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$68+ 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 1/3. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — CHI
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
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 October 14, 2025.

Round-trip from

$118
(Priceline)

One-way from

$68
(Priceline)

Popular in

December

Cheapest in

September

Average price

$319

Good round-trip deal

$113 or less

Good one-way deal

$88 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. 4% potential increase in price ($16 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 October 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 October 14, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1911:00 amJFK - ORD
Nonstop2h 45mFrontier
Fri 11/2111:48 amORD - JFK
Nonstop2h 20mFrontier
Deal found 10/13$118
This Cheapflightsfares deal was found by Cheapflights users on 10/13. 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 Cheapflightsfares 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
Sun 11/167:34 pmORD - LGA
Nonstop2h 08mSpirit Airlines
Deal found 10/13$118
This Gotogate deal was found by Cheapflights users on 10/13. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/296:29 amLGA - MDW
1 stop7h 12mFrontier
Thu 10/3012:30 pmMDW - LGA
1 stop8h 30mFrontier
Deal found 10/13$118
This Mytrip deal was found by Cheapflights users on 10/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/111:00 amJFK - ORD
Nonstop2h 45mFrontier
Mon 11/36:00 amORD - JFK
1 stop8h 00mFrontier
Deal found 10/14$119
This Mytrip deal was found by Cheapflights users on 10/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/36:00 pmLGA - ORD
1 stop16h 47mSpirit Airlines
Sat 11/83:26 pmORD - LGA
1 stop6h 55mSpirit Airlines
Deal found 10/11$119
This Trip.com deal was found by Cheapflights users on 10/13. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/286:29 amLGA - MDW
1 stop6h 09mFrontier
Tue 11/41:56 pmMDW - LGA
1 stop8h 31mFrontier
Deal found 10/13$119
This Frontier deal was found by Cheapflights users on 10/12. 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.
Mon 10/2711:00 amJFK - ORD
Nonstop2h 45mFrontier
Tue 10/2812:37 pmORD - JFK
1 stop10h 56mFrontier
Deal found 10/12$120
This Booking.com deal was found by Cheapflights users on 10/13. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/15:59 amJFK - MDW
1 stop16h 23mFrontier
Mon 11/39:32 amMDW - JFK
1 stop23h 57mFrontier
Deal found 10/13$120
This Kiwi.com deal was found by Cheapflights users on 10/12. 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.
Sat 10/2510:55 pmLGA - ORD
1 stop11h 41mMultiple Airlines
Tue 10/284:03 pmORD - LGA
Nonstop1h 57mMultiple Airlines
Deal found 10/12$120
This Kiwi.com deal was found by Cheapflights users on 10/14. 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.
Tue 10/286:29 amLGA - MDW
1 stop6h 09mFrontier
Tue 10/281:56 pmMDW - LGA
1 stop7h 25mFrontier
Deal found 10/14$120
This Frontier deal was found by Cheapflights users on 10/12. 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 10/231:01 pmJFK - ORD
1 stop11h 38mFrontier
Tue 10/286:40 amORD - JFK
Nonstop2h 23mFrontier
Deal found 10/12$121
This Priceline deal was found by Cheapflights users on 10/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/126:00 pmLGA - ORD
1 stop7h 27mSpirit Airlines
Thu 11/1310:52 amORD - LGA
1 stop11h 29mSpirit Airlines
Deal found 10/14$121

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 October 14, 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

Fri 11/14

4:59 pm-6:34 pm

Nonstop2h 35m

Chicago O'Hare Intl

Sun 11/16

7:34 pm-10:42 pm

Nonstop2h 08m

$119

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 11/1

10:15 am-11:57 am

Nonstop2h 42m

Chicago O'Hare Intl

Sat 11/1

8:00 pm-11:16 pm

Nonstop2h 16m

$137

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 11/13

7:15 am-8:45 am

Nonstop2h 30m

Chicago Midway

Wed 11/19

6:00 am-9:00 am

Nonstop2h 00m

$137

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 11/5

7:15 am-8:57 am

Nonstop2h 42m

Chicago O'Hare Intl

Wed 11/5

3:00 pm-6:07 pm

Nonstop2h 07m

$137

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 11/6

7:15 am-8:45 am

Nonstop2h 30m

Chicago Midway

Mon 11/10

8:25 pm-11:25 pm

Nonstop2h 00m

$137

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 11/11

6:15 am-7:57 am

Nonstop2h 42m

Chicago O'Hare Intl

Wed 11/12

7:00 am-10:07 am

Nonstop2h 07m

$137

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 11/12

9:10 am-10:40 am

Nonstop2h 30m

Chicago Midway

Wed 11/12

7:15 pm-10:20 pm

Nonstop2h 05m

$137

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Mon 11/10

7:22 pm-8:57 pm

Nonstop2h 35m

Chicago O'Hare Intl

Mon 11/17

6:30 pm-9:46 pm

Nonstop2h 16m

$137

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 11/1

8:15 am-9:40 am

Nonstop2h 25m

Chicago Midway

Mon 11/3

7:15 pm-10:20 pm

Nonstop2h 05m

$137

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Wed 11/19

8:00 pm-9:52 pm

Nonstop2h 52m

Chicago O'Hare Intl

Sun 11/23

6:00 am-9:17 am

Nonstop2h 17m

$138

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/14

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 October 14, 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 October 12, 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 October 14, 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 (17 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 30m. Spirit Airlines 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 JetBlue. According to our data, you can fly for as low as $69. Users have also found prices from $69 and $69 on United Airlines and Southwest, 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 (96%), ANA (90%), Qatar Airways( 90%).

  • What are the cheapest flights from Connecticut to Chicago?

    On average you can expect to pay $615 for a flight from Connecticut to Chicago. The cheapest flight overall is $117 while the most popular route, (New York John F Kennedy Intl - Chicago O'Hare Intl) is currently priced at $81.

  • 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
Merrillville
Lansing
Hammond
Porter
Benton Harbor
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
Dallas/Fort Worth to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Newark to O'Hare Intl flights
Seattle to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Baltimore to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
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John F Kennedy Intl to Midway flights
Ontario to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
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Orlando to O'Hare Intl flights
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Santa Ana to O'Hare Intl flights
Los Angeles to Midway flights
LaGuardia to Midway flights
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George Bush Intcntl to O'Hare Intl flights
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Boston to Midway flights
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LaGuardia to St. Louis flights
John F Kennedy Intl to St. Louis flights
Love Field to O'Hare Intl flights
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Miami to O'Hare Intl flights
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Seattle to Midway flights
San Francisco to Midway flights
Portland to O'Hare Intl flights
Newark to St. Louis flights
Denver to Midway flights
Cleveland to O'Hare Intl flights

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 October 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$97Average$157FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$177Average$380FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$195Average$359FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$230Average$435FlexibilityNo cancel feeOn-time69%

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