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$60+ 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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — CHI
Mar 5 — Mar 121
Thu 3/5
Thu 3/12
1 adult, Economy
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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”

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3. Compare prices and book

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Cheapflights Tip: The best prices from Hartford Bradley Intl to Chicago are usually found in October or September, 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 3, 2026.

This CheapOair deal was found by Cheapflights users on 2/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/58:31 pm
BDL
-
ORD
1 stop15h 04m
Frontier
Mon 2/911:51 am
ORD
-
BDL
1 stop22h 33m
Frontier
Deal found 2/1$253
This Frontier deal was found by Cheapflights users on 2/1. 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.
Sun 4/191:07 pm
BDL
-
ORD
1 stop10h 32m
Frontier
Mon 4/205:01 am
ORD
-
BDL
1 stop6h 14m
Frontier
Deal found 2/1$255
This JetBlue deal was found by Cheapflights users on 2/1. 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.
Sun 9/276:45 am
BDL
-
ORD
1 stop6h 35m
JetBlue
Fri 10/21:35 pm
ORD
-
BDL
1 stop7h 59m
JetBlue
Deal found 2/1$260
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 3/81:07 pm
BDL
-
MDW
1 stop7h 40m
Multiple Airlines
Mon 3/96:15 am
MDW
-
BDL
2 stops16h 01m
Multiple Airlines
Deal found 1/31$263
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 2/206:17 pm
BDL
-
MDW
1 stop21h 38m
Frontier
Sun 2/226:00 am
MDW
-
BDL
1 stop6h 32m
Frontier
Deal found 2/1$266
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 4/208:08 pm
BDL
-
ORD
1 stop12h 51m
Multiple Airlines
Wed 4/223:49 pm
ORD
-
BDL
1 stop26h 28m
Multiple Airlines
Deal found 2/1$266
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 4/69:53 pm
BDL
-
ORD
1 stop23h 10m
Multiple Airlines
Wed 4/89:06 am
ORD
-
BDL
1 stop7h 33m
Multiple Airlines
Deal found 2/1$267
This Frontier deal was found by Cheapflights users on 2/1. 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.
Mon 5/41:07 pm
BDL
-
MDW
1 stop7h 24m
Frontier
Sun 5/109:14 am
MDW
-
BDL
1 stop9h 03m
Frontier
Deal found 2/1$270
This Frontier deal was found by Cheapflights users on 2/1. 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.
Mon 5/41:07 pm
BDL
-
ORD
1 stop10h 32m
Frontier
Sun 5/1010:25 am
ORD
-
BDL
1 stop7h 52m
Frontier
Deal found 2/1$270
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 3/228:08 pm
BDL
-
ORD
1 stop20h 17m
Multiple Airlines
Tue 3/249:28 am
ORD
-
BDL
2 stops7h 43m
Multiple Airlines
Deal found 1/31$274
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 5/88:08 pm
BDL
-
ORD
1 stop20h 17m
Multiple Airlines
Mon 9/74:10 pm
ORD
-
BDL
1 stop21h 35m
Multiple Airlines
Deal found 2/1$275
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 4/268:08 pm
BDL
-
MDW
1 stop12h 56m
Frontier
Thu 4/306:00 am
MDW
-
BDL
2 stops12h 17m
Frontier
Deal found 2/1$276

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 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$255
(Frontier)

One-way from

$60
(Kiwi.com)

Popular in

May

Cheapest in

October

Average price

$361
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 ($39 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 3, 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

Tue 2/24

5:30 am-7:05 am

Nonstop2h 35m

Chicago Midway

Wed 2/25

1:25 pm-4:20 pm

Nonstop1h 55m

$289

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Tue 2/24

4:43 pm-6:35 pm

Nonstop2h 52m

Chicago O'Hare Intl

Wed 2/25

5:55 pm-9:06 pm

Nonstop2h 11m

$289

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Tue 2/24

10:05 am-11:57 am

Nonstop2h 52m

Chicago O'Hare Intl

Tue 2/24

5:55 pm-9:06 pm

Nonstop2h 11m

$289

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Wed 2/25

10:05 am-11:57 am

Nonstop2h 52m

Chicago O'Hare Intl

Wed 2/25

5:55 pm-9:06 pm

Nonstop2h 11m

$289

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Sat 6/6

6:40 am-2:20 pm

1 stop8h 40m

Chicago O'Hare Intl

Tue 6/9

3:15 pm-11:54 pm

1 stop7h 39m

$290

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Wed 7/29

5:04 pm-6:51 pm

Nonstop2h 47m

Chicago O'Hare Intl

Sat 8/1

6:30 pm-9:52 pm

Nonstop2h 22m

$300

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sat 2/28

5:00 am-6:35 am

Nonstop2h 35m

Chicago Midway

Sat 2/28

2:10 pm-10:45 pm

2 stops7h 35m

$304

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 2/24

7:00 am-11:59 am

1 stop5h 59m

Chicago Midway

Wed 2/25

6:20 pm-11:39 pm

1 stop4h 19m

$309

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Sat 2/28

6:00 am-9:34 am

1 stop4h 34m

Chicago O'Hare Intl

Sat 2/28

6:20 pm-11:59 pm

1 stop4h 39m

$309

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Mon 7/13

11:04 am-5:29 pm

1 stop7h 25m

Chicago O'Hare Intl

Wed 7/15

6:39 pm-12:41 pm

1 stop17h 02m

$315

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

Showing 1-10 of 56 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 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 January 30, 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 $286). 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 3, 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 January 31, 2026.

Travelers seeking maximum savings on their Hartford to Chicago flight should consider departing on Saturday afternoons 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 3, 2026.

The most flights from BDL to CHI are scheduled on a Monday (17 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (11 on average).

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 3, 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
4,272 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Overall

8.0

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
4,272 reviews
Southwest
8.0
Very good
4,272 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Overall

8.0

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
9,236 reviews
Southwest
8.0
Very good
4,272 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Overall

8.0

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
11,218 reviews
Southwest
8.0
Very good
4,272 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Overall

8.0

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
2,893 reviews
Southwest
8.0
Very good
4,272 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Overall

8.0

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
3,051 reviews
Southwest
8.0
Very good
4,272 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Overall

8.0

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 15 outbound flights to Chicago per day from 5 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 JetBlue fly from Hartford to Chicago in about 2h 35m. The time it takes to get you to your destination can typically vary by up to 6h 05m. 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 ($94), American Airlines ($176), and Delta ($176) offers the cheapest pricing from Hartford to Chicago. Frontier is currently priced 73% 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 $971, our data shows the cheapest flight currently is $125. When looking at the most popular route, (Hartford Bradley Intl - Chicago O'Hare Intl), you can expect to pay $169 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 $286). 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

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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 5 airlines flying from Hartford to Chicago

Discover the top 5 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 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$94Average$124FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$176Average$353FlexibilityNo cancel feeOn-time71%
DeltaCheapest$176Average$266FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$177Average$381FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$216Average$431FlexibilityNo cancel feeOn-time69%

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