Cheap flights from Chicago to Springfield from $145

The month of October is, on average, the cheapest month to fly to Hartford from Chicago, with most prices found around $292. The month of September is another great option to travel to Hartford, with average flight prices from Chicago averaging around $306.

The cheapest day to depart from Chicago to Hartford is on a Saturday when prices can be found for as low as $360. Be sure to avoid booking your departure on a Monday as prices are generally higher than usual. According to our data, the average ticket price to Hartford on Monday is $555.

According to our data, the cheapest time of day to fly to Hartford is in the morning. momondo users have found flights departing from Chicago to Hartford in the morning for as low as $408. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets in the afternoon because they tend to be around $523. Of course, these prices can vary depending on the time of year and what airport you fly to.

Fly from Chicago O'Hare Intl to Hartford Bradley Intl for the best Chicago - Hartford Bradley Intl flight prices

You are more likely to see cheaper flights to Hartford from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Hartford for around $433 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Hartford from Chicago for as low as $313 on momondo.

There are 4 cabin classes available to choose from on Chicago to Hartford flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

No. A direct flight is the cheapest option for a flight between Chicago to Hartford.

As of August 2026, prices for Chicago to Hartford flights are approximately 28% more expensive when compared to flights at the same time last year.

JetBlue, Southwest, and United Airlines are the most popular carriers operating from Chicago to Hartford Bradley Intl

American Airlines, United Airlines and Avelo Airlines are the top three most popular airlines that fly to Hartford from Chicago according to our data. American Airlines is the first choice among our users, with 72% of people opting to fly with this airline when traveling to Hartford. Keep in mind that there are 4 different airlines that fly to Hartford on a routine basis, so you have a few additional options to choose from.

As of August 2026, there are 13 flights per day flying from Chicago to Hartford. The most common time of day flights depart is 6:00PM, with 38% of flights taking off at noon.

As of August 2026, 96 flights take off from Chicago and land in Hartford each week. The most common flight departure day for this route is Fri, with 24% of weekly flights taking off on this day.