How to Plan a Multi-City Trip with Points and Miles

Traveling to more than one destination in a single trip is the dream of many frequent flyers and travel enthusiasts. Whether you’re backpacking across Europe, hopping through Asia, or visiting family across continents, a multi-city trip can make your journey more memorable and enriching. Even better? You can book much of it using points and miles, reducing your overall costs drastically.

In this comprehensive guide, we’ll show you how to plan, book, and optimize a multi-city trip using points and miles without getting overwhelmed.

What Is a Multi-City Trip?

A multi-city trip involves visiting two or more destinations on a single itinerary. Unlike a round-trip, where you fly to one destination and return from the same point, a multi-city itinerary could look like:

• New York → London
• London → Rome
• Rome → Istanbul
• Istanbul → New York

It may include stopovers, open jaws, and even multiple airline carriers. While it can be more complex to book, the experience is worth it — and can be free or nearly free using miles.

Why Book a Multi-City Trip with Points?

Using points and miles for a multi-city itinerary has several benefits:

• Save thousands of dollars on airfare
• Leverage stopovers to explore more destinations
• Use fewer miles than booking each leg separately
• Access better availability across alliances
• Enjoy added flexibility with many loyalty programs

For example, a cash ticket for a trip like this might cost US$2,500–$3,500, while the same itinerary could be booked for 80,000–120,000 points + taxes.

Choose Destinations That Make Sense Together

When planning a multi-city trip, think regionally or by travel corridor. Some good examples include:

• Western Europe (e.g., London, Amsterdam, Paris)
• Southeast Asia (e.g., Bangkok, Singapore, Bali)
• South America (e.g., Lima, Buenos Aires, Santiago)
• Middle East and Europe (e.g., Dubai, Istanbul, Rome)

Choosing destinations that are close to each other — or well-connected by air — makes your itinerary easier and cheaper to build.

Step-by-Step: How to Plan Your Trip with Points

Step 1: Decide on Your Travel Goals

Start with:

• How many days you want to travel
• How many cities or countries you want to visit
• Whether you’ll use overland transport between cities
• Your departure city and return city

Write out a rough itinerary like:

• Fly: New York → Paris
• Train: Paris → Barcelona
• Fly: Barcelona → Athens
• Return: Athens → New York

Step 2: Choose the Right Airline Alliances

Most points-friendly airline programs are part of large alliances:

Alliance	Examples	Great for:
Star Alliance	United, Lufthansa, Turkish	Europe, Asia, South America
Oneworld	American, Iberia, Qatar	Europe, Middle East, Asia
SkyTeam	Delta, KLM, Air France	Europe, Africa

You can book multi-city awards using a single loyalty account across these carriers.

Example: Use United miles to fly New York → Paris on Lufthansa, then return Athens → New York on Turkish.

Step 3: Understand Stopover and Open Jaw Rules

Each program has different rules:

• Air Canada Aeroplan: Add stopovers for 5,000 points
• Alaska Mileage Plan: 1 free stopover per one-way
• United MileagePlus: Stopovers through Excursionist Perk
• Singapore KrisFlyer: Stopovers for $100
• ANA Mileage Club: RTW ticket with 8 stopovers

These are useful for building value-packed itineraries.

Step 4: Search Award Availability

Use tools like:

• Point.me or AwardHacker to check points requirements
• Airline websites (e.g., United, Air Canada, Avios) to check award space
• ExpertFlyer (paid) for advanced seat availability

Always search segment by segment. For example:

1. New York → Paris
2. Paris → Barcelona
3. Barcelona → Athens
4. Athens → New York

Step 5: Book Strategically

When availability is limited:

• Book your longest-haul legs first
• Use one program to cover most/all legs
• Consider using multiple accounts (e.g., United for one segment, Avios for another)
• Be ready to call the airline — many multi-city awards require manual booking

Use “multi-city” search tools rather than round-trip.

Maximizing Value: Points and Miles Tips

Book in Advance

Most award seats are released 330 days in advance. Booking early helps lock in availability and lower redemption rates.

Fly Off-Peak

Award pricing is usually lower during off-peak times like:

• January to March (except holidays)
• May
• September to early December

Avoid July, August, and major holidays if possible.

Use Transferable Points

If you collect:

• Chase Ultimate Rewards
• Amex Membership Rewards
• Capital One Miles
• Citi ThankYou Points

You can transfer to dozens of airline partners for more flexibility.

Example:

• Transfer Amex points to ANA for a round-the-world ticket
• Transfer Chase points to United for Star Alliance awards
• Use Capital One to transfer to Turkish, Air France, or Etihad

Don’t Overlook Low-Cost Carriers

For short flights between cities, sometimes it’s better to pay cash for a budget airline (e.g., Ryanair, AirAsia) than burn points.

Example: Paris → Rome for US$45 on Ryanair might be cheaper than using 10,000 miles + taxes.

Example Itinerary Using Points and Miles

Let’s build a sample trip: Two weeks across Europe

• Leg 1: New York → Lisbon (TAP Portugal, 35,000 miles on Air Canada)
• Stopover: 2 days in Lisbon
• Leg 2: Lisbon → Rome (budget airline, pay cash ~US$60)
• Leg 3: Rome → Athens (Aegean Airlines, 12,500 United miles)
• Leg 4: Athens → New York (Turkish Airlines via Istanbul, 45,000 Aeroplan miles)

Total miles used: ~92,500 + US$60 cash
Approximate value of the trip: US$2,400+

Tools to Plan Your Multi-City Trip

Use these for planning:

• Google Flights: Great for comparing routes
• ITA Matrix: Advanced pricing and stopover searches
• AwardHacker: See how many points you’ll need
• FlightConnections.com: Visual route planner
• SeatGuru: Choose the best seats on long-haul flights

Mistakes to Avoid

• Waiting too long to book
• Assuming round-trip is always cheaper
• Not checking partner award space
• Ignoring fuel surcharges
• Mixing alliances (can cost more or block availability)

Final Thoughts: Travel More for Less

A multi-city trip doesn’t have to be expensive or complicated. By learning how to plan a multi-city trip with points and miles, you open up the world in a smarter, more affordable way.

With the right strategy, you can:

• Explore more destinations
• Save thousands in travel costs
• Turn a regular vacation into an epic journey

Let your points take you further — across borders, continents, and cultures.