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$59+ 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 4/11. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — CHI
Mai 4 — Mai 111
Mo 5/4
Mo 5/11
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 April 4, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/31. 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.
Di 4/216:15 pm
LGA
-
ORD
Nonstop2h 42m
Spirit Airlines
Mi 4/292:09 pm
ORD
-
LGA
Nonstop2h 11m
Spirit Airlines
Deal found 3/31$108
This Trip.com deal was found by Cheapflights users on 3/31. 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.
Mi 4/296:15 pm
LGA
-
ORD
Nonstop2h 42m
Spirit Airlines
Mi 5/61:49 pm
ORD
-
LGA
Nonstop2h 11m
Spirit Airlines
Deal found 3/31$111
This Cheapflightsfares deal was found by Cheapflights users on 3/31. 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.
Di 4/216:15 pm
LGA
-
ORD
Nonstop2h 42m
Spirit Airlines
Do 4/232:09 pm
ORD
-
LGA
Nonstop2h 11m
Spirit Airlines
Deal found 3/31$112
This Flightnetwork deal was found by Cheapflights users on 3/31. 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.
Do 4/166:15 pm
LGA
-
ORD
Nonstop2h 42m
Spirit Airlines
Mo 4/202:09 pm
ORD
-
LGA
Nonstop2h 11m
Spirit Airlines
Deal found 3/31$113
This Kiwi.com deal was found by Cheapflights users on 3/31. 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.
Mi 4/226:15 pm
LGA
-
ORD
Nonstop2h 42m
Spirit Airlines
Mo 4/272:09 pm
ORD
-
LGA
Nonstop2h 11m
Spirit Airlines
Deal found 3/31$114
This Cheapflightsfares deal was found by Cheapflights users on 3/30. 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.
Sa 4/116:30 am
LGA
-
ORD
Nonstop2h 31m
Spirit Airlines
Di 4/147:31 pm
ORD
-
LGA
Nonstop2h 05m
Spirit Airlines
Deal found 3/30$116
This Cheapflightsfares deal was found by Cheapflights users on 3/31. 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.
Mi 4/156:15 pm
LGA
-
ORD
Nonstop2h 42m
Spirit Airlines
Do 4/162:09 pm
ORD
-
LGA
Nonstop2h 11m
Spirit Airlines
Deal found 3/31$117
This Frontier deal was found by Cheapflights users on 3/31. 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.
Di 4/2111:30 am
EWR
-
MDW
Nonstop2h 30m
Frontier
Do 4/232:15 pm
MDW
-
EWR
1 stop10h 01m
Frontier
Deal found 3/31$118
This Cheapflightsfares deal was found by Cheapflights users on 3/31. 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.
Mo 4/1310:54 pm
EWR
-
ORD
Nonstop2h 28m
Spirit Airlines
So 4/1912:47 pm
ORD
-
EWR
Nonstop2h 07m
Spirit Airlines
Deal found 3/31$118
This Cheapflightsfares deal was found by Cheapflights users on 3/31. 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.
Mo 5/46:29 pm
LGA
-
ORD
Nonstop2h 42m
Spirit Airlines
Do 5/71:49 pm
ORD
-
LGA
Nonstop2h 11m
Spirit Airlines
Deal found 3/31$118
This American Airlines deal was found by Cheapflights users on 4/1. 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.
Sa 7/111:50 pm
JFK
-
ORD
Nonstop2h 56m
American Airlines
Mi 7/154:26 pm
ORD
-
JFK
Nonstop2h 34m
American Airlines
Deal found 4/1$119
This Kiwi.com deal was found by Cheapflights users on 3/30. 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.
Do 4/910:54 pm
EWR
-
ORD
Nonstop2h 28m
Spirit Airlines
Sa 4/1812:53 pm
ORD
-
EWR
Nonstop2h 07m
Spirit Airlines
Deal found 3/30$119

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 April 4, 2026.

Round-trip from

$108
(Kiwi.com)

One-way from

$59
(Cheapflightsfares)

Popular in

April

Cheapest in

January

Average price

$423

Good round-trip deal

$145 or less

Good one-way deal

$51 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. 13% potential increase in price ($54 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 April 4, 2026.
Use the filters below to find and compare flights from Connecticut to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Mi 4/22

