The first day of Benji's road trip took him winding through the windy city's downtown, from the deep dishes to the North Shore to the hipster enclave of Wicker Park.

Superb. Crowd writhing. It's a Monday night. 

Work, play, and retweeting top tippage.

Some kind words (and love for Kuma's) below the line from Hawkeye1980:

Pics brought a tear to my eye. Lived in Chicago seven years and never wanted to leave … interestingly captures this spectacular American city with an eager outsider's eye (Big props for sojourning to Kuma's) Downtown's iconic and all, but I could walk around Lincoln Park and Old Town for ages. There's a real warmth to those streets. Thanks for the postcard.

Kevinstar was also generous, also loves Kuma's, and could not be more correct about Chicagoans: "We are much more than Al Capone, Michael Jordan and Oprah".

We should not, however, forget the greatest basketball player of all time and co-star of Space Jam. 

The 90s nostalgia is strong right now.

The Chicagoan Gods are smiling on us. We followed Ryan to Double Door, where Bone Thugs-N-Harmony are playing – yes, them of the mid-90s – and we got in. I'm pretty sure I know every word to The Crossroads, and I'm going to prove that to these people.

This was named in the top 5 hipsterest nightbourhoods in the US – by Forbes no less – and there's nothing that shows your hipster credentials more than loudly shouting every word to The Crossroads by Bone Thugs-N-Harmony in public. I got this.

Three facts about Ryan, the guy with a mohawk helmet.

1. Ryan used to be a pro ballroom dancer.

2. Ryan has "lived a hard life and came out of it alive".

3. Ryan is going to a Bone Thugs-N-Harmony concert right now, at a place called Double Door, and he's gonna try to take us with him.

And as the gang heads to meet whomever's out Monday night in Chicago, we can take a quick architectural interlude courtesy @woyce, who more or less hit upon the two highlights that the team missed. 

Frank Lloyd Wright – the eccentric Beethoven-inspired fellow who designed the Guggenheim – lived and worked in Chicago's environs for many years. The fruits of his labor in the area have been recommended to us by LaVacheKyrie and others, and you can tour many of these buildings, including his home and studio out in the burbs.

What's all the fuss? Ever helpful Wiki illustrates a sample of the weirdness:

And what of the Bahá'í? The Chicago-area temple is actually the oldest of the extant seven around the world, and like its famous counterpart in Israel, gardens and fountains surround the massive central dome. The state tourism board named it "one of the seven wonders of Illinois".

While the guys are struggling to (literally) feed their carnivorous instincts, we can glance at Chicago's more naturally feral inhabitants – the city's world class collection of flora and fauna, as recommended by readers yet unseen by the Guardian's wandering trio.

@Ameritoon recommended the Lincoln Park Zoo, which from their website, seems to be full of various sorts of babies: baby gibbons, langurs, takins, gorillas, bushbabies and so on. Visitors are presumably astounded to see adorable wildlife not on internet slideshows – and for free! (Furthermore, Chicago seems to have its red pandas in check, unlike Washington DC.)

Should you find Lincoln Park a bit too dry, Chicago is also home to the Shedd Aquarium, the largest indoor aquarium in the world, per their website. Like the zoo, though, it has an enormous number of animals who don't belong anywhere near Illinois: a giant octopus, frogfish, beluga whales, a blue iguana, and, of course, sharks.

And last but not least is the Garfield Conservatory, one of the largest in the country, complete with six greenhouses and "two grand exhibition halls". There are interior deserts, rain forests and 300-year-old ferns growing here, and the glass edifice – itself around since the 1840s –stands in Garfield Park, which has everything your 19th-21st century park goer could dream of: winding paths, sport fields, a pool and a pond.

Gary, meanwhile, opted for the "Mastodon", which is only slightly more recognizable as a burger.

Whether he can bring out his inner Ice Age hunter and defeat the thing remains to be seen.

This is Pauline. Pauline has seen an actual human eat two Slayer burgers in a row.

