Take many reviews with a grain of salt. I have been working with them for 4+ years and they have been nothing short of kind and hardworking. Sean and Dana work with closely and answer every single question a driver has before purchasing their truck and they process everyone quickly. Owner/ops must always keep in mind that whether you buy a used truck or a new truck, your truck can still run into issues. That's part of owning essentially your own business as an owner/op, but thanks to their warranties and their fast response help, they make sure you're always on the road running smoothly. I have worked with and seen many drivers successfully pay off their leases, including one who has now owned his own authority for a couple years now with the truck he got from them

If I could give negative stars I would. This company is full of crooks. They sell you garbage vehicles and hound you about paying for it. I can't wait until the feds get them.

I bought a truck from them and didn’t even make it 2 months before it had a EGR cooler issue, I told them what was wrong but there mechanic said it was a head gasket, I stopped at the yard under a load going to California and let them look at it, they sent me on and when I reached California I couldn’t even operate the truck . They put it in a shop of their choice and charged me for repairs and still didn’t listen to me, when I picked up the truck I headed west and didn’t even make it 300 miles before it broke again, they had it towed to a truck stop and left me setting with not money and no plains to fix the truck,. Do not buy from them, I turned the truck in and the filed it on my credit. Nothing but Crooks

Very corrupt business practices! Please stay away at all cost, they screw good people over! I repeat, stay away, it is not worth it.

These people are thieves and liars ! Didn't make it 10 days in that piece of junk they tried to pawn off on me. I disputed ir on my credit and WON. STAY AWAY

Shortly after speaking to Steve-O from Chicago is what he called himself. These guys let me know they were just out to get your money. They did not care what they put you in in conversation show that and when I started to speak on the treatment, they worked as a team for the very poor workmanship I saw one review that said, this place needs to be put out of business. Highly agree.

SHADY JAYS is a criminal enterprise. At some point they will rip a driver off. Stay away from these crooked gangsters. You will surely regret doing business Shady Jays.

I lease a truck from this place in June. Truck went to the shop before leaving the dealership! Got the truck back not even a week later the truck breakdowns(motor blew up) didn’t have the truck 10 days in my processing! Still was getting charged for payment without the truck! Truck got repo and owner Jason will not talk to any customers so do not spend your money here please!! Bad Business..Threatening to destroy my name because I don’t want the truck!!

Wish there was a no star option! I bought my first 3 trucks from this location. New owner now, wow is all I can say. Ignored me for 20 min. standing in middle of office. Once finally asked how they could help. Don't know her name but sits by window in rear starts yelling prices across office with out even knowing what I was trying to accomplish. So unprofessional!!! I had a pocket full of cash and I own 8 trucks now. Since I don't look the part they blew a 3 truck cash deal. Wish you luck staying open, stay away we deserve better... Stop self rating; no way 5 star service, buyer beware... Jerome Carter

If you thinking about buying a truck I don’t recommend this place..bad bad bad business!! I put down on a truck and before leaving the dealership truck had major problems! Got the truck back 3 days later still had issues. Truck was down for weeks and I was told by the owner Jason I was still Accountable for my truck payments! He repo my truck just because I wanted my money back and wasn’t paying him a dime because I didn’t have the truck over a month in my Possession!!!

Got approved and made deal. Before i could get there they sold the truck. They make you pay $92.00 a week for warranty until paid off and also make you pay $150.00 a week for escrow. Christina cant remember what conversation she has had. They send you emails BUT emails arent correct and you never get them. Christina claims she calls on a certain day but i didnt answer which is wrong. I called her and had a conversation with her. Dont do business with these shady people.

I purchased a truck from Robert, and had a great experience from Jason, Robert & Dana. Had a accident and tore off my Bumper, my fault, Robert ordered a new one and installed it, at no cost to me. I recommend several friends, all are very Satisfied. On the financial side when things got slow, Barbara D. Went out of her way to assist me. Much love ❤️ to Windy City Jay. Roberson Transport LLC Skip Roberson.

Ill be returnning your piece of trash truck very soon. Joe I can tell is the only truthful and honest person at WindyCity. Sold me a truck .Jason came from landstar whose known for screwing drivers. How are these people still in buisness? Paying for a truck every week is not an owner operator, its a truck rental. This is the most stressful trucking position I have ever delt with. DRIVERS I am giving you advice DO NOT let these people trick you into buying a truck by yourself or threw a third party MC. If you purchase it through a third party MC you'll pay for two trucks. These people are getting rich off our dumb mistakes.The moment I stepped in that facility it was bad vibes all the way. Do Not deal with these crooks!

Not trustworthy. Made financial truck through their bank and 4 months ago I paid off my truck and Still didn’t get a title. Hristo sales person, very tricky, and slick opportunist, trying to sell you a pack of useless warrants. I had a major transmission repair and when I called him to find out about my warranty, his talking was kinda neglecting, and all the times he rudely disavowed my warranty claims. I have hard regret that I didn’t go with Arrow Truck Sales, when I had a chance before. I would NOT recommend this dealership

I bought my Freightliner in January and I should say I am totally satisfied. Truck is doing its job without any issues. Dana is very helpful and honest, I didn't feel any pressure, process was nice and smooth. I've been recommending them to my friends since then and I'll be heading to see them when I'm ready to buy my next truck ..

Great experience and costumer service. Not the best credit load rstes but they can help when credit is low. Bought my 4 th unit with them