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$67+ Cheap flights from Connecticut 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 10/21. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — CHI
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Connecticut to Chicago

Keep the following information in mind while searching for Connecticut to Chicago flight deals. Data was last updated September 15, 2025.

Round-trip from

$132
(Kiwi.com)

One-way from

$67
(American Airlines)

Popular in

April

Cheapest in

August

Average price

$317

Good round-trip deal

$199 or less

Good one-way deal

$77 or less
From Connecticut to Chicago (CHI)
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One-way flight from Connecticut to Chicago (CHI)
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Highest demand for flights based on searches. 5% potential increase in price ($18 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Connecticut to Chicago (CHI).
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Price to beat on a one-way flight from Connecticut to Chicago (CHI).
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Find flight deals from Connecticut to Chicago

Cheapest flights from Connecticut to Chicago
Explore the most affordable flight options available from Connecticut to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Booking.com deal was found by Cheapflights users on 9/11. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/96:59 amJFK - ORD
1 stop25h 35mFrontier
Wed 10/156:40 amORD - JFK
Nonstop2h 23mFrontier
Deal found 9/11$132
This Cheapflightsfares deal was found by Cheapflights users on 9/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2912:59 pmLGA - ORD
Nonstop2h 46mSpirit Airlines
Mon 11/311:08 amORD - LGA
Nonstop1h 55mSpirit Airlines
Deal found 9/12$132
This JetBlue deal was found by Cheapflights users on 9/12. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/3010:30 amJFK - ORD
Nonstop2h 40mJetBlue
Sat 10/48:34 amORD - JFK
Nonstop2h 30mJetBlue
Deal found 9/12$133
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/112:59 pmLGA - ORD
Nonstop2h 46mMultiple Airlines
Sun 11/25:11 amORD - LGA
1 stop5h 18mMultiple Airlines
Deal found 9/14$133
This Southwest deal was found by Cheapflights users on 9/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/39:55 pmLGA - MDW
Nonstop2h 25mSouthwest
Tue 11/412:55 pmMDW - LGA
Nonstop2h 00mSouthwest
Deal found 9/11$133
This JetBlue deal was found by Cheapflights users on 9/12. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2110:30 amJFK - ORD
Nonstop2h 52mJetBlue
Wed 10/296:45 amORD - JFK
Nonstop2h 14mJetBlue
Deal found 9/12$134
This Kiwi.com deal was found by Cheapflights users on 9/12. 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.
Mon 9/2212:56 pmLGA - ORD
1 stop7h 48mMultiple Airlines
Wed 10/111:57 amORD - LGA
1 stop10h 28mMultiple Airlines
Deal found 9/12$134
This Southwest deal was found by Cheapflights users on 9/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/56:00 amLGA - MDW
Nonstop2h 30mSouthwest
Wed 11/510:00 amMDW - LGA
2 stops6h 05mSouthwest
Deal found 9/12$134
This Priceline deal was found by Cheapflights users on 9/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2511:00 amJFK - ORD
Nonstop2h 45mFrontier
Sat 10/255:45 pmORD - JFK
1 stop5h 48mFrontier
Deal found 9/13$135
This Kiwi.com deal was found by Cheapflights users on 9/12. 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.
Thu 9/2510:56 pmLGA - ORD
1 stop11h 41mMultiple Airlines
Sat 9/2711:57 amORD - LGA
1 stop8h 08mMultiple Airlines
Deal found 9/12$135
This Booking.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/176:20 amJFK - ORD
1 stop12h 37mFrontier
Mon 10/206:40 amORD - JFK
Nonstop2h 23mFrontier
Deal found 9/14$136
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 10/110:59 amLGA - ORD
1 stop7h 40mMultiple Airlines
Sun 10/58:49 pmORD - LGA
1 stop14h 12mMultiple Airlines
Deal found 9/12$136

Cheapflights Fare Finder

 
Customize your flight search to find flights from Connecticut 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 September 15, 2025.
Use the filters below to find and compare flights from Connecticut to Chicago that are best for you.

