Booking Multi-City Flights & Hotels: A Business Guide

Your client meetings span three cities over five days, and you're staring at a dozen browser tabs trying to piece together an itinerary. Multi-city bookings expose technology limitations that simple round-trips hide: routes that don't connect properly, loyalty numbers that won't stick, pricing that makes no sense. The right booking approach eliminates most of this friction.

This guide covers how to structure multi-city reservations, maximize loyalty earning across destinations, and manage expenses when per diem rates change by city.

Understanding Multi-City Bookings

A multi-city booking is any itinerary where you fly into one city and out of another, or visit multiple destinations before returning home. Instead of the standard round-trip (City A → City B → City A), you might fly New York → Chicago → Dallas → New York, or even New York → Chicago → Dallas with no return leg at all. Airlines treat these differently than simple round-trips, and so should you.

Multi-city itineraries introduce complexity that simple round-trips don't have. You're juggling multiple departure cities, arrival times that need to align with meetings, and connections that may not exist on a single carrier. 36% of travel managers cite poor tech functionality as their biggest frustration, and multi-city bookings expose these limitations most clearly.

The challenges stack up quickly. Booking engines struggle to process thousands of route and carrier combinations, so complex trips often require agent assistance, creating delays and reducing your control. When corporate tools can't handle the itinerary, you end up booking directly with airlines or making separate reservations. That bypasses negotiated rates and creates expense reconciliation headaches when you return.

One-Way vs. Multi-City Reservations

The choice between separate one-way tickets and a single multi-city reservation affects your flexibility, pricing, and how disruptions ripple through your trip. Getting this decision right upfront saves headaches later.

When to Book Separate One-Way Tickets

Separate bookings give you maximum flexibility but require more management. Choose this approach when:

• Your return date might shift by more than a day or two
• You need to modify one leg without touching the others
• Different airlines offer significantly better routes for different segments
• You're mixing personal and business travel on the same trip
• Award availability only works for certain segments

The tradeoff: separate tickets mean separate protections. If your first flight is delayed and you miss a connection on a different reservation, the second airline owes you nothing.

When to Book a Single Multi-City Reservation

A unified reservation simplifies tracking and provides better protection during disruptions. Choose this approach when:

• Your schedule is confirmed with low probability of changes
• You want one confirmation number for expense reporting
• You need the airline to rebook your entire itinerary if something goes wrong
• You're earning status and want all segments credited together
• Corporate policy requires consolidated bookings for approval

The key advantage: when flights connect on one reservation, the airline must accommodate you through your final destination if delays cause missed connections, even if they need to book you on a competitor.

Booking Your Hotels for Multi-City Stay

When booking hotels across multiple cities, your choices around loyalty programs and location directly affect how smoothly your trip runs.

Corporate Rates and Cancellation Flexibility

Check whether your company has negotiated rates with specific hotel chains before booking. Corporate rates often include better cancellation terms than public rates, critical when multi-city schedules shift. If your company doesn't have negotiated rates, look for flexible rate options that allow free cancellation up to 24-48 hours before check-in.

Timing Your Reservations

Book hotels as soon as your flight itinerary is confirmed, especially for popular business destinations. Waiting too long can mean sold-out properties near your meeting locations, forcing you into inconvenient alternatives. For cities with major conventions or events, book even earlier. Inventory near business districts disappears fast.

Choosing Strategic Locations

Choose accommodations near central business districts or event venues. A good location saves time and money. A bad one costs you both. When you're hitting multiple cities in a week, a 45-minute commute from a cheaper airport hotel adds up fast, especially when you factor in the mental drain of fighting traffic before and after meetings.

Maximizing Loyalty Across Your Multi-City Trip

Multi-city itineraries create distinct opportunities for accelerating status in both airline and hotel programs. The key difference: airlines award status on a per-segment basis while hotels award elite night credits on a per-stay basis. That distinction shapes how you structure your bookings.

Airline Status: Earning Per Segment

Airlines award status based on segments flown and dollars spent, but the mechanics vary. United uses Premier Qualifying Points (PQP) and Premier Qualifying Flights (PQF). Delta tracks Medallion Qualifying Miles (MQMs) and Medallion Qualifying Dollars (MQDs). American Airlines uses Loyalty Points that combine spending and flying.

