Destinations/ Food Porn/ Illinois/ North America/ Spirits/ Travel/ United States

Chicago sandwich tour! From the mighty Italian beef to the elusive mother-in-law.

That’s Jim, buying me a mother-in-law out of his own goddamn pocket. He’s a saint.

I have the good fortune to be friends with Jim and Mindy Behymer. Mindy is Katy’s cousin and Jim her husband is the author of the notoriously delicious sandwich blog in which Jim is researching and making, often from scratch from the bread up, each sandwich on the Wikipedia list of sandwiches. And has agreed to be our guide to the Chicago sandwich underground. I’ve asked him to focus on the truly unique Chicago fare and was provided with a decadent foray into a wonderland of spicy meat and unhealthy calorie consumption. The world will never be the same.


Luke’s – Italian beef and the Chicago dog

On our first day out Jim agrees to meet us for lunch and suggests Luke’s, a well known Italian beef joint in the middle of the loop district where we’re staying.

An Italian beef sandwich uses a roll with a thicker than average skin.  The bread is split and then dipped into jus called gravy before the contents are added.  A healthy portion of roast beef and either ordered hot (with giardiniera) or sweet (with italian sweet peppers) shown below.

This thing is a beast to eat, no other option than grab the sopping thing up and dig in.  Apparently there’s a method to eating this over the shelf of a walk up sandwich shop by “leaning in” and letting the jus run onto the wrap.

Some places offer a variant called “gravy bread” which is just the bread dipped in jus.  I would probably eat that.  =)

Italian beef, dipped, with sweet


In addition to the sandwich I got two hot dogs.  The first your classic Chicago dog done right!  Start with a poppy seed bun, add an all beef hotdog, white onions, a pickle spear, tomato slices, neon relish, and sport peppers with some mustard and a dash of celery salt.  Ketchup is strictly forbidden.  This is like a salad on a bun.  I was skeptical to tell you the truth, but it was delicious.

Chicago dog with the works


Next the humble, the loyal, the always true, chili cheese dog.  The chili has beans here with some heat and the onions are liberal, just how I like it.  Third in line but it didn’t last long.

Chili cheese dog


Jim’s Original – Polish sausage

We only had one day to fit in the rest of the Chicago native line up and Jim was gracious enough to drive us around to all the best spots.  First up was Jim’s.  Apparently there’s a blood feud between this spot and the next door rival Maxwell’s that’s been going on since the 30’s.  He offered to do a side by side but Chicagoans are loyal and I wasn’t about to cross the line for pedestrian curiosity.

This is like half a kielbasa sausage on a bun with grilled onions and a larger variety of sport pepper than the dogs get.  And you get fries for free that they load into the bag.  At $4.70 it’s a hell of a lunch.  And Jim reminisces to when the same thing was $1.80.

I wanted to get the pork chop sandwich too but there’s only so much you can stuff into this meat sock before it pops so I take the prudent rout and save that one till next time.

Polish sausage with grilled onions and sport peppers





The Jibarito Stop – The jibarito

This is an often overlooked Chicago original.  It’s a Puerto Rican style sandwich that started in shops here.  Plantains smashed flat and grilled to form “bread” for the sandwich.  Your choice of meats with lettuce, tomato, mayo, garlic and choice of cheese.  I chose the slow roasted pork and american cheese with the yellow rice with pigeon peas and pork.  The plantains are crisp but yielding, tender pork, a great sandwich.  The fatty pork bits in the rice threw it over the top.

I also got the Good O Kola Champagne soda.  A Peurto Rico cream soda.  Excellent.






Johnny O’s – The mother in law

Jim made a special stop just for me.  (No one else had one).  Let me introduce the unholy mutant freak of a food thing.  It’s a south side Chicago original.  I guess I had mentioned this thing three times a day for the duration of the trip so we had to swing by.  And Johnny O’s liquor store has the best.

Take a low quality extruded tamale, put it on a hot dog bun, top with the usual Chicago style toppings, THEN add a mess of chile and cheese, and you have a mother in law.

I heard they call it that because it’s sure to give you indigestion.

The Mother in Law


This is the inside after chomping halfway through. It’s a challenge to eat in a moving van.





Stony Sub – The Jim Shoe

Another local original.  Though the origins seem to be a bit more murky.  The Jim Shoe aka Gym Shoe aka Jim Shoo can be found around the south side at sandwich shops.

They’re enormous.  Start with roast beef, corned beef, gyro meat, add white sauce, lettuce, tomato, mayo, cheese, onions, mustard and hot peppers.  This might have been my favorite sandwich of the trip.  Fatty, spicy, dripping with goodness.  Luckily I had saved my mother in law fork which helped get this down my gullet.

We decided to go with a Vess strawberry soda.  A perfect pairing.

Stony Sub was far enough south that it started to remind of New Orleans.  The shop had no tables and you ordered through inch thick bullet proof glass.  Put your money in the plastic box (cash only), swivel around, the sandwich goes in and back around to you.

Jim Shoe





Portillo’s – More italian beef and hot dogs

We had some time to kill before our flight on Monday so I took Jim’s suggestion and tried a chain store called Portillo’s.  I enjoyed my Luke’s meal so much I decided to do the same thing here.

This time I got a combo Italian beef, dipped, and hot, which starts with a sausage and piles on the Italian beef over it with giardiniera on the top.  Have to admit that was overkill.  I had to pull the sausage out and stick with the traditional version.

The dogs were decent too.







The Purple Pig – The JLT and more

So the Purple Pig is a holy place for porky goodness.  It’s a bit more high brow than the sandwich shops but we needed a lunch before our big day at Alinea and chose this little spot.  We were trying to go light otherwise we would have ordered several more plates to try.

I got the Jowel with lettuce, tomato, and duck egg.  This thing is a flavor bomb.  It’s like a little pork orgasm leaving duck egg sticky across your lips.  You have to make a pleasure face.  It’s involuntary.

Pork jowel, lettuce, and tomato with a duck egg.


I also got the pork neck gravy with ricotta and tomato sauce smear which is as good as it sounds.

Turkey neck gravy with ricotta and tomato sauce


Katy got the house cured sardines with fennel salad on toast.  Very good and herby.

And started with the Bobota greek cornbread with feta, mizithra cheese, and honey.  Glurb!





Kenwood Liquor Store – Malort

The last thing we needed was the true Chicago original liquor, Malort.  It’s made with wormwood and it’s bitter.  Like bile bitter.  It sticks with you.  But some people get a taste for the stuff.

We stopped at the Kenwood liquor store but they were sold out and hide to find some at a strip mall.




Monk’s Pub – Pints and shots

Throughout our trip we returned a couple of times to a local’s bar that Jim suggested, Monk’s.  Dark worn wood with a good whiskey selection.  And a lively crowd of Chicagoans caught up in lively debates about the issues of the day.  It’s a peanuts on the floor kind of place.




You Might Also Like


  • Reply
    Chicago – Winter 2018 – the Wandering Hedonist
    February 20, 2018 at 9:57 pm

    […] Chicago – Winter 2018 – All the sandwiches! […]

  • Reply
    Sausage Sandwiches | Sandwich Tribunal
    January 28, 2019 at 6:10 pm

    […] after a marathon day of trying various local lowbrow culinary delights (which Daniel wrote about here), he and I discussed the Seattle style hot […]

  • Leave a Reply