HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$70+ 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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — CHI
Mar 14 — Mar 211
Sat 3/14
Sat 3/21
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Hartford to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.
Cheapflights Tip: The best prices from Hartford Bradley Intl to Chicago are usually found in January or October, booked 66 days in advance, depart on a Wednesday or Thursday 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 February 12, 2026.

This Frontier deal was found by Cheapflights users on 2/12. 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.
Thu 3/121:12 pm
BDL
-
ORD
1 stop10h 27m
Frontier
Thu 3/195:01 am
ORD
-
BDL
1 stop6h 16m
Frontier
Deal found 2/12$290
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/238:08 pm
BDL
-
MDW
1 stop12h 56m
Frontier
Sun 4/266:00 am
MDW
-
BDL
2 stops21h 05m
Frontier
Deal found 2/11$292
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Fri 3/67:00 am
BDL
-
ORD
2 stops16h 39m
Multiple Airlines
Sun 3/85:01 am
ORD
-
BDL
1 stop6h 11m
Multiple Airlines
Deal found 2/9$292
This Southwest deal was found by Cheapflights users on 2/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/177:30 am
BDL
-
MDW
Nonstop2h 30m
Southwest
Wed 3/187:40 am
MDW
-
BDL
Nonstop2h 00m
Southwest
Deal found 2/9$293
This United Airlines deal was found by Cheapflights users on 2/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/95:00 pm
BDL
-
ORD
Nonstop2h 51m
United Airlines
Tue 5/127:35 am
ORD
-
BDL
Nonstop2h 19m
United Airlines
Deal found 2/9$293
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Thu 3/53:40 pm
BDL
-
ORD
1 stop7h 59m
Multiple Airlines
Fri 3/68:42 pm
ORD
-
BDL
2 stops15h 50m
Multiple Airlines
Deal found 2/9$294
This JetBlue deal was found by Cheapflights users on 2/9. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:45 am
BDL
-
ORD
1 stop6h 35m
JetBlue
Tue 10/131:35 pm
ORD
-
BDL
1 stop7h 59m
JetBlue
Deal found 2/9$295
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/298:00 am
BDL
-
ORD
1 stop31h 47m
Multiple Airlines
Mon 5/44:28 pm
ORD
-
BDL
2 stops22h 52m
Multiple Airlines
Deal found 2/11$296
This Kiwi.com deal was found by Cheapflights users on 2/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:29 pm
BDL
-
ORD
1 stop23h 27m
Multiple Airlines
Sat 4/113:00 pm
ORD
-
BDL
1 stop21h 58m
Multiple Airlines
Deal found 2/12$297
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/148:08 pm
BDL
-
MDW
1 stop12h 56m
Frontier
Mon 5/186:00 am
MDW
-
BDL
2 stops21h 05m
Frontier
Deal found 2/10$298
This Expedia deal was found by Cheapflights users on 2/11. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:00 am
BDL
-
ORD
1 stop6h 54m
Multiple Airlines
Mon 3/23:50 pm
ORD
-
BDL
1 stop16h 33m
Multiple Airlines
Deal found 2/11$298
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Mon 3/238:08 pm
BDL
-
MDW
1 stop20h 25m
Multiple Airlines
Mon 3/309:51 pm
MDW
-
BDL
1 stop17h 29m
Multiple Airlines
Deal found 2/9$300

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 February 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$290
(Frontier)

One-way from

$70
(Mytrip)

Popular in

May

Cheapest in

January

Average price

$374
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. 10% potential increase in price ($40 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 February 12, 2026.
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 4/8

