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$79+ Cheap flights from Hartford (BDL) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/24. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — CHI
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheapflights Tip: The best prices from Hartford Bradley Intl to Chicago are usually found in August or September, booked 77 days in advance, depart on a Thursday or Wednesday and return on a Wednesday

Cheap flight deals from Hartford to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Hartford (BDL) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated July 31, 2025.

Round-trip from

$186
(United Airlines)

One-way from

$79
(Southwest)

Popular in

April

Cheapest in

August

Average price

$352
From Hartford Bradley Intl to Chicago (CHI)
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One-way flight from Hartford Bradley Intl to Chicago (CHI)
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Highest demand for flights based on searches. 3% potential increase in price ($14 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find flight deals from Hartford to Chicago

Cheapest flights from Hartford to Chicago
Explore the most affordable flight options available from Hartford to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 31, 2025.

This United Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/186:10 amBDL - ORD
Nonstop2h 43mUnited Airlines
Mon 9/228:48 amORD - BDL
Nonstop2h 32mUnited Airlines
Deal found 7/31$186
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/195:20 pmBDL - MDW
Nonstop2h 20mSouthwest
Wed 9/36:10 pmMDW - BDL
Nonstop2h 10mSouthwest
Deal found 7/29$187
This Mytrip deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/125:58 pmBDL - ORD
2 stops24h 41mSpirit Airlines
Sun 9/146:44 pmORD - BDL
2 stops21h 09mSpirit Airlines
Deal found 7/30$188
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/217:00 amBDL - MDW
1 stop5h 48mDelta
Tue 8/261:08 pmMDW - BDL
1 stop3h 38mDelta
Deal found 7/29$197
This Delta deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/218:00 amBDL - ORD
1 stop7h 19mDelta
Tue 8/269:47 amORD - BDL
1 stop5h 31mDelta
Deal found 7/30$197
This American Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/512:07 pmBDL - ORD
Nonstop2h 51mAmerican Airlines
Thu 9/116:55 pmORD - BDL
Nonstop2h 20mAmerican Airlines
Deal found 7/31$199
This CheapOair deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2511:44 amBDL - ORD
1 stop7h 57mMultiple Airlines
Thu 8/2810:12 amORD - BDL
1 stop5h 47mMultiple Airlines
Deal found 7/29$202
This Frontier deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1612:27 pmBDL - ORD
1 stop12h 02mFrontier
Sun 8/175:01 amORD - BDL
1 stop5h 40mFrontier
Deal found 7/31$208
This FlightHub deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/309:54 amBDL - MDW
1 stop9h 24mFrontier
Sat 11/13:59 pmMDW - BDL
1 stop20h 05mFrontier
Deal found 7/30$215
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/49:15 amBDL - ORD
1 stop4h 30mSouthwest
Sun 9/71:50 pmORD - BDL
1 stop7h 55mSouthwest
Deal found 7/29$232
This Mytrip deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/196:10 amBDL - RFD
2 stops9h 15mMultiple Airlines
Mon 9/2210:37 amRFD - BDL
2 stops11h 10mMultiple Airlines
Deal found 7/30$240

Cheapflights Fare Finder

 
Customize your flight search to find flights from Hartford to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 31, 2025.
Use the filters below to find and compare flights from Hartford to Chicago that are best for you.

Fly from

Hartford

Fly to

Chicago

Route

Depart

Return

Price

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Thu 9/18

6:10 am-7:53 am

Nonstop2h 43m

Chicago O'Hare Intl

Mon 9/22

8:48 am-12:20 pm

Nonstop2h 32m

$186

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 8/19

5:20 pm-6:40 pm

Nonstop2h 20m

Chicago Midway

Wed 9/3

6:10 pm-9:20 pm

Nonstop2h 10m

$187

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Fri 9/12

5:58 pm-5:39 pm

2 stops24h 41m

Chicago O'Hare Intl

Sun 9/14

6:44 pm-4:53 pm

2 stops21h 09m

$188

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 8/21

7:00 am-11:48 am

1 stop5h 48m

Chicago Midway

Tue 8/26

1:08 pm-5:46 pm

1 stop3h 38m

$197

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Thu 8/21

7:00 am-2:19 pm

1 stop8h 19m

Chicago O'Hare Intl

Tue 8/26

11:15 am-8:28 pm

1 stop8h 13m

$197

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Fri 9/5

12:07 pm-1:58 pm

Nonstop2h 51m

Chicago O'Hare Intl

Thu 9/11

6:55 pm-10:15 pm

Nonstop2h 20m

$199

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Mon 8/25

11:44 am-6:41 pm

1 stop7h 57m

Chicago O'Hare Intl

Thu 8/28

10:12 am-4:59 pm

1 stop5h 47m

$202

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Sat 8/16

12:27 pm-11:29 pm

1 stop12h 02m

Chicago O'Hare Intl

Sun 8/17

5:01 am-11:41 am

1 stop5h 40m

$208

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 9/11

10:30 am-3:58 pm

1 stop6h 28m

Chicago Midway

Sun 9/14

10:13 am-7:52 pm

1 stop8h 39m

$218

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Thu 9/4

9:15 am-12:45 pm

1 stop4h 30m

Chicago O'Hare Intl

Sun 9/7

1:50 pm-10:45 pm

1 stop7h 55m

$232

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 22 results
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The best insider tips for Hartford to Chicago flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Hartford to Chicago trip
Airlines
United Airlines

United offers Economy Plus seats with extra legroom, perfect for added comfort.