The segment strategy works across all three major carriers. Each awards credit per flight segment regardless of distance. A route like LAX→DEN→ORD→EWR (3 segments) earns more qualifying credits than nonstop LAX→EWR, even though you're traveling the same distance. For frequent travelers chasing status, this can mean the difference between mid-tier and top-tier elite status by year's end.

Hotel Status: Earning Per Stay

Hotels award elite nights per stay (check-in to check-out at a single property) rather than per night stayed. This creates opportunities for strategic booking.

Consider splitting your stays strategically. A business traveler visiting Chicago for 3 nights could book 1 night at a Marriott near the airport and 2 nights at a downtown Marriott, generating 2 elite night credits instead of 1. If you're changing locations for meetings anyway, the hassle is minimal.

Hotel credit cards can accelerate your progress significantly. The Marriott Bonvoy Business American Express card delivers automatic Gold status and 15 elite night credits annually, making Platinum realistic at 50 nights. For a traveler making 12 multi-city trips annually with 3-night average stays (36 qualifying nights), the credit card benefit bridges most of the gap to Platinum status.

Managing Expense Tracking Across Multiple Cities

When you're traveling to multiple cities, you need to track different per diem rates for each location and follow the 75% first/last day rule. The GSA defines per diem by locality, and you must identify and apply the correct rate for each distinct city visited.

Understanding the 75% Rule

Your first and last travel days only qualify for 75% of the Meals & Incidental Expenses (M&IE) rate for each respective location.

For a 6-day, 2-city trip:

• Day 1 gets 75% of City A's rate
• Days 2-3 get 100% of City A's rate
• Days 4-5 get 100% of City B's rate
• Day 6 gets 75% of City B's rate

Receipt Requirements

The IRS wants receipts for any single business expense of $75 or more, with a critical exception: lodging expenses always require receipts regardless of amount. Even if a hotel stay costs less than $75, the receipt is mandatory.

The IRS accepts physical receipts, digital copies, credit card statements, and bank records. Submit receipts within 48 hours of each transaction. Documenting while traveling beats reconstructing expenses later.

How Otto Simplifies Multi-City Booking

Most booking tools make you start from scratch for each segment: entering your Delta SkyMiles number for the third time this month, re-selecting window seats, comparing dozens of flight combinations across multiple browser tabs.

Otto the Agent learns your preferences once and applies them automatically. Book a multi-city trip from Atlanta to Chicago to Boston, and Otto already knows you want Delta nonstops when available, right-side window seats on eastbound flights, and your Marriott number attached to every hotel.

The difference is immediate: no repetitive data entry, no forgotten loyalty numbers, no comparing hundreds of flight combinations manually. You book complex three-city itineraries in the same time it currently takes you to book a simple round-trip.

Take Control of Your Multi-City Bookings

Multi-city business travel exposes the gaps in most booking tools. You've seen the pain points: booking engines that can't handle complex itineraries, loyalty numbers that disappear between segments, and hours lost comparing flight combinations across multiple tabs. These aren't minor inconveniences when you're trying to coordinate meetings across three cities in five days.

Otto solves the core problem by remembering everything you shouldn't have to. Your airline preferences, seat selections, loyalty numbers, and hotel memberships stay attached to every booking automatically. Instead of starting from scratch each time you add a segment, you pick from options that already match how you travel.

Start with Otto to book your next multi-city itinerary with your preferences already applied and loyalty numbers attached to every flight and hotel. You'll spend minutes instead of hours building complex trips, and you'll never lose points to forgotten account numbers again.

FAQ

Should I book multi-city flights as one reservation or separate one-way tickets?

It depends on schedule certainty and flexibility needs. One reservation offers better disruption protection; separate tickets let you modify legs independently. United and Delta eliminated change fees on standard Economy and above, reducing the flexibility gap between these approaches.

How can I quickly manage complex itineraries across multiple cities?

Otto saves your preferences, compares itineraries, monitors flight status, and provides expense-ready receipts automatically, eliminating the manual coordination that makes multi-city booking tedious.

How do hotel loyalty programs work when I'm staying in different cities?

Hotels count stays, not nights. Concentrate bookings within one program across all cities to accelerate status, and consider strategic split stays when changing locations for meetings.

What is an open-jaw flight and how does it relate to multi-city bookings?

An open-jaw flight means flying into one city and out of another, covering the gap yourself by train or car. It falls under multi-city booking and can reduce costs or improve award redemption value.