When is the cheapest time to visit Chicago? If you want short lines and cheaper hotel and flight rates, and don't mind cold weather, coming in January, February, or November might be the best choice for you. These are considered the low season months when deals such as Chicago Restaurant Week take place.
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Is there a cheapest month to fly? If you're looking for a bargain month to travel, February is your best bet. Flights in January closely follow February for being most affordable.
Tuesdays and Wednesdays are the cheapest days to fly domestically. The cheapest days to depart if you're flying within the U.S. are midweek — generally Tuesday or Wednesday.
Timing plays an important part. Specifically, plane tickets usually don't get cheaper closer to the departure date. Instead, flights tend to be the most inexpensive when you book between four months and three weeks before your departure date.
According to a recent study by Expedia, the cheapest day to book flights is Sunday. When comparing Sunday flight prices to Friday, Expedia found that travelers save 5% on domestic flights and 15% on international flights. For the past four years, Sunday has been the best day of the week to book flights.
Tuesday Around Midnight is the Cheapest Time to Book
In general, flights were slightly cheaper at midnight earlier in the week (Monday through Wednesday). However, this is only applicable to about 1.6% of U.S. markets, meaning that it's not likely you'll find the same savings on your specific route.
The general rule is that for domestic flights, travelers should start searching for flight tickets one to three months in advance. For international flights, the best prices are typically available from two to eight months in advance.
“For domestic flights, if you're talking peak season, it's about three to seven months in advance,” he says. “For international flights — [it's] four to 10 months.”