$58 Cheap Flights from Hartford (BDL) to Chicago (ORD)

View $58 flight on Wed, Aug 20, 2025Opens in a new window

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

  • Plan, book, fly with confidence

  • trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon
    Book smarter
    Save up to 30% on select hotels after you book a flight*
  • one key icon
    Earn twice
    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

Cheap Flights from Hartford to Chicago (BDL-ORD)

Prices were available within the past 7 days and start at $58 for one-way flights and $115 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Thu, Aug 28 - Sat, Aug 30
BDL
Hartford
ORD
Chicago
$115 Roundtrip, found 1 hour ago
$115
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Thu, Aug 28 from Hartford to Chicago, returning Sat, Aug 30, priced at $115 found 1 hour ago
American Airlines
Fri, Sep 5 - Tue, Sep 9
BDL
Hartford
ORD
Chicago
$120 Roundtrip, just found
$120
Roundtrip
just found
Select American Airlines flight, departing Fri, Sep 5 from Hartford to Chicago, returning Tue, Sep 9, priced at $120 just found
American Airlines
Thu, Aug 28 - Sat, Aug 30
BDL
Hartford
ORD
Chicago
$124 Roundtrip, found 1 hour ago
$124
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Thu, Aug 28 from Hartford to Chicago, returning Sat, Aug 30, priced at $124 found 1 hour ago
American Airlines
Sat, Aug 30 - Thu, Sep 4
BDL
Hartford
ORD
Chicago
$126 Roundtrip, found 6 hours ago
$126
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Sat, Aug 30 from Hartford to Chicago, returning Thu, Sep 4, priced at $126 found 6 hours ago
United
Thu, Oct 2 - Mon, Oct 6
BDL
Hartford
ORD
Chicago
$126 Roundtrip, just found
$126
Roundtrip
just found
Select United flight, departing Thu, Oct 2 from Hartford to Chicago, returning Mon, Oct 6, priced at $126 just found
American Airlines
Sat, Aug 30 - Tue, Sep 2
BDL
Hartford
ORD
Chicago
$128 Roundtrip, found 6 hours ago
$128
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Sat, Aug 30 from Hartford to Chicago, returning Tue, Sep 2, priced at $128 found 6 hours ago
United
Wed, Sep 17 - Sun, Sep 21
BDL
Hartford
ORD
Chicago
$129 Roundtrip, just found
$129
Roundtrip
just found
Select United flight, departing Wed, Sep 17 from Hartford to Chicago, returning Sun, Sep 21, priced at $129 just found
Southwest Airlines
Thu, Sep 4 - Mon, Sep 8
BDL
Hartford
ORD
Chicago
$131 Roundtrip, just found
$131
Roundtrip
just found
Select Southwest Airlines flight, departing Thu, Sep 4 from Hartford to Chicago, returning Mon, Sep 8, priced at $131 just found
Spirit Airlines
Thu, Aug 7 - Thu, Aug 14
BDL
Hartford
ORD
Chicago
$204 Roundtrip, found 2 hours ago
$204
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Thu, Aug 7 from Hartford to Chicago, returning Thu, Aug 14, priced at $204 found 2 hours ago
JetBlue Airways
Tue, Aug 12 - Wed, Aug 20
BDL
Hartford
ORD
Chicago
$216 Roundtrip, just found
$216
Roundtrip
just found
Select JetBlue Airways flight, departing Tue, Aug 12 from Hartford to Chicago, returning Wed, Aug 20, priced at $216 just found

Find the cheapest month to fly from Hartford (BDL) to Chicago (ORD)

November is typically the cheapest month to fly

From $119 - $393 per traveler.

Graph displaying average flight prices per month

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. Cheapest and Closest option available. Average driving time to city center is 16 minutes. Flights from $197
MDW
Midway Intl.
CheapestClosest
Average driving time to city center16 min
Flights from $197
Flights from Hartford (BDL) to Chicago (ORD)
Origin airport
Bradley Intl.
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, Frontier Airlines, JetBlue Airways, Southwest Airlines, Spirit Airlines, Sun Country Airlines, United
Roundtrip price
$115
Distance
780 mi
Average flight time
1 hour 44 mins

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 2025. You can also book with separate airlines for your outbound and return journeys, from $58 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.

