Romantic places of my past:
With only one drinker you could get away under 100 at Geja's...my favorite romantic spot. I remember having to split the bill with one date years back in order to go...I'm a feminist.
One problem is you smell like bubbling oil after so, if that is a problem....
Joe's Prime Steak and Seafood is a special night out in my book. Our service there was top notch as was the food. Fun atmosphere. Expensive.
You could eat like kings or queens at Cafe Iberico. This is my absolute favorite Chicago restaurant. It's a night out, but you have to like crowds. We go at off times...or start at Iberico for apps and drinks, then eat somewhere else.
I've walked from Iberico to Frontera where it's fun to eat and be. You get to see the chef walking around stopping to talk to people. I think Bayless is the coolest guy--wish he was my dad so I could go on his show and eat from his garden. Some people complain about it, but I found it to be a worthwhile experience. The $9+ margaritas are small, but killer to sip. It might be tough to get a decent reservation there, though. I find the Frontera Kitchens website a marketing nightmare.
Have fun and report back!
Cafe Iberico
Geja's
Frontera, et. al.
Joe's Seafood
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