Chicago Alone cover

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Chicago
Alone

A solo travel guide for women 50 and over
By Jennifer Brandt

Sailboats cut across Lake Michigan, and the lakefront is the city's backyard. Spend a morning among the Loop's architectural canyons, an afternoon on Lincoln Park's leafy streets, and pack a good jacket for the wind.

$6.99 ebook

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Ebook · Updated Q4 2026

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Where you might stay

  • BudgetHampton Inn Majestic Chicago Theatre Districtbreakfast included, with museums within reach
  • Mid-rangeLondonHouse Chicago, Curio Collection by Hiltondining and spa without going back out
  • A treatNobu Hotel Chicagorestaurant and rooftop bar in the building

Two places to eat alone

  • The GageAmerican gastropub with bar seating.
  • Miller's PubHistoric bar and restaurant with bar seating.

SAMPLE

A City Ready to Meet You

The city rises from Lake Michigan with confidence, a place that has survived fire, reinvented itself, and built something extraordinary in the rebuilding. This guide is written for the woman traveling alone, 50 and over. The grid is logical, the lake keeps you oriented, and the neighborhoods let you choose your own pace.

The architecture speaks plainly, and lunch can be an Italian beef sandwich eaten at a counter on Taylor Street.

The lake is the first thing to understand. Lake Michigan is vast, one of five Great Lakes, and from Chicago’s shore the water stretches to the horizon. The lakefront is the city’s backyard, its escape valve, its place to think. Many visitors end up sitting on the rocks and watching sailboats cut through the water. The lake is also the reason Chicago’s wind is so insistent, so pack a good jacket.

A free excerpt from Chicago Alone.

PRACTICAL SAMPLE

How Chicago Dining Works

Counter Seating: restaurants with prominent counter seating are ideal. You can watch your food being prepared and have a more engaged meal than at a table. Ramen counters, sushi counters, and tapas-style bars are all good options.

Bars: Bar-top seating is common in Chicago restaurants and is a normal way to eat alone. The bar is where conversation is easiest if you want it, and the atmosphere is less formal than table service.

Open Layouts: Busy, open rooms tend to be more comfortable to eat alone in than intimate, quiet ones. The energy makes you feel part of something rather than isolated.

Lunch: Lunch is the easiest time to eat alone. Restaurants are full of workers and casual diners, the pace is faster, and there is no sense of occasion. Lunch alone is entirely unremarkable.

A free excerpt from Chicago Alone.

Inside this book

  • Chicago Awaits
  • A City Shaped by History
  • Planning Your Escape
  • The Solo Woman’s Chicago
  • Where to Stay
  • Neighborhood by Neighborhood
View the chapter contents
  • Chicago Awaits
  • A City Shaped by History
  • Planning Your Escape
  • The Solo Woman’s Chicago
  • Where to Stay
  • Neighborhood by Neighborhood
  • Days in Chicago
  • Art, Culture & Creativity
  • The Pleasures of the Table
  • Evening & After Dark
  • Retail Therapy
  • Beyond the City: Day Trips
  • Practical Matters
  • Final Reflections

BUY THE GUIDE

Chicago Alone

Sailboats cut across Lake Michigan, and the lakefront is the city's backyard. Spend a morning among the Loop's architectural canyons, an afternoon on Lincoln Park's leafy streets, and pack a good jacket for the wind.

$6.99 ebook

Buy the ebook, $6.99

Ebook · Updated Q4 2026

Instant download · Secure checkout by Payhip

THE GUIDE + YOUR OWN PLANS

Ready to settle your plans?

The Loop or River North? The kit sets them side by side before you book.

See inside the Chicago kit →
A page from the free sample of the Chicago kitRead the free 3-page sample (PDF) →
Do I need the kit as well?

No. The guide stands on its own. The kit is a separate, optional pack of decisions, day plans and a booking list. Read the free 3-page sample to see whether it suits the way you plan.

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