The most affordable time to visit Chicago is usually January through early March and late November through early April, excluding major holidays. During these months, airfare and hotel prices tend to be lower due to colder weather and reduced tourism.
Midweek flights often deliver the lowest fares.

Spring and fall provide moderate weather and occasional flight deals.

Summer months bring festivals and peak tourism, often with higher prices.
Booking early and remaining flexible with your travel dates helps maximize savings.