Prepay for checked bags to save money on fees.

Read more about United Airlinesby Harriet Baskas
Southwest

Enjoy free snacks and non-alcoholic drinks on board, enhancing your travel experience.


Two free checked bags included, ideal for travelers with extra luggage needs.

Read more about Southwestby Marisa Garcia
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on United Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Marisa Garcia

Marisa Garcia

Expert on Southwest

Marisa Garcia

Marisa Garcia

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Read more

Best time to book a flight from Hartford to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Hartford with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Hartford to Chicago

How far ahead should I book a flight from Hartford to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Hartford to Chicago. Price data was last updated on July 25, 2025.

To ensure you get the cheapest price possible for a flight from Hartford to Chicago, you should look to book at least 77 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Hartford to Chicago?

Currently, August is the cheapest month in which you can book a flight from Hartford to Chicago (average of $245). Flying from Hartford to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from BDL to CHI?

Find hourly flight availability from Hartford to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 31, 2025.

It’s typically best to fly out from Hartford to Chicago in the afternoon. Doing so could potentially save you 8% on the flight price compared to flying in the morning, which is usually more expensive.

What is the cheapest day to fly from Hartford to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Hartford to Chicago. Price data was last updated on July 27, 2025.

Travelers seeking maximum savings on their Hartford to Chicago flight should consider departing on Thursday at noon when fares are most often at their lowest. Tuesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Hartford to Chicago

Explore weekly flight availability from Hartford to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 31, 2025.

The most flights from BDL to CHI are scheduled on a Thursday (23 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (8 on average).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated July 31, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Hartford to Chicago. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,900 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Spirit Airlines
6.3
Okay
8,048 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

Related info for your journey

Find useful and relevant information for your journey from Hartford to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Hartford to Chicago?

    Most people fly from Hartford Bradley Intl (BDL) if they book a flight from Hartford to Chicago. On average, Bradley Intl has 14 outbound flights to Chicago per day from 6 airlines. Hartford Bradley Intl is conveniently located just 11.9 mi from Hartford’s city center.

  • What are the cheapest airlines flying from Hartford to Chicago round-trip?

    According to our current data, United Airlines ($186), Southwest ($187), and Spirit Airlines ($188) offers the cheapest pricing from Hartford to Chicago. United Airlines is currently priced 48% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Hartford to Chicago one-way?

    One-way options have recently been found by users for as low as $79 on Southwest. Other airlines that offer cheap prices include American Airlines from $79 and Spirit Airlines from $90 one-way.

  • What are the most popular routes from Hartford to Chicago?

    Most travelers choose Hartford Bradley Intl - Chicago O'Hare Intl, Hartford Bradley Intl - Chicago Midway or Hartford Bradley Intl - Chicago Greater Rockford when deciding on the best route from Hartford to Chicago.

  • What are the most reliable airlines from Hartford to Chicago?

    The top 3 most reliable airlines when flying from Hartford to Chicago are Republic Airways (90%), ANA (87%) and Envoy Air (74%).

  • What are the cheapest flights from Hartford to Chicago?

    While on average a flight from Hartford to Chicago is generally $1,010, our data shows the cheapest flight currently is $92. When looking at the most popular route, (Hartford Bradley Intl - Chicago O'Hare Intl), you can expect to pay $137 for that flight.

  • Can I find deals for flights from Hartford to Chicago that include hotel bookings?

    Yes. In addition to deals on Hartford to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Hartford to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Hartford to Chicago.

  • Can I find deals for business class flights from Hartford to Chicago?

    Yes. Cheapflights offers flight deals from Hartford to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Hartford to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Hartford to Chicago (average of $245). Flying from Hartford to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

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Alternative routes for Hartford to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Hartford to Chicago

Discover the top 6 airlines that operate flights from Hartford to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$116Average$192FlexibilityNo cancel feeOn-time62%
DeltaCheapest$176Average$276FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$177Average$362FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$184Average$356FlexibilityNo cancel feeOn-time71%
Spirit AirlinesCheapest$202Average$280FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$227Average$407FlexibilityNo cancel feeOn-time69%

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