TripSpotter Get early access

Flight search for digital nomads

Flight deals that fit
around your work week.

TripSpotter finds flights that leave when you’re free and land with time to settle in before work. It checks cash fares and award seats every day to find options within your budget and shows what each flight costs in cash or the miles and points you already have.

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8:00 PMFri Nov 6, 2026Chicago time

7 h 50 min · Nonstop

9:50 AMSat Nov 7, 2026Lisbon time3:50 AM Chicago time

TAP Air PortugalTP 248

Arrives 53 h 10 min before your next work shiftMon Nov 9, 2026, 3:00 PM Lisbon time · 9:00 AM Chicago time

$612Economy · Cash fareLowest fare

30,000 United miles + $48.20Uses miles you haveStrong redemption

45,000 Air Canada points + $91.40Needs a transferTransfer 45,000 points from American Express or Capital One

One flight as TripSpotter shows it, with sample data.

A deal you can’t take
isn’t a deal.

That $400 fare in your inbox leaves at 2:00 PM on a Tuesday. A cheap flight doesn’t help if it takes off in the middle of your workday. TripSpotter searches cash fares and award seats, then shows you only the options that fit your schedule, budget and the points and miles you already have.

How it works

From your workweek
to a flight that fits.

Here’s one example of using TripSpotter, from setting work hours and adding miles and points to finding a flight and choosing how to book it.

  1. Your scheduleSet your work hours and time zone, along with holidays and other days off.
  2. Your budget & pointsAdd your airline miles and bank points balances, then set how much cash or how many miles you’d spend.
  3. Flights that fitChoose your destinations and dates. TripSpotter checks cash fares and award seats daily for flights that fit your schedule and limits.
  4. Ways to bookCompare cash and award prices for the same flight, including fees and points-transfer options, with direct links to book.

The fares and balances in this walkthrough are illustrative.

01

Your workweek and days off

Workdays
  • Mon
  • Tue
  • Wed
  • Thu
  • Fri
  • Sat
  • Sun
Work starts
9:00 AM
Work ends
5:00 PM
Work time zone
Chicago
Holidays and days off
Thanksgiving
Christmas Day
New Year’s Day

Work hours stay on the Chicago clock, wherever you travel. Days off open up extra departure dates.

02

Your miles and points

19 airline programs and 4 bank rewards programs. The balances you hold determine which award options TripSpotter can find for you.

Airline miles and points

United MileagePlus
84,000miles
American AAdvantage
62,500miles
Alaska Atmos Rewards
48,000points

Bank rewards

Chase Ultimate Rewards
135,000points
American Express Membership Rewards
90,000points
Capital One Miles
64,000miles
Citi ThankYou Rewards
41,000points

Balances are entered for the programs you collect and updated as they change. Bank points can also cover awards through eligible airline transfers.

Airline programs available

United MileagePlus · American AAdvantage · Delta SkyMiles · Alaska Atmos Rewards · Air Canada Aeroplan · Air France-KLM Flying Blue · ANA Mileage Club · Virgin Atlantic Flying Club · Avianca LifeMiles · Qantas Frequent Flyer · JetBlue TrueBlue · Turkish Airlines Miles&Smiles · Lufthansa Miles & More · Etihad Guest · SAS EuroBonus · Aeromexico Rewards · Aerolíneas Plus · Ethiopian ShebaMiles · Virgin Australia Velocity

03

Your travel plans

Company holidays included
When flights can leaveFriday after 7:30 PM · SaturdayOutside work, with time to get to the airport.
Time after landingAt least 24 hours before workA full day to get settled before the next shift.
Travel datesNovember 6, 2026–January 30, 2027Company holidays add more dates to search.
From Chicago to

Lisbon · Porto · Bangkok · Tokyo

Economy cash limits

Portugal $900 · Bangkok $1,300 · Tokyo $1,400

Budgets by destination and cabin

Cash limits

Portugal: $900 Economy · $2,000 Premium economy · $6,000 Business

Bangkok: $1,300 Economy · $3,200 Premium economy · $7,000 Business

Tokyo: $1,400 Economy · $3,500 Premium economy · $7,500 Business

Miles limits

60,000 Economy · 90,000 Premium economy · 120,000 Business

04

The places those dates could take you.

Cash fares and award options, across your destinations and cabins. One view of the trips worth looking at.