Oh my days. This is barely a burger. This is an edible autonomous state. This burger could legitimately operate own legal system. There's a mound of cheese on top of a mound of meat on top of a mound of other stuff that I can't really make out because it's dim-lit in here and I've taken my glasses off because I might cry.

They've just delivered a "side" of mac n' cheese. It could comfortably feed a family of three. I'm a peculiar mix of scared and exhilarated. I'm also slightly worried that if I don't finish this someone here will put me in a headlock.

We're inside, and we've met the manager, Frank DeBose. Brilliantly, he's telling us about his love of Manchester City – he lived in Didsbury for seven years in the 80s.

He's also running us though the menu, recommending the "Slayer": 10oz of beef, chili, caremalized onions, andouille (what's that?!), cherry pepper, Monterrey jack, scallions, anger. Yup, anger. apparently it really ties the burger together. I've ordered one. Braced for impact.

[Editor's note: andouille is a kind of sausage popular in Cajun cooking, and also what a French epicurean sort might idiomatically call you for ordering a dish named the "Slayer".]

Arrived in Avondale … a distinct neighbourhood feel. Low orange light, low-rise, grungy.

 We're loitering outside of Kuma's. We can hear the music inside pumping. They're playing a kung-fu movie above the bar in which everyone is dying. I'm hungry.

Does not much amuse their cab driver …

Or Hollis.

From here we'll head to Avondale, for dinner at Kuma's Corner, a highly endorsed tip kicked off by @MarkPakulski and re-suggested by many since. It's a heavy metal burger joint. I don't fully get this. Must I mosh as I munch? 

The Yelp page is overwhelming – people love this place. 

But what of Avondale? Is it a one-metal-burger-joint town? Tips welcome. From there we'll aim for Wicker Park, Chicago's hippest hood. I just said "hippest hood". Will they not let me in now? 

J Parker's is not bad at all … 

but the road awaits, so we'll have to look back fondly after coming back down to earth.

Callie, our waitress, is from Indy – currently sharing tips off the I65.

A bit of the sunset hour at J Parker …

And an update on Gary: he took American prescription cold medicine an hour ago. 

Tip of the day so far, from @karlazimmerman.

We're up on the roof of the J Parker, as witching hour turns to sunset hour. The savvy locals are up here too, none as sweaty as me. They've been home and re-humanised. 

It's a well-dressed crowd, scattered across the rooftop with sensible indie wafting from the speakers. The view … lordy. 

We've entered the American "witching hour", the time between work and everything else. These folk go home, refresh, re-apply, before heading out.

We Brits, mistakenly I think, have no time for such temperance – we hit the pub and go hard, early. Lincoln Park is full of strollers now, ambling up and down Wells Street. I like.

The guys plan on venturing into Wicker Park after dinner for the flavor of Chicago's breweries, music and nightlife. (They're deciding between a couple options – Big Star? Velvet Hour? Map Room? – so you can still help make up Benji's mind for him @BenjiLanyado.)

But readers have supplied plenty of choices all around the city:

Nellie DeBruyn recommends "the West Loop for meals and cocktails. Check out Aviary and … If the price of admission is too frightening, stroll up the street to Publican, or over a ways to Au Cheval for the best burgers in town and amazing music to accompany."

ianmichaelgumby disagrees about Aviary, and throws in a counteroffer: "Aviary is over priced. And over rated. Or you could hit Matchbox on Milwaukee"

johnakirk101 suggests Owen and Engine, "winner of best fish and chips in Chicago", would appeal to anyone with a taste for craft beer and pub food.

missMM has suggested a slew around Logan Square and the West Loop: The Whistler ("a bar, gallery, record label, and venue") Scofflaw (a gin bar), Three Dots and A Dash (tiki!), Longman and Eagle (an inn), The Drawing Room (a restaurant), as well as the "divine"
rooftop of Little Goat (a diner below and a bar atop). She also recommends the "good dive" Delilah's.