10:24 am-12:26 pm

Nonstop3h 02m

Chicago O'Hare Intl

Fr 4/24

1:06 pm-4:29 pm

Nonstop2h 23m

$177

NewarkChicago

EWR - ORD

EWRORD

Newark

Do 6/11

6:00 am-7:42 am

Nonstop2h 42m

Chicago O'Hare Intl

Di 6/16

9:19 pm-12:42 am

Nonstop2h 23m

$177
Quickest round-trip

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sa 5/9

7:35 am-9:00 am

Nonstop2h 25m

Chicago Midway

Mo 5/11

5:15 am-8:15 am

Nonstop2h 00m

$177

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Mi 5/20

8:05 am-9:44 am

Nonstop2h 39m

Chicago O'Hare Intl

So 5/24

6:00 am-9:11 am

Nonstop2h 11m

$177

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sa 6/13

5:55 pm-8:02 pm

Nonstop3h 07m

Chicago O'Hare Intl

Di 6/16

6:00 am-9:12 am

Nonstop2h 12m

$177

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Fr 4/24

7:30 am-9:23 am

Nonstop2h 53m

Chicago O'Hare Intl

Mo 4/27

6:00 am-9:14 am

Nonstop2h 14m

$177

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Mi 5/27

6:00 am-7:47 am

Nonstop2h 47m

Chicago O'Hare Intl

Fr 6/5

7:10 pm-10:32 pm

Nonstop2h 22m

$177

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

So 5/3

6:00 am-7:25 am

Nonstop2h 25m

Chicago Midway

So 5/10

5:20 am-8:20 am

Nonstop2h 00m

$187

NewarkChicago

EWR - ORD

EWRORD

Newark

So 8/23

7:00 am-8:43 am

Nonstop2h 43m

Chicago O'Hare Intl

Di 8/25

5:00 am-8:12 am

Nonstop2h 12m

$187

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Do 4/23

6:00 am-7:25 am

Nonstop2h 25m

Chicago Midway

Sa 4/25

6:10 pm-9:15 pm

Nonstop2h 05m

$187

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/3

Showing 1-10 of 60 resultsSorted by cheapest first
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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, February is the cheapest month in which you can book a flight from Connecticut to Chicago (average of $76). Flying from Connecticut to Chicago in April is currently the most expensive (average of $294). 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 April 4, 2026.

Unlike in the evening, when flights are generally more expensive, you can save up to 25% on flights from Connecticut to Chicago by exploring options for tickets in the afternoon.

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 April 4, 2026.

Travelers seeking maximum savings on their Connecticut to Chicago flight should consider departing on Wednesday 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 April 4, 2026.

The most flights from USCT to CHI are scheduled on a Friday (17 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (7 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 25m. Delta provides one of the quickest options available for as low as $177. 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 Avelo Airlines. According to our data, you can fly for as low as $37. Users have also found prices from $68 and $78 on Southwest and American Airlines, 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: Copa Airlines (89%), ANA (78%), Qatar Airways( 78%).

  • What are the cheapest flights from Connecticut to Chicago?

    On average you can expect to pay $921 for a flight from Connecticut to Chicago. The cheapest flight overall is $142 while the most popular route, (New York John F Kennedy Intl - Chicago O'Hare Intl) is currently priced at $172.

  • 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, February is the cheapest month in which you can book a flight from Connecticut to Chicago (average of $76). Flying from Connecticut to Chicago in April is currently the most expensive (average of $294). 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.
John F Kennedy Intl to O'Hare Intl flights
Newark to O'Hare Intl flights
Seattle to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
Boston to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Denver to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Newark to Midway flights
John F Kennedy Intl to Midway flights
Sky Harbor Intl to O'Hare Intl flights
Ontario to O'Hare Intl flights
Orlando to O'Hare Intl flights
Austin to O'Hare Intl flights
Dulles Intl to Midway flights
Santa Ana to O'Hare Intl flights
Baltimore to Midway flights
Charlotte to O'Hare Intl flights
Tampa to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Los Angeles to Midway flights
San Diego to O'Hare Intl flights
LaGuardia to Midway flights
San Francisco to Midway flights
Atlanta to Midway flights
Minneapolis to O'Hare Intl flights
San Jose to O'Hare Intl flights
Minneapolis to Midway flights
Burbank to O'Hare Intl flights
Denver to Midway flights
Sacramento to O'Hare Intl flights
Portland to O'Hare Intl flights
Miami to O'Hare Intl flights
Newark to St. Louis flights
Fort Lauderdale to O'Hare Intl flights
Philadelphia to Midway flights
Boston to Midway flights
Hartford to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
LaGuardia to St. Louis flights
Las Vegas to O'Hare Intl flights
Hobby to O'Hare Intl flights
Orlando to Midway flights

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 April 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$76Average$143FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$167Average$361FlexibilityNo cancel feeOn-time71%
DeltaCheapest$176Average$292FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$177Average$390FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$218Average$401FlexibilityNo cancel feeOn-time69%

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