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$77+ 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 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — CHI
ago. 25 — sep. 11
lun. 8/25
lun. 9/1
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 agosto 20, 2025.

Round-trip from

$138
(Priceline)

One-way from

$77
(Cheapflightsfares)

Popular in

April

Cheapest in

September

Average price

$316

Good round-trip deal

$199 or less

Good one-way deal

$101 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 ($15 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in August 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 agosto 20, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 8/20. 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.
mié. 10/811:00 amJFK - ORD
Nonstop2h 45mFrontier
dom. 10/125:05 amORD - JFK
1 stop5h 54mFrontier
Deal found 8/20$139
This Kiwi.com deal was found by Cheapflights users on 8/19. 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.
sáb. 9/133:12 pmLGA - ORD
Nonstop2h 38mSpirit Airlines
mar. 9/167:09 pmORD - LGA
3 stops24h 20mSpirit Airlines
Deal found 8/19$139
This Cheapflightsfares deal was found by Cheapflights users on 8/20. 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.
vie. 10/2411:00 amJFK - ORD
Nonstop2h 45mFrontier
lun. 10/275:05 amORD - JFK
1 stop5h 54mFrontier
Deal found 8/20$140
This Booking.com deal was found by Cheapflights users on 8/19. 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.
sáb. 9/131:29 pmLGA - ORD
1 stop9h 29mSpirit Airlines
lun. 9/155:05 amORD - LGA
1 stop9h 54mSpirit Airlines
Deal found 8/19$140
This Justfly.com deal was found by Cheapflights users on 8/18. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/3111:00 amJFK - ORD
Nonstop2h 45mFrontier
mar. 11/412:37 pmORD - JFK
1 stop10h 56mFrontier
Deal found 8/18$141
This FlightHub deal was found by Cheapflights users on 8/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/2712:59 pmLGA - ORD
Nonstop2h 44mSpirit Airlines
jue. 10/3011:08 amORD - LGA
Nonstop1h 55mSpirit Airlines
Deal found 8/19$141
This Frontier deal was found by Cheapflights users on 8/19. 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.
dom. 10/261:01 pmJFK - ORD
1 stop12h 10mFrontier
dom. 11/25:40 amORD - JFK
Nonstop2h 23mFrontier
Deal found 8/19$142
This American Airlines deal was found by Cheapflights users on 8/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/25:45 amLGA - ORD
Nonstop2h 38mAmerican Airlines
mar. 9/3011:16 amORD - LGA
Nonstop2h 14mAmerican Airlines
Deal found 8/19$142
This Southwest deal was found by Cheapflights users on 8/18. 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.
mar. 9/29:35 pmLGA - MDW
Nonstop2h 20mSouthwest
mar. 9/95:55 pmMDW - LGA
Nonstop2h 15mSouthwest
Deal found 8/18$142
This FlightHub deal was found by Cheapflights users on 8/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/811:00 amJFK - ORD
Nonstop2h 45mFrontier
lun. 10/136:37 pmORD - JFK
1 stop14h 47mFrontier
Deal found 8/20$143
This Flightnetwork deal was found by Cheapflights users on 8/19. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/36:30 amLGA - ORD
1 stop10h 20mFrontier
vie. 10/105:50 amORD - LGA
1 stop9h 18mFrontier
Deal found 8/19$143
This Mytrip deal was found by Cheapflights users on 8/18. 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.
jue. 9/186:30 amLGA - MDW
1 stop10h 28mFrontier
vie. 9/195:15 pmMDW - LGA
1 stop5h 42mFrontier
Deal found 8/18$143

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 agosto 20, 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

sáb. 9/13

7:30 am-9:02 am

Nonstop2h 32m

Chicago O'Hare Intl

lun. 9/15

8:20 pm-11:38 pm

Nonstop2h 18m

$138

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

jue. 9/4

10:30 am-12:10 pm

Nonstop2h 40m

Chicago O'Hare Intl

mar. 9/16

6:45 am-9:59 am

Nonstop2h 14m

$142

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

jue. 11/6

1:24 pm-2:56 pm

Nonstop2h 32m

Chicago O'Hare Intl

mar. 11/11

8:41 am-7:11 pm

1 stop9h 30m

$142

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

mar. 9/2

5:45 am-7:23 am

Nonstop2h 38m

Chicago O'Hare Intl

mar. 9/9

1:02 pm-4:14 pm

Nonstop2h 12m

$142

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

sáb. 9/20

6:25 am-8:02 am

Nonstop2h 37m

Chicago O'Hare Intl

sáb. 9/20

5:00 pm-8:17 pm

Nonstop2h 17m

$142

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

mié. 10/1

3:13 pm-4:51 pm

Nonstop2h 38m

Chicago O'Hare Intl

jue. 10/9

6:00 am-4:29 pm

1 stop9h 29m

$142

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

sáb. 11/1

11:59 am-6:24 pm

1 stop7h 25m

Chicago O'Hare Intl

lun. 11/3

4:03 pm-7:00 pm

Nonstop1h 57m

$142

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

sáb. 10/4

7:28 am-9:05 am

Nonstop2h 37m

Chicago O'Hare Intl

sáb. 10/4

5:00 pm-8:17 pm

Nonstop2h 17m

$142

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

sáb. 10/18

6:35 am-11:35 am

1 stop6h 00m

Chicago O'Hare Intl

mar. 10/21

3:12 pm-10:21 pm

1 stop6h 09m

$143

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

mié. 9/24

6:30 am-5:39 pm

1 stop12h 09m

Chicago O'Hare Intl

mié. 10/1

11:45 am-11:57 pm

1 stop11h 12m

$143

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/19

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 agosto 20, 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 agosto 20, 2025.

The most flights from USCT to CHI are scheduled on a Monday (27 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (11 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 32m. Delta provides one of the quickest options available for as low as $138. 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 Frontier. According to our data, you can fly for as low as $77. Users have also found prices from $79 and $79 on JetBlue and Delta, 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 Newark - Chicago O'Hare Intl or New York LaGuardia - 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 (90%), ANA (89%), Envoy Air( 83%).

  • What are the cheapest flights from Connecticut to Chicago?

    On average you can expect to pay $730 for a flight from Connecticut to Chicago. The cheapest flight overall is $99 while the most popular route, (New York John F Kennedy Intl - Chicago O'Hare Intl) is currently priced at $86.

  • 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.
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Top 5 airlines flying from Connecticut to Chicago

Discover the top 5 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 agosto 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$77Average$167FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$115Average$192FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$177Average$369FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$185Average$357FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$234Average$416FlexibilityNo cancel feeOn-time69%

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