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$103+ 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 7/20. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 7 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 June 12, 2025.

Round-trip from

$229
(Expedia)

One-way from

$103
(United Airlines)

Popular in

April

Cheapest in

August

Average price

$393
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 ($4 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This United Airlines deal was found by Cheapflights users on 6/12. 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.
Tue 7/156:00 amBDL - ORD
Nonstop2h 48mUnited Airlines
Wed 7/165:56 pmORD - BDL
1 stop5h 03mUnited Airlines
Deal found 6/12$227
This American Airlines deal was found by Cheapflights users on 6/12. 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.
Wed 11/57:19 amBDL - ORD
Nonstop2h 46mAmerican Airlines
Mon 11/108:00 amORD - BDL
Nonstop2h 09mAmerican Airlines
Deal found 6/12$229
This Southwest deal was found by Cheapflights users on 6/11. 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.
Sat 11/89:45 amBDL - MDW
2 stops10h 00mSouthwest
Mon 11/1011:55 amMDW - BDL
Nonstop2h 00mSouthwest
Deal found 6/11$230
This FlightHub deal was found by Cheapflights users on 6/12. 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.
Fri 7/114:08 pmBDL - ORD
1 stop17h 47mSpirit Airlines
Sun 7/1311:11 amORD - BDL
1 stop21h 09mSpirit Airlines
Deal found 6/12$230
This FlightHub deal was found by Cheapflights users on 6/12. 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.
Sat 6/2112:38 pmBDL - ORD
1 stop12h 36mMultiple Airlines
Sat 6/288:19 amORD - BDL
1 stop9h 29mMultiple Airlines
Deal found 6/12$237
This Delta deal was found by Cheapflights users on 6/10. 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.
Sun 8/315:35 amBDL - MDW
1 stop4h 00mDelta
Wed 9/36:00 amMDW - BDL
1 stop6h 36mDelta
Deal found 6/10$245
This Delta deal was found by Cheapflights users on 6/10. 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.
Sun 8/318:00 amBDL - ORD
1 stop7h 19mDelta
Wed 9/39:45 amORD - BDL
1 stop5h 33mDelta
Deal found 6/10$245
This Southwest deal was found by Cheapflights users on 6/10. 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 7/316:05 amBDL - ORD
1 stop12h 50mSouthwest
Sun 8/311:25 amORD - BDL
1 stop12h 10mSouthwest
Deal found 6/10$263
This Frontier deal was found by Cheapflights users on 6/11. 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 - MDW
1 stop11h 08mFrontier
Mon 8/188:35 amMDW - BDL
1 stop10h 18mFrontier
Deal found 6/11$267
This Mytrip deal was found by Cheapflights users on 6/10. 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.
Sat 8/24:08 pmBDL - RFD
2 stops17h 23mMultiple Airlines
Thu 8/79:21 amRFD - BDL
2 stops36h 36mMultiple Airlines
Deal found 6/10$306
This Frontier deal was found by Cheapflights users on 6/12. 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 6/2112:38 pmBDL - ORD
1 stop12h 36mFrontier
Mon 6/239:43 amORD - BDL
1 stop9h 05mFrontier
Deal found 6/12$360

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 June 12, 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

Tue 7/15

6:00 am-7:48 am

Nonstop2h 48m

Chicago O'Hare Intl

Wed 7/16

5:56 pm-11:59 pm

1 stop5h 03m

$227

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Wed 11/5

7:19 am-9:05 am

Nonstop2h 46m

Chicago O'Hare Intl

Mon 11/10

8:00 am-11:09 am

Nonstop2h 09m

$229

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sat 11/8

9:45 am-6:45 pm

2 stops10h 00m

Chicago Midway

Mon 11/10

11:55 am-2:55 pm

Nonstop2h 00m

$230

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Fri 7/11

4:08 pm-8:55 am

1 stop17h 47m

Chicago O'Hare Intl

Sun 7/13

11:11 am-9:20 am

1 stop21h 09m

$230

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Mon 7/7

10:58 am-5:21 pm

1 stop7h 23m

Chicago O'Hare Intl

Thu 7/10

11:11 am-9:20 am

1 stop21h 09m

$239

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sun 8/31

1:00 pm-6:37 pm

1 stop6h 37m

Chicago Midway

Wed 9/3

10:11 am-5:59 pm

1 stop6h 48m

$245

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Sun 8/31

8:00 am-2:19 pm

1 stop7h 19m

Chicago O'Hare Intl

Wed 9/3

9:45 am-4:18 pm

1 stop5h 33m

$245

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Thu 7/31

6:05 am-5:55 pm

1 stop12h 50m

Chicago O'Hare Intl

Sun 8/3

11:25 am-12:35 am

1 stop12h 10m

$263

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sat 8/16

12:27 pm-10:35 pm

1 stop11h 08m

Chicago Midway

Mon 8/18

8:35 am-7:53 pm

1 stop10h 18m

$267

HartfordChicago

BDL - RFD

BDLRFD

Hartford Bradley Intl

Sat 8/2

4:08 pm-8:31 am

2 stops17h 23m

Chicago Greater Rockford

Thu 8/7

9:21 am-10:57 pm

2 stops36h 36m

$306

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 25 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 June 9, 2025.

To ensure you get the cheapest price possible for a flight from Hartford to Chicago, you should look to book at least 7 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 June 12, 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 June 8, 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. Sunday at noon 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 June 12, 2025.

The most flights from BDL to CHI are scheduled on a Wednesday (26 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (11 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 June 12, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and United Airlines from Hartford to Chicago to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,946 reviews
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,790 reviews
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
JetBlue
7.3
Good
2,925 reviews
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 19 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, Southwest ($230), Spirit Airlines ($230), and American Airlines ($232) offers the cheapest pricing from Hartford to Chicago. Southwest is currently priced 36% 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 $103 on United Airlines. Other airlines that offer cheap prices include Spirit Airlines from $106 and Delta from $109 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 Japan Airlines (92%), ANA (91%) and United Airlines (83%).

  • What are the cheapest flights from Hartford to Chicago?

    While on average a flight from Hartford to Chicago is generally $772, our data shows the cheapest flight currently is $113. When looking at the most popular route, (Hartford Bradley Intl - Chicago O'Hare Intl), you can expect to pay $157 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 Hartford?

Book flights to Hartford if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$108Average$224FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$125Average$434FlexibilityNo cancel feeOn-time69%
Spirit AirlinesCheapest$144Average$263FlexibilityNo cancel feeOn-time65%
DeltaCheapest$176Average$346FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$202Average$352FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$232Average$379FlexibilityNo cancel feeOn-time63%

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