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I’ve moved a few times in the past few years. Cheapest option is to rent a truck yourself, I recommend Penski, and driving to Chicago. You can rent a car carrier and tow one car and have your significant other drive the other. One way truck rentals with car carrier can be had for well under $1,000 with miles included. I’ve done this 4 times with little issue.
Another way I have moved is to use PODS. I used them because I had a 3-month timeframe where I didn’t have a permanent home. Process was pretty straightforward but more expensive. The POD shows up and you load it and they take care the moving. The harder part is moving into a city will require getting permits because PODs does not do same day drop off and pickup and they do not guarantee timing until the day before.
For loading / unloading labor, I always use Uhaul Moving Help. Let’s you book moving companies who will load and unload your truck. Definitely read the reviews and be willing to spend a little more to get good movers.
I moved from Chicago to Charlotte in 2021. I had a moving company come to my one bedroom apartment in a Chicago and box everything up and take it to my charlotte apartment. Cost me $5,000 and delivery took ~30 days.
Unfortunately for moving companies that about the right timeframe but pretty cheap all considered.
If you’re looking for a cost-effective option, I honestly recommend using a U-Haul U-Box. Moved from Boston and especially for just an apartment worth of furniture, 2-3 boxes is enough. The boxes arrived just a few days after we drove down and were picked up out of our driveway as soon as we were done unpacking. I think you can also hire companies to pack/unpack your belongings through U-Haul, but we just did it ourselves. Also if you’re already considering selling one of the cars, I’d just do that instead of paying to ship it up there.
Thank you for the recommendations! I don't think I'll be able to get the desk out of the apartment by myself (getting it in was a nightmare), so I'll investigate companies to help pack.