We flew in to the midway airport then rented a car and stayed at the Comforr Inn in Gurnee. I highly recommend the Comfort Inn in Gurnee. Don't stay in Waukeegan. The hotels there are not good. Also, if you are going to rent a car, make sure you talk to the car rental place about the iPass option for the tollways.
Chicago or Milwaukee have airports. Both are around 50 miles away. There are quite a few motels near the Naval base. Info will come with your letter from your sailor.
Do not stay at the red carpet inn. It's off limits to sailors. I booked there not realizing. They almost didn't let me take me son on liberty.
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