And finally, Hiro111 throws in an entire list of beers to try, since "Chicago is all about the local beer these days … [besides] Goose Island, other fine Midwestern brews to sample include:

Revolution (Chicago)
Two Brothers (Chicago suburbs)
Three Floyds (Indiana)
New Glarus (Wisconsin, admittedly hard to find in Chicago)
Capital (Wisconsin)
Great Lakes (Ohio)
Founders (Michigan)
Boulevard (Missouri)

A playlist in part for @missMM, who wouldn't let us get away with omitting Sufjan Stevens.

With the day winding down in the windy city, the team is starting to think about tomorrow's plan. What should they see on the road to Indy? Are there strange Midwestern foods to try? Bizarre roadside attractions to behold? People to meet and detours to make? 

Tell us below the line or by tweeting to @BenjiLanyado, #TwiTrips, @GuardianTravel

Recharging batteries – both literally and figuratively – on Well St, Lincoln Park. It's the post-work witching hour, restaurants opening and prepping for the evening.

Meanwhile on Twitter, two major food tips are emerging: Kuma's Corner for burgers, and Hot Dougs for, yup, hot dogs. @MarkPakulski makes a convincing case for the burgers:

Gary's belly update: tranquil. His sinuses, less so. He's got a minor cold, an just dipped into a Walgreens for some meds. They IDed him for looking under 40 – what they have him taking includes an active ingredient of meth. Look forward to Flying Gary in T-minus 30 mins.

Lest we forget the other all-time movie filmed and set in Chicago, The Blues Brothers.

At St Michael's Church in Old Town.

We're in Lincoln Park, where we found ourselves walking in sync with Mike Robinson, who lives here.

[Editor's note: the people of Illinois are, unsurprisingly, rather proud of Abraham Lincoln, who served their state in the Senate before becoming president. This 12ft statue has a double in Parliament Square, and its title more or less reflects how Chicagoans feel about the Civil War leader: 'Abraham Lincoln: The Man.')

We wander past Twin Anchors, a dive bar with blackened windows – Mike tells us about how the area used to be home to dozens of German brewers, and the area proliferated with speakeasies during Prohibition.

Twin Anchors was one of them. It's totally different here – low-rise and leafy, lined with old stone and wooden slat houses. Mike explains – this was the northern limit of the Great Chicago Fire in 1871. 

Sadly, there's not nearly enough time to make the Chi Art Institute, which has come highly recommended by @mouseboy33 and johnakirk101, among others. Among the collection – which is massive, ranges from ancient artifacts the world over, and generally looks spectacular – is one particularly (in)famous painting: American Gothic, by Grant Wood.

Courtesy Wiki:

At this point, though, parodies of the painting may have become more famous than the original; they feature zombies, presidents, Muppets, TV characters, Legos and go on and on and on. Have any of your own?

Your whims are Benji's command, readers – tell us where to go!

From a 95th floor lookout over Chicago's sprawling downtown … to the beach, in under 10 minutes. Great tip from @MaxineSheppard. We're currently perched at Castaways Bar and Grill. 

It's shaped like a giant boat and they're playing One Direction, but we'll forgive them that, because the views are beautiful – clean blonde sand with a sprinkling of people laid out along the shore, some swimming out between wooden pylons in the water. I repeat: we're 10 mins from downtown. Bravo Chicago.

In case vicariously touring Chicago with Benji doesn't quite have the delinquent kick you're looking for, two classics of the 80s show the city from three very different points of view: students playing hooky, gangsters brewing hooch, and the authority figures trying to catch them. Ferris Bueller's Day Off and The Untouchables.

Below the line, @johnakirk101 has suggested that the crew reenact two iconic scenes: leaning down from the Sears Tower (which @mouseboy33 tells us is not to be called the Willis Tower) and the Union Station shootout. Without time to run hijack parade floats or rob banks, however, we're left with YouTube to console us.

