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$70+ 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 1/17. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — CHI
déc. 27 — janv. 31
ven. 12/27
ven. 1/3
1 adult, Economy
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Cheap flight deals from Connecticut to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Connecticut (USCT) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated décembre 22, 2024.

Round-trip from

$127
(Mytrip)

One-way from

$70
(Frontier)
From Connecticut to Chicago (CHI)
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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 décembre 22, 2024.

This Cheapflightsfares deal was found by Cheapflights users on 12/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/319:05 pmLGA - ORD
Nonstop2h 38mSpirit Airlines
sam. 1/44:45 pmORD - LGA
Nonstop2h 15mSpirit Airlines
Deal found 12/20$132
This CheapOair deal was found by Cheapflights users on 12/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 12/288:35 amLGA - ORD
Nonstop2h 32mMultiple Airlines
lun. 1/610:59 amORD - LGA
1 stop27h 57mMultiple Airlines
Deal found 12/21$165
This FlightHub deal was found by Cheapflights users on 12/21. 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.
lun. 12/305:35 pmEWR - ORD
Nonstop2h 44mSpirit Airlines
dim. 1/51:24 pmORD - EWR
Nonstop2h 16mSpirit Airlines
Deal found 12/21$176
This Delta deal was found by Cheapflights users on 12/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 12/286:00 amEWR - ORD
1 stop4h 09mDelta
jeu. 1/306:45 amORD - EWR
1 stop4h 26mDelta
Deal found 12/21$203
This United Airlines deal was found by Cheapflights users on 12/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/318:10 pmEWR - ORD
Nonstop2h 42mUnited Airlines
jeu. 1/29:45 pmORD - EWR
Nonstop2h 12mUnited Airlines
Deal found 12/21$205
This Delta deal was found by Cheapflights users on 12/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/315:45 pmJFK - ORD
1 stop6h 07mDelta
mer. 1/82:03 pmORD - JFK
Nonstop2h 26mDelta
Deal found 12/21$234
This American Airlines deal was found by Cheapflights users on 12/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 12/287:05 amEWR - ORD
Nonstop2h 36mAmerican Airlines
jeu. 1/308:40 amORD - EWR
Nonstop2h 16mAmerican Airlines
Deal found 12/21$237
This American Airlines deal was found by Cheapflights users on 12/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 12/288:40 amJFK - ORD
1 stop4h 21mAmerican Airlines
jeu. 1/3011:40 amORD - JFK
Nonstop2h 15mAmerican Airlines
Deal found 12/21$247
This Gotogate deal was found by Cheapflights users on 12/21. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/315:29 pmLGA - MDW
1 stop15h 52mFrontier
jeu. 1/28:00 amMDW - LGA
1 stop13h 00mFrontier
Deal found 12/21$253
This Southwest deal was found by Cheapflights users on 12/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 12/286:00 amLGA - MDW
Nonstop2h 30mSouthwest
dim. 1/56:00 amMDW - LGA
Nonstop2h 05mSouthwest
Deal found 12/21$256
This eDestinos deal was found by Cheapflights users on 12/20. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/3110:00 pmEWR - ORD
2 stops35h 37mMultiple Airlines
sam. 1/47:25 amORD - EWR
1 stop24h 35mMultiple Airlines
Deal found 12/20$266
This Trip.com deal was found by Cheapflights users on 12/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/316:00 amLGA - ORD
1 stop14h 14mFrontier
jeu. 1/22:19 pmORD - LGA
1 stop8h 25mFrontier
Deal found 12/21$273

