Bellow. Ginsberg. Sontag. Stein. Wilder... And that’s only the beginning. Though it’s not a Jewish institution, the sheer range of Semitic scribes honoured at Chicago’s newly opened American Writers Museum is impressive.

It’s a perfect metaphor for Chicago itself. America’s third-largest city feels less Jewishly in your face than New York or Los Angeles, where nouveau delicatessens and hip Sephardic joints seem as common as coffee bars.

But there’s distinct Jewish flavor here, and an equally rich history. The mayor, after all, is boisterously Jewish former Clinton confidante Rahm Emanuel. There’s a downtown monument to Haym Salomon, the Polish-born financier of the American Revolution. And Chicago gave the world luminaries from CBS founder William Paley and Hadassah co-founder Pearl Franklin to big-band boss Benny Goodman and author Saul Bellow.

The latter is just one of those honoured at the new museum, in downtown’s aptly named Magnificent Mile. The first of its kind of the US, the museum showcases American letters through highly interactive exhibits with evocative titles like Visionaries and Troublemakers and A Nation of Writers, all of which feature Jews in disproportionate numbers.

But the Jewish presence is most strikingly felt in a softly lit Hall of Fame where just 100 writers are saluted — many of them members of the tribe. The pantheon includes giants like Arthur Miller and Isaac Bashevis Singer, feminist Tillie Olsen, and Jewish Daily Forward founder Abe Cahan.

And as a starting point to explore the Windy City’s Jewish heritage, it’s perfect too; just 15 minutes on foot from some of Chicago’s most august Jewish landmarks. One of them, the Chicago Loop Synagogue, was founded in 1929 to serve Jews whose business activities brought them downtown. Destroyed by a fire in the early 50s, it was reopened in 1957 with a soaring modern design that been called “perhaps the most beautiful synagogue interior in the United States”.

Indeed, the shul boasts some museum-quality art. Abraham Rattner’s dazzling Let There Be Light stained-glass window dominates the sanctuary. Outside, the building is instantly recognisable by Hands of Peace, an abstract bronze sculpture by Israeli artist Henry Azaz that adorns its façade. Stylized hands in prayer encompass Hebrew and English words that spell out a blessing from the Book of Numbers.

An influx of young professionals to the downtown core has revitalized the 21st century congregation, and it remains the city’s central shul. Not always open to the public, the best way to see inside is to attend Shabbat services, register for one of its cultural programmes, or visit during October’s Open House Chicago festival with trips to significant buildings.

In the same downtown cluster — which got its local name of The Loop for the endless circles its streetcars would make — you’ll also find the acclaimed Spertus Institute for Jewish Learning and Leadership.

Primarily an academic and research hub, the Spertus operates a terrific ground-floor exhibition space — political cartoonist Ben Shahn was a recent subject — and a vibrant array of cultural programmes, from Sephardic music concerts to documentaries on David Ben-Gurion and works by local artists.

It would be easy to spend an entire trip in the Loop. But that’s just a small part of the Chicago story so hop on an L — as the magnificent elevated subway is known — and explore. Train rides are an attraction on their own, with the Pink and Brown lines snaking between hulking downtown buildings, and offering postcard skyline views further out.

With its inexpensive places to eat and indie shops, Lakeview has plenty of reasons to tempt you out there — not least being home to what may be the world’s only Rambam-inspired eatery. Milt’s Kosher BBQ for the Perplexed draws a mixed city and suburban crowd for expertly prepared meats and lively atmosphere. While there’s tofu and salad on the menu, it’s almost mandatory to order a BBQ Combo — half a chicken, a half-slab of ribs, coleslaw, and your choice of sides like potato salad or corn bread. Resign yourself to schlepping leftovers back to your hotel room.

Milt’s choice of location isn’t an accident. The eastern part of Lakeview has attracted a growing Orthodox population, including a busy Chabad outpost. Their arrival is just the latest twist in Chicago’s long Jewish story, with the first Jews settling here soon after the city’s incorporation in 1833, drawn by the promise of opportunity after landing on the east coast.

German and Eastern European Jews built their own communities, friendship societies, and synagogues; the first shul, Kehilath Anshe Ma’ariv, opened above a clothing store in 1847.

Many Jewish settlers toiled as peddlers, often in the bustling Maxwell Street Market, before opening businesses downtown. Some of those blossomed into still-thriving commercial powerhouses like Florsheim, Spiegel, Alden’s, and Brunswick. In a modern-day spin on tradition, Maxwell Street Market still operates on Sundays as a bargain-priced outdoor flea market.

By 1940, Chicago’s Yiddish landscape rivaled New York’s or Montreal’s, with 15 publishing houses and a vibrant cultural life that included an effervescent poetry scene — last year The University of Chicago hosted an entire exhibition dedicated to that history.

These days, more Jews live in nearby suburbs like Glencoe, West Rogers Park, and Skokie, which at one point housed the world’s largest per-capita population of Holocaust survivors. outside Israel About 40 minutes north of downtown by car, or 90 by public transit, it’s a fitting home for the world-renowned Illinois Holocaust Museum and Education Center.

Launched as a tiny storefront in 1981, the museum now occupies 65,000 square feet in an award-winning building designed by Chicago architect Stanley Tigerman as a literal journey from darkness to light. Its permanent exhibition includes more than 500 artifacts, including a German rail car used to deport Jews. The museum also has a special focus on post-war life in Skokie itself.

If you make the trip, there’s another sight to make time for here. The area is also home to what may be the world’s only kosher, 1950s-inspired classic diner. Ken’s Diner, tucked into a strip mall ten minutes by car from the museum, draws locals and visitors for its giant burgers and the “Mt. Trashmore”, an all-American, off-the-menu monstrosity of chili, eggs, mustard, and potatoes.

It sounds, and looks, as overwhelming as Chicago itself. A good reason to consider the city’s size — if not Mt. Trashmore’s — as an excuse to start planning another visit.