Many New Upside Updates + $100 Gift Card for your Next Flight/Travel Package Purchase

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I’ve written about Upside Business Travel many times over the past year and for a few very good reasons: 1) Their site (and mobile app) is very user friendly and incredibly easy to use; 2) Their customer service is phenomenal; 3) They’ve offered some great promotions to save you a ton of money when booking a flight/hotel/rental car/rideshare packages. For those who have no idea what I am talking about when referring to Upside, here you go.

“Upside is a travel site for business travelers who aren’t part of a traditional corporate travel program and need a solution with great pricing and quality customer service–they even reward you for booking travel packages for your work trips.” (Learn more)

Essentially, Upside is a one-stop shop for those looking for a cost-effective and seamless business travel experience. Now you can book all your work trip reservations in one place, get (free) expert human customer service 24/7, and get gift card rewards when you package 2+ reservations in one trip. I’ve found that when I use Upside, it’s easier than ever to book, manage, and change my work trip.

I personally tried Upside for the first time about a year ago for a business trip I was taking to Chicago and had a great experience. I also had the opportunity to stay in one of Upside’s priority partner hotels in New York back in May and was highly impressed. It is definitely a business travel solution I recommend looking into, especially since they’ve rolled out two massive upgrades recently which will be huge for booking business flights!

Book Southwest Flights Through Upside!

This is a huge win as Upside is the only business travel site I’ve found that has access to Southwest flights! Typically if you were to do a quick search on Kayak or Expedia, no Southwest flight options will appear and you’ll instead need to go directly to to see their availability, flight schedule, and pricing. So being able to see Southwest flights outside of Southwest’s site directly is HUGE! Not only that, you’ll earn Southwest Rapid Reward points even when you book with Upside. To search for Southwest Airlines flights you must be registered with your work email address and looking to book a work trip with travel dates between Sunday-Friday (for leisure trips, using is your best option).

Book Multi-City Flights

Upside now supports multi-city flight itineraries which is a real game changer for frequent business travelers! While this is for domestic flights only, this will allow you to book business trips that require you to be in multiple cities throughout the week and potentially save even more money!

First Time User? Get $100!

If you are a first time Upside business traveler, new customers can receive a $100 gift card when booking their first $600 or more flight/travel package. You can redeem your gift cards at 50+ top retailers (i.e.,, Target, Home Depot, Whole Foods, Nordstrom, Gap, etc.) and I consider Amazon gift cards the same as cash since I shop there quite often! You can book here and use my referral code DEALSWELIKE at checkout.

Offer valid for first time customers with required pre-tax purchase minimum of $600+ paid at time of booking, see for terms and conditions. “Pay Later” prices are not eligible towards minimum package price. Gift cards redeemable after travel is completed.



The responses below are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser's responsibility to ensure all posts and/or questions are answered.


  1. I just did a mock booking. It did not save me a ton of money. In fact, I can do much, much better on my own. The hotel rates were much higher than on the hotel sites, which means they would be even cheaper on Expedia. I found trying to use the website on my phone extremely difficult as it kept resetting.

  2. I agree with above comment. I find their prices very high so there is no savings. Plus i lose elite benefits from other portals. And for business travel, it may not matter (yet?) but times are changing and budgets are tighter.

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