TripSpotterFlights Chicago departuresOne-way fares
Flight prices by departure date, destination and cabin. Dollar figures are cash fares. Award options list the program’s miles or points plus fees.
Friday, November 6, 2026
DestinationEconomyPremium economyBusiness
LisbonLIS · PortugalThis flight $612 30,000 United miles + $48.20 45,000 Air Canada points + $91.40 $1,240 55,000 United miles + $48.20 $3,460 70,000 United miles + $48.20
PortoOPO · Portugal $598 25,000 Flying Blue miles + $86.40 $1,290 45,000 Flying Blue miles + $154.20 $3,980 60,000 Flying Blue miles + $218.60
BangkokBKK · Thailand $864 40,000 United miles + $52.10 $1,780 $4,960 88,000 United miles + $52.10
Saturday, November 7, 2026
DestinationEconomyPremium economyBusiness
TokyoHND · Japan $892 35,000 United miles + $35.30 $2,140 60,000 United miles + $35.30 55,000 ANA miles + $142.80 $5,840 75,000 ANA miles + $142.80 88,000 United miles + $35.30
TokyoNRT · Japan $918 35,000 American miles + $35.30 45,000 Alaska points + $35.30 $2,210 50,000 American miles + $35.30 $6,120 60,000 American miles + $35.30
LisbonLIS · Portugal $574 45,000 Air Canada points + $91.40 $1,386 50,000 Air Canada points + $108.60 $3,320 70,000 Air Canada points + $134.60

Cash fares in gold · Green highlights a strong redemption.

One of those options, up closeFriday evening to Lisbon$612 cash or 30,000 United miles + $48.20

05A flight that fits

Friday after work.
A weekend in Lisbon
before Monday’s shift.

TripSpotter’s flight card. TAP Air Portugal TP 248 leaves Chicago Friday November 6, 2026 at 8:00 PM and arrives Lisbon Saturday November 7 at 9:50 AM, or 3:50 AM Chicago time. There are 53 hours 10 minutes before the next shift. The same flight costs $612, 30,000 United miles plus $48.20, or 45,000 Air Canada points plus $91.40 through a transfer.
TripSpotter shows the options. You book flights and make any points transfers yourself.

  1. Arrival on both clocks

    Saturday at 9:50 AM in Lisbon is 3:50 AM on your Chicago work clock.

  2. 53 h 10 min before work

    The weekend to settle in before Monday’s 3:00 PM Lisbon start. Your search required at least 24 hours.

  3. The cash fare, with a booking link

    $612 in Economy, with a link to Google Flights.

  4. Miles or transferable points

    Use 30,000 of your 84,000 United miles, or transfer 45,000 Amex or Capital One points to Air Canada. Taxes and fees appear beside each option.

06The search keeps going

Your next trip doesn’t need another evening of searching.

TripSpotter keeps checking the dates and places in your searches. Your options are there in the dashboard when you want them, or in a scheduled email at the time you choose.

One way or coming back: return flights can be searched too, with cash, miles or a combination across the trip.

View the full email
TripSpotterScheduled email

Your flight options

Flights around your workweek

LisbonFriday, November 6, 2026$612or 30,000 United miles + $48.20
PortoFriday, November 6, 2026$598or 25,000 Flying Blue miles + $86.40
Tokyo HanedaSaturday, November 7, 2026$892or 35,000 United miles + $35.30

Selected options from the email

Why I built it

I could work from anywhere.
I wanted to make the most of it.

DanielFounder, TripSpotter

I wanted to finish work on Friday, fly somewhere new, and have the weekend to settle in before Monday. With a remote job and fixed hours, that was possible. Finding the right flights took work.

I’d spend hours going through fare alerts, checking flight times, searching for award seats, and figuring out whether to use cash or points. Every trip meant working through the same questions before I could book.

I built TripSpotter to keep looking for me, with my schedule, budget, and points already taken into account. It found flights I could actually take, with time to get settled before work started again.

That’s helped me travel around the world while keeping my work schedule. The freedom I had became something I could use.

Now I’m making TripSpotter available to other digital nomads with places they want to go and a workweek to plan around.

A few practical questions

Before your next trip.

Does TripSpotter book flights?

No. Cash fares link to where they’re sold, and award seats link to their airline program. You make the booking there.

Do I need miles or points?

No. Cash fares work on their own. With your balances added, eligible award options appear alongside them.

Does it connect to my airline or credit card accounts?

You enter your balances yourself. TripSpotter uses those balances to work out which awards they can cover. It shows the transfers that could be needed; you make any transfer yourself.

What if I work in a different time zone?

Your work hours stay on the work clock you set. TripSpotter checks arrivals against that schedule and shows the work time alongside local flight times.

Can it search one-way and round-trip travel?

Yes. It can search the way out and the way home, with cash, miles or a combination for the two directions. Your trip length and availability shape the return search.

When can I start using it?

TripSpotter is in development. People on the early-access list will hear when it opens.

Early access

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