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$43+ 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 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — CHI
Feb 27 — Mrz 61
Do 2/27
Do 3/6
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 Februar 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$89
(FlightHub)

One-way from

$43
(Cheapflightsfares)

Good round-trip deal

$387 or less

Good one-way deal

$171 or less
Provider with most accurate pricing for Springfield (SFY)-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Springfield (SFY)-Chicago (CHI) flights.
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From Connecticut to Chicago (CHI)
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One-way flight from Connecticut to Chicago (CHI)
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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 Februar 22, 2025.

This FlightHub deal was found by Cheapflights users on 2/21. 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.
Fr 5/169:33 pmEWR - ORD
Nonstop2h 37mSpirit Airlines
Mo 5/195:10 pmORD - EWR
Nonstop2h 18mSpirit Airlines
Deal found 2/21$89
This Cheapflightsfares deal was found by Cheapflights users on 2/21. 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 3/1110:58 amLGA - ORD
1 stop13h 58mSpirit Airlines
Do 3/1312:31 pmORD - LGA
Nonstop2h 04mSpirit Airlines
Deal found 2/21$95
This Cheapflightsfares deal was found by Cheapflights users on 2/21. 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 3/2511:01 amJFK - MDW
1 stop5h 52mFrontier
Di 4/14:40 pmMDW - JFK
1 stop7h 03mFrontier
Deal found 2/21$98
This Justfly.com deal was found by Cheapflights users on 2/21. 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.
Fr 3/76:00 amEWR - ORD
Nonstop2h 44mMultiple Airlines
Sa 3/82:25 pmORD - EWR
1 stop5h 44mMultiple Airlines
Deal found 2/21$99
This Mytrip deal was found by Cheapflights users on 2/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 3/181:01 pmJFK - ORD
1 stop21h 04mFrontier
Di 4/19:22 amORD - JFK
1 stop23h 38mFrontier
Deal found 2/20$100
This Kiwi.com deal was found by Cheapflights users on 2/21. 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 5/15:30 pmLGA - ORD
1 stop6h 41mMultiple Airlines
Mo 5/55:55 amORD - LGA
Nonstop2h 05mMultiple Airlines
Deal found 2/21$100
This Frontier deal was found by Cheapflights users on 2/21. 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.
Mi 3/510:00 pmLGA - MDW
1 stop14h 31mFrontier
Di 3/117:50 amMDW - LGA
1 stop12h 09mFrontier
Deal found 2/21$100
This Frontier deal was found by Cheapflights users on 2/21. 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.
Mo 5/1210:00 pmEWR - MDW
1 stop11h 19mFrontier
Sa 5/1710:48 amMDW - EWR
1 stop9h 18mFrontier
Deal found 2/21$104
This Frontier deal was found by Cheapflights users on 2/22. 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.
Mo 3/310:00 pmLGA - ORD
1 stop12h 51mFrontier
Di 3/42:25 pmORD - LGA
1 stop7h 35mFrontier
Deal found 2/22$117
This Frontier deal was found by Cheapflights users on 2/21. 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 2/2510:10 pmEWR - ORD
1 stop10h 18mFrontier
Mi 3/59:08 amORD - EWR
1 stop11h 02mFrontier
Deal found 2/21$123
This KAYAK deal was found by Cheapflights users on 2/21. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mo 4/288:00 amJFK - ORD
Nonstop2h 55mDelta
Mi 4/307:20 amORD - JFK
Nonstop2h 19mDelta
Deal found 2/21$145
This JetBlue Airways deal was found by Cheapflights users on 2/22. 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 JetBlue Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 5/110:35 amJFK - ORD
Nonstop2h 42mJetBlue
So 5/46:20 amORD - JFK
Nonstop2h 13mJetBlue
Deal found 2/22$147

Find flights from Connecticut to Chicago within your budget

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 Februar 22, 2025.

