I've been reading on this site and a few others, so I think I have our game plan, but I wanted to run it by you folks before booking and ask a few questions. It's my husband's 60th birthday and we plan to take the CZ from CHI to EMY. Since it's a special trip for him, I'd like it to be as nice as possible! 
-We'll be flying into MDW and I found the directions on getting to Union Station. My plan is to check our carry-ons with the attendant in the Metropolitan Lounge, since we'll arrive several hours before departure. Any lunch suggestions near the station?
- I'm still debating on whether to book a roomette or bedroom. The price differnce is huge! $485 versus $1268. Is there much difference in the experience? Yes, it's a special trip, but geez.
- We'll each have a backpack and one roller bag between us since we plan to spend a few days in the Bay area before flying home. Should we leave the roller bag in the bag room, and just take our backpacks to our room?
- My husband said he would prefer to be on the upper level, but I can't make that request online, right? If I call reservations, how do I get my tickets. I'd prefer to book online and not hassle with lines on day of travel.
-My husband likes a particular flavor of beer,
so if there is place close to the station in CHI, I thought we could buy some of his favorite beer to take with us. Shouldn't be a problem if he only drinks it in our room, right? Is there a store close to the station? I can pack a small soft-sided cooler that lays flat, but what about ice onboard?
- What are the dining car hours? We prefer to eat dinner later than many people. What are the hours for the cafe car for snacks and drinks?
- Do you tip your room attendant daily, or on the last day, like on a cruise?
Thanks in advance for helping me make this a special birthday trip for my husband! Any and all tips are appreciated.
-We'll be flying into MDW and I found the directions on getting to Union Station. My plan is to check our carry-ons with the attendant in the Metropolitan Lounge, since we'll arrive several hours before departure. Any lunch suggestions near the station?
- I'm still debating on whether to book a roomette or bedroom. The price differnce is huge! $485 versus $1268. Is there much difference in the experience? Yes, it's a special trip, but geez.
- We'll each have a backpack and one roller bag between us since we plan to spend a few days in the Bay area before flying home. Should we leave the roller bag in the bag room, and just take our backpacks to our room?
- My husband said he would prefer to be on the upper level, but I can't make that request online, right? If I call reservations, how do I get my tickets. I'd prefer to book online and not hassle with lines on day of travel.
-My husband likes a particular flavor of beer,
- What are the dining car hours? We prefer to eat dinner later than many people. What are the hours for the cafe car for snacks and drinks?
- Do you tip your room attendant daily, or on the last day, like on a cruise?
Thanks in advance for helping me make this a special birthday trip for my husband! Any and all tips are appreciated.