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$104+ 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 11/27. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — CHI
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheapflights Tip: The best prices from Hartford Bradley Intl to Chicago are usually found in September or August, booked 66 days in advance, depart on a Wednesday or Thursday and return on a Saturday

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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$212
(Kiwi.com)

One-way from

$104
(Delta)

Popular in

December

Cheapest in

September

Average price

$319
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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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. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/162:06 pmBDL - MDW
2 stops19h 26mMultiple Airlines
Wed 11/191:56 pmMDW - BDL
1 stop18h 56mMultiple Airlines
Deal found 10/28$212
This United Airlines deal was found by Cheapflights users on 10/28. 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 12/116:10 amBDL - ORD
Nonstop2h 51mUnited Airlines
Sun 12/146:13 pmORD - BDL
Nonstop2h 18mUnited Airlines
Deal found 10/28$212
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/128:05 amBDL - MDW
1 stop26h 07mMultiple Airlines
Wed 11/191:56 pmMDW - BDL
1 stop18h 56mMultiple Airlines
Deal found 10/28$213
This Southwest deal was found by Cheapflights users on 10/28. 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.
Wed 12/175:15 amBDL - MDW
Nonstop2h 30mSouthwest
Thu 1/221:25 pmMDW - BDL
Nonstop1h 55mSouthwest
Deal found 10/28$215
This American Airlines deal was found by Cheapflights users on 10/28. 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 12/175:46 pmBDL - ORD
Nonstop3h 09mAmerican Airlines
Thu 1/225:35 pmORD - BDL
Nonstop2h 16mAmerican Airlines
Deal found 10/28$215
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/211:30 pmBDL - ORD
2 stops10h 36mMultiple Airlines
Mon 11/246:15 pmORD - BDL
1 stop24h 17mMultiple Airlines
Deal found 10/28$216
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/232:24 pmBDL - ORD
1 stop21h 11mMultiple Airlines
Thu 11/276:48 amORD - BDL
1 stop11h 44mMultiple Airlines
Deal found 10/29$217
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/198:05 amBDL - ORD
1 stop16h 01mMultiple Airlines
Thu 11/206:48 amORD - BDL
1 stop11h 44mMultiple Airlines
Deal found 10/28$218
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/173:07 pmBDL - ORD
1 stop8h 59mMultiple Airlines
Thu 11/276:48 amORD - BDL
1 stop11h 44mMultiple Airlines
Deal found 10/29$219
This Trip.com deal was found by Cheapflights users on 10/27. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/141:36 pmBDL - MDW
1 stop9h 34mFrontier
Sat 11/1511:36 amMDW - BDL
1 stop24h 05mFrontier
Deal found 10/27$220
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/511:59 amBDL - ORD
1 stop24h 55mMultiple Airlines
Mon 12/83:23 pmORD - BDL
2 stops26h 43mMultiple Airlines
Deal found 10/30$220
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/255:42 pmBDL - MDW
1 stop24h 15mMultiple Airlines
Tue 12/27:44 amMDW - BDL
2 stops30h 05mMultiple Airlines
Deal found 10/28$221

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 October 30, 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 - MDW

BDLMDW

Hartford Bradley Intl

Wed 12/17

5:15 am-6:45 am

Nonstop2h 30m

Chicago Midway

Thu 1/22

1:25 pm-4:20 pm

Nonstop1h 55m

$215

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Thu 12/11

6:10 am-8:01 am

Nonstop2h 51m

Chicago O'Hare Intl

Mon 1/12

6:25 pm-9:48 pm

Nonstop2h 23m

$227

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 12/16

12:10 pm-5:35 pm

2 stops6h 25m

Chicago Midway

Wed 1/21

6:50 am-5:15 pm

1 stop9h 25m

$243

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 3/3

11:50 am-4:25 pm

1 stop5h 35m

Chicago Midway

Wed 3/4

6:00 am-1:18 pm

1 stop6h 18m

$245

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Thu 11/13

6:10 am-8:02 am

Nonstop2h 52m

Chicago O'Hare Intl

Sun 11/16

6:20 pm-9:38 pm

Nonstop2h 18m

$247

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Mon 2/23

5:40 am-8:50 am

1 stop4h 10m

Chicago Midway

Thu 2/26

9:30 am-3:58 pm

1 stop5h 28m

$262

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Mon 12/8

5:10 pm-8:35 pm

1 stop4h 25m

Chicago O'Hare Intl

Sat 1/17

6:50 am-12:04 pm

1 stop4h 14m

$262

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Wed 12/24

2:00 pm-9:00 pm

1 stop8h 00m

Chicago Midway

Wed 12/31

6:15 pm-9:25 pm

Nonstop2h 10m

$267

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 1/20

5:30 am-7:05 am

Nonstop2h 35m

Chicago Midway

Thu 1/22

6:00 am-2:50 pm

1 stop7h 50m

$267

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Thu 11/13

7:00 am-12:19 pm

1 stop6h 19m

Chicago O'Hare Intl

Sun 11/16

6:45 am-12:12 pm

1 stop4h 27m

$267

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 50 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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Hartford-Chicago flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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.

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 October 24, 2025.

To ensure you get the cheapest price possible for a flight from Hartford to Chicago, you should look to book at least 66 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, February is the cheapest month in which you can book a flight from Hartford to Chicago (average of $130). Flying from Hartford to Chicago in March is currently the most expensive (average of $285). 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 October 30, 2025.

It’s typically best to fly out from Hartford to Chicago in the evening. Doing so could potentially save you 9% on the flight price compared to flying at noon, 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 October 26, 2025.

Travelers seeking maximum savings on their Hartford to Chicago flight should consider departing on Wednesday 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.

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 October 30, 2025.
Read reviews from past customers who have flown Southwest, United Airlines, and American 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
4,242 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,998 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,030 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
JetBlue
7.2
Good
2,906 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,123 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 10 outbound flights to Chicago per day from 4 airlines. Hartford Bradley Intl is conveniently located just 11.9 mi from Hartford’s city center.

  • How long is the flight from Hartford to Chicago?

    Airlines like Southwest, United Airlines, and Delta fly from Hartford to Chicago in about 2h 30m. The time it takes to get you to your destination can typically vary by up to 1h 55m. The distance between Hartford and Chicago is about 773 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    According to our current data, Frontier ($97), Southwest ($177), and American Airlines ($191) offers the cheapest pricing from Hartford to Chicago. Frontier is currently priced 72% 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 $104 on Southwest. Other airlines that offer cheap prices include Delta from $104 and United Airlines from $114 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 (93%), ANA (87%) and Qatar Airways (85%).

  • What are the cheapest flights from Hartford to Chicago?

    While on average a flight from Hartford to Chicago is generally $957, our data shows the cheapest flight currently is $115. 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, February is the cheapest month in which you can book a flight from Hartford to Chicago (average of $130). Flying from Hartford to Chicago in March is currently the most expensive (average of $285). 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
Porter
Benton Harbor

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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 4 airlines flying from Hartford to Chicago

Discover the top 4 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$97Average$182FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$177Average$382FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$191Average$357FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$225Average$434FlexibilityNo cancel feeOn-time69%

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