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$146+ 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 6/15. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — CHI
Jun 9 — Jun 161
Tue 6/9
Tue 6/16
1 adult, Economy
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Cheapflights Tip: The best prices from Hartford Bradley Intl to Chicago are usually found in January or September, booked 85 days in advance, depart on a Wednesday or Saturday and return on a Thursday

Cheap 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 May 10, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/9. 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 8/2612:33 pm
BDL
-
ORD
1 stop11h 41m
Multiple Airlines
Sat 8/297:55 am
ORD
-
BDL
2 stops13h 17m
Multiple Airlines
Deal found 5/9$348
This JetBlue deal was found by Cheapflights users on 5/6. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:15 am
BDL
-
ORD
1 stop8h 15m
JetBlue
Mon 6/16:15 am
ORD
-
BDL
1 stop16h 40m
JetBlue
Deal found 5/6$349
This JetBlue deal was found by Cheapflights users on 5/7. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/217:25 am
BDL
-
ORD
1 stop8h 20m
JetBlue
Sun 5/243:27 pm
ORD
-
BDL
1 stop7h 28m
JetBlue
Deal found 5/7$350
This Kiwi.com deal was found by Cheapflights users on 5/9. 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 8/116:05 pm
BDL
-
ORD
1 stop12h 23m
Multiple Airlines
Wed 8/197:55 am
ORD
-
BDL
2 stops13h 17m
Multiple Airlines
Deal found 5/9$351
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 5/295:40 pm
BDL
-
RFD
1 stop16h 41m
Multiple Airlines
Mon 6/18:35 am
RFD
-
BDL
2 stops31h 35m
Multiple Airlines
Deal found 5/5$352
This KAYAK deal was found by Cheapflights users on 5/8. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/237:10 am
BDL
-
ORD
Nonstop2h 50m
American Airlines
Thu 6/257:26 pm
ORD
-
BDL
Nonstop2h 20m
American Airlines
Deal found 5/8$352
This Southwest deal was found by Cheapflights users on 5/7. 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 6/212:25 pm
BDL
-
MDW
Nonstop2h 25m
Southwest
Wed 6/177:50 am
MDW
-
BDL
Nonstop2h 10m
Southwest
Deal found 5/7$353
This United Airlines deal was found by Cheapflights users on 5/7. 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 6/26:09 am
BDL
-
ORD
Nonstop2h 45m
United Airlines
Wed 6/176:25 pm
ORD
-
BDL
Nonstop2h 23m
United Airlines
Deal found 5/7$353
This Southwest deal was found by Cheapflights users on 5/7. 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 6/17:20 pm
BDL
-
MDW
Nonstop2h 25m
Southwest
Tue 6/212:55 pm
MDW
-
BDL
Nonstop2h 05m
Southwest
Deal found 5/7$354
This JetBlue deal was found by Cheapflights users on 5/7. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/87:15 am
BDL
-
ORD
1 stop8h 15m
JetBlue
Wed 6/103:39 pm
ORD
-
BDL
1 stop7h 13m
JetBlue
Deal found 5/7$354
This Southwest deal was found by Cheapflights users on 5/7. 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 5/2811:40 am
BDL
-
MDW
Nonstop2h 25m
Southwest
Mon 6/17:40 am
MDW
-
BDL
Nonstop2h 00m
Southwest
Deal found 5/7$355
This United Airlines deal was found by Cheapflights users on 5/6. 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 6/48:47 am
BDL
-
ORD
Nonstop2h 53m
United Airlines
Mon 6/87:15 am
ORD
-
BDL
Nonstop2h 21m
United Airlines
Deal found 5/6$355

Find 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 May 10, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$348
(Kiwi.com)

One-way from

$146
(Kiwi.com)

Popular in

May

Cheapest in

January

Average price

$427
Provider with most accurate pricing for Hartford Bradley Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Hartford Bradley Intl-Chicago (CHI) flights.
Search Deals
From Hartford Bradley Intl to Chicago (CHI)
Search Deals
One-way flight from Hartford Bradley Intl to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($54 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals

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 May 10, 2026.
Use the filters below to find and compare flights from Hartford to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

