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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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BDL
Apr 5 — Apr 122
Sat 4/5
2 travelers, Economy
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Cheap flight deals from Chicago to Connecticut

Keep the following information in mind while searching for Chicago to Connecticut flight deals. Data was last updated March 31, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$91
(Expedia)

One-way from

$55
(Cheapflightsfares)

Good round-trip deal

$351 or less

Good one-way deal

$196 or less
Provider with most accurate pricing for Chicago (CHI)-Springfield (SFY) flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Springfield (SFY) flights.
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From Chicago (CHI) to Connecticut
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One-way flight from Chicago (CHI) to Connecticut
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Price to beat on a round-trip flight from Chicago (CHI) to Connecticut.
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Price to beat on a 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 March 31, 2025.

This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/65:55 amORD - LGA
Nonstop2h 05mSpirit Airlines
Sun 5/117:59 pmLGA - ORD
1 stop13h 51mSpirit Airlines
Deal found 3/31$91
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.
Tue 5/135:05 amORD - EWR
1 stop10h 29mSpirit Airlines
Wed 5/145:55 amEWR - ORD
Nonstop2h 32mSpirit Airlines
Deal found 3/31$103
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/66:15 amORD - JFK
Nonstop2h 15mJetBlue
Tue 5/612:00 pmJFK - ORD
1 stop7h 36mJetBlue
Deal found 3/31$121
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/305:55 amORD - LGA
Nonstop2h 05mMultiple Airlines
Mon 5/55:30 pmLGA - ORD
1 stop6h 41mMultiple Airlines
Deal found 3/31$139
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/104:44 pmORD - JFK
Nonstop2h 16mAmerican Airlines
Tue 5/279:00 amJFK - ORD
Nonstop3h 09mAmerican Airlines
Deal found 3/30$140
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/215:50 pmMDW - LGA
Nonstop2h 10mSouthwest
Mon 5/266:30 amLGA - MDW
Nonstop2h 20mSouthwest
Deal found 3/31$143
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/302:00 pmORD - LGA
Nonstop2h 15mUnited Airlines
Sun 5/47:25 amLGA - ORD
Nonstop2h 41mUnited Airlines
Deal found 3/31$149
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/86:17 amORD - LGA
Nonstop2h 06mAmerican Airlines
Mon 5/127:29 pmLGA - ORD
Nonstop2h 44mAmerican Airlines
Deal found 3/31$151
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/217:00 amORD - JFK
Nonstop2h 25mDelta
Tue 5/278:00 amJFK - ORD
Nonstop2h 51mDelta
Deal found 3/31$153
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/287:00 amORD - LGA
Nonstop2h 12mDelta
Sat 5/315:25 pmLGA - ORD
Nonstop2h 55mDelta
Deal found 3/31$157
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/248:11 amORD - EWR
1 stop11h 54mMultiple Airlines
Tue 4/298:59 pmEWR - ORD
1 stop13h 25mMultiple Airlines
Deal found 3/31$157
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/63:46 pmORD - EWR
Nonstop2h 14mAmerican Airlines
Tue 5/137:19 amEWR - ORD
Nonstop2h 42mAmerican Airlines
Deal found 3/31$159

Cheapflights Fare Finder

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 March 31, 2025.
Use the filters below to find and compare flights from Chicago to Connecticut that are best for you.

Fly from

Chicago

Fly to

Connecticut

Route

Depart

Return

Price

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Tue 5/6

7:47 pm-10:00 am

1 stop13h 13m

New York LaGuardia

Wed 5/14

6:30 pm-8:07 pm

Nonstop2h 37m

$91

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Tue 4/29

5:45 pm-9:07 pm

Nonstop2h 22m

Newark

Thu 5/1

8:59 pm-9:24 am

1 stop13h 25m

$103

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Tue 5/6

6:15 am-9:30 am

Nonstop2h 15m

New York John F Kennedy Intl

Tue 5/6

12:00 pm-6:36 pm

1 stop7h 36m

$121

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Wed 4/30

5:55 am-9:00 am

Nonstop2h 05m

New York LaGuardia

Mon 5/5

5:30 pm-11:11 pm

1 stop6h 41m

$139

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Sat 5/10

4:44 pm-8:00 pm

Nonstop2h 16m

New York John F Kennedy Intl

Tue 5/27

9:00 am-11:09 am

Nonstop3h 09m

$140

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 5/21

5:50 pm-9:00 pm

Nonstop2h 10m

New York LaGuardia

Mon 5/26

6:30 am-7:50 am

Nonstop2h 20m

$143

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Thu 5/1

4:00 pm-7:15 pm

Nonstop2h 15m

New York LaGuardia

Sun 5/4

6:25 am-8:00 am

Nonstop2h 35m

$149

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Thu 5/8

6:00 am-9:10 am

Nonstop2h 10m

New York LaGuardia

Mon 5/12

8:55 pm-10:41 pm

Nonstop2h 46m

$150

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Wed 5/21

7:00 am-10:25 am

Nonstop2h 25m

New York John F Kennedy Intl

Wed 5/28

8:00 am-9:51 am

Nonstop2h 51m

$153

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Thu 4/24

8:11 am-9:05 pm

1 stop11h 54m

Newark

Tue 4/29

8:59 pm-9:24 am

1 stop13h 25m

$157

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/30

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.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Connecticut

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 March 31, 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 March 31, 2025.

The most flights from CHI to USCT are scheduled on a Monday (20 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (6 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 March 31, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest 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.
Alaska Airlines
8.0
Very good
9,818 reviews

Food

7.1

Boarding

8.2

Overall

8.0

Comfort

7.9

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,818 reviews
Alaska Airlines
8.0
Very good
9,818 reviews

Food

7.1

Boarding

8.2

Overall

8.0

Comfort

7.9

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Southwest
8.0
Very good
4,276 reviews
Alaska Airlines
8.0
Very good
9,818 reviews

Food

7.1

Boarding

8.2

Overall

8.0

Comfort

7.9

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,899 reviews
Alaska Airlines
8.0
Very good
9,818 reviews

Food

7.1

Boarding

8.2

Overall

8.0

Comfort

7.9

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
United Airlines
7.4
Good
8,614 reviews
Alaska Airlines
8.0
Very good
9,818 reviews

Food

7.1

Boarding

8.2

Overall

8.0

Comfort

7.9

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
JetBlue
7.3
Good
2,924 reviews
Alaska Airlines
8.0
Very good
9,818 reviews

Food

7.1

Boarding

8.2

Overall

8.0

Comfort

7.9

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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 Spirit Airlines. You may also be able to find cheap deals on Delta and Southwest, with prices starting from $69 and $69, respectively.

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

    While some choose either Chicago O'Hare Intl - New York John F Kennedy Intl or Chicago O'Hare Intl - Newark, Chicago O'Hare Intl - New York LaGuardia 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 SkyWest Airlines (100%), Copa Airlines (100%) or Air New Zealand (92%) 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 $316, our data shows the cheapest flight currently is $150. When looking at the most popular route, (Chicago O'Hare Intl - New York LaGuardia), you can expect to pay $64 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.

See more FAQs

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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 March 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$84Average$168FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$116Average$199FlexibilityNo cancel feeOn-time65%
FrontierCheapest$124Average$211FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$197Average$334FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$208Average$353FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$228Average$412FlexibilityNo cancel feeOn-time69%
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