7:50 am-9:15 am

Nonstop2h 25m

Chicago Midway

Wed 4/8

6:00 pm-9:05 pm

Nonstop2h 05m

$293

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Tue 3/10

10:28 am-2:34 pm

1 stop5h 06m

Chicago O'Hare Intl

Tue 3/17

6:05 pm-9:16 pm

Nonstop2h 11m

$303

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 3/17

5:55 am-9:50 am

1 stop4h 55m

Chicago Midway

Wed 3/18

7:40 am-10:40 am

Nonstop2h 00m

$303

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 4/21

3:15 pm-10:15 pm

1 stop8h 00m

Chicago Midway

Wed 4/22

12:55 pm-4:00 pm

Nonstop2h 05m

$303

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Wed 4/8

6:00 am-11:27 am

1 stop6h 27m

Chicago O'Hare Intl

Wed 4/8

6:01 pm-11:59 pm

1 stop4h 58m

$313

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 3/26

1:07 pm-7:47 pm

1 stop7h 40m

Chicago Midway

Mon 3/30

9:51 pm-6:11 pm

2 stops19h 20m

$318

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Mon 4/20

6:00 am-7:49 am

Nonstop2h 49m

Chicago O'Hare Intl

Wed 4/22

6:20 pm-9:37 pm

Nonstop2h 17m

$327

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Wed 3/11

6:10 pm-7:40 pm

Nonstop2h 30m

Chicago Midway

Sat 3/14

7:45 am-10:45 am

Nonstop2h 00m

$327

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Wed 4/8

6:00 am-7:49 am

Nonstop2h 49m

Chicago O'Hare Intl

Mon 4/13

11:00 am-2:15 pm

Nonstop2h 15m

$327

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 4/2

7:05 pm-8:35 pm

Nonstop2h 30m

Chicago Midway

Tue 4/7

7:40 am-10:40 am

Nonstop2h 00m

$327

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/12

Showing 1-10 of 51 results
1
2
3
...
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 February.
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?

Use this chart to determine the optimal time to book a round-trip flight from Hartford to Chicago. Price data was last updated on February 6, 2026.

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, August is the cheapest month in which you can book a flight from Hartford to Chicago (average of $166). Flying from Hartford to Chicago in March is currently the most expensive (average of $279). 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 February 12, 2026.

It’s typically best to fly out from Hartford to Chicago in the afternoon. Doing so could potentially save you 12% 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 February 7, 2026.

Travelers seeking maximum savings on their Hartford to Chicago flight should consider departing on Thursday 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 February 12, 2026.

The most flights from BDL to CHI are scheduled on a Thursday (20 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 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 February 12, 2026.
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
4,283 reviews

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,283 reviews
Southwest
8.0
Very good
4,283 reviews

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,283 reviews
Southwest
8.0
Very good
4,283 reviews

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,277 reviews
Southwest
8.0
Very good
4,283 reviews

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
JetBlue
7.2
Good
2,896 reviews
Southwest
8.0
Very good
4,283 reviews

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.7
Fair
3,052 reviews
Southwest
8.0
Very good
4,283 reviews

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 7 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 and United Airlines 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 2h 41m. 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 ($176), Delta ($176), and Southwest ($177) offers the cheapest pricing from Hartford to Chicago. American Airlines is currently priced 49% 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 Frontier from $77 and American Airlines from $78 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 Envoy Air (100%), SkyWest Airlines (89%) and ANA (76%).

  • What are the cheapest flights from Hartford to Chicago?

    While on average a flight from Hartford to Chicago is generally $988, our data shows the cheapest flight currently is $128. When looking at the most popular route, (Hartford Bradley Intl - Chicago O'Hare Intl), you can expect to pay $195 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 $166). Flying from Hartford to Chicago in March is currently the most expensive (average of $279). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Hartford to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to O'Hare Intl flights
Newark to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Newark to Midway flights
LaGuardia to Midway flights
Newark to St. Louis flights
LaGuardia to St. Louis flights
Hartford to O'Hare Intl flights
John F Kennedy Intl to St. Louis flights
Providence to O'Hare Intl flights
Hartford to Midway flights
Providence to Midway flights
Hartford to St. Louis flights
Providence to St. Louis flights
New Haven to O'Hare Intl flights
LaGuardia to Moline flights
Newark to Moline flights
LaGuardia to Peoria flights
John F Kennedy Intl to Evansville flights
LaGuardia to Bloomington flights
John F Kennedy Intl to Moline flights
Newark to Bloomington flights
LaGuardia to Evansville flights
Newark to Evansville flights
John F Kennedy Intl to Bloomington flights
Providence to Moline flights
Newark to Paducah flights
Newark to Champaign flights
LaGuardia to Paducah flights
LaGuardia to Champaign flights
Newark to Peoria flights
Hartford to Peoria flights
John F Kennedy Intl to Peoria flights
Hartford to Rockford flights
John F Kennedy Intl to Champaign flights
LaGuardia to Springfield flights
John F Kennedy Intl to Springfield flights
Newark to Marion flights
Hartford to Evansville flights
Newark to Springfield flights
New Haven to St. Louis flights
Hartford to Moline flights
LaGuardia to Marion flights
Providence to Evansville flights
Providence to Peoria flights
LaGuardia to Decatur flights
Hartford to Springfield flights
LaGuardia to Dubuque flights

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 February 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$176Average$356FlexibilityNo cancel feeOn-time71%
DeltaCheapest$176Average$242FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$177Average$381FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$216Average$431FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.