Bookish Escapes: Great Travel Reads for Your Trip

At Milwaukee Fly Limo, we’ve noticed something over the years: the best trips often start with a great book. Whether you’re settling into the comfort of your ride from Milwaukee to O’Hare or beginning the journey from Chicago back home, there’s something special about cracking open a compelling read as the scenery rolls by—and continuing it at 35,000 feet.

We asked our drivers, frequent flyers, and road warriors what books they’d recommend for that perfect journey. Here’s what made the list.

Classic Literature

“The Great Gatsby” by F. Scott Fitzgerald
At just 180 pages, Fitzgerald’s masterpiece is perfectly sized for a round trip. The jazz-age glamour and Midwestern sensibilities (Nick Carraway is from the Midwest, after all) make this a fitting choice for travelers moving between two great American cities.

“East of Eden” by John Steinbeck
If you’re a frequent traveler on our route, this epic tale of family, morality, and the American dream rewards multiple reading sessions. Rich enough to get lost in during your limo ride, deep enough to ponder during your flight.

Adventure & Thriller

“The Martian” by Andy Weir
Mark Watney’s survival story on Mars turns science into edge-of-your-seat entertainment. Fast-paced chapters make it easy to pick up and put down between limo and plane, and it’s the rare book that makes you laugh out loud in transit.

“Into Thin Air” by Jon Krakauer
This harrowing account of the 1996 Everest disaster is gripping from page one. Perfect for armchair adventurers who prefer their journeys at ground level and cruising altitude rather than at 29,000 feet without oxygen.

Science Fiction

“Project Hail Mary” by Andy Weir
Another winner from Weir, this standalone novel about a lone astronaut trying to save Earth combines humor, hard science, and genuine emotion. You’ll find yourself annoyed when boarding announcements interrupt your reading.

“Neuromancer” by William Gibson
The cyberpunk classic that predicted the internet. Dense and atmospheric, it’s perfect for that contemplative mood that hits during a nighttime drive through the Midwest, city lights fading in the rearview mirror.

Fantasy

“The Name of the Wind” by Patrick Rothfuss
This beautifully written fantasy follows Kvothe, an innkeeper with a legendary past. The storytelling is so immersive that you’ll barely notice the miles passing. Warning: you’ll want the sequel immediately.

“Piranesi” by Susanna Clarke
A shorter, mesmerizing fantasy about a man living in an impossible house. Strange, beautiful, and complete in under 300 pages—ideal for a single journey with time to reflect on what you just read.

Romance

“The Seven Husbands of Evelyn Hugo” by Taylor Jenkins Reid
A Hollywood icon recounts her scandalous life to an unknown magazine reporter. This page-turner about love, ambition, and identity works beautifully for travelers who want to get swept away from the moment they leave their driveway.

“Beach Read” by Emily Henry
Two writers with opposite genres challenge each other to switch styles for the summer. It’s witty, warm, and set partially in a Michigan beach town—fellow Midwest travelers will recognize the landscape flying by below.

Biographies & Memoirs

“Educated” by Tara Westover
A stunning memoir about a woman who grew up in a survivalist family in Idaho and eventually earned a PhD from Cambridge. Her journey from isolation to education is both inspiring and thought-provoking—perfect for travelers pursuing their own ambitions.

“The Wright Brothers” by David McCormick
For anyone sitting in an airport or flying through the sky, the story of how two bicycle mechanics from Ohio achieved powered flight never gets old. It adds a certain appreciation to your boarding process.

Business & Professional Development

“Atomic Habits” by James Clear
Small changes, remarkable results. This practical guide to building good habits is structured in digestible chunks—ideal for business travelers who want actionable insights they can implement immediately upon landing.

“The Hard Thing About Hard Things” by Ben Horowitz
Silicon Valley veteran Horowitz doesn’t sugarcoat the struggles of building a business. It’s honest, practical, and perfect for entrepreneurs and executives traveling between Milwaukee and Chicago’s business hubs.

Mystery & Crime

“The Thursday Murder Club” by Richard Osman
Four retirees meet weekly to investigate cold cases—until they find themselves in the middle of a real murder. Charming, clever, and genuinely funny. You’ll be smiling through your entire journey.

“Gone Girl” by Gillian Flynn
The Midwest-set thriller that defined a generation of psychological suspense. Set partially in Missouri, Flynn captures middle-America perfectly while delivering twist after jaw-dropping twist.

Short Story Collections

“Tenth of December” by George Saunders
When you want variety or aren’t sure about your attention span for the trip, Saunders delivers. His stories are profound, weird, and deeply human—each one perfect for the length of a ride or a flight segment.

“What We Talk About When We Talk About Love” by Raymond Carver
Minimalist masterpieces that pack emotional punches. These spare, haunting stories about ordinary people are the literary equivalent of watching the Midwest roll past your window—simple surfaces hiding complex depths.

Light & Humorous

“The Hitchhiker’s Guide to the Galaxy” by Douglas Adams
The ultimate travel book, even if your destination is just O’Hare. Arthur Dent’s accidental journey through space is absurd, hilarious, and somehow comforting—especially when your own travel plans go sideways.

“Bossypants” by Tina Fey
Fey’s memoir about her journey from suburban Pennsylvania to SNL and 30 Rock is laugh-out-loud funny. Warning: you might snort-laugh in your limo or on your plane. We apologize in advance to your fellow passengers.

A Final Note from the Road

The beauty of a good book is that it travels with you—from the moment you settle into your seat in Milwaukee or Chicago, through the quiet miles of highway, past airport security, and up into the clouds. Your journey becomes part of the story, and the story becomes part of your journey.

Safe travels, and happy reading.

Milwaukee Fly Limo serves the Milwaukee-Chicago corridor with comfortable, reliable transportation. Whether you’re heading to Mitchell International or O’Hare, we’ll get you there with time to spare—and maybe finish a chapter or two.