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The Great Literary Tour of Chicago

Arts, Culture & History

3 Days 60 Miles


Chicago, Oak Park

The Great Literary Tour of Chicago

Explore the city’s literary legends

Bookworms can take in the rich culture of Chicago’s literary history. Take the Devil in the White City Tour, inspired by Erik Larson’s best seller. Pay tribute to Chicago’s brightest authors at the very first crowd-sourced exhibition, Chicago Authored. Head to Oak Park to Ernest Hemingway’s Birthplace Museum and see where the author’s roots began. Extend your trip outside the city for experiences surrounding other writers like Carl Sandburg in Galesburg, Ray Bradbury in Waukegan and many more.

Day 1:


  • People staring at a wall of words

Your literary-themed adventure begins at the American Writers Museum in Chicago - the only national museum dedicated to American writers and their works featuring informative, interactive exhibits honoring notable U.S. writers throughout history. Just blocks away, browse through the After-Words Bookstore offering new and used books featuring fiction, literature, poetry and children’s books. Next, stroll by the nearby Art Institute of Chicago to take a picture with the iconic Lions that guard the building. The Art Institute of Chicago is where the main character, Russell Stone, works in the popular Richard Powers’ novel, Generosity: An Enchantment

Nearby Grant Park – a sprawling open space featuring picturesque skyline views and known as “Chicago’s Front Yard” – is home to Buckingham Fountain and was featured in the popular novel, The Time Traveler’s Wife. Not far from Grant Park, just across Chicago’s famous Michigan Avenue, you can get lost for hours inside the Harold Washington Library Center, the Chicago Public Library’s main branch. Inside the building, discover the Winter Garden that features incredible natural light that makes for a great photo op. Next, head north to stop for lunch at Beatnik on the River, known for its chic, Bohemian decor along with progressive, globetrotting dishes and cocktails. 

Continue north across the Chicago River and take in the city’s incredible architecture as you make your way to the Poetry Foundation in the River North area. The first space in Chicago dedicated solely to the art of poetry, the Poetry Foundation is a 30,000-volume poetry library that features an exhibition gallery and performance space for live poetry readings and public events. Head west across the Chicago River to Semicolon Bookstorein the nearby Chicago’s River West area. Semicolon is Chicago’s only Black and woman-owned bookstore and gallery that focuses on both community and literacy, with an emphasis on supporting Black book-buying and bookselling. 

The day would be incomplete without a literary-themed dinner at one of Chicago’s many quaint restaurants dedicated to creating the feeling of wanting to curl up with a good book. At Wilde Bar & Restaurant in the Lakeview area, named after Oscar Wilde, you can enjoy an extensive beer list and Irish pub food under a stained glass ceiling dome, along with a charming library nook and two cozy fireplaces. If you plan to stay around the River North area, the Library at Gilt Bar is a low-lit basement bar offering red-velvet booths along shelves of vintage books, perfect for a romantic dinner for two. 

Chicago offers numerous hotels to complete a literary-themed getaway, like Freehand Chicago, which boasts a gathering room decorated with one-of-a-kind Mid-century modern furnishings and decor along with a well-curated selection of books on Midwestern art, design and architecture. Stay in the hip Publishing House Bed and Breakfast - an industrial-style boutique B&B situated inside a former publishing house. Along the city’s famous Magnificent Mile, you can stay at the Four Seasons Hotel - Chicago, where a stylish “Author Suite” sits on the 46th floor offering sweeping panoramic views of Lake Michigan. The suite includes an extensive library filled with signed works by Stephen King, Margaret Thatcher, Oliver Stone and Anne Rice – all former guests of the hotel!

Day 2:


  • A neon sign over an old car in the Chicago History Museum

Kick off your second day aboard Weird Chicago’s Devil in the White City Tour and experience the dark history of the infamous serial killer, H.H. Holmes, and the remains of the 1893 World’s Fair, like the Museum of Science and Industry. Next, discover rare books and manuscripts at the The Newberry Library - a stately five-story research library that served as the main character’s place of employment in the novel The Time Traveler’s Wife.

Your second day calls for branching out and discovering more Chicago neighborhoods. Head north to Lincoln Park to discover the Chicago History MuseumChicago Authored exhibit highlighting authors that helped define and navigate the character and complexity of Chicago as a whole. Stop for lunch at The Red Lion Pub, also in Lincoln Park featuring roaring fireplaces and shelves adorning an impressive collection of British literature. Next, discover Oz Park, an entire park dedicated to The Wizard of Oz, a book that was written by Chicago reporter L. Frank Baum. Oz Park brings the book's characters to life as statues are peppered throughout the park. Continue north and grab a bite to eat or drink at The Monkey’s Paw in Lincoln Park, a gastropub that’s reminiscent of a high-school English classroom and named after the famous short story of the same name by W.W. Jacobs. Head northeast to the Northalsted neighborhood home to Unabridged Bookstore - the city’s go-to-bookstore for LGBTQ literature. 

Make your way even further north to the Andersonville and Edgewater areas. Lady Gregory’s is another literary-themed gastropub to discover in Andersonville, featuring a library and over 300 whiskeys to choose from. Edgewater offers a couple unique bookstores, Women & Children First – a feminist and kid-focused book shop, and Unchartered Books – a rare and used bookstore, along with the City Lit Theater Company, dedicated to the vitality and accessibility of the literary imagination with concert readings and full-stage productions of adaptations of literary material, scripted plays and more. 

If you visit in September, be sure to stop by the annual Printers Row Literary Fest, a two-day festival featuring carefully selected offerings from over 100 booksellers – everything from the tattered to the rare to ‘hot off the press,’ newly published works.

Day 3:


  • Exterior of a house

On your last day, head to the charming town of Oak Park, a half hour drive west from Chicago. Start with a delicious brunch at Hemmingway’s Bistro which offers classic French fare, an extensive wine list and Sunday brunch buffet with live jazz music. Discover more Hemingway at the Ernest Hemingway Birthplace Home and Museum - the ideal place to explore the roots of the author’s life and work. The history in Oak Park doesn’t stop there though. You can get an in depth look into the life of famed architect, Frank Lloyd Wright, at his Home & Studio  one of the stops along the Illinois’ Frank Lloyd Wright Trail that highlights 13 architectural gems he built around the state. Make sure to also plan a visit to Edgar Rice Burroughs’ former Oak Park home where he wrote 11 novels including his most famous book, Tarzan of the Apes. Learn more about well-known Oak Park writers, architects, artists, scientists, social activists and more at the Oak Park River Forest Museum and Oak Park Public Library.

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