New to business travel out of ORD? Buckle up!

Business travel is a mixed bag. On the one hand, traveling to a new city is exciting (both for the city & the work experiences you’ll have there)! What’s not as much fun is the unknown of business travel. That is, stress, being away from family & friends, airport logistics, transportation, and getting settled into your hotel. In the event you’re in Chicago for business anytime soon, here are some of my experiences and best tips for one of the busiest U.S. airports – Chicago O’Hare International Airport (ORD).


I’ve been traveling for business nearly seven years, the last five of which have been in and out of Chicago, and my impressions of ORD have varied greatly these past few years. In its favor, Chicago is smack dab in the middle of the U.S., which means traveling to most domestic destinations involves a 2 to 4 hour flight. Not too shabby! Especially compared to my former home city of Seattle, where it was a commute to get anywhere in the US. However, the other major consideration of flying out of O’Hare is getting to the airport.


Transportation to the airport boils down to the time of day. Weighing your options of using public transportation or a car depends on cost and timing.

  • Train. If you work Downtown Chicago, the ‘L’ has the Blue line to O’Hare for approximately 45 minutes. The fare is very reasonable and a one-way ticket costs $2.50. Which is super cost effective and great during the rush hours (6-9am and 3-7pm).
  • Taxi. But if you need to get to the airport mid-morning or early afternoon, taxi or rideshare apps are optimal. Usually the cost is around $20-25 dollars and takes 15-20 minutes to get to the airport.

Once you arrive, security typically takes anywhere from 15 minutes to an hour. Generally, ORD is the busiest at the end of the week, especially Thursdays, so be warned.


But this is Chicago so another major factor in your decision is weather. Any seasoned business traveler will tell you their favorite story of being delayed or stuck in Chicago due to inclement weather. In my short five years here, I’ve been delayed enough times that if you added up all of the hours I could probably take 2 weeks of PTO (no, I am not exaggerating – it’s bad). Terrible weather finds itself in the Windy City – yes that is an obvious pun, but it’s the truth. If you ever find yourself watching the Weather Channel, notice how they put up the radar for the U.S. At any given time, you’re bound to see three to five air streams making their way through Chicago. Plus, this area sits at the bottom of the Great Lakes, which is called the Third Coast for a reason. Locals love to talk about how much Lake Michigan affects their weather; it’s either the rain, the wind, the snow, the humidity – whatever weather term you can find, Lake Michigan is the cause for it. Consider yourself warned if you have to fly in and out of Chicago, you might want to invest in a club pass from your favorite airline.


To put it all into perspective, take my maddening story of flying out of O’Hare to Kansas City. This trip had all of the stresses of business travel – weather delays, gate changes, crew delays and even a missing pilot. It was my first visit to Kansas City to meet new clients, so you can imagine the anxiety of trying to get out before the airline canceled the flight. When I got to O’Hare at 4:30pm, the flight was schedule to depart at 6pm (I usually give myself an hour and half to two hours before departure). It didn’t matter as our flight out to MCI was delayed 5 hours, taking off at 11 pm. Once we landed, it was 1:15am and I had to decide how to get to the hotel. I had a rental car scheduled for pickup, which I called to cancel and reschedule the pick up at their downtown location. At the time, Uber/Lyft were not operating out of the airport, so I called a taxi (pretty painful at 1:30am), which I waited 30 minutes for. Tip: there are very few taxis that time of night. Once the taxi arrived, it took 30 minutes to get to the downtown area, and I checked into my hotel at 2:30am. To add insult to injury, my first appointment was set at 8:30am, so I barely got 5 hours of sleep. It was a long day of introduction meetings, but I powered through and got to recover by going to bed early, only to embark on a second day of intro meetings.


So, to share a few tips when arriving in your destination to get your business trip off to a good start:

  • Understand the available ground transportation options available at the airport. It’s helpful to have a couple options in the event you get delayed.
  • Once you arrive to your hotel, I encourage you to set up a routine to make your trip as easy as possible. Settling into your hotel is critical for a successful business trip.
    • My first order of business is putting my luggage in order to ensure I keep my sanity for the next couple of days. This includes unpacking all of my clothes, getting my toothbrush in the proper arrangement – usually a towel down next to the sink along with my shaving cream and razor.
    • One additional step – set aside your clothes for the new day.
    • Mornings are important – find your gym, your coffee spot, or your best Wi-Fi spot.


Good luck and safe travels!


– Matthew Salmon, Hotwire Hotel Account Manager

  • Over 10 years in sales, account management and business development
  • 7 years in on-line travel, specifically consulting with hotel groups on revenue management, content support and customer acquisition
  • Board Member of the HSMAI Chicago Chapter for 2 years, supporting the chapter’s efforts with Fundraising, Sponsorship & Event Management
  • Recent MBA Graduate from DePaul University with a concentration in Entrepreneurship & Change Leadership


Leave a Reply

Your email address will not be published. Required fields are marked *