Southwest and Multi-City Flights Have Landed!

We’ve heard you loud and clear over the past few months: You want more flight options to choose from! We’re excited to announce a few major updates that will help finding the perfect flight easier (and faster) than ever before.


First, Upside now offers Southwest Airlines as an airline option for business trips!

How can you find Southwest Airlines on Upside Travel?

  1. Make sure you are registered with your work email address
  2. Search for a trip for work (for leisure trips, is still your best bet!)

With Southwest bookings on Upside, you’ll also be able to apply your Rapid Rewards # and earn points, just like you can on

Additionally, when you book on Upside, you’ll benefit from Southwest Airlines’ generous baggage policy (2 bags free) and you won’t be subject to additional change fees if you need to make a last minute change to your Southwest flight.

On top of all of these great Southwest benefits, we’re most excited to offer you Southwest’s impressive non-stop route coverage across the United States, with over 4,000 flights every day.

Best for Business Sorting

In addition to adding Southwest, our Machine Learning and Data Science teams have been busy optimizing the “Best for Business” flight sort to better surface the perfect, personalized, flight results just for you.

Do you prefer early morning flights or to arrive the night before? Are you always looking for the lowest price or are you comfortable paying a little bit more for a shorter flight? We’ll take your preferences into account and return matching flight results that save you time, every time.

Flight Amenities

Finally, if you’ve searched for a flight on Upside in the past few weeks, you may have noticed a few new icons with each flight result.

For every flight, we now provide detailed information on the Wi-Fi, power outlets, and legroom you can expect on your trip. With this additional information about your plane, you can make a more informed (and more comfortable!) decision on the perfect flight!

Feature Release: Multi-City Flights

Do you try to maximize the efficiency of your business trips? Of course you do!

Hopefully, our new Multi-City Domestic Flight feature makes maximizing your business travel even easier! With this feature on Upside, you can now book a two or three leg multi-city trip.

Need to travel from Washington to San Diego and then back from San Francisco to Washington? With Upside, that’s now possible.

Need to travel from Boston to Chicago to Dallas and then back to Boston? It’s possible with Upside!

Need to travel from Orlando to New York then Newark to Maine and then New Hampshire to Miami? I’m not sure what kind of a trip you’re on, but it’s possible with Upside!

You can book your next multi-city flight with Upside at or by selecting “Flight” on the left side of our homepage and then the “Multi-City” toggle.

We’d love to hear your feedback on this new feature and we hope it helps you build a better business trip with Upside.