When booking a flight to Chicago, the cheapest time to book can vary depending on a few factors.
 
First, it is important to consider the time of year you plan to travel. Typically, the off-peak seasons for travel to Chicago are in the winter and early spring, while peak season is during the summer months. During the off-peak seasons, you may find lower prices on flights.
 
Another factor to consider is the day of the week. Tuesdays and Wednesdays are typically the cheapest days to book a flight, as many people tend to book flights for the weekend.
 
It's also important to book your flight well in advance. Generally, the earlier you book, the better the deal you can find. Most airlines release their flight schedules several months in advance, so you can plan ahead and book your flight as soon as possible.
 
Additionally, being flexible with your travel dates can also help you find cheaper flights. If you're not tied to a specific date, consider searching for flights on different days of the week or at different times of the day. Many airlines also offer lower prices for flights that have more layovers or longer flight times.
 
Another tip is to sign up for fare alerts from airlines or travel websites. These alerts will notify you when the price of a flight to Chicago drops, so you can take advantage of any deals that become available.
 
Price comparison sites such as Kayak, Expedia, Priceline and many others are a great resource to find the cheapest flights to Chicago. These sites allow you to compare prices from different airlines, so you can find the best deal.
 
Lastly, you can also consider booking a package deal that includes your flight, hotel, and rental car. Often, these package deals can save you money compared to booking each component separately.
 
In summary, the cheapest time to book a flight to Chicago can vary depending on the time of year, day of the week, and how far in advance you book. Being flexible with your travel dates and considering package deals can also help you find a cheaper flight. Additionally, signing up for fare alerts and using price comparison sites can help you stay informed about the best deals on flights to Chicago.

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