I’m finally out of the Southwest! And in Chicago for a little less than a week, predictably crazed as I try to see all my friends and eat the entire city.

This post is a thursday throw back to 2014 during the polar vortex when the Chicago river looked like this

And my friends Corey, Matt, Rob and I did a progressive dinner on Randolph Street along with Cardboard Ryan. I look insane or super excited…

The original Progressive Dinner group is Corey, Matt, Ryan and me but Ryan couldn’t make Chicago so we created a cardboard cutout o bring along with us so he wouldn’t miss anything. You want an interesting big city experience? Try bringing along a cardboard cutout as a dining companion. Photo ops for days!

I’ve written about Progressive Dinners before and described them as the perfect solution to an excess of restaurant options with a minimum of time. Why eat three courses at one place when you can eat at three places? Or five?

We’ve now had progressive dinners in New York, Chicago, Atlanta, New Orleans, Dallas, San Francisco and Zurich. If I were a really responsible blogger I’d have written about all of them. Clearly that hasn’t happened. But over these years of eating and drinking (a lot), we’ve argued (a lot) about how Progressive Dinners actually work and last summer in Zurich we sat down and tried to hammer out Progressive Dinner rules, written very officially on the back of a coaster. The conversation went something like this…

Kaitlyn: first rule is “start early.”

Matt: Second rule is the first course has to be champagne or something sparkly.

Corey: Is there a rule about beverages? Do they have to be alcoholic?

Matt: the first one has to be sparkly.

Ryan: just because we’ve had something sparkly at the last two dinners, doesn’t mean it’s a rule.

Kaitlyn: let’s call it a trend.

Corey: Second rule, one course at each restaurant.

Matt: third rule: one course has to be tapas.

Corey: no it doesn’t, we don’t always have tapas.

Matt: but we mostly have. New Orleans, New York, Chicago…

Ryan: but we don’t have to.

Kaitlyn: Ok, tapas is a trend. Not a rule.

Ryan: Third rule: one person is in charge of each dinner. Not Matt.

Matt: What?!

Ryan: kidding! You can be in charge. As long as there’s something sparkly and some tapas.

Matt: there needs to be a photobooth so we can take pictures.

Kaitlyn: Can we start a new coaster called “Matt’s Trends?”

Ryan: Fourth rule, Matt doesn’t get to make rules.

Don’t you just want to have dinner with us as we eat all night and argue?

Basically the Progressive Dinner rules came down to these:

1. The number of restaurants in a dinner is only limited to how much you can eat in a given night.

2. Chips and salsa is a course and woe betide the dinner planner that omits this course.

3. Every dinner course has to have a drink pairing, sparkly or otherwise.

I will say that walking between restaurants is preferred since there’s so much eating and drinking and I heartily advise that you start early because everything takes longer than you think.

I planned Progressive Dinner Chicago 2014 and picked a series of restaurants on Randolph Street because it’s all very walkable and most of Chicago’s solid fantastic restaurants are centered here right now.

We started at my favorite cocktail bar in all of Chicago, Aviary

Swanky fancy cocktails with spectacular presentation, like “In the Rocks” where the booze comes inside an ice ball. The server places a slingshot over the top of the glass, one snap of the rubber band and the ice breaks, creating drink on the rocks.

Brilliant. Aviary gets more online chatter than any other cocktail bar in Chicago, with good reason; so I won’t go on and on here but I highly recommend a visit if you’re in Chicago. Make reservations, bring a camera and plan to hang out for awhile. It’s totally worth the time and the money.

RM Champagne Salon was stop #2

For oysters and sparkly drinks (just for Matt!) as well as lobster deviled eggs, which were divine. Deviled eggs are slowly sliding out of restaurant fashion – overtaken by cauliflower, me thinks – but I’ve enjoyed every creamy spicy sensational bite I’ve had across the nation this past year. Some time on a slow news day I’ll post a deviled egg retrospective. Aren’t you looking forward to that?

Anyway, RM is a cozy brick walled intimate space, perfect for romantic dates… or as course #2 with 4 people and a cardboard cutout. Wherever you might be in life.

Course #3 was supposed to be de cero but… it was closed.

I know. Progressive Dinner fail! And trust me, I’ll never hear the end of it. I neglected to photograph the outrage so you’ll just have to imagine it. Cardboard Ryan got particularly pouty…

Moving on to Course #4, Avec, another of my favorite places in the city

The restaurant looks like Ikea designers were cut loose in a closet and instructed to only use blond wood and straight lines, but the chorizo-stuffed medjool dates wrapped in bacon (above) are the stuff of Chicago food legend. Magic spicy sweet crispy roasted bites of heaven. My mouth literally waters as I type. I also highly recommend the whipped brandade with garlic bread, crunchy flat bread with oozy melted salty potatoes that just might change your life.

We drank a lot of wine and my friend Rob joined us

And then we progressed to course #5, Randolph Street’s piece de resistance Girl and the Goat

Also my favorite Cardboard Ryan photo op of the evening. I’ve written about Girl and the Goat before and I took better pictures then so I won’t repeat myself. Suffice it to say that the food is still splendid, reservations are still needed and order the pig face. Really.

Post Girl and the Goat we ran into problems of time with my planned nightcap location, so instead of Maude’s we went to Lone Wolf

Where they mix really good brown liquor cocktails and offer a drink called Zombie Dust.

After Lone Wolf it had already been a long evening of drinks and hilarity so why we felt like we needed yet another nightcap is beyond me. I think it was Cardboard Ryan’s idea

But it was the Berkshire Room, conveniently situated in the bottom floor of our hotel. I guess that made a demented drunken amount of sense. Plus Cardboard Ryan never passes up a photo op with a pretty girl. I’m gonna say that one nightcap was probably enough and it was good we were already home by that point.

6 hours, 6 courses, 4 humans and 1 cardboard cutout. And so concluded Progressive Dinner Chicago 2014 on Randolph Street! Long night, great eats and some of the best company anywhere.

More Chicago tomorrow!