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$57+ 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 3/15. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — CHI
Feb 27 — Mar 61
Fri 2/27
Fri 3/6
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 January 28, 2026.

This Booking.com deal was found by Cheapflights users on 1/28. 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.
Tue 2/2412:02 pm
EWR
-
ORD
1 stop10h 11m
Spirit Airlines
Wed 2/258:16 pm
ORD
-
EWR
1 stop13h 41m
Spirit Airlines
Deal found 1/28$89
This Frontier deal was found by Cheapflights users on 1/27. 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 4/2311:30 am
EWR
-
MDW
Nonstop2h 30m
Frontier
Sun 4/267:30 am
MDW
-
EWR
Nonstop2h 08m
Frontier
Deal found 1/27$90
This Spirit deal was found by Cheapflights users on 1/25. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1211:05 pm
EWR
-
ORD
Nonstop2h 35m
Spirit Airlines
Mon 2/166:51 pm
ORD
-
EWR
Nonstop2h 09m
Spirit Airlines
Deal found 1/25$90
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Sun 2/84:04 pm
JFK
-
ORD
Nonstop3h 00m
Frontier
Mon 2/912:05 pm
ORD
-
JFK
Nonstop2h 24m
Frontier
Deal found 1/26$91
This Spirit deal was found by Cheapflights users on 1/27. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2612:02 pm
EWR
-
ORD
1 stop8h 09m
Spirit Airlines
Fri 2/276:51 pm
ORD
-
EWR
Nonstop2h 09m
Spirit Airlines
Deal found 1/27$91
This Priceline deal was found by Cheapflights users on 1/28. 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 2/184:59 pm
LGA
-
ORD
1 stop7h 48m
Spirit Airlines
Wed 2/255:58 pm
ORD
-
LGA
Nonstop2h 01m
Spirit Airlines
Deal found 1/28$91
This Expedia deal was found by Cheapflights users on 1/27. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2311:03 am
JFK
-
ORD
Nonstop3h 00m
Frontier
Wed 2/256:02 pm
ORD
-
JFK
1 stop6h 01m
Frontier
Deal found 1/27$92
This Super.com deal was found by Cheapflights users on 1/26. 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 2/117:30 am
LGA
-
ORD
Nonstop2h 42m
Spirit Airlines
Mon 2/165:58 pm
ORD
-
LGA
Nonstop2h 01m
Spirit Airlines
Deal found 1/26$92
This Frontier deal was found by Cheapflights users on 1/27. 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.
Tue 2/246:05 am
JFK
-
ORD
1 stop11h 47m
Frontier
Sun 3/16:40 am
ORD
-
JFK
Nonstop2h 24m
Frontier
Deal found 1/27$93
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/285:15 am
EWR
-
ORD
1 stop6h 36m
Multiple Airlines
Sun 3/16:51 pm
ORD
-
EWR
Nonstop2h 09m
Multiple Airlines
Deal found 1/27$93
This Cheapflightsfares deal was found by Cheapflights users on 1/26. 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 2/107:30 am
LGA
-
ORD
Nonstop2h 42m
Spirit Airlines
Sat 2/145:58 pm
ORD
-
LGA
Nonstop2h 01m
Spirit Airlines
Deal found 1/26$93
This Booking.com deal was found by Cheapflights users on 1/26. 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.
Mon 2/2311:03 am
JFK
-
ORD
Nonstop3h 00m
Frontier
Sat 2/284:42 pm
ORD
-
JFK
1 stop7h 26m
Frontier
Deal found 1/26$94

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 January 28, 2026.

Round-trip from

$89
(Booking.com)

One-way from

$57
(Trip.com)

Popular in

May

Cheapest in

October

Average price

$331

Good round-trip deal

$378 or less

Good one-way deal

$182 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 ($39 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 January 2026
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 January 28, 2026.
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

NewarkChicago

EWR - ORD

EWRORD

Newark

Thu 2/12

11:05 pm-12:40 am

Nonstop2h 35m

Chicago O'Hare Intl

Mon 2/16

6:51 pm-10:00 pm

Nonstop2h 09m

$90

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sun 3/8

7:40 am-9:22 am

Nonstop2h 42m

Chicago O'Hare Intl

Wed 3/11

12:44 pm-11:21 pm

1 stop9h 37m

$98

NewarkChicago

EWR - ORD

EWRORD

Newark

Tue 4/14

10:39 pm-12:07 am

Nonstop2h 28m

Chicago O'Hare Intl

Tue 4/21

4:47 pm-7:55 pm

Nonstop2h 08m

$100

NewarkChicago

EWR - ORD

EWRORD

Newark

Sat 2/7

9:05 pm-10:42 pm

Nonstop2h 37m

Chicago O'Hare Intl

Sun 2/8

4:38 pm-7:46 pm

Nonstop2h 08m

$103

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 3/12

7:30 am-9:10 am

Nonstop2h 40m

Chicago O'Hare Intl

Sat 3/21

6:01 pm-8:59 pm

Nonstop1h 58m

$105

NewarkChicago

EWR - ORD

EWRORD

Newark

Thu 5/7

9:05 pm-10:43 pm

Nonstop2h 38m

Chicago O'Hare Intl

Sun 5/10

4:47 pm-7:55 pm

Nonstop2h 08m

$123

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 2/7

7:30 am-9:12 am

Nonstop2h 42m

Chicago O'Hare Intl

Sun 2/8

8:43 pm-10:00 am

1 stop12h 17m

$125

NewarkChicago

EWR - MDW

EWRMDW

Newark

Wed 5/6

1:45 pm-8:04 am

1 stop19h 19m

Chicago Midway

Sat 5/9

7:30 am-10:38 am

Nonstop2h 08m

$129

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 5/21

12:59 pm-2:41 pm

Nonstop2h 42m

Chicago O'Hare Intl

Tue 5/26

7:05 am-7:00 pm

1 stop10h 55m

$136

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Wed 2/25

3:52 pm-5:43 pm

Nonstop2h 51m

Chicago O'Hare Intl

Sat 2/28

7:00 am-10:34 am

Nonstop2h 34m

$137

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

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 $246). 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 January 28, 2026.

Unlike in the evening, when flights are generally more expensive, you can save up to 24% on flights from Connecticut to Chicago by exploring options for tickets in the morning.

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 January 24, 2026.

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 January 28, 2026.

The most flights from USCT to CHI are scheduled on a Monday (16 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (8 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 35m. Spirit Airlines provides one of the quickest options available for as low as $90. Airlines will cover a distance of 716 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 $37. 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 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: ANA (80%), American Airlines (75%), Japan Airlines( 75%).

  • What are the cheapest flights from Connecticut to Chicago?

    On average you can expect to pay $846 for a flight from Connecticut to Chicago. The cheapest flight overall is $125 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 $246). 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.
Dallas/Fort Worth to O'Hare Intl flights
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John F Kennedy Intl to Midway flights
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LaGuardia to Midway flights
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Atlanta to Midway flights
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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 January 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$94Average$124FlexibilityNo cancel feeOn-time62%
Avelo AirlinesCheapest$104Average$199FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$176Average$353FlexibilityNo cancel feeOn-time71%
DeltaCheapest$176Average$242FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$177Average$381FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$216Average$430FlexibilityNo cancel feeOn-time69%

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