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$55+ Cheap flights from Chicago (CHI) to Connecticut

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 3/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BDL
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
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Cheap flight deals from Chicago to Connecticut

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Connecticut (USCT). 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 January 21, 2025.

Round-trip from

$97
(Cheapflightsfares)

One-way from

$55
(Frontier)
From Chicago (CHI) to Connecticut
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One-way flight from Chicago (CHI) to Connecticut
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Find flight deals from Chicago to Connecticut

Cheapest flights from Chicago to Connecticut
Explore the most affordable flight options available from Chicago to Connecticut. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 21, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 1/20. 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.
Tue 2/47:00 amORD - LGA
Nonstop2h 04mSpirit Airlines
Wed 2/510:59 amLGA - ORD
Nonstop2h 40mSpirit Airlines
Deal found 1/20$97
This Frontier deal was found by Cheapflights users on 1/19. 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 1/282:59 pmORD - LGA
1 stop6h 01mFrontier
Sat 2/110:00 pmLGA - ORD
1 stop12h 04mFrontier
Deal found 1/19$100
This Frontier deal was found by Cheapflights users on 1/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/198:12 amMDW - LGA
1 stop5h 48mFrontier
Wed 2/1910:00 pmLGA - MDW
1 stop14h 28mFrontier
Deal found 1/20$100
This Booking.com deal was found by Cheapflights users on 1/18. 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.
Fri 2/710:02 pmORD - LGA
1 stop16h 58mMultiple Airlines
Wed 2/1210:59 amLGA - ORD
Nonstop2h 38mMultiple Airlines
Deal found 1/18$102
This Gotogate deal was found by Cheapflights users on 1/19. 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.
Tue 2/186:20 amORD - JFK
1 stop26h 55mFrontier
Tue 2/2511:15 amJFK - ORD
1 stop28h 10mFrontier
Deal found 1/19$106
This Frontier deal was found by Cheapflights users on 1/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/303:20 pmMDW - JFK
1 stop8h 13mFrontier
Wed 5/76:00 amJFK - MDW
1 stop12h 18mFrontier
Deal found 1/20$110
This Cheapflightsfares deal was found by Cheapflights users on 1/20. 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.
Thu 3/205:22 pmORD - EWR
Nonstop2h 17mSpirit Airlines
Sat 3/229:55 amEWR - ORD
1 stop9h 57mSpirit Airlines
Deal found 1/20$119
This Priceline deal was found by Cheapflights users on 1/19. 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 1/291:45 pmORD - EWR
1 stop6h 25mMultiple Airlines
Thu 1/307:59 amEWR - ORD
Nonstop2h 35mMultiple Airlines
Deal found 1/19$122
This American Airlines deal was found by Cheapflights users on 1/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2011:45 amORD - JFK
Nonstop2h 10mAmerican Airlines
Mon 2/243:50 pmJFK - ORD
Nonstop2h 52mAmerican Airlines
Deal found 1/20$146
This United Airlines deal was found by Cheapflights users on 1/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/201:00 pmORD - LGA
Nonstop2h 13mUnited Airlines
Sun 2/236:00 amLGA - ORD
Nonstop2h 47mUnited Airlines
Deal found 1/20$147
This Southwest deal was found by Cheapflights users on 1/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/118:05 pmMDW - LGA
Nonstop2h 05mSouthwest
Wed 2/129:35 pmLGA - MDW
Nonstop2h 30mSouthwest
Deal found 1/20$147
This Delta deal was found by Cheapflights users on 1/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/510:05 amORD - JFK
Nonstop2h 25mDelta
Wed 3/57:29 pmJFK - ORD
Nonstop2h 55mDelta
Deal found 1/20$147

Find flights from Chicago to Connecticut within your budget

Customize your flight search to find flights from Chicago to Connecticut 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 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Sat 2/1

