: $126
Food: $100
Transportation: $100
Baggage Fee: $65

Total: $1,285 – that leaves an extra $43 for entertainment!

This is a budget stopover, but it could actually save you money on your trip if you’re thrifty. Sure, you could spend more, but the real goal here is to get you thinking differently about how you select flights and book travel—especially when planning a multi city trip or navigating a multi leg booking.

Don’t just settle for the first option you find—explore alternatives and see what you can create using tools like Flight Connections, Google Flights, or anything else that helps you piece together a smarter route. You don’t have to do a three-day stopover; that’s just what we chose. If we only stayed one night and kept costs low, our stopover in Manila could have cost as little as $1,000.

CV Points – “Multi City Trips are THE BEST!!!”