It’s about the journey, not the destination…

…said someone who’s never been through Chicago O’Hare on November 23rd.

Travel for work, pleasure or holiday can be a difficult, busy and hectic process, and with Thanksgiving, winter holidays, and New Year’s Eve approaching fast, it’s likely that you’re going to have to hit the road or airport at some point in coming months.

To help you make that journey a little easier to handle, we reached out to some of Chicago tech’s most prolific travelers for advice. They shot us back notes from across the country–LA to New York City–with tips on the best margarita at O’Hare, how to pack your luggage so you never have to check a bag, and the best website for cheap airline tickets.

Raaja Nemani, cofounder of Bucketfeet (Courtesy of Nemani)
Raaja Nemani, cofounder of Bucketfeet (Courtesy of Nemani)

Raaja Nemani, cofounder of Bucketfeet

For his international brand of artist-designed sneakers, Nemani estimates he travels at least three to five days a month. He wrote to us from Boston (en route to New York City) and will be heading to Hong Kong in a few weeks.

I would always argue packing and then taking out at least 50% of what you packed. The beauty of packing light is that you realize it forces you to explore a new city if you’re missing something you need, and you get more [comfortable] with traveling and new places knowing you can pretty much get everything you need anywhere you go.

More specifically, if you’re visiting London (a city I love and maybe the only equivalent to New York City), go to Brick Lane Market for ethnic food, boutique chocolate shops, vintage record stores, breweries, etc. So a bit more of a different London experience but also great for unique gifts for a special someone.

Amanda Signorelli, CEO of Techweek (Courtesy of Amanda Signorelli)
Amanda Signorelli, CEO of Techweek (Courtesy of Amanda Signorelli)

Amanda Signorelli, CEO of Techweek

Techweek hosts events across eight cities in the US and Canada, so Signorelli is constantly on the go. She wrote us her travel tips from Los Angeles, where TechweekLA is underway.

Productivity: Don’t forget to charge all of your devices the night before or the day of, bring a back up charger for your phone and computer. When you’re stuck on a long flight or in transit you don’t want it to put you behind [on] the work that needs to get done just because your computer dies.

Nutrition: Airport food more than often is terrible for you and it can be incredibly difficult to find something healthy to eat so pack 2-3 protein bars, an apple, and a piece of chocolate, if you’ve got a sweet tooth like me and don’t want to consistently spend $5 on a snickers bar at the airport. 

Roll your clothes when you’re packing

Accessories: My two pet peeves when flying is when an airline won’t turn off the cabin lights on early morning flights when you’re trying to sneak in some sleep before a big day and when it’s too cold to fall asleep. To get around this I carry a pair of warm fluffy socks, (yes I look ridiculous), plus an eye mask and I always wear a heavy coat.

Luggage: Do not underestimate the power of a great carry-ons, messenger bags and phone case. If you can avoid it, never check a bag it will slow you down. Roll your clothes when you’re packing to save space and avoid wrinkles. For a messenger bag, find some thing where you can hide an extra pair of shoes to swap between heels and flats. Your bag should also ideally have a strap to go over your carry on handle (I personally use a Lo & Son’s bag, they have great sales). Lastly, avoid digging in your purse for your ID at TSA by using a phone case like this.

Matt Meltzer's travel accessories (Courtesy of Meltzer)
Matt Meltzer’s travel accessories (Courtesy of Meltzer)

Matt Meltzer, founder of Sage Corps  

Meltzer runs a college study abroad program that sends students to work with global startups everywhere from Argentina to South Korea, and has an extensive domestic and international travel schedule.

I try to fly Tuesday-Thursday, when fares tend to be cheapest. I love day trips (other than to LA), so that I can save hotel costs and sleep in my own bed. Wherever I travel, I have my macbook air, water bottle with carabiner, and of course an external phone/computer battery charger. For international flights, when I need to sleep (I’m sitting upright in coach), the travel pillow actually works (with a couple beers). If I have some free time, I love getting lost alongside Google maps and after skimming the NYT “36 hours in [global city]” column. And when I’m really lost, Uber has saved me in multiple cities worldwide.

Katy Lynch, founder of SocialKaty, and Craig Ulliott, cofounder of Belly

Katie Lynch and Craig Ulliot (Courtesy of Katy Lynch)
Katie Lynch and Craig Ulliott (Courtesy of Katy Lynch)

The wife-husband Chicago tech duo, who travel together at least once per month, wrote to us from their current destination–Los Angeles. 

1. The best real tip I can offer is travel is the most important time to be organized. Get TSA-Pre, don’t be late, and pack super light.

2. Don’t wear work out gear or pajamas when you’re traveling to and from the airport. It’s sloppy and lazy.

On top of that, manners and smiles go a long way. Lots of stuff goes wrong when you are traveling. When you approach customer service with a positive attitude, you get a lot more accomplished. Craig and I have been given upgrades just from being polite.

3. Business travel is time we get to spend together, which is really nice. We always get to the airport early enough to fulfill a hilarious tradition of a margarita at Chili’s. (Chicago O’Hare is the only Chili’s we go to.)

Airports can be miserable places for some people. So, find a place you can relax (Chili’s!!!) and amuse yourself for hours by people watching or getting work done.

Nicole Vasquez in Santa Catalina, Panama (Courtesy of Vasquez)
Nicole Vasquez in Santa Catalina, Panama (Courtesy of Vasquez)

Nicole Vasquez, founder of The Shift

As founder of coworking space The Shift and travel blogger at Why the World, Vasquez takes at least one to two international trips and up to 10 trips within the US. Recently she’s traveled to Croatia, Slovenia, and San Francisco and coming up, she’s headed to Puerto Rico on a surf trip.

My current obsession is the Kayak Explore feature. For me, I want to go everywhere at least once, so destination is not important, but my budget and when I travel is high priority. With Explore, you can input the month or season you can travel, what your flight budget is, and it will show you anywhere in the world you can go for that price during that specified time window. There’s even a sidebar that will let you filter by category (ex: beach, romantic, foodie, family-friendly, etc.)

I feel like its a modern day approach to the ol’ spinning of the globe and letting your finger pick your next destination. It’s also quite dangerous for travel addicts….I’ve spent many late nights browsing Explore (perhaps with a glass of wine)…and then ended up booking a trip.