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$66+ 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 10/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BDL
Jul 6 — Jul 131
Sun 7/6
Sun 7/13
1 adult, 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 July 1, 2025.

Round-trip from

$118
(Cheapflightsfares)

One-way from

$66
(Expedia)

Good round-trip deal

$178 or less

Good one-way deal

$78 or less
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 July 1, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 6/29. 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.
Sat 7/195:51 amORD - LGA
Nonstop2h 09mSpirit Airlines
Tue 7/226:30 pmLGA - ORD
Nonstop2h 30mSpirit Airlines
Deal found 6/29$118
This Priceline deal was found by Cheapflights users on 6/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/410:42 amORD - LGA
1 stop10h 29mFrontier
Sat 9/66:30 amLGA - ORD
1 stop5h 57mFrontier
Deal found 6/30$121
This Priceline deal was found by Cheapflights users on 6/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/25:07 pmORD - JFK
1 stop6h 35mFrontier
Tue 8/59:00 amJFK - ORD
1 stop8h 38mFrontier
Deal found 6/30$121
This Priceline deal was found by Cheapflights users on 7/1. 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.
Fri 9/125:04 pmMDW - JFK
1 stop6h 38mFrontier
Mon 9/159:00 amJFK - MDW
1 stop7h 58mFrontier
Deal found 7/1$122
This Priceline deal was found by Cheapflights users on 6/29. 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.
Sat 8/2310:22 amORD - LGA
Nonstop2h 17mMultiple Airlines
Wed 8/276:30 amLGA - ORD
1 stop8h 03mMultiple Airlines
Deal found 6/29$130
This Delta deal was found by Cheapflights users on 7/1. 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 9/36:00 amORD - LGA
Nonstop2h 10mDelta
Wed 9/36:55 pmLGA - ORD
Nonstop2h 52mDelta
Deal found 7/1$137
This Southwest deal was found by Cheapflights users on 7/1. 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 9/36:00 amMDW - LGA
Nonstop2h 00mSouthwest
Wed 9/39:35 pmLGA - MDW
Nonstop2h 20mSouthwest
Deal found 7/1$137
This JetBlue deal was found by Cheapflights users on 6/29. 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 9/211:35 amORD - JFK
Nonstop2h 23mJetBlue
Tue 9/28:30 pmJFK - ORD
Nonstop2h 58mJetBlue
Deal found 6/29$137
This Priceline deal was found by Cheapflights users on 6/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/88:00 amMDW - LGA
1 stop11h 59mFrontier
Sun 10/1211:30 amLGA - MDW
1 stop7h 48mFrontier
Deal found 6/30$142
This Priceline deal was found by Cheapflights users on 6/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/25:07 pmORD - EWR
1 stop6h 37mFrontier
Wed 8/611:04 amEWR - ORD
1 stop6h 00mFrontier
Deal found 6/30$144
This Priceline deal was found by Cheapflights users on 6/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/155:04 pmMDW - EWR
1 stop6h 30mFrontier
Sun 9/2111:15 amEWR - MDW
1 stop5h 43mFrontier
Deal found 6/30$145
This Justfly.com deal was found by Cheapflights users on 6/28. 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.
Sat 10/185:45 pmORD - EWR
1 stop5h 49mMultiple Airlines
Tue 10/219:33 pmEWR - ORD
Nonstop2h 37mMultiple Airlines
Deal found 6/28$146

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 July 1, 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

Sat 7/19

5:51 am-9:00 am

Nonstop2h 09m

New York LaGuardia

Tue 7/22

6:30 pm-8:00 pm

Nonstop2h 30m

$118

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Thu 9/4

10:42 am-10:11 pm

1 stop10h 29m

New York LaGuardia

Sat 9/6

6:30 am-11:27 am

1 stop5h 57m

$121

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Sat 8/2

5:07 pm-12:42 am

1 stop6h 35m

New York John F Kennedy Intl

Tue 8/5

9:00 am-4:38 pm

1 stop8h 38m

$121

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Fri 9/12

5:04 pm-12:42 am

1 stop6h 38m

New York John F Kennedy Intl

Mon 9/15

9:00 am-3:58 pm

1 stop7h 58m

$122

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Sat 8/23

10:22 am-1:39 pm

Nonstop2h 17m

New York LaGuardia

Wed 8/27

6:30 am-1:33 pm

1 stop8h 03m

$130

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Wed 9/3

6:00 am-9:10 am

Nonstop2h 10m

New York LaGuardia

Wed 9/3

6:55 pm-8:47 pm

Nonstop2h 52m

$137

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 9/3

6:00 am-9:00 am

Nonstop2h 00m

New York LaGuardia

Wed 9/3

9:35 pm-10:55 pm

Nonstop2h 20m

$137

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Tue 9/2

11:35 am-2:58 pm

Nonstop2h 23m

New York John F Kennedy Intl

Tue 9/2

8:30 pm-10:28 pm

Nonstop2h 58m

$137

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Sat 8/2

5:07 pm-12:44 am

1 stop6h 37m

Newark

Wed 8/6

11:04 am-4:04 pm

1 stop6h 00m

$144

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Mon 9/15

5:04 pm-12:34 am

1 stop6h 30m

Newark

Sun 9/21

11:15 am-3:58 pm

1 stop5h 43m

$145

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

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 December is currently the most expensive (average of $351). 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 July 1, 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 July 1, 2025.

The most flights from CHI to USCT are scheduled on a Monday (23 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 on average).

How much does it cost to fly round-trip from Chicago to Connecticut?

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 July 1, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Chicago to Connecticut by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,273 reviews

Boarding

8.2

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,273 reviews
Southwest
8.0
Very good
4,273 reviews

Boarding

8.2

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,973 reviews
Southwest
8.0
Very good
4,273 reviews

Boarding

8.2

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,858 reviews
Southwest
8.0
Very good
4,273 reviews

Boarding

8.2

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
JetBlue
7.3
Good
2,919 reviews
Southwest
8.0
Very good
4,273 reviews

Boarding

8.2

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,273 reviews

Boarding

8.2

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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?

    $66 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 Frontier and JetBlue, with prices starting from $67 and $77, 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 SkyWest Airlines (86%), Envoy Air (84%) or Air New Zealand (82%) 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 $322, our data shows the cheapest flight currently is $78. When looking at the most popular route, (Chicago O'Hare Intl - New York John F Kennedy Intl), you can expect to pay $144 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 December is currently the most expensive (average of $351). 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 4 airlines flying from Chicago to Connecticut

Discover the top 4 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 July 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$84Average$169FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$192Average$367FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$197Average$351FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$235Average$419FlexibilityNo cancel feeOn-time69%

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