Intelligent Travel Sidekicks
Travel is too much for one person. Get a team.
Sidekick and a crew of specialists watch fares, chase expiring points and pull the whole trip into one plan. They do the digging. You say yes.
Free to start
Runs in your browser, installs like an app
Never books, sends or pays without your yes
Connect what you already hold
Fly · Watching−$118Tulsa → Maui now $612
14 – 21 Mar, round trip via Dallas
Expiring30,000 points expire 31 March
The Wailea beach stay would keep them.
02How it works
Jump in. Three steps, zero tabs.
No forms and no app store. Tell it where you want to be and let the team go to work.
01about a minute
Say the trip
Type it or say it: “Tandem skydive over Interlaken, two of us, late June.” Connect the programs you hold and Sidekick sees what you are sitting on.
02while you wait
The specialists pile in
Fly prices Zurich, Train times the run up to Interlaken, Lodge shortlists stays by the landing field. Answers land as cards, every price with its source.
03your call
You say yes
One plan, every part, in cash or points, with a link to book each one. Nothing is booked, sent or paid without your yes.
03Meet the team
One lead. A whole roster of specialists.
Sidekick runs point and pulls in the right specialist for every part of the trip. Tap one to hear what it's working on.
Sidekick
Your lead
Runs point, keeps the plan and pulls in the right specialist for each part. Name it anything you like. Ours answers to Pip.
Latest in Orlando parks week
Park tickets for your Orlando week go up on 1 Dec. Want me to lock them in?
Fly
Flights
Watches cash fares and award seats against the miles you hold, and tells you when to book.
Latest in Orlando parks week
Tulsa to Orlando dropped to $238. That is $64 under what you saw.
Lodge
Stays
Shortlists stays and applies what your status tier includes, where the program says so.
Latest in Orlando parks week
Three stays for 14 – 19 Mar, all with early park entry.
Drive
Road trips
Routes, fuel and the lunch stop worth making.
Latest in Orlando parks week
A rental with two car seats from Orlando airport, $312 for the week.
Dine
Tables
Finds tables that fit your nights and watches for the ones that open.
Latest in Orlando parks week
The character breakfast opens bookings 60 days out. I will tell you the moment it does.
Train
Rail
Stitches rail and ground routes into your plan, door to door.
Latest in Orlando parks week
Brightline runs Orlando to Miami in about 3 h 30 min if you want a beach day.
Cruise
Cruises
Lines up cabins, ports and the card credits you already hold.
Latest in Orlando parks week
A 3-night Bahamas sailing leaves Port Canaveral the day after the parks.
Ski
Snow days
Watches snow and lift prices and tells you which days to go.
Latest in Orlando parks week
Nothing to watch on this one. I will pick up again when winter fares open.
Timeshare
Weeks & points
Lists your weeks and points with their expiry dates and finds where they go furthest.
Latest in Orlando parks week
Your vacation club points can cover four nights near the parks.
Spa
The quiet
Finds a quiet place to land after the big trip.
Latest in Orlando parks week
Two hotel spas near the parks have openings for your rest day.
Camp
Outdoors
Sites, seasons and gear for nights outside.
Latest in Orlando parks week
A lakeside campground 30 minutes from the parks has cabins open.
Japan
Destinations
Destination specialists know the local rules, the seasons and the best hours.
Latest in Orlando parks week
Osaka’s parks are quieter in early December. Want me to look?
04Trip chat → plan
From group-chat chaos to a plan you can book.
Austin City Limits, four people, a weekend that sells out. Watch the team turn it into four parts with prices, deadlines and links to book.
Answers come as cards, not walls of text
Change anything by saying so and the plan updates
Every price shows where it came from
Deadlines surface before they bite
05For you
Deals don't wait. Neither does your team.
Fares drop at 2 am. Points expire on a Tuesday. Your specialists watch it all and put what matters on one board, with what needs you first.
−$640
Business class, Dallas → London, caught by Fly while you slept.
Fare dropsAward seatsHotel ratesReservation openingsAny page you pick
Needs youUrgent
Upgrade to First, DFW → LHR
Window closes in 6 h. 40,000 miles.
Watching−$640
Dallas → London fell to $2,190
Business class, 14 – 21 Mar.
IdeasNew
Empty-leg jet: Teterboro → Aspen
Seats from $1,850 on Fri 20 Feb.
06Points & accounts
See what you're already sitting on.
Connect your programs and Sidekick lines up every balance, certificate and timeshare week, with what expires soonest at the top.
Browser extension
Reads balances on pages you are already signed in to.
Mail you share
Confirmations and statements, nothing else.
Saved logins
Encrypted to your own vault, used only on sites you allow.
07Cloud computer
It does the clicking. You keep the keys.
