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Flaut.Travel was designed and developed by a team dedicated to making the process of searching, comparing and booking airline tickets as easy and convenient as possible. Our service helps travelers to find and buy the cheapest flights from Hartford to Chicago. We have connected more than 40 airlines and airline ticketing agencies to help you find the most suitable and affordable flight option.
A non-stop flight is the most convenient and comfortable way to fly from Hartford to Chicago, despite the fact that sometimes flights with transfers can cost significantly less.
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Answers to questions about the route that travelers are most interested in.
We keep tight track on airlines' pre-holidays sales and other special offers occurences all the time to let you save maximum amount of funds while traveling to your family or just going out on vacation.
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We carefully collect statistics on the search and pricing of airlines and, based on these data, we make an assumption about future prices. Thus, you can better understand which season is the cheapest to fly from Hartford to Chicago
Hartford — Chicago
05/20/2026
Departure
Direct flight
WN588
starting at $423
starting at $423
starting at $145
The route Hartford — Chicago is served by several airlines: Southwest Airlines and Frontier Airlines. This gives passengers more freedom in choosing flights. You can consider not only the price but also schedules, baggage policies, and onboard service. Our service compares all offers so you can find tickets from $145 and choose the most convenient option. Thanks to airline competition, you may also find promotional fares or special offers, helping you save even more. Plan your trip in advance and choose the best flights without overpaying.
The cheapest flight ticket from Hartford to Chicago according to data for the last 48 hours costs $145
Often the best time to buy tickets from Hartford to Chicago is 2 months before departure.
Based on statistics over the past years, the lowest prices for flights from Hartford to Chicago can be found flying in these months: May.
The fastest flights from Hartford to Chicago start from 17 hours 46 minutes in the air.
The following airlines operate direct flights on the route Hartford — Chicago: Southwest Airlines
The cheapest one-way flight from Hartford to Chicago departs on 05/20/2026, is operated by Frontier Airlines and costs $145
There is no information about the cheapest roundtrip flight from Hartford to Chicago
Fastest flight from Hartford to Chicago takes 17h 46m
There are direct flights on this route 1 day a week: We
The distance between Hartford and Chicago is 1235km (766 miles). There are 19 direct flights from Hartford to Chicago. The time difference between Hartford and Chicago is 1h. Flights from Hartford begin at 6:00 AM. The latest flight from Hartford departs at 7:29 PM
We couldn't find any special offers for flights from Hartford to Chicago