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$62+ 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 1/22. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — CHI
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
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 November 6, 2025.

Round-trip from

$95
(Frontier)

One-way from

$62
(Frontier)

Popular in

December

Cheapest in

September

Average price

$384

Good round-trip deal

$347 or less

Good one-way deal

$49 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. 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 November 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 November 6, 2025.

This Frontier deal was found by Cheapflights users on 11/6. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/224:07 pmJFK - ORD
Nonstop2h 52mFrontier
Sat 12/61:24 pmORD - JFK
1 stop10h 35mFrontier
Deal found 11/6$95
This Mytrip deal was found by Cheapflights users on 11/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/46:20 amLGA - ORD
1 stop12h 07mMultiple Airlines
Sat 12/64:38 pmORD - LGA
Nonstop2h 04mMultiple Airlines
Deal found 11/6$95
This Frontier deal was found by Cheapflights users on 11/4. 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.
Fri 12/121:00 pmJFK - ORD
Nonstop2h 57mFrontier
Wed 12/174:01 pmORD - JFK
1 stop7h 58mFrontier
Deal found 11/4$96
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:37 pmLGA - ORD
Nonstop2h 30mSpirit Airlines
Sat 1/246:19 pmORD - LGA
Nonstop2h 10mSpirit Airlines
Deal found 11/6$96
This Frontier deal was found by Cheapflights users on 11/4. 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.
Fri 11/1411:00 amJFK - ORD
Nonstop2h 45mFrontier
Tue 11/1812:37 pmORD - JFK
1 stop10h 56mFrontier
Deal found 11/4$97
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 11/2012:59 pmLGA - ORD
Nonstop2h 32mSpirit Airlines
Thu 12/184:38 pmORD - LGA
Nonstop2h 04mSpirit Airlines
Deal found 11/3$97
This Priceline deal was found by Cheapflights users on 11/4. 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.
Mon 11/1711:00 amJFK - ORD
Nonstop2h 45mFrontier
Tue 11/186:40 amORD - JFK
Nonstop2h 23mFrontier
Deal found 11/4$98
This Super.com deal was found by Cheapflights users on 11/5. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1412:59 pmLGA - ORD
Nonstop2h 32mSpirit Airlines
Fri 11/147:34 pmORD - LGA
Nonstop2h 08mSpirit Airlines
Deal found 11/5$98
This Frontier deal was found by Cheapflights users on 11/5. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/31:00 pmJFK - ORD
Nonstop2h 57mFrontier
Sat 12/68:36 amORD - JFK
Nonstop2h 24mFrontier
Deal found 11/5$99
This Mytrip deal was found by Cheapflights users on 11/5. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/134:59 pmLGA - ORD
Nonstop2h 35mMultiple Airlines
Wed 12/108:00 amORD - LGA
1 stop7h 29mMultiple Airlines
Deal found 11/5$99
This Frontier deal was found by Cheapflights users on 11/4. 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.
Wed 12/101:00 pmJFK - ORD
Nonstop2h 57mFrontier
Mon 12/158:36 amORD - JFK
Nonstop2h 24mFrontier
Deal found 11/4$100
This Cheapflightsfares deal was found by Cheapflights users on 11/3. 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.
Sat 12/68:41 pmLGA - ORD
Nonstop2h 30mSpirit Airlines
Fri 12/124:38 pmORD - LGA
Nonstop2h 04mSpirit Airlines
Deal found 11/3$100

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 November 6, 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

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sat 12/6

8:01 am-9:56 am

Nonstop2h 55m

Chicago O'Hare Intl

Mon 12/8

1:23 pm-4:47 pm

Nonstop2h 24m

$137

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Wed 12/10

8:00 pm-9:52 pm

Nonstop2h 52m

Chicago O'Hare Intl

Tue 12/16

7:00 am-10:17 am

Nonstop2h 17m

$137

NewarkChicago

EWR - ORD

EWRORD

Newark

Sat 12/6

9:00 am-10:44 am

Nonstop2h 44m

Chicago O'Hare Intl

Tue 12/16

4:25 pm-7:48 pm

Nonstop2h 23m

$137

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 12/4

9:55 pm-11:20 pm

Nonstop2h 25m

Chicago Midway

Thu 12/11

7:15 pm-10:20 pm

Nonstop2h 05m

$137

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Wed 11/19

10:50 am-12:39 pm

Nonstop2h 49m

Chicago O'Hare Intl

Wed 11/19

6:33 pm-10:05 pm

Nonstop2h 32m

$137

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sat 12/13

8:00 pm-9:52 pm

Nonstop2h 52m

Chicago O'Hare Intl

Tue 12/16

7:00 am-10:17 am

Nonstop2h 17m

$137

NewarkChicago

EWR - ORD

EWRORD

Newark

Sat 12/6

2:25 pm-4:04 pm

Nonstop2h 39m

Chicago O'Hare Intl

Mon 12/8

9:15 am-12:28 pm

Nonstop2h 13m

$137

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Thu 12/11

8:01 am-9:56 am

Nonstop2h 55m

Chicago O'Hare Intl

Tue 12/16

10:36 am-1:59 pm

Nonstop2h 23m

$137

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 12/25

7:15 pm-9:03 pm

Nonstop2h 48m

Chicago O'Hare Intl

Wed 12/31

6:00 pm-9:14 pm

Nonstop2h 14m

$137

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Tue 12/16

8:01 am-9:56 am

Nonstop2h 55m

Chicago O'Hare Intl

Tue 12/16

6:30 pm-10:04 pm

Nonstop2h 34m

$137

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

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, September is the cheapest month in which you can book a flight from Connecticut to Chicago (average of $115). Flying from Connecticut to Chicago in May is currently the most expensive (average of $273). 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 November 6, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 15% on flights from Connecticut to Chicago by exploring options for tickets in the evening.

What is the cheapest day to fly from Connecticut to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Connecticut to Chicago. Price data was last updated on November 2, 2025.

Travelers seeking maximum savings on their Connecticut to Chicago flight should consider departing on Sunday afternoons when fares are most often at their lowest. Tuesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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 November 6, 2025.

The most flights from USCT to CHI are scheduled on a Monday (22 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (19 on average).

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 25m. Delta provides one of the quickest options available for as low as $137. Airlines will cover a distance of 722 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 Frontier. According to our data, you can fly for as low as $65. Users have also found prices from $69 and $69 on Delta and JetBlue, 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: ANA (89%), Qatar Airways (89%), Republic Airways( 86%).

  • What are the cheapest flights from Connecticut to Chicago?

    On average you can expect to pay $879 for a flight from Connecticut to Chicago. The cheapest flight overall is $115 while the most popular route, (New York John F Kennedy Intl - Chicago O'Hare Intl) is currently priced at $91.

  • 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, September is the cheapest month in which you can book a flight from Connecticut to Chicago (average of $115). Flying from Connecticut to Chicago in May is currently the most expensive (average of $273). 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
Hammond
Porter
Benton Harbor
Merrillville

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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.
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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 November 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$97Average$182FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$177Average$383FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$185Average$357FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$224Average$434FlexibilityNo cancel feeOn-time69%

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