Fly from

Connecticut

Fly to

Chicago

Route

Depart

Return

Price

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 9/27

8:36 pm-10:11 pm

Nonstop2h 35m

Chicago O'Hare Intl

Sun 9/28

5:05 am-3:59 pm

1 stop9h 54m

$132

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Wed 12/10

8:00 pm-9:48 pm

Nonstop2h 48m

Chicago O'Hare Intl

Tue 12/16

7:00 am-10:13 am

Nonstop2h 13m

$133

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Tue 10/21

10:30 am-12:22 pm

Nonstop2h 52m

Chicago O'Hare Intl

Wed 10/29

6:45 am-9:59 am

Nonstop2h 14m

$134

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Tue 10/14

9:00 am-10:35 am

Nonstop2h 35m

Chicago Midway

Tue 10/21

6:10 am-9:15 am

Nonstop2h 05m

$137

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Tue 10/7

6:05 am-7:30 am

Nonstop2h 25m

Chicago Midway

Wed 10/8

7:20 pm-10:25 pm

Nonstop2h 05m

$137

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Thu 2/19

7:40 pm-9:33 pm

Nonstop2h 53m

Chicago O'Hare Intl

Wed 2/25

7:00 am-10:23 am

Nonstop2h 23m

$139

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 10/22

11:20 am-12:57 pm

Nonstop2h 37m

Chicago O'Hare Intl

Fri 10/24

6:30 pm-9:54 pm

Nonstop2h 24m

$141

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sun 10/19

9:30 pm-11:07 pm

Nonstop2h 37m

Chicago O'Hare Intl

Wed 10/22

5:00 pm-8:17 pm

Nonstop2h 17m

$141

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 10/1

10:59 am-10:48 pm

1 stop12h 49m

Chicago O'Hare Intl

Sun 10/5

6:58 pm-9:00 am

1 stop13h 02m

$142

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 12/5

9:55 pm-11:20 pm

Nonstop2h 25m

Chicago Midway

Wed 12/10

7:15 pm-10:20 pm

Nonstop2h 05m

$142

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 60 results
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Best time to book a flight from Connecticut to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Connecticut 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 Connecticut to Chicago

What is the cheapest month to book a flight from Connecticut to Chicago?

Currently, August is the cheapest month in which you can book a flight from Connecticut to Chicago (average of $245). Flying from Connecticut to Chicago in March is currently the most expensive (average of $321). 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 CT to CHI?

Find hourly flight availability from Connecticut 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 September 15, 2025.

When flying from Connecticut to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Connecticut to Chicago

Explore weekly flight availability from Connecticut 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 September 15, 2025.

The most flights from USCT to CHI are scheduled on a Monday (23 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (15 on average).

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

Related info for your journey

Find useful and relevant information for your journey from Connecticut to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Connecticut to Chicago?

    A quick flight from Connecticut to Chicago can take about 2h 35m. Spirit Airlines provides one of the quickest options available for as low as $132. Airlines will cover a distance of 731 mi. All flights are typically nonstop.

  • What are the cheapest airlines to fly from Connecticut to Chicago one-way?

    For one-way options, check prices for JetBlue. According to our data, you can fly for as low as $70. Users have also found prices from $70 and $78 on Southwest and United Airlines, respectively.

  • What are the most popular routes from Connecticut to Chicago?

    The most popular route from Connecticut to Chicago is New York John F Kennedy Intl - Chicago O'Hare Intl. You may also consider New York LaGuardia - Chicago O'Hare Intl or Newark - Chicago O'Hare Intl.

  • What are the most reliable airlines from Connecticut to Chicago?

    Before booking your flight to Chicago from Connecticut, check out the most reliable airlines to get you to your destination on time: Republic Airways (93%), ANA (89%), Qatar Airways( 86%).

  • What are the cheapest flights from Connecticut to Chicago?

    On average you can expect to pay $673 for a flight from Connecticut to Chicago. The cheapest flight overall is $113 while the most popular route, (New York John F Kennedy Intl - Chicago O'Hare Intl) is currently priced at $80.

  • Can I find deals for flights from Connecticut to Chicago that include hotel bookings?

    Yes. In addition to deals on Connecticut to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Connecticut to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Connecticut to Chicago.

  • Can I find deals for business class flights from Connecticut to Chicago?

    Yes. Cheapflights offers flight deals from Connecticut 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 Connecticut to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Connecticut to Chicago (average of $245). Flying from Connecticut to Chicago in March is currently the most expensive (average of $321). 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
Benton Harbor
Porter
Chesterton

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Alternative routes for Connecticut 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
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Top 4 airlines flying from Connecticut to Chicago

Discover the top 4 airlines that operate flights from Connecticut 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$108Average$195FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$177Average$381FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$186Average$358FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$230Average$417FlexibilityNo cancel feeOn-time69%

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