Long weekends are great for quick trips to nearby cities. Chicago is perfect: Porter flies there, meaning there’s not a massive amount of standard airport bullshit to deal with. Our dollar is strong right now. It’s a big city but not so big that a weekend feels like too short a period of time.

I went, mostly to eat and walk around. I did lots of both. Don’t let anyone tell you different: Chicago is the most beautiful big city in North America. The architecture is insane; the streets are wide; the rivers mean there are stunning vistas even in the middle of a densely packed urban area; Millennium Park, while not enormous, is really well designed; and the waterfront is terrific, too. I love you, Toronto, but seeing another big city on one of the Great Lakes do almost everything right makes me realise how much we’ve screwed up.

But let’s talk about food and drink. I like to - no, love to - make a Google Map whenever I take a trip. I especially like this because, if you’re traveling with people who aren’t jerks, everyone can share a common itinerary and and add to it as they see fit. Every restaurant, bar, store and attraction is in one place; and it’s accessible on a mobile device. If you’re going to Chicago - or New York, or London, or San Fran/The PCH - feel free to send me an e-mail. You’ll get a map, and a sense of my itinerary, and reviews for everywhere, too. Nice!

I guess if I know anything, it’s sarcasm. But after that, it’s food and drink. My two favourite things in the world, really. So here’s where we ate, and drank, and what I thought of them all. Did some shopping and a ton of walking around but you don’t need my help for that.

The Best Experience was at Aviary. It’s a bar run by the folks who do Alinea, which is probably Chicago’s best restaurant. It’s certainly the city’s most involved restaurant, in that meals take hours and are a minimum of 15 courses. Aviary applies a softer version of that approach to drinking - the cocktails are involved but delicious. We did a ridiculously expensive bourbon flight - 6 whiskeys that are simply unavailable in Canada. Delicious. Best of all there, there’s a 10 item menu of ridiculously upscale bar snacks. Almost all were amazing - tiny little bites of molecular goodness. A fried ball of clam chowder that maintained a liquid centre. A little bonbon of foie gras that tasted like the most upscale peanut butter and jelly sandwich, ever. A bite of chocolate brioche that somehow kept a cool, liquid ice cream middle. And more. We sat in a dark room listening to great music, with terrific service, and got drunkish. Eventually, we were asked if we wanted to go to The Office, the most exclusive bar in Chicago (ooh, la la). It’s a 20 person capacity speakeasy in the basement: we were either charming, or had spent enough money (my guess is it was a bit of both) to be invited. And again, an extraordinary cocktail menu, and some more great food. The whole night was super expensive but we will never, ever forget it. Amazing.

The Best Food was probably The Purple Pig. An excellent, excellent restaurant. Vibrating with energy, we sat at a long communal table and devoured everything we ordered. This place was like a more mainstream combo of The Black Hoof and Hoof Cafe - meat-centred, with house-made charcuterie, but a tonne of other items. An insanely good octopus salad; a great red sauce gravy with pork on crostini; and an absolutely delicious salt-roasted beet dish. Crispy pigs ears with duck egg; chorizo stuffed olives; panini with coppa and grainy mustard. All wonderful. We didn’t want this to end. Casual, hip service that was really informed - and a killer wine and beer list. Also a gorgeous patio. This is the model of what a restaurant should be in 2011: flavour-forward, casual but professional, fun and completely able to service customers who want just a little something, as well as those looking for a multi-course meal.

The Best Food that wasn’t at Purple Pig was at Frontera Grill. One of Rick Bayless restaurants, his places in River North are probably the best upscale Mexican food being served in the US. There just aren’t any flavours like it in Toronto, so it was a huge treat for us. This place will make you rethink what Mexican can be. We went for lunch and had brunch items as well as dinner-style mains. Everything was excellent, but there were a few things that had such a layering and depth of flavour that they made us all stand up and take notice. The Chilaquiles (a quick-simmered tortilla casserole) with fried egg were amazing; and the Mole was just the best any of us had ever had.

The Best Cheap Eats were at Big Star Tacos in Bucktown. This is an awesome restaurant. Massive patio, super casual and fun, it’s a taco place that also has a long and wonderful spirit list and a great selection of beers. We spent a lot of time in River North and right in the Loop, so getting to Bucktown was great and something we should have done earlier. I wish to God, as much as I adore Harbord Room; that the boys there would get off their asses and open something like this is Toronto. Tacos were amazing and $3 a piece. We sat and had lunch and all wished we’d arrived at 7pm instead - to stay to 2 in the morning. It was that sort of place.

The Best Room  was The Girl and The Goat. Top Chef Season 4 winner Steph Izard has a sensational restaurant in Greektown. It’s in a converted loft space - expansive, dark but lively, open without being too overwhelming, this was the sort of place one goes to for food and energy at the same time. The cooking was excellent, too - and it’s a huge hit, this place, being pretty much full (at about 200 seats!) at 10:00 on a Sunday. Lots of flavours from all around the world. We had a delicious chicken served with naan that was pure upscale Indian - but then a completely Asian-feeling dish, and then something that was Greek-influenced. But everything was good, and it was a lovely place to sit. On a busy Saturday it must feel like the centre of the universe.

Other very good and great meals were at Grahame Eliot, for inventive, whimsical molecular-gastronomy-inspired dishes and the best popcorn I have ever had; Art Smith’s TABLE 52, for an excellent brunch of shrimp and grits, fried chicken and waffles; iCream, for excellent made-to-order ice cream; Lou Malnati’s for a classic Chicago Deep Dish pizza that I ordered from the cab on the way to the hotel from the airport as we arrived; and even the food at US Cellular Field, where we saw the White Sox play, was great. The only miss was Blackbird. It’s a bit of an institution - right next to Avec and owned by the same people (we wanted to go to Avec but they don’t take reservations, and it was a 2 hour wait). The food was curiously flat. Almost everything, actually. It all felt under-seasoned, and even boring. We’ll give Avec a shot next time we’re there - if only to sit in that room! - but I can’t recommend Blackbird at all.

This trip cemented something: Chicago is a great food city. It’s not quite New York, but it’s closer than a lot of people night think. On the high end, it might not compare. But for the sort of eating that people want to do in 2011 - great food in a more casual environment, with less prescriptive menus that invite sharing and smaller plates - it’s pretty spot-on. There’s a great energy to the city, and a Midwestern friendliness. Chicago closes a bit earlier than New York, of course - it’s the City that Eventually Sleeps Because it Has to Get Up in the Morning - but that just meant we went out a bit earlier. It’s missing a little in terms of boutique coffee places (America, especially middle America, really does run on Dunkins) and, as in Toronto, the commitment to local and seasonal means that in the winter you’ll be missing some things. But who cares? It’s a great town with an interestingly earthy food history - comfort food in Chicago is just food, I think - meaning that the chefs who honour that are making wonderfully modern versions of the food we all want to eat. I’ll be back, Chicago, you stay classy.