Itineraries
Chicago in Winter
Cold-weather Chicago done right: indoors, outdoors, and the Christmas market.
Chicago Itineraries: Day Plans by Trip Length
One day means the Loop, the lakefront and one big view. Two days add a museum and a river cruise. Three days let you reach the neighborhoods and the food. Pick the plan that matches your time, and check the month, because a Chicago winter rewrites the order.
Itineraries
Weekend Itinerary
A Friday-to-Sunday plan for Chicago with real prices, fares, and booking shortcuts.
Planning
Rainy Day in Chicago
Museums, indoor attractions and wet-weather itineraries for a rained-out day in Chicago.
Itineraries
3 Days in Chicago
A day-by-day 3-day Chicago itinerary with real prices, transit fares and where to eat.
Planning
First Time in Chicago
The practical first-visit plan: days, neighborhoods, costs and bookings.
Itineraries
4 Days in Chicago
A four-day Chicago itinerary with real prices, transit fares and neighborhood picks.
Itineraries
Romantic Chicago
A couples itinerary for Chicago: cruises, viewpoints, dinners and free walks.
Itineraries
5 Days in Chicago
A five-day Chicago plan: downtown icons, museums, neighborhoods, food, and a day trip.
Itineraries
O'Hare Layover Guide
How long your O'Hare layover needs to be before downtown Chicago is worth the trip, and what to do when it isn't.
Itineraries
Chicago on a Budget
A 3-day cheap Chicago plan: free museums, lakefront days, pass math and under-$100 days.
Itineraries
Chicago with Kids
A three-day family plan built around what children actually enjoy, with costs and transit worked out.
Itineraries
Two Days in Chicago
A realistic two-day plan: downtown day one, lakefront and neighborhoods day two.