 

Frequently asked questions

How much does a flight from Bradley Intl. Airport (BDL) to O'Hare Intl. Airport (ORD) cost?
Book cheap return flights starting from $132 from Bradley Intl. Airport (BDL) to O'Hare Intl. Airport (ORD). This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a United flight leaving BDL on July 29 2025 and touching down at ORD. The price was last updated on July 6 2025 and has not changed since.
What is the cheapest month to fly from BDL to ORD?
The cheapest flights from BDL to ORD are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Bradley Intl. Airport (BDL) to O'Hare Intl. Airport (ORD)?
When setting off from Bradley Intl. Airport (BDL), you can take a direct flight to O'Hare Intl. Airport (ORD) with American Airlines.
What is the cheapest airline that flies from BDL to ORD?
Travel from BDL to ORD with American Airlines. This airline currently has the lowest one-way fare for this route, starting from $69. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from BDL on September 21 2025. Prices were last updated on July 6 2025 and have not changed since.
How many flights per day from Bradley Intl. Airport (BDL) to O'Hare Intl. Airport (ORD)?
When taking off from Bradley Intl. Airport (BDL), you can pick from an average of 4 daily nonstop flights to O'Hare Intl. Airport (ORD).
What are the most popular departure times for flights from Bradley Intl. Airport (BDL) to O'Hare Intl. Airport (ORD)?
The 5 PM departures from BDL to ORD are typically the busiest. These flights can come with a higher price due to their popularity. If you want to save on your trip, pick a less crowded time to fly.
What day of the week has the most flights from BDL to ORD?
Fly on a Friday if you're after the biggest selection of flights from Bradley Intl. Airport (BDL) to O'Hare Intl. Airport (ORD).
What is the earliest flight from Bradley Intl. Airport (BDL) to O'Hare Intl. Airport (ORD)?
Hop on the earliest flight at around 6:00AM UTC-5, leaving from Bradley Intl. Airport (BDL). You'll be flying for around 2h 47m, reaching O'Hare Intl. Airport (ORD) at approximately 7:47AM UTC-6.
How long does it take to fly from Bradley Intl. Airport (BDL) to O'Hare Intl. Airport (ORD)?
It usually takes 2 hours and 47 minutes to cover the 780 mi from BDL to ORD.
What airline has the least delays from BDL to ORD?
With 82% of flights typically landing on schedule, Alaska Airlines has the best on-time performance for direct flights from Bradley Intl. Airport (BDL) to O'Hare Intl. Airport (ORD). To keep track of your flight status and receive notifications if anything changes, use the Expedia App.
What is the best time to fly from Bradley Intl. Airport (BDL) to O'Hare Intl. Airport (ORD)?
To arrive at O'Hare Intl. Airport (ORD) without delays, pick a flight that leaves Bradley Intl. Airport (BDL) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**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 Chicago from Bradley Intl. Airport (BDL)?
If you're leaving on a direct flight from Bradley Intl. Airport (BDL) to Chicago, you can land at either O'Hare Intl. Airport (ORD) or Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Bradley Intl. Airport (BDL) to O'Hare Intl. Airport (ORD) last-minute?
Booking your ticket from BDL to ORD shortly before your trip is usually more expensive. But if you're flexible with your departure times and dates, you could bag a cheap last-minute fare.
Is it cheaper to book a BDL to ORD flight and hotel package?
Opting for a BDL to ORD flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your trip in one place. Choose from our extensive range of stays and then add car rentals, activities and flights to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Bradley Intl. Airport (BDL) to O'Hare Intl. Airport (ORD)?
It's usually possible to cancel or reschedule your BDL to ORD flight. However, for bookings made more than 24 hours ago, additional charges may apply. Refer to your airline's policies in your itinerary to see what changes are possible and whether any costs are involved. You'll also find more details on our Customer Service portal.

Explore a world of travel with Expedia

*Available to One Key members.