Oddly enough, both films center around a battle of wits: Sean Connery's hard-boiled cop v Robert De Nero's vicious Al Capone, and Matthew Broderick eponymous Ferris v his high school's Ahab-like dean of students. Not sure what all these defiant rule-breakers say about Chicago …

And curiously, Chicago Magazine tells us that Ferris' famous house – glass walls intact – is for sale if you want it … only $1.5m.

The guys are heading up to North Avenue Beach, so to accompany them (and us) we've compiled reader requests and bands with ties to the windiest of cities. Tells us your picks in the comments below, @GuardianTravel, and we'll add them to the next one!

Oh wow, this is incredible. We were walking north toward Lincoln Park, right next to the famous John Hancock Tower. Our photographer Hollis had a superb diversion. Tourists here are usually corralled towards the "observatory" on the 94th floor, for $20 a pop.

One floor above that, fairly unmarked at street level, is the Signature Room, free for all. I'm currently sipping a coffee next to floor-to-ceiling windows with the most astonishing views of the city. 

My ears are popping a little. To my left, a vast ridge of skyscrapers stretch from the shores of Lake Michigan to the edges of the downtown district. East Chicago is sprawling in front of me, dissolving into the clouds in the distance. Magnificent.

No dilemma for Benji, who needed little persuasion...we're now looking for Lincoln Park tips!

While Benji and the boys have been shoeing in the pie, we have a split vote on what to do next.

Some readers are pointing us in the direction of history and the arts downtown:

@woyce says: Jane Addams' Hull House is undervisited & close to downtown.

@mouseboy33 reckons: "Chi History Museum. Chi Art Insitute."

Others reckon a trip to the burbs and Frank Lloyd Wright architecture is in order:

LaVacheKyrie: "for a Brit, I'd recommend a visit to the Frank Lloyd Wright buildings in Oak Park (especially the octagon shaped studio, and Robie House in Hyde Park)."

While @MaxineSheppard pushes for the beach: "Fairly busy beach, but North Avenue Beach House is shaped like an ocean liner".

Gah! So much to do, so little time. Advice please?

We've made it to Gino's East. OK, let's talk about the deep dish. You know what? It's fine. In fact, I'd go as far as saying its good. These guys clearly know what they're doing - the crust is big, but not offensively so. And the stuff in the middle, it's upside down (sauce over cheese), but the sauce is rich and sweet. 

Also, a new mantra from our photographer Hollis: if in doubt, "dip it in ranch". This improves the deep dish experience by approx. 20%.

Gino's East is great fun - almost entirely daubed in graffiti from visitors.

I found a friendly face, and added my own.

Our photographer Hollis Bennett has taken over the Guardian News Instagram feed for this trip from Chicago to Memphis, and you can also leave tips there

@chicagofoodlord has offered:

my Wicker Park favs are Lockdown Bar and Grill, Antique Taco, and Mana Food Bar (vegetarian but still delicious)

For all you never ever wanted or needed to know about the evolution of the deep-dish pizza/pie in Chicago, we point you in the direction of the chicagoeater.com blog archives:

Deep dish pizza first appeared in a commercial setting when Ike Sewell and Ric Riccardo (born Richard Novaretti) opened the restaurant now known as Pizzeria Uno in 1943...Sewell pushed for something much more substantial than the Neapolitan version and the two came up with deep dish pizza.

The only problem being:

there is zero evidence to support the notion that two guys with no known cooking acumen came up with the recipe for deep dish pizza.

Enough said. Over to @grantkmartin on Twitter:

Deep dish is a scam, a tourist trap. Some people like it, some don't

Or maybe @curlyadamb has it down pat:

Italians cooking pizzas in frying pans in their tenement ovens after leaving the old country... I think

Appears Benji is being led by his belly. And despite professing a distrust for all things deep-dish - "Fact fans: why does Chicago do this deep-dish pizza thing? Who started this madness? Was it a mistake? It's ok you can tell me" - he's doing the deep-dish thing.

