“So this is where it all starts? This is how my new life begins?”
Jess stood beneath the red-and-blue Begin Route 66 sign at Adams and Michigan Avenue. People hurried past her in every direction, but she stood still, feeling as if the bronze lions in front of the Art Institute were watching her. She’d been here dozens of times before, yet somehow she’d never really seen the sign — the one that marked the start of America’s most legendary road.
It seemed like the right time for something symbolic. She walked up to the sign, took a quick selfie, and then turned the corner onto Adams. She only made it fifty feet before stopping to look back at the Art Institute. Her heart was pounding — maybe from excitement, maybe anxiety — but she knew those first few steps had changed something inside her.
She’d be in Chicago for a few more days before officially starting her trip, but she’d already made up her mind: she wasn’t turning back.
Her father was still at the hotel with her little brother, Cameron, giving her a chance to explore the city alone. There was one place she wanted to visit before she left — technically on the inbound side of Route 66, but close enough. Lou Mitchell’s. Every Chicagoan knew it; every Route 66 traveler stopped there at least once.
The walk west on Adams wasn’t far, but on a hot June morning it felt like an adventure. She passed The Berghoff — where she and her dad planned to have dinner that night — and what felt like nineteen Starbucks. She crossed under the shadow of Willis Tower, smelling a mix of diesel exhaust, fried food, flowers, and coffee. When she finally reached Union Station, she crossed Canal Street and turned down Jackson. Lou Mitchell’s waited on the corner of Jackson and Clinton, glowing like a neon postcard from another era.
Inside, a hostess seated her right away and set down a little box of Milk Duds. The waitress looked like she’d been part of the place forever — gray hair, quick wit, and a smile that could disarm a mobster.
“Good morning, young lady,” the waitress said. “What’ll you have to drink?”
“Coffee,” Jess answered automatically — though she was really craving a Diet Coke.
“Coffee?” the waitress teased. “You even old enough for that?”
Jess laughed. “Maybe not. Diet cola, please.”
“That’s more like it,” the woman said with a wink. “Lunch menu, then?”
Jess glanced at her phone. 11:14. Her heart skipped. I’m running behind already.
She flipped through the menu, indecisive — burger? salad? something “classic”? Anxiety bubbled up. This was supposed to be her first Route 66 meal, and she hadn’t even researched what travelers ordered here.
Then she heard laughter — warm, genuine — from the booth across the aisle.
Two women sat side by side: one with chestnut-brown hair, the other blonde. They looked around her dad’s age, confident and kind, with the easy familiarity of lifelong friends. Something about them — maybe the sound of their laughter — reminded her of her mom.
Before she could overthink it, Jess set her menu down and leaned toward them.
“Pardon me, ladies… can you help me?”
Both turned toward her and smiled.
“Maybe,” said the brown-haired woman.
“I’ve never been here before,” Jess said. “What’s good?”
“Just about everything,” the brunette replied. “Depends what you’re into.”
“I’m starting a Route 66 trip,” Jess said, trying not to sound too eager. “I was wondering what travelers usually order.”
“My husband drove the whole thing a few years before we met,” said the brunette. “Swore it was life-changing. One of these days, when we’re both retired, we’ll do it together.”
The blonde laughed. “I don’t think that’s what she asked. She asked what’s good.”
She turned to Jess with a grin. “Don’t mind her. She’s a storyteller — comes with the territory.”
Jess smiled. “I like storytellers.”
“Then you’re in the right place,” said the brunette. “You can’t go wrong with a burger or their skirt steak.”
“The chicken Caesar’s good too,” added the blonde. “Used to be they had a pot pie the size of an actual pie — you could feed a family with it.”
Jess hesitated, then asked, “Are you two sisters?”
They both laughed.
“Sort of,” the brunette said.
“Our husbands are brothers,” the blonde explained. “So we’re sisters-in-law — though most days we just skip the in-law part.”
Jess smiled. “I never had a sister, but if I did, I think it’d look a lot like you two.”
They exchanged a quick, knowing glance. Then the brunette said, “You know, we do have the same color eyes. How did we never notice that?”
The blonde laughed. “Mine are darker — and prettier.”
“You wish,” the brunette shot back, laughing.
“I’m Ginny,” she said finally, gesturing to her friend. “And this is Charlie.”
“Jess,” she replied.
Ginny grinned. “Well, Jess — move over, Charlie. Let’s not make our new friend eat alone.”
The three of them spent the next two hours talking — about travel, families, music, and the small surprises that make ordinary days feel alive. Jess learned that the two women had lived out west for a time before coming back to Chicago, following work and family and the usual twists of life.
They told stories with warmth and humor and an honesty Jess hadn’t felt in a long while. There was something about them — something motherly without being condescending. She felt like she was sitting with two of her mom’s oldest friends, people who somehow knew the shape of her grief and wanted to send her off with a little of her mother’s spirit.
As lunch wound down and the check arrived, Ginny and Charlie exchanged one of those silent glances that seemed to say now’s the time.
Charlie leaned forward, her eyes kind. “You don’t have to know where you’re going,” she said. “Just be the kind of person who pays attention. That’s all the road ever asks of you.”
Ginny tapped her coffee cup and added, “And don’t rush through the little places. That’s where the good stuff hides. Your mother probably would’ve told you that too.”
Jess blinked, unsure whether to smile or cry.
Charlie reached across the table and touched her wrist. “Be careful with your kindness,” she said. “It’s your best compass — but people notice it first when they’re looking for someone to use.”
Ginny nodded, softer now. “The road doesn’t test your feet, Jess. It tests your heart — how much of it you can give, and how much you can keep for yourself.”
They paid their bill and stood to go, their laughter fading into the city’s hum.
Jess stayed behind a moment, tracing a fingertip around her empty coffee cup. Then she looked toward the door, sunlight spilling across the tiles, and whispered to herself, “Guess this is where it all really begins.”
Epilogue to Chapter One
Jess found herself making her way east along Jackson on the long, hot trek back toward Michigan Avenue. The whole time, she felt as if she were walking in a daze. She nearly missed the iconic Chicago Board of Trade Building, the statue of the goddess Ceres gleaming faintly atop it.
Her mind kept circling back to the two women — their warmth, their kindness, their motherly advice. Maybe it was a sign, she thought. Maybe this was Mom’s way of telling me she was down for the ride.
As she reached Michigan Avenue, passing the End of Route 66 sign along the way, she turned north toward the Drake Hotel. Everything seemed to click into place at once.
Funny, she thought. I started the day looking for a sign — and found three. Two of them literal.
She smiled to herself as she moved through the flow of shoppers, street musicians, and tourists, a new lightness in her step.
This is going to be a good trip, she thought. Then, with a half-smirk: Too bad both of them were married — they were exactly Dad’s type.
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