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$60+ 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 12/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BDL
Nov 25 — Dec 21
Mon 11/25
Mon 12/2
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 November 20, 2024.

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 November 20, 2024.

This Cheapflightsfares deal was found by Cheapflights users on 11/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/64:19 pmORD - LGA
Nonstop2h 05mSpirit Airlines
Wed 12/1112:59 pmLGA - ORD
1 stop9h 08mSpirit Airlines
Deal found 11/19$96
This Cheapflightsfares deal was found by Cheapflights users on 11/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/37:39 pmORD - EWR
1 stop12h 21mSpirit Airlines
Tue 12/1010:55 pmEWR - ORD
Nonstop2h 39mSpirit Airlines
Deal found 11/19$109
This Booking.com deal was found by Cheapflights users on 11/19. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/104:19 pmORD - LGA
Nonstop2h 05mMultiple Airlines
Thu 12/125:59 pmLGA - ORD
1 stop16h 55mMultiple Airlines
Deal found 11/19$111
This Booking.com deal was found by Cheapflights users on 11/19. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/910:59 amORD - LGA
1 stop29h 01mFrontier
Wed 12/115:59 pmLGA - ORD
1 stop15h 25mFrontier
Deal found 11/19$116
This Frontier deal was found by Cheapflights users on 11/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/97:15 amMDW - LGA
1 stop13h 45mFrontier
Tue 1/1410:59 amLGA - MDW
1 stop6h 15mFrontier
Deal found 11/18$123
This Frontier deal was found by Cheapflights users on 11/19. 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.
Mon 12/95:01 amMDW - JFK
1 stop28h 15mFrontier
Thu 12/1211:19 amJFK - MDW
1 stop25h 22mFrontier
Deal found 11/19$128
This CheapOair deal was found by Cheapflights users on 11/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/166:07 pmORD - JFK
1 stop18h 52mFrontier
Tue 12/313:00 pmJFK - ORD
1 stop19h 24mFrontier
Deal found 11/20$138
This American Airlines deal was found by Cheapflights users on 11/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/78:25 pmORD - LGA
Nonstop2h 08mAmerican Airlines
Tue 12/1010:15 amLGA - ORD
Nonstop2h 52mAmerican Airlines
Deal found 11/18$147
This JetBlue deal was found by Cheapflights users on 11/20. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/1010:14 amORD - JFK
Nonstop2h 16mJetBlue
Thu 12/127:29 amJFK - ORD
Nonstop2h 49mJetBlue
Deal found 11/20$147
This Southwest deal was found by Cheapflights users on 11/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/107:55 pmMDW - LGA
Nonstop2h 05mSouthwest
Thu 12/126:30 amLGA - MDW
Nonstop2h 30mSouthwest
Deal found 11/19$148
This KAYAK deal was found by Cheapflights users on 11/19. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/112:50 pmORD - LGA
Nonstop2h 12mDelta
Thu 12/127:25 amLGA - ORD
Nonstop2h 45mDelta
Deal found 11/19$150
This American Airlines deal was found by Cheapflights users on 11/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/146:47 pmORD - EWR
Nonstop2h 12mAmerican Airlines
Wed 1/87:00 amEWR - ORD
Nonstop2h 46mAmerican Airlines
Deal found 11/19$152

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 2,629,791 searches. Data last updated November 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Wed 1/15

7:00 am-10:04 am

Nonstop2h 04m

New York LaGuardia

Sat 1/18

9:15 pm-10:55 pm

Nonstop2h 40m

$95

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Thu 1/9

10:35 am-3:56 pm

1 stop28h 21m

New York LaGuardia

Tue 1/14

10:59 am-12:39 pm

Nonstop2h 40m

$104

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Thu 2/6

6:36 pm-6:30 am

1 stop10h 54m

New York John F Kennedy Intl

Wed 2/12

11:01 am-4:56 pm

1 stop6h 55m

$104

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Thu 1/30

12:43 pm-6:30 am

1 stop16h 47m

New York John F Kennedy Intl

Mon 2/3

11:00 am-3:43 pm

1 stop5h 43m

$108

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Tue 12/3

7:39 pm-9:00 am

1 stop12h 21m

Newark

Tue 12/10

10:55 pm-12:34 am

Nonstop2h 39m

$109

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Thu 1/16

7:25 am-5:00 pm

1 stop8h 35m

New York LaGuardia

Wed 1/22

5:59 pm-3:13 pm

1 stop22h 14m

$114

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Mon 12/9

10:59 am-5:00 pm

1 stop29h 01m

New York LaGuardia

Wed 12/11

5:59 pm-8:24 am

1 stop15h 25m

$116

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Wed 2/12

8:12 am-9:10 pm

1 stop11h 58m

Newark

Tue 2/18

10:10 pm-7:07 am

1 stop9h 57m

$116

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Wed 1/22

1:45 pm-9:10 pm

1 stop6h 25m

Newark

Thu 1/23

7:59 am-9:34 am

Nonstop2h 35m

$123

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Thu 1/9

11:00 am-2:12 pm

Nonstop2h 12m

New York LaGuardia

Sun 1/12

6:00 am-7:42 am

Nonstop2h 42m

$147

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

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, December is the cheapest month in which you can book a flight from Chicago to Connecticut (average of $280). Flying from Chicago to Connecticut in June is currently the most expensive (average of $359). 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 November 20, 2024.

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 November 20, 2024.

The most flights from CHI to USCT are scheduled on a Wednesday (17 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (10 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 November 20, 2024.
Get a feel of what it's like to fly with JetBlue, American Airlines and Frontier 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
5,014 reviews

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,014 reviews
Southwest
8.1
Very good
5,014 reviews

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,756 reviews
Southwest
8.1
Very good
5,014 reviews

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Alaska Airlines
8.0
Very good
9,461 reviews
Southwest
8.1
Very good
5,014 reviews

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Porter Airlines
7.8
Good
288 reviews
Southwest
8.1
Very good
5,014 reviews

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Air Transat
7.8
Good
389 reviews
Southwest
8.1
Very good
5,014 reviews

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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?

    $60 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 United Airlines, with prices starting from $61 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 (100%), Envoy Air (96%) or United Airlines (93%) 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 $324, our data shows the cheapest flight currently is $139. When looking at the most popular route, (Chicago O'Hare Intl - New York John F Kennedy Intl), you can expect to pay $132 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, December is the cheapest month in which you can book a flight from Chicago to Connecticut (average of $280). Flying from Chicago to Connecticut in June is currently the most expensive (average of $359). 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 2,629,791 searches. Data last updated November 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$84Average$168FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$116Average$199FlexibilityNo cancel feeOn-time65%
FrontierCheapest$148Average$238FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$191Average$373FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$207Average$399FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$207Average$349FlexibilityNo cancel feeOn-time71%
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