Course→Lesson 14

Booking Your First Award: Full Walkthrough

Lesson 14 of 19•15 min•By Austin Nguyen•Updated Oct 16, 2026

Complete booking flow: search award space, transfer points (1-3 days), book on airline site, enter passenger info, pay taxes ($50-400 depending on route), save confirmation number. Select seats after booking, check cancellation policy, add to calendar.

Key Takeaways

  • ✓ Search award space first, then transfer points
  • ✓ Transfers take 1-3 days (Chase instant, Amex 1-3 days)
  • ✓ Award tickets require taxes/fees ($50-400 depending on route)
  • ✓ Save confirmation number and ticket number immediately
  • ✓ Select seats after booking (free for most awards)
  • ✓ Most airlines allow free changes/cancellations on award tickets

Step-by-Step: Booking Your First Award Flight

This walkthrough uses a United MileagePlus award as an example, but the process is similar across airlines.

Step 1: Search for Award Availability

  1. Log in to United.com
  2. Toggle "Book with miles" at the top
  3. Enter origin (e.g., NYC JFK), destination (e.g., LAX), dates, and cabin class
  4. Enable flexible dates to see ±3 days of availability
  5. Click "Find flights"

Review the results. Look for "Saver" awards (lowest mileage cost). If your dates have no saver awards, try nearby dates or consider everyday awards if the price is reasonable.

Step 2: Verify the Award Cost and Taxes

Before transferring points, confirm the exact cost:

  • Miles required: e.g., 12,500 United miles one-way
  • Taxes and fees: Displayed below the miles cost. Domestic U.S. flights typically cost $5.60 one-way. International flights cost $50-400 depending on route and country taxes.

Make sure you have enough miles in your United account PLUS enough cash/credit to cover taxes.

Step 3: Transfer Points to the Airline

If you don't have enough miles yet, transfer Chase Ultimate Rewards points to United:

  1. Log in to Chase.com and go to Ultimate Rewards
  2. Click "Transfer to Travel Partners"
  3. Select "United MileagePlus"
  4. Enter the exact number of miles you need (e.g., 12,500)
  5. Confirm your United MileagePlus account number is correct
  6. Submit the transfer

Chase transfers are usually instant (1-5 minutes). Amex transfers take 1-3 days. DO NOT transfer until you've confirmed award space exists—award availability can disappear while you wait.

Step 4: Book the Award Flight

Once your miles post to your United account:

  1. Return to United.com and search for the same flight
  2. Select the flight and click "Select" or "Continue"
  3. Enter passenger information (name must match government-issued ID exactly)
  4. Review the booking details (dates, times, miles cost, taxes)
  5. Enter payment method for taxes and fees
  6. Click "Purchase" or "Complete booking"

You'll receive a confirmation screen with a 6-character confirmation number (e.g., ABC123) and a 13-digit ticket number. Save both immediately—screenshot or write them down.

Step 5: Confirm the Booking

Check your email for the confirmation email from United. It should arrive within 5-10 minutes. If you don't receive it:

  • Check spam/junk folders
  • Log in to United.com and go to "My Trips" to view the booking
  • Call United customer service with your confirmation number

Selecting Seats After Booking

Most airlines let you select seats for free after booking award tickets. Premium economy, business, and first class awards include seat selection.

To select seats on United:

  1. Go to "My Trips" on United.com
  2. Enter your confirmation number and last name
  3. Click "Choose seats"
  4. Select available seats (green = free, blue = extra legroom for a fee, gray = occupied)
  5. Save your selection

If your preferred seat isn't available, check back closer to departure. Seat maps update as other passengers change or cancel.

Understanding Award Ticket Rules

Changes and Cancellations

According to United's change/cancel policy, award tickets allow:

  • Free cancellations: Cancel online and miles redeposit immediately (no fee as of 2024)
  • Free changes: Change dates or flights online for no fee (you pay any difference in miles if the new flight costs more)
  • No partial cancellations on round-trips: If you booked round-trip as one ticket, you must cancel the entire reservation. Book one-way segments separately for flexibility.

Southwest has the most flexible policy: no change fees, no cancellation fees, full refund of points when you cancel.

Stopovers and Open Jaws

Stopover: A layover longer than 24 hours. Some airlines allow free stopovers on international awards. United allows one stopover on round-trip international awards.

Open jaw: Flying into one city and returning from another. Example: NYC to London, Paris to NYC. Most airlines allow free open jaws (price is based on total distance).

What Happens After Booking?

  1. 24 hours before departure: Check in online and receive boarding pass
  2. At the airport: Show boarding pass and ID at security. Board the plane like any other ticket.
  3. On the plane: Award tickets are treated identically to cash tickets. You board in your assigned group, earn flight miles if you're a member, and receive the same service.

Award tickets are NOT second-class tickets. They're the same seats as cash passengers with the same rights (meal service, baggage allowance, elite benefits if you have status).

Common Booking Mistakes

  • Transferring points before confirming award space: Points transfer to the airline, then award space disappears. You're stuck with miles in the wrong program.
  • Misspelling passenger name: Name must match ID exactly. Fixing name errors costs $50-200 per ticket.
  • Forgetting to budget for taxes: You need miles PLUS cash for taxes. Domestic U.S. flights are cheap ($5.60), but international routes charge $100-400 in taxes per person.
  • Not saving confirmation number: If you lose your confirmation, you must call the airline to retrieve it
  • Booking round-trip when you want flexibility: Book one-way segments separately so you can change or cancel one direction without affecting the other

What If Something Goes Wrong?

Award Space Disappears Before You Book

Book immediately after transferring points. Award seats can disappear in seconds if another traveler books them. If space is gone, your options:

  • Check alternate dates or routes
  • Call the airline to see if they can manually add availability (rare but sometimes works)
  • Use the miles for a different redemption

Flight Schedule Changes

Airlines change schedules 1-6 months before departure. If your award flight changes by 60+ minutes, the airline must:

  • Notify you via email
  • Allow you to change to a different flight for free
  • Allow you to cancel for a full refund (miles redeposit + taxes refunded)

Check your email and "My Trips" periodically after booking to catch schedule changes early.

Booking Partner Awards (Advanced)

When you book a partner airline (e.g., Lufthansa flight using United miles), the process is similar but with nuances:

  • Search on the airline where your miles are (United.com if you have United miles)
  • Partner flights may not show online and require calling the airline's phone line
  • Phone booking fees ($25-50) may apply for partner awards
  • Partner airlines' cancellation policies may differ from the issuing airline

Should You Book Now or Wait?

Book now if you find saver award space and your dates are set. Award space can disappear anytime. Don't wait hoping for better availability—it usually gets worse, not better.

Wait if:

  • Your dates are very flexible and you're searching 6+ months out
  • The current award price is everyday/standard (wait for saver to open)
  • You're waiting for a transfer bonus to appear (but don't wait forever)

Next Steps

Now you know how to book award flights. The next lesson covers hotel points (focusing on Hyatt, the best hotel transfer partner) and elite status basics.

Move to Lesson 15: Hotel Points (Hyatt) & Elite Status Basics.

← Lesson 13Next: Lesson 15 →