$82 Cheap Flights from Chicago (ORD) to Hartford (HFD)

View $82 flight on Wed, May 21, 2025Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Hartford - Brainard Airport (HFD)

Find available prices by choosing your travel dates.

Cheap Flights from Chicago to Hartford (ORD-HFD)

Prices were available within the past 7 days and start at $82 for one-way flights and $182 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

JetBlue Airways
Tue, May 20 - Tue, Jun 10
ORD
Chicago
BDL
Hartford
$182 Roundtrip, found 14 hours ago
$182
Roundtrip
found 14 hours ago
Select JetBlue Airways flight, departing Tue, May 20 from Chicago to Hartford, returning Tue, Jun 10, priced at $182 found 14 hours ago
Frontier Airlines
Sat, May 3 - Sat, May 10
ORD
Chicago
BDL
Hartford
$188 Roundtrip, found 13 hours ago
$188
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Sat, May 3 from Chicago to Hartford, returning Sat, May 10, priced at $188 found 13 hours ago
JetBlue Airways
Thu, May 29 - Sat, May 31
ORD
Chicago
BDL
Hartford
$205 Roundtrip, found 7 hours ago
$205
Roundtrip
found 7 hours ago
Select JetBlue Airways flight, departing Thu, May 29 from Chicago to Hartford, returning Sat, May 31, priced at $205 found 7 hours ago
JetBlue Airways
Tue, Sep 16 - Sat, Sep 27
ORD
Chicago
BDL
Hartford
$208 Roundtrip, found 16 hours ago
$208
Roundtrip
found 16 hours ago
Select JetBlue Airways flight, departing Tue, Sep 16 from Chicago to Hartford, returning Sat, Sep 27, priced at $208 found 16 hours ago
JetBlue Airways
Tue, May 20 - Wed, May 28
ORD
Chicago
BDL
Hartford
$208 Roundtrip, found 14 hours ago
$208
Roundtrip
found 14 hours ago
Select JetBlue Airways flight, departing Tue, May 20 from Chicago to Hartford, returning Wed, May 28, priced at $208 found 14 hours ago
JetBlue Airways
Thu, Sep 18 - Sat, Sep 27
ORD
Chicago
BDL
Hartford
$213 Roundtrip, found 16 hours ago
$213
Roundtrip
found 16 hours ago
Select JetBlue Airways flight, departing Thu, Sep 18 from Chicago to Hartford, returning Sat, Sep 27, priced at $213 found 16 hours ago
JetBlue Airways
Wed, May 14 - Fri, May 16
ORD
Chicago
BDL
Hartford
$214 Roundtrip, found 5 hours ago
$214
Roundtrip
found 5 hours ago
Select JetBlue Airways flight, departing Wed, May 14 from Chicago to Hartford, returning Fri, May 16, priced at $214 found 5 hours ago
United
Fri, May 30 - Sat, May 31
ORD
Chicago
BDL
Hartford
$237 Roundtrip, found 8 hours ago
$237
Roundtrip
found 8 hours ago
Select United flight, departing Fri, May 30 from Chicago to Hartford, returning Sat, May 31, priced at $237 found 8 hours ago
American Airlines
Tue, May 27 - Thu, May 29
ORD
Chicago
BDL
Hartford
$273 Roundtrip, just found
$273
Roundtrip
just found
Select American Airlines flight, departing Tue, May 27 from Chicago to Hartford, returning Thu, May 29, priced at $273 just found
Sun Country Airlines
Sun, Jun 1 - Fri, Jun 13
ORD
Chicago
BDL
Hartford
$277 Roundtrip, found 1 day ago
$277
Roundtrip
found 1 day ago
Select Sun Country Airlines flight, departing Sun, Jun 1 from Chicago to Hartford, returning Fri, Jun 13, priced at $277 found 1 day ago
Flights from Chicago (ORD) to Hartford (BDL)
Origin airport
O'Hare Intl.
Destination airport
Bradley Intl.
Roundtrip price
$181
Distance
780 mi

Chicago to Hartford Flights

The cheapest times to fly from Chicago to Hartford

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Hartford are during the month of May. You can find some of the cheapest flights from Chicago to Hartford with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Chicago to Hartford

Sunday is one of the best days to book for cheap flights from Chicago to Hartford: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

How to find cheap round-trip tickets from Chicago to Hartford

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Hartford in 2025. You can also book with separate airlines for your outbound and return journeys, from $82 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Hartford flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Hartford airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

*Terms apply.

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Hartford, CT (HFD-Hartford - Brainard) cost?
Discover the latest flight deals from ORD to HFD by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from ORD to HFD?
The cheapest flights from ORD to HFD are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from ORD to HFD?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that’ll take you from ORD to HFD. Sort your results by “Price (lowest to highest)” to snap up a great deal.
How many flights per day from O'Hare Intl. Airport (ORD) to Hartford, CT (HFD-Hartford - Brainard)?
You’ll need to take a flight with a layover when traveling from O’Hare Intl. Airport (ORD) to Hartford, CT (HFD-Hartford - Brainard). There are no daily direct flights on this route. However, simply filter your search to include one or two stops to find an option that works for you.
What day of the week has the most flights from ORD to HFD?
Generally you’ll find the most flight options available on a Friday. Tuesdays are often the quietest.* But this can vary based on the airline, time of year and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Hartford, CT (HFD-Hartford - Brainard)?
To avoid potential delays on the O’Hare Intl. Airport (ORD) to Hartford, CT (HFD-Hartford - Brainard) route, fly before 3 PM. Later flights are 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.
What airports do you fly into for Hartford from O'Hare Intl. Airport (ORD)?
If you’re boarding a direct flight from O’Hare Intl. Airport (ORD) to Hartford, Bradley Intl. Airport (BDL) is the only airport you can touch down at.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Hartford, CT (HFD-Hartford - Brainard) last-minute?
Last-minute bookings from ORD to HFD are typically more expensive. To lock in the cheapest rates, start searching for flights well in advance. That being said, if you’re flexible with your travel dates, it’s possible to score a cheap ticket right before your trip.
Is it cheaper to book an ORD to HFD flight and hotel package?
Securing an ORD to HFD flight and hotel package tends to be cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your travels in one place. Select from our impressive range of stays and then add activities, car rentals and flights to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Hartford, CT (HFD-Hartford - Brainard)?
If you reserved your ORD to HFD flight in the last 24 hours, you may be able to modify or cancel it without fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal for more details.

Explore a world of travel with Expedia

*Available to One Key members.