Fly from

Connecticut

Fly to

Chicago

Route

Depart

Return

Price

NewarkChicago

EWR - ORD

EWRORD

Newark

Fr 5/16

9:33 pm-11:10 pm

Nonstop2h 37m

Chicago O'Hare Intl

So 5/18

5:10 pm-8:28 pm

Nonstop2h 18m

$89

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Di 3/11

10:58 am-11:56 pm

1 stop13h 58m

Chicago O'Hare Intl

Do 3/13

12:31 pm-3:35 pm

Nonstop2h 04m

$95

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Di 3/25

11:01 am-3:53 pm

1 stop5h 52m

Chicago Midway

Di 4/1

4:40 pm-12:43 am

1 stop7h 03m

$98

NewarkChicago

EWR - ORD

EWRORD

Newark

Fr 3/7

6:00 am-7:44 am

Nonstop2h 44m

Chicago O'Hare Intl

Sa 3/8

2:25 pm-9:09 pm

1 stop5h 44m

$99

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Di 3/18

1:01 pm-9:05 am

1 stop21h 04m

Chicago O'Hare Intl

Di 4/1

9:22 am-10:00 am

1 stop23h 38m

$100

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Do 5/1

5:30 pm-11:11 pm

1 stop6h 41m

Chicago O'Hare Intl

Mo 5/5

5:55 am-9:00 am

Nonstop2h 05m

$100

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Mi 3/5

10:00 pm-11:31 am

1 stop14h 31m

Chicago Midway

Di 3/11

7:50 am-8:59 pm

1 stop12h 09m

$100

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Di 4/1

10:00 pm-10:40 am

1 stop13h 40m

Chicago O'Hare Intl

Sa 4/5

7:20 am-10:32 am

1 stop26h 12m

$103

NewarkChicago

EWR - MDW

EWRMDW

Newark

Mo 5/12

10:00 pm-8:19 am

1 stop11h 19m

Chicago Midway

Sa 5/17

10:48 am-9:06 pm

1 stop9h 18m

$104

NewarkChicago

EWR - ORD

EWRORD

Newark

Di 2/25

10:10 pm-7:28 am

1 stop10h 18m

Chicago O'Hare Intl

Mi 3/5

9:08 am-9:10 pm

1 stop11h 02m

$123

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/22

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.

Travel insights for flights from Connecticut to Chicago

Get recent, data-driven insights about flights from Connecticut to Chicago including ideal travel times, pricing trends, and more.

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 Februar 22, 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 Februar 22, 2025.

The most flights from USCT to CHI are scheduled on a Thursday (20 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (5 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated Februar 22, 2025.
Peruse reviews from past customers who have flown with Southwest, Alaska Airlines and Delta from Connecticut to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,395 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Entertainment

7.6

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,395 reviews
Southwest
8.1
Very good
4,395 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Entertainment

7.6

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,700 reviews
Southwest
8.1
Very good
4,395 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Entertainment

7.6

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,203 reviews
Southwest
8.1
Very good
4,395 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Entertainment

7.6

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,068 reviews
Southwest
8.1
Very good
4,395 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Entertainment

7.6

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,754 reviews
Southwest
8.1
Very good
4,395 reviews

Food

7.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Entertainment

7.6

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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.

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

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $43. Users have also found prices from $51 and $74 on Frontier 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: SkyWest Airlines (89%), Envoy Air (86%), ANA( 84%).

  • What are the cheapest flights from Connecticut to Chicago?

    On average you can expect to pay $792 for a flight from Connecticut to Chicago. The cheapest flight overall is $144 while the most popular route, (New York John F Kennedy Intl - Chicago O'Hare Intl) is currently priced at $83.

  • 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 Connecticut?

Book flights to Connecticut if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
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
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San Francisco to O'Hare Intl flights
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Los Angeles to Midway flights
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Burbank to O'Hare Intl flights
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Charlotte to O'Hare Intl flights
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Baltimore to Midway flights
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Orlando to O'Hare Intl flights
Love Field to O'Hare Intl flights
Atlanta to Midway flights
George Bush Intcntl to O'Hare Intl flights
Seattle to Midway flights
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Cleveland to O'Hare Intl flights
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Newark to St. Louis flights
Portland to O'Hare Intl flights
Boston to Midway flights
Minneapolis to Midway flights
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Hobby to Midway flights
Philadelphia to Midway flights
LaGuardia to St. Louis flights
Reagan-National to Midway flights

Top 7 airlines flying from Connecticut to Chicago

Discover the top 7 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 Februar 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$77Average$204FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$115Average$224FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$117Average$225FlexibilityNo cancel feeOn-time65%
DeltaCheapest$175Average$322FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$198Average$339FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$217Average$397FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$257Average$377FlexibilityNo cancel feeOn-time63%
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