HartfordChicago

BDL - RFD

BDLRFD

Hartford Bradley Intl

Fri 7/10

12:24 pm-9:15 am

1 stop21h 51m

Chicago Greater Rockford

Mon 7/13

7:50 pm-12:41 am

1 stop27h 51m

$347
Quickest round-trip

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Mon 6/1

7:20 pm-8:45 pm

Nonstop2h 25m

Chicago Midway

Tue 6/2

12:55 pm-4:00 pm

Nonstop2h 05m

$354

HartfordChicago

BDL - RFD

BDLRFD

Hartford Bradley Intl

Fri 6/12

12:38 pm-9:17 am

1 stop21h 39m

Chicago Greater Rockford

Mon 6/15

7:53 pm-12:41 am

1 stop27h 48m

$362

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 5/26

11:20 am-4:15 pm

1 stop5h 55m

Chicago Midway

Thu 5/28

7:00 pm-10:05 pm

Nonstop2h 05m

$364

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Thu 6/4

6:00 am-11:53 am

1 stop6h 53m

Chicago O'Hare Intl

Mon 6/8

6:26 pm-9:49 pm

Nonstop2h 23m

$365

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Wed 9/30

12:45 pm-2:05 pm

Nonstop2h 20m

Chicago Midway

Sat 10/3

6:30 am-2:55 pm

2 stops7h 25m

$370

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 6/4

7:10 pm-8:40 pm

Nonstop2h 30m

Chicago Midway

Mon 6/8

2:45 pm-12:15 am

2 stops8h 30m

$370

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 6/2

5:30 am-8:43 am

1 stop4h 13m

Chicago Midway

Wed 6/3

6:23 am-1:00 pm

1 stop5h 37m

$373

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sat 5/30

4:55 pm-8:40 pm

1 stop4h 45m

Chicago Midway

Wed 6/3

9:50 am-7:00 pm

2 stops8h 10m

$379

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 8/4

3:05 pm-10:20 pm

2 stops8h 15m

Chicago Midway

Tue 8/18

7:40 am-5:10 pm

2 stops8h 30m

$383

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/5

Showing 1-10 of 60 resultsSorted by cheapest first
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6

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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 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.

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?

To ensure you get the cheapest price possible for a flight from Hartford to Chicago, you should look to book at least 83 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, April is the cheapest month in which you can book a flight from Hartford to Chicago (average of $86). Flying from Hartford to Chicago in March is currently the most expensive (average of $252). 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 May 10, 2026.

It’s typically best to fly out from Hartford to Chicago in the afternoon. Doing so could potentially save you 18% 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 May 9, 2026.

Travelers seeking maximum savings on their Hartford to Chicago flight should consider departing on Saturday evenings 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 May 10, 2026.

The most flights from BDL to CHI are scheduled on a Friday (28 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (18 on average).

How much does it cost to fly round-trip from Hartford to Chicago?

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 May 10, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andJetBlue from Hartford to Chicago. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,301 reviews

Crew

8.6

Food

7.0

Overall

7.9

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
7.9
Good
4,301 reviews
Southwest
7.9
Good
4,301 reviews

Crew

8.6

Food

7.0

Overall

7.9

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,694 reviews
Southwest
7.9
Good
4,301 reviews

Crew

8.6

Food

7.0

Overall

7.9

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
JetBlue
7.2
Good
2,976 reviews
Southwest
7.9
Good
4,301 reviews

Crew

8.6

Food

7.0

Overall

7.9

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,668 reviews
Southwest
7.9
Good
4,301 reviews

Crew

8.6

Food

7.0

Overall

7.9

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.6
Fair
2,955 reviews
Southwest
7.9
Good
4,301 reviews

Crew

8.6

Food

7.0

Overall

7.9

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 21 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 25m. The time it takes to get you to your destination can typically vary by up to 4h 28m. 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, American Airlines ($158), Delta ($176), and Southwest ($177) offers the cheapest pricing from Hartford to Chicago. American Airlines is currently priced 55% 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 $68 on Southwest. Other airlines that offer cheap prices include American Airlines from $78 and Frontier from $99 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 Copa Airlines (100%), ANA (86%) and SkyWest Airlines (85%).

  • What are the cheapest flights from Hartford to Chicago?

    While on average a flight from Hartford to Chicago is generally $771, our data shows the cheapest flight currently is $166. When looking at the most popular route, (Hartford Bradley Intl - Chicago O'Hare Intl), you can expect to pay $239 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, April is the cheapest month in which you can book a flight from Hartford to Chicago (average of $86). Flying from Hartford to Chicago in March is currently the most expensive (average of $252). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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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 May 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$158Average$369FlexibilityNo cancel feeOn-time71%
DeltaCheapest$176Average$244FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$177Average$402FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$217Average$410FlexibilityNo cancel feeOn-time69%

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