6 Biggest Business Travel Challenges and How to Fix Them

Most business travelers have accepted travel chaos as normal: flights get disrupted and you spend hours rebooking, preferences get re-entered endlessly into every booking form, confirmation numbers hide across five different apps, and travel costs climb while budgets shrink.

These business travel challenges can cost you hours and budget on every trip. But they don’t have to. The next six sections break down each issue and offer practical fixes. We’ll also show you how AI travel agents like Otto the Agent can help seamlessly solve your travel challenges, so you can reclaim those hours. 

1. Rising Travel Costs

Challenge: Rising travel costs rank as a top challenge for business travelers in 2025. The average ticket price in the United States and Canada climbed from $668 in 2023 to $721 in 2024 due to fuel costs, labor shortages, and demand for flexible fares. Cost management has become a primary concern across U.S. and global business travel markets, forcing companies and travelers to find value without sacrificing the flexibility business trips require.

Fix: Track the real cost before you book, not after you land. Add up the base fare plus the hidden extras like preferred seating, checked bags, or airport transfers. Compare that real number across options instead of the lowest advertised price. Book refundable fares when meetings might shift, so you don’t pay twice when plans change. And make sure to apply your loyalty numbers consistently so the miles and points you earn offset future costs. For hotels, check if properties near your meeting location offer free breakfast or airport shuttles, which cut your daily spend without forcing you into inconvenient locations.

2. Handling Business Travel Disruptions

Challenge: Twenty percent of flights got delayed in 2025, with another 1-2% cancelled outright. Travel disruptions include flight delays, cancellations, gate changes, and equipment failures that force you to rebook mid-trip. Your flight gets delayed by three hours, and your connection becomes impossible. By the time you realize the original routing won't work, you're hunting through airline apps for alternatives while boarding announcements blare overhead. Most road warriors accept reactive scrambling as normal, but this approach burns hours on logistics when you need to focus on tomorrow's presentation.

Fix: Monitor your flight status starting 24 hours before departure. Set up alerts for delays, gate changes, and cancellations through your airline app or flight tracking service. When disruptions hit, search for alternative flights on the same airline first, then check partner carriers if your ticket allows changes. Know your ticket rules before problems hit: can you change without fees? Will you get credit if cancelled? Having this information ready will help you rebook later. It’s also important to understand your company’s policy when it comes to travel discruptions. 

3. Wasting Time on Data Entry While Booking

Challenge: How many times have you typed your frequent flyer number into booking forms this year? Every site asks for your aisle seat preference, your hotel loyalty program, and your preferred airline or airport. This repetitive data entry leads to downstream errors and it bleeds time from actual work.

Fix: Use the same booking platform consistently instead of switching between sites, which forces you to rebuild your profile every time. Most platforms let you save preferences, but only if you create an account and use it religiously. Store your loyalty numbers in your password manager or phone notes so you can copy-paste instead of scrambling through your inbox for your numbers 

4. Juggling Disconnected Tools for Calendar, Bookings, and Expenses

Challenge: Most business travelers manage trips across several disconnected apps. Your calendar is in Google Workspace, boarding pass in the airline app, hotel confirmation buried in email, and now your manager is pinging you on Slack asking when you land in Boston. Pretty quickly, Sunday nights become receipt reconstruction sessions as you piece together itineraries from scattered confirmations.

Fix: Create one place where all travel information lives. Forward every booking confirmation to a dedicated email folder or use a travel app that automatically imports reservations from your inbox. Add flights and hotels to your calendar immediately after booking, including confirmation numbers in the event details. For expenses, photograph or screenshot receipts the moment you get them instead of saving that work for later. Set up email rules that automatically tag travel confirmations so they're easy to find later. Some expense tools can scan and categorize receipts directly from your phone, which eliminates manual entry entirely. The goal is to reduce the number of places you need to check when someone asks "when do you land?" or finance asks for documentation.

5. Planning Complex Multi-City Business Trips

Challenge: Building a multi-city business trip means juggling half a dozen browser tabs. You need to visit clients in three cities across four days, and every booking site treats these as separate one-way flights with no connection between them. You're trying to figure out whether flying from NYC to Boston to Chicago makes more sense than routing through Atlanta, considering your meeting times, hotel checkout schedules, and minimum connection windows. Hours disappear into this logistics puzzle, and you eventually book something that works "well enough" because optimizing the full route gets too complex.

Fix: Map your meeting locations and times first, then build the route around those fixed points. Look for patterns: if two cities are close together, can you take ground transportation instead of a second flight? Can you arrange meetings to flow geographically instead of bouncing between coasts? Use multi-city search tools that let you enter all destinations at once rather than pricing each leg separately, which often reveals routing options and cost savings you'd miss booking segment by segment. Check if one airline can handle the entire itinerary, which simplifies rebooking if disruptions hit. When you optimize the route before clicking buy, the complex trip becomes manageable.

6. Integrating Rapidly Evolving AI Travel Technology

Challenge: Eighty percent of travelers now use generative AI tools to research, book, and manage trip itineraries, but implementation complexity remains a barrier for business travelers. To be useful, AI travel tools must integrate with existing, often fragmented technology ecosystems: your calendar system, expense platform, company booking policies, loyalty programs, and communication tools. 

Fix: An AI travel agent that handles business travel challenges and integration complexity for you. But make sure you choose a platform that connects all these pieces reliably while also ensuring the recommendations are personalized to your preferences and secure enough for corporate data. 

How Otto the Agent Can Help

Otto works like the best executive assistant, managing all six business travel challenges across your existing platforms without requiring you to rebuild your workflow.

For rising travel costs: Otto shows you the real total upfront (base fare plus your typical extras like preferred seats and checked bags).

For travel disruptions: Otto monitors your flights and immediately presents alternative routings when delays or cancellations hit, eliminating the hours you'd spend on hold with airlines. Otto also understands what's in or out of your company’s travel policy and can make instant decisions to help you rebook, while remaining compliant.

For repetitive data entry: Otto learns your preferences as you travel (aisle seats, specific airlines, hotel chains, frequent flyer numbers) and pre-loads them automatically on every booking. And when you’re ready to commit, Otto fills out booking and payment forms for each transaction, so getting that plane ticket is as simple as typing “book it.”

For disconnected tools: Otto syncs bookings to your calendar automatically, generates expense-ready receipts in importable PDF format, and works through the platforms you already use: email, Slack, Teams, SMS, WhatsApp, and mobile apps.

For complex multi-city trips: Otto considers your meeting times, connection logistics, and route preferences to build complete itineraries in one conversation. You avoid manually searching and pricing each city-to-city segment separately.

For AI integration complexity: Otto is accessible through channels you already check daily instead of requiring another login or platform to manage. It syncs with your calendar automatically and generates receipts ready for your expense system.

Available on web, iOS, and Android, Otto handles the coordination work automatically so you focus on getting your work done. 

Business Travel Needs Better Tools, Not More Workarounds

Road warriors have accepted these six business travel challenges as just part of the job. And fixing them on your own requires tracking hidden fees, monitoring flights continuously, maintaining preferences across platforms, syncing bookings with calendars and expense tools, optimizing multi-leg routes, and integrating AI into existing workflows. That level of coordination is difficult to maintain when you're also trying to manage client relationships and prepare for meetings.

Otto handles that coordination for you, so you can focus on what you're actually paid to do: show up ready and close deals.