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$51+ 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 3/10. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — CHI
Jan 8 — Jan 151
Thu 1/8
Thu 1/15
1 adult, Economy
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Cheap 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 December 9, 2025.

This Super.com deal was found by Cheapflights users on 12/7. 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.
Wed 12/318:37 pmLGA - ORD
Nonstop2h 30mSpirit Airlines
Mon 1/54:38 pmORD - LGA
Nonstop2h 04mSpirit Airlines
Deal found 12/7$84
This Frontier deal was found by Cheapflights users on 12/8. 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 12/171:00 pmJFK - ORD
Nonstop2h 57mFrontier
Wed 1/78:35 amORD - JFK
Nonstop2h 24mFrontier
Deal found 12/8$89
This Super.com deal was found by Cheapflights users on 12/8. 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.
Wed 12/171:00 pmJFK - ORD
Nonstop2h 57mFrontier
Mon 12/226:40 amORD - JFK
Nonstop2h 24mFrontier
Deal found 12/8$90
This Frontier deal was found by Cheapflights users on 12/7. 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 12/171:00 pmJFK - ORD
Nonstop2h 57mFrontier
Fri 12/196:40 amORD - JFK
Nonstop2h 24mFrontier
Deal found 12/7$91
This Frontier deal was found by Cheapflights users on 12/7. 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 12/151:00 pmJFK - ORD
Nonstop2h 57mFrontier
Fri 12/196:40 amORD - JFK
Nonstop2h 24mFrontier
Deal found 12/7$97
This Cheapflightsfares deal was found by Cheapflights users on 12/7. 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.
Tue 12/168:41 pmLGA - ORD
Nonstop2h 30mSpirit Airlines
Sat 1/37:20 amORD - LGA
Nonstop2h 01mSpirit Airlines
Deal found 12/7$99
This Cheapflightsfares deal was found by Cheapflights users on 12/8. 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 12/318:37 pmLGA - ORD
Nonstop2h 30mSpirit Airlines
Sat 1/37:20 amORD - LGA
Nonstop2h 01mSpirit Airlines
Deal found 12/8$100
This Cheapflightsfares deal was found by Cheapflights users on 12/8. 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.
Tue 12/168:41 pmLGA - ORD
Nonstop2h 30mSpirit Airlines
Wed 12/174:38 pmORD - LGA
Nonstop2h 04mSpirit Airlines
Deal found 12/8$101
This Super.com deal was found by Cheapflights users on 12/8. 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.
Sat 12/131:00 pmJFK - ORD
Nonstop2h 57mFrontier
Sat 1/1712:00 pmORD - JFK
Nonstop2h 24mFrontier
Deal found 12/8$102
This Kiwi.com deal was found by Cheapflights users on 12/7. 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 12/131:00 pmJFK - ORD
Nonstop2h 57mFrontier
Tue 1/135:57 pmORD - JFK
1 stop6h 16mFrontier
Deal found 12/7$106
This Frontier deal was found by Cheapflights users on 12/7. 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 12/131:00 pmJFK - ORD
Nonstop2h 57mFrontier
Wed 12/178:36 amORD - JFK
Nonstop2h 24mFrontier
Deal found 12/7$108
This Priceline deal was found by Cheapflights users on 12/7. 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 12/131:00 pmJFK - ORD
Nonstop2h 57mMultiple Airlines
Tue 1/139:40 amORD - JFK
Nonstop2h 16mMultiple Airlines
Deal found 12/7$109

Find flight deals from Connecticut to Chicago

Keep the following information in mind while searching for Connecticut to Chicago flight deals. Data was last updated December 9, 2025.

Round-trip from

$84
(CheapOair)

One-way from

$51
(CheapOair)

Popular in

May

Cheapest in

October

Average price

$367

Good round-trip deal

$98 or less

Good one-way deal

$50 or less
From Connecticut to Chicago (CHI)
Search Deals
One-way flight from Connecticut to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($42 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 December 2025
Search Deals
Price to beat on a round-trip flight from Connecticut to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Connecticut to Chicago (CHI).
Search Deals

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 December 9, 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

Thu 1/8

7:00 am-5:52 pm

1 stop11h 52m

Chicago O'Hare Intl

Thu 1/15

5:53 pm-8:59 pm

Nonstop2h 06m

$97

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 2/26

9:55 am-5:28 pm

1 stop8h 33m

Chicago O'Hare Intl

Sat 2/28

5:51 pm-8:59 pm

Nonstop2h 08m

$98

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Thu 1/8

5:25 pm-7:36 pm

Nonstop3h 11m

Chicago O'Hare Intl

Sat 1/10

8:35 am-11:59 am

Nonstop2h 24m

$99

NewarkChicago

EWR - ORD

EWRORD

Newark

Wed 1/7

12:01 pm-8:59 pm

1 stop9h 58m

Chicago O'Hare Intl

Fri 1/9

8:43 pm-11:42 am

1 stop13h 59m

$123

NewarkChicago

EWR - ORD

EWRORD

Newark

Fri 1/23

1:00 pm-7:38 pm

1 stop7h 38m

Chicago O'Hare Intl

Fri 1/30

12:44 pm-11:27 pm

1 stop9h 43m

$124

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 1/15

9:55 am-5:52 pm

1 stop8h 57m

Chicago O'Hare Intl

Sun 1/18

10:48 am-8:00 pm

1 stop8h 12m

$124

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Fri 1/16

4:24 pm-6:24 pm

Nonstop3h 00m

Chicago O'Hare Intl

Sun 1/18

7:45 am-2:58 pm

1 stop6h 13m

$126

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Mon 1/5

8:37 pm-10:07 pm

Nonstop2h 30m

Chicago O'Hare Intl

Thu 1/8

5:53 pm-8:59 pm

Nonstop2h 06m

$127

NewarkChicago

EWR - MDW

EWRMDW

Newark

Thu 1/15

10:30 pm-12:02 am

Nonstop2h 32m

Chicago Midway

Sun 1/18

8:19 pm-11:30 pm

2 stops26h 11m

$130

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Thu 1/15

7:50 am-9:49 am

Nonstop2h 59m

Chicago O'Hare Intl

Sun 1/18

6:25 pm-9:59 pm

Nonstop2h 34m

$139

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/6

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 $238). 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 December 9, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 16% 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 December 6, 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 December 9, 2025.

The most flights from USCT to CHI are scheduled on a Friday (21 on average). You will have fewer flight options on Saturday, 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 59m. Spirit Airlines provides one of the quickest options available for as low as $139. Airlines will cover a distance of 738 mi. This flight may include one or multiple stops.

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

    For one-way options, check prices for Avelo Airlines. According to our data, you can fly for as low as $40. Users have also found prices from $68 and $77 on Southwest and Frontier, 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 (87%), Qatar Airways (85%), Japan Airlines( 79%).

  • What are the cheapest flights from Connecticut to Chicago?

    On average you can expect to pay $923 for a flight from Connecticut to Chicago. The cheapest flight overall is $124 while the most popular route, (New York John F Kennedy Intl - Chicago O'Hare Intl) is currently priced at $69.

  • 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 $238). 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 Connecticut to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Connecticut to Chicago

Discover the top 6 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 December 9, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$97Average$232FlexibilityNo cancel feeOn-time62%
Avelo AirlinesCheapest$104Average$199FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$176Average$287FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$177Average$372FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$178Average$355FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$218Average$431FlexibilityNo cancel feeOn-time69%

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