Fly opens the airline site, signs in with your saved login and reads the points fares, in a browser you can watch live. It searches and prices. You book.
LIVE · delta.com
Opened delta.com
Signed in with your saved login
Reading award fares for Fri 11 Dec
Stops before booking and hands it to you
Take overStop the run
08Live & Apple Watch
Talk it through. Glance at your wrist.
Live is voice-first planning, one question at a time, with notes as you go. On your wrist: the next leg, a fare drop, a quick reply.
Voice first
Talk it out. One question at a time.
Noted as you go
Everything said lands in the plan.
Next leg, glanced
Gate, boarding time and seats.
Wrist alerts
Fare drops and fresh snow.
Apple Watch app is coming
09Your travel map
Every trip, every stamp, one map.
Upcoming trips, places you've been and home, together. Tap a pin to jump into that trip's chat.
H
Hallstatt & Salzburg
10 – 17 Jun 2027
C
Cinque Terre
2 – 8 Sep 2027
B
Bruges at Christmas
18 – 22 Dec 2026
K
Kyoto old town
2 – 9 Apr 2027
Been there
Positano2024
Sintra2023
Colmar2022Takayama2022
10Made for your kind of trip
Whoever's going, there's a specialist for that.
Squeeze every point.
Balances, certificates and expiry dates in one wallet, ranked by what lapses first. Ideas flags the stay that keeps them alive.
Award seats watched against the miles you hold
Status perks applied where the program says so
Point values shown as estimates next to cash
Everyone’s preferences, one plan.
Friends keeps what each traveler likes, needs and can’t stand next to the plan. School checks term dates before you pick a week.
Preferences kept for each traveler
Break dates checked first
Planning together in one family chat is coming
Stop leaving weeks on the table.
Your weeks and points listed with their expiry dates, and what they would get you now against the same stay in cash.
Weeks about to lapse flagged early
Cash-versus-points estimate for each stay
Asks before it books, exchanges or pays
Upgrades you’re owed. Lounges you can use.
Business checks your status tiers, certificates and card benefits and tells you exactly what to ask for, and when.
Lounge access from your cards and status
Upgrade requests written for you to send
Your calendar connected, so trips line up
Beat the on-sale.
Music watches lineups and on-sale dates and tells you before tickets go, then lines up the flights and the stay so the weekend works.
On-sale alerts for the shows you follow
Dates matched to flights and stays
Choosing together with friends is coming
Just tell it where.
Say a place and a week. Sidekick pulls in the right specialists and hands back one plan with prices and links to book.
One chat, one plan
Every price with its source
Nothing happens without your yes
11Privacy & trust
Your trip. Your accounts. Your call.
Nothing happens without your yes
ITS gets everything ready and asks before it books, sends or pays. You can watch any task and take over.
ITS reads only what a task needs
The pages you are signed in to, the accounts you connect and the mail you share. You can see what ITS remembers, edit it and delete it.
Your logins stay yours
Logins are encrypted to your own vault. The ITS servers relay them but cannot read them, and the model never sees a password.
12Early travelersPLACEHOLDER CONTENT
They stopped leaving points on the table.
$000
found per traveler in the first week
000k
points saved from expiring
0.0★
average rating from early travelers
“Fly caught a $118 drop on our Scottsdale fares while I was asleep. I booked before my first tee time.”
Placeholder Name
Weekend golfer, Tulsa
“It told me 30,000 Marriott points were about to lapse and found the golf resort that saved them.”
Placeholder Name
Points collector
“A Pebble Beach tee time opened at 6 am. Sidekick told me before anyone in the group chat had seen it.”
Placeholder Name
Golf trip organizer
“Our timeshare week was about to go to waste. Now it’s four rounds in Palm Springs.”
Placeholder Name
Vacation club owner
13PricingPLACEHOLDER TIERS
Free to start. Upgrade when it pays for itself.
Free
Everything you need to plan a trip.
$0$0forever
Sidekick and every specialist
Unlimited trip chats and plans
Wallet with expiry alerts
3 active watches
PlusMost popular
For deal hunters who want everything watched.
$7$9per month
Billed $84 a year
Billed monthly
Everything in Free
Unlimited watches
Cloud computer runs
Live voice planning
FamilyComing soon
One plan, everyone heard.
$12$15per month
Up to 6 travelers
Up to 6 travelers
Everything in Plus
Shared family trip chat
Preferences for each traveler
Pooled perks across the group
14FAQ
Straight answers.
Still wondering? Ask Sidekick. It's free to start.
Your team is ready. Where to?
Meet Sidekick and see what you are already sitting on.
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Intelligent Travel Sidekicks
Travel is too much for one person. ITS is your team of proactive specialists.
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