Sample guide

A Chicago weekend for two

Friday, May 7 to Sunday, May 9, 2027. Architecture, baseball, classical music and good food, at a balanced pace, with one vegetarian traveler. Practical, usable information, no fluff.

This is a sample. Jordan and Sam are made-up travelers, and their flight and hotel are placeholders. Every venue, event, price and date in the guide is real and was checked on November 14, 2026, with sources listed in the guide. Times not yet published (like 2027 Cubs game times) are marked TBA.

What they asked for

Form questionAnswer
DestinationChicago
DatesFri May 7 to Sun May 9, 2027
Travelers2 adults
InterestsArchitecture, baseball, classical music, food
BudgetComfortable
PaceBalanced
Special needsOne vegetarian

What they got

  • The Cubs' three home games that weekend, with a rule for picking the one that doesn't clash with the Symphony
  • Saturday's Chicago Symphony concert and a Sunday piano recital, with times and prices
  • A "book first" list, including the boat tour with no refunds and the Mother's Day brunch that goes early
  • Three timed day plans, each with a plan B
  • Trains, passes and costs, from O'Hare to Wrigley
  • May weather averages, sunrise and sunset, a packing list and a cost estimate
Open the full sample (PDF, 12 pages)

Your own guide can come as a PDF, a printed book, or both. A printed book adds the print fee from our printer at cost, plus shipping. You get an estimated quote first, nothing is charged until you approve it, and the 5-business-day turnaround starts once you do.

Inside the sample

Cover
Cover
About this guide and trip at a glance
About this guide · your trip at a glance
What's on
What's on during your dates
Book first
Book first
Day 1
Day 1, Friday
Day 2
Day 2, Saturday
Day 3
Day 3, Sunday
Weather
Weather and daylight

Order a guide like this: from $49