$107 Cheap Flights from Hartford (BDL) to Chicago (ORD)

View $107 flight on Wed, Sep 23, 2026Opens in a new window

Popular airlines from Bradley Intl. Airport (BDL) to Chicago O'Hare Intl. Airport (ORD)

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Cheap Flights from Hartford to Chicago (BDL-ORD)

Prices were available within the past 7 days and start at $107 for one-way flights and $210 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Wed, Aug 26 - Tue, Sep 1
BDL
Hartford
ORD
Chicago
$210 Roundtrip, found 6 days ago
$210
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, Aug 26 from Hartford to Chicago, returning Tue, Sep 1, priced at $210 found 6 days ago
JetBlue Airways
Thu, Sep 10 - Mon, Sep 14
BDL
Hartford
ORD
Chicago
$216 Roundtrip, just found
$216
Roundtrip
just found
Select JetBlue Airways flight, departing Thu, Sep 10 from Hartford to Chicago, returning Mon, Sep 14, priced at $216 just found
Frontier Airlines
Sat, Jul 11 - Tue, Jul 14
BDL
Hartford
ORD
Chicago
$218 Roundtrip, found 4 hours ago
$218
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sat, Jul 11 from Hartford to Chicago, returning Tue, Jul 14, priced at $218 found 4 hours ago
Frontier Airlines
Sat, Aug 8 - Thu, Aug 13
BDL
Hartford
ORD
Chicago
$221 Roundtrip, just found
$221
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Aug 8 from Hartford to Chicago, returning Thu, Aug 13, priced at $221 just found
Frontier Airlines
Sat, Aug 22 - Mon, Aug 31
BDL
Hartford
ORD
Chicago
$224 Roundtrip, found 6 days ago
$224
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Aug 22 from Hartford to Chicago, returning Mon, Aug 31, priced at $224 found 6 days ago
Frontier Airlines
Mon, Aug 3 - Thu, Aug 13
BDL
Hartford
ORD
Chicago
$226 Roundtrip, found 15 hours ago
$226
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Mon, Aug 3 from Hartford to Chicago, returning Thu, Aug 13, priced at $226 found 15 hours ago
Frontier Airlines
Wed, Sep 2 - Sat, Sep 5
BDL
Hartford
ORD
Chicago
$227 Roundtrip, found 3 days ago
$227
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Sep 2 from Hartford to Chicago, returning Sat, Sep 5, priced at $227 found 3 days ago
American Airlines
Wed, Jun 10 - Wed, Jun 24
BDL
Hartford
ORD
Chicago
$353 Roundtrip, found 2 hours ago
$353
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Wed, Jun 10 from Hartford to Chicago, returning Wed, Jun 24, priced at $353 found 2 hours ago
United
Wed, Jun 10 - Wed, Jun 24
BDL
Hartford
ORD
Chicago
$353 Roundtrip, found 2 hours ago
$353
Roundtrip
found 2 hours ago
Select United flight, departing Wed, Jun 10 from Hartford to Chicago, returning Wed, Jun 24, priced at $353 found 2 hours ago
Delta
Wed, Jun 10 - Wed, Jun 24
BDL
Hartford
ORD
Chicago
$373 Roundtrip, found 2 hours ago
$373
Roundtrip
found 2 hours ago
Select Delta flight, departing Wed, Jun 10 from Hartford to Chicago, returning Wed, Jun 24, priced at $373 found 2 hours ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $530
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $530

Frequently asked questions

How much does a flight from Hartford, CT (BDL-Bradley Intl.) to Chicago, IL (ORD-O'Hare Intl.) cost?
You can find cheap one-way flights from $107 and cheap return flights from $210 Hartford, CT (BDL-Bradley Intl.) to Chicago, IL (ORD-O'Hare Intl.) with Expedia. One-way flights typically cost between $132 and $812, and return flights often range between $287 and $1294. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Hartford, CT (BDL-Bradley Intl.) to Chicago, IL (ORD-O'Hare Intl.) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Hartford, CT (BDL-Bradley Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
September is the cheapest month to fly from Hartford, CT (BDL) to Chicago, IL (ORD), with average return fares around $276. This is about 20% lower than the average price throughout the year, as travel demand typically drops after the summer. Other budget-friendly months to consider are August and October.*Averages based on flights available on Expedia in the last year.
Which airlines fly direct from Hartford, CT (BDL-Bradley Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
There are 2 airlines offering direct flights from BDL to ORD:

  • United operates around 39 direct flights from BDL to ORD every week
  • American Airlines operates around 31 direct flights from BDL to ORD every week

