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$61+ 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 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — CHI
Jan 21 — Jan 281
Tue 1/21
Tue 1/28
1 adult, Economy
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The best prices from Hartford Bradley Intl to Chicago are usually found in September or August, booked 70 days in advance, depart on a Saturday 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 January 16, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$277
(Delta)

One-way from

$61
(Frontier)

Popular in

April

Cheapest in

September

Average price

$347
Provider with most accurate pricing for Hartford Bradley Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Hartford Bradley Intl-Chicago (CHI) flights.
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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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High demand for flights, 6% potential price rise
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Best time to find cheap flights, 1% potential price drop
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Average for round-trip flights in January 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 January 16, 2025.

This Delta deal was found by Cheapflights users on 1/14. 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.
Tue 2/1812:55 pmBDL - ORD
1 stop6h 30mDelta
Wed 2/196:45 amORD - BDL
1 stop4h 25mDelta
Deal found 1/14$277
This Mytrip deal was found by Cheapflights users on 1/16. 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.
Sun 2/26:00 pmBDL - ORD
2 stops21h 23mMultiple Airlines
Wed 2/53:56 pmORD - BDL
3 stops21h 10mMultiple Airlines
Deal found 1/16$278
This FlightHub deal was found by Cheapflights users on 1/15. 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 4/258:59 pmBDL - ORD
1 stop27h 39mFrontier
Sun 4/274:21 pmORD - BDL
1 stop17h 32mFrontier
Deal found 1/15$280
This Frontier deal was found by Cheapflights users on 1/16. 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.
Thu 3/1312:02 pmBDL - MDW
1 stop8h 33mFrontier
Mon 3/246:20 amMDW - BDL
1 stop6h 39mFrontier
Deal found 1/16$290
This United Airlines deal was found by Cheapflights users on 1/14. 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.
Fri 2/710:40 amBDL - ORD
2 stops22h 25mUnited Airlines
Sat 2/810:55 amORD - BDL
Nonstop2h 12mUnited Airlines
Deal found 1/14$294
This Sun Country Air deal was found by Cheapflights users on 1/16. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/3111:42 amBDL - ORD
1 stop8h 29mSun Country Air
Sun 8/38:10 pmORD - BDL
1 stop13h 37mSun Country Air
Deal found 1/16$295
This Mytrip deal was found by Cheapflights users on 1/15. 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.
Sun 3/911:36 amBDL - ORD
2 stops23h 08mSpirit Airlines
Wed 3/125:55 amORD - BDL
3 stops27h 46mSpirit Airlines
Deal found 1/15$300
This Southwest deal was found by Cheapflights users on 1/16. 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.
Mon 3/37:30 amBDL - MDW
Nonstop2h 45mSouthwest
Tue 3/412:25 pmMDW - BDL
Nonstop2h 00mSouthwest
Deal found 1/16$317
This American Airlines deal was found by Cheapflights users on 1/15. 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.
Thu 2/137:00 amBDL - ORD
Nonstop2h 51mAmerican Airlines
Mon 2/177:36 pmORD - BDL
Nonstop2h 00mAmerican Airlines
Deal found 1/15$317
This Southwest deal was found by Cheapflights users on 1/16. 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 2/135:50 amBDL - ORD
1 stop9h 10mSouthwest
Thu 2/204:00 pmORD - BDL
1 stop5h 45mSouthwest
Deal found 1/16$336
This Delta deal was found by Cheapflights users on 1/16. 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.
Wed 2/267:00 amBDL - MDW
1 stop7h 05mDelta
Wed 3/59:33 amMDW - BDL
1 stop5h 36mDelta
Deal found 1/16$337
This Mytrip deal was found by Cheapflights users on 1/16. 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.
Sun 2/27:00 amBDL - RFD
1 stop10h 10mMultiple Airlines
Thu 2/612:44 pmRFD - BDL
1 stop16h 28mMultiple Airlines
Deal found 1/16$403

Find flights from Hartford to Chicago within your budget

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 January 16, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Tue 2/18

