Old Town Ale House, Chicago.

The dive bar that doubles as an art gallery.

Old Town Ale House opened in 1958 as a Second City after-show bar, three doors down from the Second City stage. Bill Murray drank here. John Belushi drank here. Roger Ebert sat at the same table by the window for twenty years and called it his second office. The room itself is unchanged: dark wood, low yellow lighting, sticky tile floor, and one of the most peculiar interior decorations on this entire list.

The walls are covered, ceiling to floor, with original oil paintings by the owner Beth Spencer. Most of them are nude political satire. Sarah Palin nude. Donald Trump nude. Vladimir Putin nude with a small bear. Mitch McConnell as a turtle. The artwork is for sale, prices written under each frame, profits go to the bar.

Why this matters. Old Town Ale House is the rare dive that has a coherent point of view. Beth Spencer has not changed it for the room. She has changed it because she is angry at the news.

Beth Spencer's nude political portraits.

Spencer started painting in the 1990s after her husband Bruce died. The first paintings were of regulars. Then the politicians. Now there are over five hundred portraits on the walls. New ones go up every two or three weeks, painted in her studio above the bar. The compositions get more pointed each election cycle.

You will spend the first thirty minutes of your visit walking the perimeter, glass in hand, working out who is who. The painting of Hillary Clinton in a fox costume is famous enough to have its own Wikipedia citation. The painting of Barack Obama as Caesar is hung above the bar.

The paintings are for sale. Prices range from two hundred to fifteen hundred dollars. Beth signs them at the bar if you buy one. She accepts cards, but slowly.

Old Style and a shot of Powers.

The Ale House has the deepest beer list of any Chicago dive, but the regulars order Old Style, the Chicago lager that has been on tap here since the bar opened. It is honest at five dollars a pint. The regulars know what to do.

• The first drink: Old Style draft. Order it without thinking.
• The shot: Powers Irish whiskey, four dollars. The Chicago Irish drink Powers, not Jameson.
• The deeper move: the bar's whisky list is forty deep. Ask the bartender what came in this month from a small distillery. They will pour something at six dollars that costs twelve elsewhere.
• The cocktail: there is no cocktail menu. If you must, an Old Fashioned at eight dollars, made with the cheapest decent rye on the rail.
• The thing nobody knows: the bar serves complimentary popcorn from a 1970s machine in the corner. It is salty and good. Take a small bowl.

Tuesday at 3pm. The classic Chicago move.

Old Town Ale House opens at 8am every day except Sunday, when it opens at noon. Closing is 4am Monday through Friday and 5am on Saturday. The Sunday close is 2am. The classic move is Tuesday at 3pm: the room is empty, Beth is often at the bar painting, the regulars are drinking slowly with paperbacks, and the light through the front window hits the political portraits at exactly the right angle.

The peak hour is Friday and Saturday between 11pm and 1am, when the Second City show ends and the cast and the audience pour over. The bar doubles in volume in fifteen minutes. The booths fill. The bartenders turn into machines.

If you want the Roger Ebert experience, sit at the window table on a Sunday afternoon. He used the second seat from the door, looking out at North Avenue, and reread Hemingway on rainy days.

Why this bar is on every Chicago itinerary.

Roger Ebert was a regular for twenty years. He praised the bar in his Chicago Sun-Times column eight separate times. After his death the bar hung a small framed photograph above his preferred table. The brass plate beneath says "his table." The regulars do not sit there on the anniversary of his death, by silent agreement.

Ebert wrote in his memoir that the Ale House was the only bar in Chicago where you could read for three hours without anyone bothering you. That is still true. The staff will refill your coffee in the afternoons without asking and will look at the cover of your book before they look at your face.

For two people, sixty dollar afternoon.

Pints are five dollars. Shots are four. A four-pint, two-shot afternoon for two people runs forty-eight dollars before tip. Plan sixty dollars total with a twenty percent tip and a popcorn bowl.

The kitchen does not exist in the dinner sense. There are bagged crisps, popcorn, and the small assortment of microwave items that have been on the back counter since the Carter administration. Do not eat at the Ale House. Eat next door at Topo Gigio for cheap Italian, or two blocks west at the Wieners Circle if you want to fight a stranger over a Polish sausage.

The painting prices are the only volatile cost. Beth is a fair seller and the prices are written, but the average sale is six hundred dollars and you may leave the bar with a wrapped canvas if she likes you.

The Old Town crowd, by the hour.

Mornings bring retired North Side teachers, occasional Second City staff sleeping off opening night, and a small contingent of newspaper veterans who still write a column from the back booth. Afternoons bring readers. Evenings bring a younger Old Town crowd. Late nights bring the comedy crowd, including, on a typical Friday, two or three current Saturday Night Live cast members on a Chicago weekend.

The bar has a long tradition of welcoming political journalists. Mike Royko wrote here. Studs Terkel held court. Today the Chicago Tribune metro desk uses the third booth as an after-deadline office. The bar is, in this way, a working artefact of the Chicago newspaper era.

How to be welcome at Old Town Ale House.

• Do not photograph the paintings without buying a drink. Beth has banned photographers in the past. Buy a beer first, then take a photo with your phone, no flash.
• Do not sit at Ebert's table on April 4th. That is the anniversary of his death and the regulars hold the table empty out of respect.
• Do not haggle on the painting prices. Beth will tell you the price is the price and the conversation will stop.
• Do not order anything blended or muddled. The bartenders do not own a blender.
• Do not ask the staff which paintings are most controversial. They will say "all of them" and they will be correct.
• Do not bring a group of more than four to a Friday night. The bar is small and your group will block the back booth row.
• Do not, under any circumstances, bring up your political views. Beth has heard them all and painted most of them. Your opinions are not new and not interesting in this room.

Eat at Topo Gigio, drink at Old Town, walk home through the neighbourhood.

Old Town as a neighbourhood is the rare Chicago corridor where dive and fine still coexist. Eat at Topo Gigio next door for a forty dollar Italian dinner, then walk three doors east to the Ale House. After 11pm, walk west to the Old Town School of Folk Music's monthly late session, or south to the Hideout, which keeps a different crowd on the same dive standard.

For more bars in the area, see our Chicago city guide, especially the hidden gems list and the live music bars.

Yes. The most coherent dive bar in America.