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 décembre 22, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

sam. 1/11

11:02 am-3:16 pm

1 stop29h 14m

Chicago Midway

lun. 1/13

11:33 am-1:59 pm

1 stop25h 26m

$129

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

ven. 1/24

10:59 am-8:57 pm

1 stop10h 58m

Chicago O'Hare Intl

mar. 1/28

7:00 am-10:04 am

Nonstop2h 04m

$129

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

jeu. 1/9

10:59 am-6:37 pm

1 stop8h 38m

Chicago Midway

lun. 1/13

6:15 am-3:10 pm

1 stop7h 55m

$129

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

jeu. 2/6

11:00 am-10:27 pm

1 stop12h 27m

Chicago O'Hare Intl

dim. 2/9

10:59 am-1:59 pm

1 stop26h 00m

$130

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

jeu. 1/9

10:59 am-12:39 pm

Nonstop2h 40m

Chicago O'Hare Intl

jeu. 1/9

2:02 pm-11:26 pm

1 stop8h 24m

$133

NewarkChicago

EWR - ORD

EWRORD

Newark

jeu. 1/9

7:59 am-9:34 am

Nonstop2h 35m

Chicago O'Hare Intl

dim. 1/12

6:06 pm-8:04 am

1 stop12h 58m

$134

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

lun. 2/10

4:00 pm-10:27 pm

1 stop7h 27m

Chicago O'Hare Intl

jeu. 2/13

12:59 pm-11:59 pm

1 stop10h 00m

$138

NewarkChicago

EWR - ORD

EWRORD

Newark

mer. 1/29

6:29 pm-8:13 pm

Nonstop2h 44m

Chicago O'Hare Intl

lun. 2/3

6:20 pm-9:32 pm

Nonstop2h 12m

$143

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

lun. 1/13

7:29 pm-9:28 pm

Nonstop2h 59m

Chicago O'Hare Intl

lun. 1/20

7:05 am-10:31 am

Nonstop2h 26m

$147

NewarkChicago

EWR - ORD

EWRORD

Newark

ven. 1/24

2:45 pm-4:26 pm

Nonstop2h 41m

Chicago O'Hare Intl

dim. 1/26

6:00 am-9:11 am

Nonstop2h 11m

$147

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

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 $317). 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 décembre 22, 2024.

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 décembre 22, 2024.

The most flights from USCT to CHI are scheduled on a Saturday (18 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (4 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 décembre 22, 2024.
Peruse reviews from past customers who have flown with Frontier, United Airlines and JetBlue 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
4,804 reviews

Overall

8.1

Entertainment

7.7

Crew

8.7

Comfort

8.1

Food

7.2

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,804 reviews
Southwest
8.1
Very good
4,804 reviews

Overall

8.1

Entertainment

7.7

Crew

8.7

Comfort

8.1

Food

7.2

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,537 reviews
Southwest
8.1
Very good
4,804 reviews

Overall

8.1

Entertainment

7.7

Crew

8.7

Comfort

8.1

Food

7.2

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,594 reviews
Southwest
8.1
Very good
4,804 reviews

Overall

8.1

Entertainment

7.7

Crew

8.7

Comfort

8.1

Food

7.2

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,265 reviews
Southwest
8.1
Very good
4,804 reviews

Overall

8.1

Entertainment

7.7

Crew

8.7

Comfort

8.1

Food

7.2

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
9,028 reviews
Southwest
8.1
Very good
4,804 reviews

Overall

8.1

Entertainment

7.7

Crew

8.7

Comfort

8.1

Food

7.2

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 Frontier. According to our data, you can fly for as low as $70. Users have also found prices from $70 and $73 on Spirit Airlines 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 (100%), Japan Airlines (95%), Republic Airways( 95%).

  • What are the cheapest flights from Connecticut to Chicago?

    On average you can expect to pay $1,038 for a flight from Connecticut to Chicago. The cheapest flight overall is $153 while the most popular route, (New York John F Kennedy Intl - Chicago O'Hare Intl) is currently priced at $135.

  • 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 $317). 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

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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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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 décembre 22, 2024.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$77Average$204FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$108Average$225FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$117Average$225FlexibilityNo cancel feeOn-time65%
DeltaCheapest$175Average$295FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$195Average$341FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$217Average$401FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$232Average$374FlexibilityNo cancel feeOn-time63%
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