5:06 pm-8:10 pm

Nonstop2h 04m

New York LaGuardia

Mon 2/3

10:59 am-12:39 pm

Nonstop2h 40m

$97

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Tue 2/4

2:59 pm-10:00 pm

1 stop6h 01m

New York LaGuardia

Sat 2/8

10:00 pm-9:04 am

1 stop12h 04m

$100

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 2/19

8:12 am-3:00 pm

1 stop5h 48m

New York LaGuardia

Wed 2/19

10:00 pm-11:28 am

1 stop14h 28m

$100

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Wed 2/19

8:33 am-3:00 pm

1 stop5h 27m

New York LaGuardia

Wed 2/26

7:55 pm-9:33 pm

Nonstop2h 38m

$104

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Tue 2/18

6:20 am-10:15 am

1 stop26h 55m

New York John F Kennedy Intl

Tue 2/25

11:15 am-2:25 pm

1 stop28h 10m

$106

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Tue 3/4

8:30 am-12:02 pm

1 stop26h 32m

New York John F Kennedy Intl

Tue 3/11

11:01 am-3:53 pm

1 stop5h 52m

$110

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Sat 3/1

5:15 am-8:23 am

Nonstop2h 08m

Newark

Mon 3/3

9:11 pm-10:40 am

1 stop14h 29m

$119

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Wed 2/19

8:33 am-9:10 pm

1 stop11h 37m

Newark

Fri 2/21

10:10 pm-7:18 am

1 stop10h 08m

$122

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Thu 3/6

11:55 am-9:09 pm

1 stop8h 14m

Newark

Sun 3/9

6:00 am-7:44 am

Nonstop2h 44m

$124

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Tue 3/4

8:47 am-9:10 pm

1 stop11h 23m

Newark

Tue 3/11

10:09 pm-4:55 pm

1 stop19h 46m

$130

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Showing 1-10 of 60 results
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Best time to book a flight from Chicago to Connecticut

Have a flexible travel schedule? Discover the best time to fly to Connecticut from Chicago 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 Chicago to Connecticut

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

What is the cheapest month to book a flight from Chicago to Connecticut?

Currently, November is the cheapest month in which you can book a flight from Chicago to Connecticut (average of $287). Flying from Chicago to Connecticut in June is currently the most expensive (average of $357). 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 CHI to CT?

Find hourly flight availability from Chicago to Connecticut. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 21, 2025.

When flying from Chicago to Connecticut, 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 Chicago to Connecticut

Explore weekly flight availability from Chicago to Connecticut. 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 21, 2025.

The most flights from CHI to USCT are scheduled on a Monday (18 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (8 on average).

Rainfall in Connecticut by month

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

In terms of precipitation, rainfall in Connecticut ranges from 3.1 - 4.1 inches per month. September is typically the wettest month, when rainfall can reach 4.1 in. February is typically the driest time to visit Connecticut when rainfall is around 3.1 in.

Temperature in Connecticut by month

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

If weather is an important factor for your trip to Connecticut, 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 24.8 F).

Reviews of airlines servicing Connecticut

Get insights into the airlines that provide service to Connecticut. 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 Connecticut. Reviews last updated January 21, 2025.
Get a feel of what it's like to fly with JetBlue, Frontier and Delta from Chicago to Connecticut by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,659 reviews

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Crew

8.7

Food

7.2

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
4,659 reviews
Southwest
8.1
Very good
4,659 reviews

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Crew

8.7

Food

7.2

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
9,696 reviews
Southwest
8.1
Very good
4,659 reviews

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Crew

8.7

Food

7.2

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
8,521 reviews
Southwest
8.1
Very good
4,659 reviews

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Crew

8.7

Food

7.2

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
3,201 reviews
Southwest
8.1
Very good
4,659 reviews

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Crew

8.7

Food

7.2

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
8,982 reviews
Southwest
8.1
Very good
4,659 reviews

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Crew

8.7

Food

7.2

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 Chicago to Connecticut. 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 Chicago to Connecticut one-way?

    $55 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Spirit Airlines and Delta, with prices starting from $59 and $74, respectively.

  • What are the most popular routes from Chicago to Connecticut?

    While some choose either Chicago O'Hare Intl - New York LaGuardia or Chicago O'Hare Intl - Newark, Chicago O'Hare Intl - New York John F Kennedy Intl is the most popular route from Chicago to Connecticut.

  • What are the most reliable airlines from Chicago to Connecticut?

    No one likes to see their flight delayed. When booking a flight from Chicago to Connecticut consider choosing Republic Airways (90%), Envoy Air (84%) or Qatar Airways (83%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Chicago to Connecticut?

    While on average a flight from Chicago to Connecticut is generally $395, our data shows the cheapest flight currently is $128. When looking at the most popular route, (Chicago O'Hare Intl - New York John F Kennedy Intl), you can expect to pay $126 for that flight.

  • Can I find deals for flights from Chicago to Connecticut that include hotel bookings?

    Yes. In addition to deals on Chicago to Connecticut flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Connecticut?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Connecticut.

  • Can I find deals for business class flights from Chicago to Connecticut?

    Yes. Cheapflights offers flight deals from Chicago to Connecticut 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 Chicago to Connecticut?

    Currently, November is the cheapest month in which you can book a flight from Chicago to Connecticut (average of $287). Flying from Chicago to Connecticut in June is currently the most expensive (average of $357). 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.

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Alternative routes for Chicago to Connecticut

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

Discover the top 6 airlines that operate flights from Chicago to Connecticut. 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 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$84Average$168FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$116Average$199FlexibilityNo cancel feeOn-time65%
FrontierCheapest$124Average$215FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$191Average$369FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$208Average$403FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$212Average$351FlexibilityNo cancel feeOn-time71%
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