Can I leave security and then go back through security at the Chicago O Hare airport during my layover?

I will have a longer layover at the O Hare airport on Sept 11. I have a friend who lives in Chicago who would like to possibly meet me for a drink. I know he won't be able to meet me at the terminals, but can I meet him on the other side of security and then go back through security to catch my connecting flight? Also is there anywhere to get a drink on other side of security in the airport? If not is there anything right outside the airport? This will be my first time at O Hare airport and I'm unfamiliar with it. Any help would be great.

Can my Mastiff fly in-cabin?

I have a 100lb mastiff who is relocating across the country with me. I discovered recently that there's an air travel embargo on mastiffs, and they are banned from flying cargo on every airline I can find.

She is clearly too large to fly in-cabin. Do I have any other options for air travel? My only other option is to use a service such as citizen shipper where a complete stranger would drive her clear across the country for 5 days.

I DO NOT want to go that route but I'm not sure if I have any other options. Does anyone know?

Can i make a flight with 30 minute layover?

I'm flying from iowa to chicago and then to philadelphia in october, it says we're scheduled to land at chicago at 1245pm and leave to philly by 135pm… We land at T3 and leave from T3 also, american airlines, so i won't have to transfer terminals but i have only been thru chicago a few times, i know every flight is different, usually they land late even when the weather is perfect, but does this seem like enough time? I will run as fast as i can but what does everyone think? Is this reasonable amount of time to make it to my gate in time? Maybe i can have them call the pilot and tell them to wait?