Rather than list them, I'll provide you with some good resources.

A gluten free blog run by a fellow paleo Chicagoan:

http://chiangcw.blogspot.com/

Here is what happens when you search "grass fed beef" into Yelp:

http://www.yelp.com/search?find_desc=grass+fed+beef&find_loc=Lakeview,+Chicago,+IL#cflt=restaurants&find_desc=%22grass+fed%22&find_loc=Chicago,+IL

I can vouch for:

DMK ($8 grass fed burgers with fried egg)

Lula (hip, creative new American; once saw a whole skinned deer delivered through the front door)

Great Lake Pizza: The ultimate cheat meal if you can get a table. It's the place that GQ rated best in America. The thought of it has me repeating Ba Ba Ba while gobs of spit fall from my lips.

And I'll second the person who said Fogo de Chao: make sure you (i) avoid the salad bar, (ii) avoid the carbage they bring to the table automatically, and (iii) request small pieces of each meat so that you have room to try them all.

Rick Bayless has a couple restaurants, some paleo options, uses grass fed beef :) http://www.fronterakitchens.com/restaurants/restaurants.html

I know this is an old topic but I just went to two restaurants that are Paleo Friendly (though many things on the menu are not).

The first is called HB (aka HomeBistro) at 3404 North Halsted Street Chicago, IL 60657. It had a lot of unusual meat cuts and choices on the menu such as pheasant and lamb and also featured liver, sweetbreads, and cow tongue. This makes for a nice variety and the dishes didn't have a lot of carbohydrates. If you're with nonpaleo people it's also BYOB. It's more of a nice/higher end type of place.

For more casual dining I went to Aloha Eats at 2534 North Clark Street Chicago, IL 60614. It's Hawaiian fast food and had grilled salmon and some other fish dishes and there were a few interesting side dishes, including Kimchi which I think is paleo friendly.

Chicago has good options for Paleo.

Skip Fogo de Chao (and skip Giordanos...) -- check out Las Tablas up in Lincoln Park. Get the skirt steak with the spicy chimichurri and some grilled plantains if you want some carbs. SO GOOD. There might be a Groupon for it too if you're lucky!

I gotta put in my vote for Carnivale, a Latin American fusion restaurant. Here's my review from my first visit. http://www.yelp.com/biz/carnivale-chicago-2#hrid:tNdeVgomTZIB4IisFMOukQ I had been raving about it to Cherry since last October and so we went again tonight. Same great experience.

I love Joe's Stone Crab, but I cannot guarantee their beef is grass fed. The Brazilian Steak Houses listed above are solid choices for the carne.

I would also recommend the Gage on Michigan Avenue in the Loop. With a few minor adjustments, their menu has quite a few "meat" options.

I see a lot of posts inquiring about Paleo-friendly restaurants. I just assume most are not and aim for a place where I can get a steak or, less desirably, piece of broiled fish. If there are any gravies or sauces on it, I just order it without. Sometimes I'll ask for some crumbled blue cheese on the side.

I know blood glucose is not the only measure of whether something is Paleo, but taking your BG 60 or 90 minutes after you eat gives you a decent shot of knowing whether there was flower or sugar in something. If a restaurant is one I might frequent, I go there, eat something, then test my BG later. If it didn't rise much, I put that on my list of "safe" restaurants.

Anyone ever consider giving X-Marks or a similar "underground restaurant" a chance? I've visited X-Marks a number of times before going Paleo and they do wonderful things with food. They cater to any dietary requests, and if a large enough group attend on a night, they'll customize an entire 5 course menu to meet any request.

I think it's about 20-25 people to rent out the place for a night to do a fully customized Paleo menu (i.e., not just remove gluten from the current item, but they'll design the menu from scratch to meet the requirements based on what is in season and available that day in the market). If you just show up on any other night, they'll take their existing menu and adapt it meet dietary requests. It's around $70 per person, BYOB, great service, great atmosphere, and great food.

They also can meet individual requirements if you do rent it out.. If we did a Paleo night, some people can choose dairy free, some (or all) could do gluten free, vegetarian, vegan, etc.. they'll happily meet any or all requests on a per person basis.

Fogo de Chao is national chain we have that in the DC/MD/VA area.

Go to Giordano's!!!!

Pizano's has a gluten-free pizza in which the crust is made out of sausage.