Trip Motivation
We have several close friends who live in Chicago, IL. On various occasions, we have driven or flown for trips to this city. Below, I lay out what both options look like and the costs and benefits for each. For our most recent trip in November 2021, we decided to fly, but overall we think this trip is better as a drive if you have any flexibility.
November 2021 Trip
We had a few unique considerations as we made our November 2021 trip. Ben recently fractured his toe and was in a boot and on crutches. Prior to the trip, we conferred and decided that even if we wouldn’t get to “do” the city as much as typical, this trip was still worth doing so we could visit friends. We initially thought the flight would be better than driving due to the time involved (and I don’t like to drive). However, after taking the trip, driving would have probably been a better option so that Ben could stretch and move his foot and so that I wouldn’t have to carry things through multiple airports (like a sleeping Ellie) on my own.
Another consideration that won’t apply to other trips was that we had booked this flight to take advantage of a Southwest promotion (expired now) to fly in November to earn a companion pass in Jan/Feb. Paying more now meant we could save the same or more in the spring.
Driving: Nashville, TN to Chicago, IL (7.25 hours plus stops)
The total drive time is about 8 hours with quick stops. For more on how we handle long road trips with kids, read more here.
Option 1: Leisurely drive in daylight. With the length of the drive, it’s nice to do on a full day starting around 9 and arriving in Chicago for dinner. This option has been harder for us lately due to not wanting to use a PTO day for work. Also, Carter has not been excited to be pulled out of school because he has FOMO (fear of missing out) on what they’re doing in class. A holiday weekend or teacher day for Carter would be a good way to have that extra time for driving. Starting in the morning also gives us flexibility for longer stops. On several trips, we’ve made a stop half-way in Columbus, IN, a little south of Indianapolis. This small city, a few miles off of I-65, has a pizza restaurant with beer and outdoor seating, a small food court with a cool playground, and an inexpensive ($7) little children’s museum!
Option 2: After work drive. If we’re watching vacation day counts or have work tasks that we can’t escape, we have also done this drive on a Friday afternoon starting closer to 1p. Both Ben and I have jobs that are flexible about us committing to a 4 hour day and not taking a vacation day if we leave early. An 8 hour drive gets us to Chicago with just enough time to sleep.
Option 3: Split the drive in half. If the opposite applies and we have days to spare or two half-days of work and half-days of driving make more sense for our schedules, there are multiple options to stop overnight in a city like Louisville, KY or Indianapolis, IN or any hotel along the interstate.
Chicago, IL to Nashville, TN
On the way back, we usually leave in the early afternoon, often after a morning race for Ben. On previous trips, we like to break up the drive back with a quick stop in Louisville, KY to visit friends. This stop is about 5 hours from Chicago and the 3-hour end of the drive after Louisville post dinner is not too bad (probably with some iPad watching time). In the past, if we were flush with vacation days, we would stay overnight in Louisville after a Chicago trip and enjoy a visit to the zoo in the morning before leisurely heading back to Nashville.
Driving recap: 8 hours each way door to door, options for stops in Columbus, IN, Louisville, KY
Pros: Cheaper (Gas <$100),
Cons: Potential missed work and school, short period in Chicago, lots of time in the car.
Flight details
We purchased tickets for this November 2021 trip from Southwest Airlines for $210 RT/person. We had a little bit of unused travel funds from re-checking previous flight prices, but mostly paid this trip with cash. One of the main reasons we flew, even though the cost was high, was due to Southwest’s promotion (expired now) to fly in November to earn a companion pass in Jan/Feb. The fine print specifically stated that this trip couldn’t be on points. If you’re flying at any other time, you can usually find better deals ($100 RT) or use Southwest points (around 6k RT). You can earn Southwest points from Southwest credit cards or by transferring Chase points using the Chase portal. Read more about tips for airline trips here.
Getting There: Nashville (BNA) to Chicago (MDW) Fri 4:20p – 5:50p (1hr 30 m)
Coming Back: Chicago to Nashville Sun 9:45p – 11:10p (1hr 25m)
Flight recap: 1.5-hour flight each way. 5 hours door to door (2 h preflight/1.5h flight/1h airport walking+baggage+car rental/0.5h driving from airport to city)
Pros: Able to do a partial work/school day on Friday, more time in Chicago, less time in a car.
Cons: Higher costs (flights + car rental ~$1,000), airport navigation difficulties, and also Covid is still a thing.
Airport Lounges
When traveling with layovers or to new cities, we always check the local airport website and the Priority Pass Lounge website prior to the trip. The Chase Sapphire Reserve card (in addition to others) comes with Priority Pass access. This card gets you access to various airport lounges. It is much more common internationally. In Nashville, there is a Minute Suites lounge in terminal D. No lounge available in Midway Airpot.
Other travel perks
Another perk you can get from several credit cards we have used is Global Entry/Pre-Check. This is always helpful for avoiding long lines and spending as little time as possible with others. After you activate your credit card, you’ll use it to pay for the Global Entry fee and get reimbursed immediately. If you want more on this particular benefit and how to use a credit card to receive it for free, check out our tips here. The cards below are ones that we’ve used and are very pleased with, but there are definitely more options if something else suits your family and travel goals better.
Driving in Chicago
Since we chose to fly, we had the additional cost of a car rental. We like to use costcotravel.com and continue to check in on the prices and will rebook if the price lowers. Our cost for the car rental was $140 for 3 days. For more on car rentals, including the best card to use, see here.
After arriving, we had to collect our checked bags and car seats, take a shuttle to the car rental center, wait in a long line, and drive to our hotel. This is another thing to keep in mind when comparing time differences between flying and driving. It’s not just the flying time but the time arriving earlier to the departing airport and time spent at the destination airport as well. For this trip, flying took us 5 hours door to door, so there’s much more than the 1.5 hour flight time to consider.
Parking is also grossly expensive in Chicago. If you are able to taxi and use public transportation, that may be an additional consideration to flying rather than driving your own car. Our hotel gave us free parking due to our hotel status.
Other Considerations for Driving versus Flying
After taking this recent November 2021 trip, we concluded that driving would have probably been a better option so that Ben could stretch and move his broken foot and so that I wouldn’t have to carry things through multiple airports (like a sleeping Ellie) on my own.
Also consider that if you have items such as bikes for races, fishing, or skiing items, the ease of driving vs. flying may be something to consider in your decision-making. In addition, if we had driven instead, we could have considered bringing our puppy along for the trip if we had a pet-friendly hotel and a safe place to leave her while we went on adventures. But that wasn’t an option we considered on our flight, so we paid for a dog-sitter in Nashville, an added cost that may or may not have applied if driving.