12:55 pm-6:25 pm

1 stop6h 30m

Chicago O'Hare Intl

Wed 2/19

6:45 am-12:10 pm

1 stop4h 25m

$277

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Sun 2/2

6:00 pm-2:23 pm

2 stops21h 23m

Chicago O'Hare Intl

Wed 2/5

3:56 pm-2:06 pm

3 stops21h 10m

$278

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Fri 4/25

8:59 pm-11:38 pm

1 stop27h 39m

Chicago O'Hare Intl

Sun 4/27

4:21 pm-10:53 am

1 stop17h 32m

$280

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 3/13

12:02 pm-7:35 pm

1 stop8h 33m

Chicago Midway

Mon 3/24

6:20 am-1:59 pm

1 stop6h 39m

$290

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Fri 2/7

10:40 am-8:05 am

2 stops22h 25m

Chicago O'Hare Intl

Sat 2/8

10:55 am-2:07 pm

Nonstop2h 12m

$294

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Sun 3/9

11:36 am-9:44 am

2 stops23h 08m

Chicago O'Hare Intl

Wed 3/12

5:55 am-10:41 am

3 stops27h 46m

$300

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Mon 3/3

7:30 am-9:15 am

Nonstop2h 45m

Chicago Midway

Tue 3/4

12:25 pm-3:25 pm

Nonstop2h 00m

$317

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Thu 2/13

7:00 am-8:51 am

Nonstop2h 51m

Chicago O'Hare Intl

Mon 2/17

2:07 pm-5:20 pm

Nonstop2h 13m

$317

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Thu 2/13

5:50 am-2:00 pm

1 stop9h 10m

Chicago O'Hare Intl

Thu 2/20

4:00 pm-10:45 pm

1 stop5h 45m

$336

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Wed 2/26

7:00 am-1:05 pm

1 stop7h 05m

Chicago Midway

Thu 3/6

6:00 am-1:18 pm

1 stop6h 18m

$337

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/16

Showing 1-10 of 24 results
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Compare providers for flights from Hartford to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Hartford to Chicago in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy2 starsTrust Score*3 stars
FareScanPrice Accuracy3 starsTrust Score*1 star
MytripPrice Accuracy3 starsTrust Score*3 stars
KAYAKPrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Hartford-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Hartford-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Hartford-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Hartford-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Hartford-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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.

Travel insights for flights from Hartford to Chicago

Get recent, data-driven insights about flights from Hartford to Chicago including ideal travel times, pricing trends, and more.

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 January 10, 2025.

To ensure you get the cheapest price possible for a flight from Hartford to Chicago, you should look to book at least 70 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 $320). 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 January 16, 2025.

It’s typically best to fly out from Hartford to Chicago at noon. Doing so could potentially save you 27% on the flight price compared to flying in the afternoon, 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 December 16, 2024.

Travelers seeking maximum savings on their Hartford to Chicago flight should consider departing on Wednesday evenings when fares are most often at their lowest. Monday afternoons 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 January 16, 2025.

The most flights from BDL to CHI are scheduled on a Thursday (15 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (6 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 January 16, 2025.
Peruse reviews from past customers who have flown with Delta, United Airlines and Southwest 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
8.1
Very good
4,659 reviews

Entertainment

7.7

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,659 reviews
Southwest
8.1
Very good
4,659 reviews

Entertainment

7.7

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,511 reviews
Southwest
8.1
Very good
4,659 reviews

Entertainment

7.7

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,964 reviews
Southwest
8.1
Very good
4,659 reviews

Entertainment

7.7

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,659 reviews

Entertainment

7.7

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Sun Country Air
7.0
Good
384 reviews
Southwest
8.1
Very good
4,659 reviews

Entertainment

7.7

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 12 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, Delta ($277), Frontier ($280), and United Airlines ($294) offers the cheapest pricing from Hartford to Chicago. Delta is currently priced 24% 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 $61 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $74 and Delta from $139 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 (90%), Republic Airways (87%) and ANA (86%).

  • What are the cheapest flights from Hartford to Chicago?

    While on average a flight from Hartford to Chicago is generally $1,243, our data shows the cheapest flight currently is $164. When looking at the most popular route, (Hartford Bradley Intl - Chicago O'Hare Intl), you can expect to pay $149 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 $320). 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
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 January 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$108Average$225FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$117Average$225FlexibilityNo cancel feeOn-time65%
DeltaCheapest$175Average$296FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$197Average$340FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$218Average$401FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$232Average$364FlexibilityNo cancel feeOn-time63%
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