Chicago Dive Charters (Burnham Harbor) 312-842-1480
http://www.chicagodivecharter.com/
Great boat, unfortunately Cap't. Hank sold it this winter and hasn't replaced it yet. Rats.
Discovery Dive Charters (Burnham Harbor) 815-786-1337
Decent boat, it was in the harbor last year but I never saw it leave it's mooring. The Cap't has a reputation for canceling at the first sign of inclement weather.
Enterprise Marine (Waukegan Harbor) 847-520-4689
http://www.captaindales.com/enterprise_marine.htm
Big old boat, slow as molasses but gets you where you're going with plenty of room. Cap't Dale is a nice guy, I'll dive with him most any day.
Shipwreck Adventures (Winthrop Harbor) 815-222-3069
http://www.shipwreckadventures.com
Smaller boat that trailers to Winthrop and other harbors. Cap't Greg Such is a terrific diver and TDI instructor, I've done a couple of advanced classes with him. If you're DIR inclined, this is your guy.
The Lender (Milwaukee) 414-482-1430
http://www.pcdiving.com/about_charters.htm
Two boats, the Len-Der and the Reef Diver. The Reef Diver is the better of the two but has had some mechanical problems and hasn't been running for awhile. The Len-Der is a giant tug with a very slow top end but gets the job done. Cap't Jerry is one of the old-time masters and knows the Milwaukee wrecks like the back of his hand. Recreational diving only.
A few more to consider:
The Nordic Diver (Milwaukee) 630-880-4606
http://www.nordicdiver.com/
Excellent service from Cap't Bill, compressor on-board, runs some decent technical trips, nice wooden cruiser. I like this boat and the Cap't.
N'Pursuit (East Chicago) 219-942-5767
http://www.npursuitcharters.com/index.html
Haven't been out with him but there is a group from this board planning a trip this summer - look for a thread about a Chicago Dive Party in 2004. I've met Cap't. Mike and he's a nice guy.
Great Lakes Explorer (Burnham Harbor) 312-922-5090
http://www.divechicago.com/
Maybe the only dive charter running out of Burnham Harbor this year. The Cap't has been around for ages and is renowned for being a little crusty but knowing his stuff.
WreckXpress (Milwaukee) 414-659-6350
www.wreckXpress.com
28 ft Trojan seats 4 - 6. Another new boat that I haven't dived with but I will fix that problem this summer. I watched this boat last year and the guys on it know their stuff, a friend has been on a Truk trip with the principals and speaks highly of their diving skills, too. Technically inclined.
L'Attitude (various Wisconsin Eastern shore) 608-345-0758
www.diversions-scuba.com/pointsnorth
Trailered 28 ft SeaRay trailered to various harbors. I've never been out with this guy but met him and I'm going to give him a try this summer if time permits.
LCM Charters (Racine) 262-412-8259
I've never been out with these folks and don't really know anything about them. 44ft trawler seats 6.