What is the cheapest airline that flies from Hartford, CT (BDL-Bradley Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
United is one of the cheapest airlines offering nonstop flights from Bradley Intl. (BDL) to O'Hare Intl. (ORD), with round-trip tickets starting from around $106. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from Hartford, CT (BDL-Bradley Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
To find a cheap flight from Hartford, CT (BDL-Bradley Intl.) to Chicago, IL (ORD-O'Hare Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best airline to fly with from Hartford, CT (BDL-Bradley Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The best airline to fly with from Hartford, CT (BDL) to Chicago, IL (ORD) will differ from traveler to traveler. If you like to fly early, United offers early morning flights. If price is the most important factor, American Airlines typically offers the lowest fares. American Airlines also offers the most daily flights from Hartford to Chicago, which is great if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from Hartford, CT (BDL-Bradley Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The best times to fly from Hartford, CT (BDL) to Chicago, IL (ORD) are in August and September. These months provide the most affordable return flights at around $276. August is great for summer activities in Chicago, while September offers a lovely fall atmosphere.*Prices based on flights available on Expedia in the last year.
How many flights per day from Hartford, CT (BDL-Bradley Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
On average, there are around 10 nonstop flights per day from Bradley Intl. (BDL) to O'Hare Intl. (ORD). For more options, look at flights that include layovers.
What is the earliest flight from Hartford, CT (BDL-Bradley Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The earliest flight from Bradley International Airport (BDL) in Hartford to O'Hare International Airport (ORD) in Chicago usually departs at around 5:00 AM, operated by American Airlines. This service is seasonal, active in April and May, which can help you make the most of your time in Chicago. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from Hartford, CT (BDL-Bradley Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The most popular departure times for flights from Hartford, CT (BDL) to Chicago, IL (ORD) are from 6am to 9am. About 29% of passengers prefer this time window. Many major carriers, including American Airlines and Delta Airlines, offer flights during this window. This timing is favored because it lets you arrive in Chicago with plenty of time to start your day.
How long does it take to fly from Hartford, CT (BDL-Bradley Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Direct flights from BDL to ORD usually take about 2 hours 50 minutes, traveling roughly 781 miles. If you opt for a connecting flight, expect to add around 4 hours 40 minutes to your journey. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Hartford, CT (BDL-Bradley Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
You can fly first class between BDL and ORD. First class cabins are available on:

  • United Airlines
  • American Airlines
  • Delta Air Lines

How much is a business class flight from Hartford, CT (BDL-Bradley Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
A direct, return business class ticket from Hartford, CT (BDL) to Chicago, IL (ORD) typically costs between $949 - $1,386. Prices often fluctuate based on seasonality and how early you book. You may also be able to find a cheaper business class journey between Hartford, CT (BDL-Bradley Intl.) to Chicago, IL (ORD-O'Hare Intl.) if you opt for a connecting flight.*Prices based on flights available on Expedia in the last year.
How do I earn miles on a Hartford, CT (BDL-Bradley Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight with Expedia?
It's easy to earn miles on a Hartford, CT (BDL-Bradley Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago from Bradley Intl. (BDL)?
When traveling from Bradley Intl. (BDL) to Chicago, you can fly into Midway Intl. (MDW) and O'Hare Intl. (ORD). Some flights may connect through major hubs like Baltimore Washington Intl. Thurgood Marshall (BWI), Orlando Intl. (MCO), Washington Dulles Intl. (IAD) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Hartford, CT (BDL-Bradley Intl.) to Chicago, IL (ORD-O'Hare Intl.) at the last minute?
Typically, booking a last minute flight from Hartford, CT (BDL-Bradley Intl.) to Chicago, IL (ORD-O'Hare Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Hartford, CT (BDL-Bradley Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package?
Securing a Hartford, CT (BDL-Bradley Intl.) to Chicago, IL (ORD-O'Hare Intl.) Chicago Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Hartford, CT (BDL-Bradley Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
If you booked your Hartford, CT (BDL-Bradley Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Bradley Intl.
Destination airport
O'Hare Intl.
Roundtrip price
$210
Distance
780 mi
Average flight time
1 hour 48 mins

Book with confidence

Hartford to Chicago Flights

The cheapest times to fly from Hartford to Chicago

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 Hartford to Chicago are during the month of August. You can find some of the cheapest flights from Hartford to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Hartford to Chicago

Sunday is one of the best days to book for cheap flights from Hartford to Chicago: 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 Hartford to Chicago

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 Hartford to Chicago in 2026. You can also book with separate airlines for your outbound and return journeys, from $107 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 Hartford to Chicago 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 Hartford to Chicago 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.

 

Hartford to Chicago Flights

*Flight schedules are subject to change.

*Available to One Key members.

 

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