Lots of food tips coming in - for deep-dish pizza at Gino's East, tacos on the patio at Big Star in Wicker Park, for Franks N Dawgs in Lincoln Park (shark bacon, eggs, and scallop sausages) and Devil Dawgs. Thanks to all on Twitter and below ... but it feels like indigestion could be approaching after that breakfast. And we're mindful of poor Gary's constitution!

What else should our crew SEE and DO?

Great story: in the late 1800s, Chicago had a dirty water problem - all the city's waste was, erm, dumped into the Chicago River, which flowed into Lake Michigan, where they got their drinking water from. Euw.

So, in 1889, the city's planners reversed the flow of the river, using "engineering and gravity", according to our guide. They reversed the river!!

Everyone was happy and healthy. Apart from the city of St Louis, who were the proud new downstream inheritants of Chicago's cumulative crap. St Louis sued Chicago, but it all ended OK. "In fact, by the time the waste water hit St Louis, it was fine because it had been 'naturally aerated' on the journey" says our guide.

The Chicago Architecture Foundation River Cruise takes in some of the greatest architecture in the world - in every style - in a few short blocks. From the Tribune Tower to the Wrigley Tower to Trump Tower - from Deco to Gothic to Modern to Spanish Renaissance. Mind blown again!

35 West Wacker - a post-modern Goliath that houses the Leo Burnett advertising company. This is where Tony the Tiger was invented. MIND BLOWN.

We're indebted to A View on Cities for this background on the Tribune building:

In 1922, the Chicago Daily Tribune organized a competition for the 'most beautiful and eye-catching building in the world'. Raymond Hood - who would later build the Rockefeller Center in New York - and John Howell won the first place due to their Gothic design...

The award was very much criticized at the time as the Gothic design went against the modernizing trend set by the Chicago School and against the ideas of the more functional European architecture, later known as the International Style, which reduced decorations to the bare minimum. It would in fact be the second place design from Eliel Saarinen and another major contender from Walter Gropius which would greatly influence later skyscraper designs.

The Tribune Tower was completed in 1925 and reaches a height of 141m.

Sitting on the banks, braced for a boat trip on the Chicago River. Can't stop staring at the Tribune Building across the water. I just love this stuff, built in an era of 1920s showing-off exuberance, when frills and grand flourishes were the foundations of anything big. The top 10 floors look like a cathedral. Doing neck exercises.

Looks like they're heading for a boat tour of Chicago architecture - despite them eating enough at breakfast to sink an architectural tour boat

With breakfast all but over ... what should Benji do next?

In our expert Q&A last week, Chicago resident ChrisdesGarennes suggested a feast for the eyes:

Some of the best tours in Chicago are offered by the Chicago Architecture Foundation. They offer a variety of different kinds (walking, boat, elevated train) and I recommend for first-time visitors to take the classic river architectural boat tour for a good overview of Chicago architecture

Seconded by @klemieur and thirded by @Ameritoon on Twitter. Fourthed by Nellie De Bruyn in the comments below.

Appears to be winning by a country mile. Any advances? Tips to the usual places, please: @BenjiLanyado, #TwiTrips, @GuardianTravel or below in the comments

Swimming in ingredients at Yolk. This is breakfast as our American God intended. Nothing is straight up - there are five different eggs Benedict, ranging from "caprese" (mozzarella, pesto etc) to "south of the border benny" featuring chipotle, cilantro (CORIANDER!) and chorizo.

Jetlagged Gary is almost crying with joy. I have a rabbit in the headlights moment, and somehow order three slices of cake slathered in cheese then deep fried and grilled. I'm eating deep-fried cheesy cake for breakfast.

So far: EXCELLENT.

Left to right: Gary (the driver), Benji (knee-knacked blogger), Hollis (the photographer)

While we're waiting for Benji and the team to get their first coffee rush going, let's spin a few tunes courtesy of our resident DJ @jaimeblack at Dynasty Podcasts.

We will be taking requests throughout the trip, so tell us what you want to hear, and we'll put it up on our daily playlists - in the comments below, or @GuardianTravel, #TwiTrips