OK, so I did this trip from AZ to OH at almost this exact time of year a few years back! The hard part is when your stop at a hotel overnight and it's cold. You can leave the plants if it's not below 55 you are ok, but most of your drive will be in colder weather. It got below that temp in our car for two of the nights and I just couldn't manage everything we had with us, our dog, our suitcases, so I let the plants stay in the car. Oh, and we got into a very bad snow storm coming out of AZ, with low profile summer tires, and that was so harrowing I really lost track of the plants' needs.
Then, it was a huge adjustment for those plants, and took at least 6 month for them to acclimate, the following spring. The jade adjusted (had a bout of mealy bugs that winter but got past it), the money tree adjusted over a year, the staghorn never really did so that is gone. I can't remember the other two I brought but they didn't make it either. The bulk of the plants (about 50) I have now, I've purchased at my new place.
Looking back now, even though that happened, I'm glad I brought the jade and the money tree because that was a big challenge and it always reminds me of AZ! So it's doable! I just wanted to let you know about the cold weather issue.
How many are you planning to take? It seems to me you have a monstera? Pretty hearty. What are the other plants?
P.S. I pretty much guarantee it won't take you long to find a new plant shop in Chicago, lol.
