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$73+ 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 10/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BDL
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
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 August 18, 2025.

Round-trip from

$115
(Priceline)

One-way from

$73
(Priceline)

Popular in

December

Cheapest in

August

Average price

$265

Good round-trip deal

$157 or less

Good one-way deal

$86 or less
From Chicago (CHI) to Connecticut
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One-way flight from Chicago (CHI) to Connecticut
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Highest demand for flights based on searches. 8% potential increase in price ($33 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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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 August 18, 2025.

This Priceline deal was found by Cheapflights users on 8/17. 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 9/47:40 amORD - LGA
1 stop7h 49mMultiple Airlines
Sat 9/63:12 pmLGA - ORD
Nonstop2h 38mMultiple Airlines
Deal found 8/17$115
This FlightHub deal was found by Cheapflights users on 8/16. 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.
Wed 10/156:40 amORD - JFK
Nonstop2h 23mFrontier
Fri 10/1711:00 amJFK - ORD
Nonstop2h 45mFrontier
Deal found 8/16$115
This Cheapflightsfares deal was found by Cheapflights users on 8/16. 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 11/136:40 amORD - JFK
Nonstop2h 23mFrontier
Mon 11/1711:00 amJFK - ORD
Nonstop2h 45mFrontier
Deal found 8/16$116
This Cheapflightsfares deal was found by Cheapflights users on 8/17. 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 9/2011:57 amORD - LGA
1 stop10h 28mSpirit Airlines
Sat 9/276:00 amLGA - ORD
1 stop12h 39mSpirit Airlines
Deal found 8/17$117
This Booking.com deal was found by Cheapflights users on 8/17. 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.
Wed 10/111:45 amORD - JFK
1 stop12h 23mFrontier
Wed 10/811:00 amJFK - ORD
Nonstop2h 45mFrontier
Deal found 8/17$117
This Priceline deal was found by Cheapflights users on 8/17. 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 10/186:40 amORD - JFK
Nonstop2h 23mFrontier
Mon 10/2011:00 amJFK - ORD
Nonstop2h 45mFrontier
Deal found 8/17$119
This Priceline deal was found by Cheapflights users on 8/16. 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 9/1311:57 amORD - LGA
1 stop10h 28mMultiple Airlines
Mon 9/156:30 amLGA - ORD
1 stop10h 20mMultiple Airlines
Deal found 8/16$120
This Frontier deal was found by Cheapflights users on 8/17. 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.
Thu 10/306:40 amORD - JFK
Nonstop2h 23mFrontier
Sun 11/211:00 amJFK - ORD
Nonstop2h 45mFrontier
Deal found 8/17$120
This Cheapflightsfares deal was found by Cheapflights users on 8/17. 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 9/134:35 pmORD - LGA
Nonstop2h 06mSpirit Airlines
Sun 9/147:59 pmLGA - ORD
1 stop14h 19mSpirit Airlines
Deal found 8/17$121
This Cheapflightsfares deal was found by Cheapflights users on 8/17. 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.
Wed 10/86:40 amORD - JFK
Nonstop2h 23mFrontier
Mon 10/1311:00 amJFK - ORD
Nonstop2h 45mFrontier
Deal found 8/17$121
This FlightHub deal was found by Cheapflights users on 8/16. 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.
Fri 9/55:05 amORD - LGA
1 stop9h 54mSpirit Airlines
Sat 9/610:59 amLGA - ORD
1 stop7h 40mSpirit Airlines
Deal found 8/16$122
This Cheapflightsfares deal was found by Cheapflights users on 8/17. 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 10/176:40 amORD - JFK
Nonstop2h 23mFrontier
Mon 10/2011:00 amJFK - ORD
Nonstop2h 45mFrontier
Deal found 8/17$122

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 August 18, 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

Thu 9/4

7:40 am-4:29 pm

1 stop7h 49m

New York LaGuardia

Tue 9/9

10:59 am-5:39 pm

1 stop7h 40m

$115

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Tue 9/16

10:27 am-11:03 pm

1 stop11h 36m

New York LaGuardia

Tue 9/23

11:30 am-5:39 pm

1 stop7h 09m

$115

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Sat 9/13

4:35 pm-7:41 pm

Nonstop2h 06m

New York LaGuardia

Sat 9/13

10:56 pm-9:37 am

1 stop11h 41m

$120

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Wed 9/17

10:27 am-11:03 pm

1 stop11h 36m

New York LaGuardia

Mon 9/22

6:30 am-3:50 pm

1 stop10h 20m

$120

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Fri 9/5

10:27 am-11:03 pm

1 stop11h 36m

New York LaGuardia

Wed 9/10

9:59 am-9:58 pm

1 stop12h 59m

$122

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Sat 11/1

6:40 am-10:03 am

Nonstop2h 23m

New York John F Kennedy Intl

Tue 11/4

11:00 am-12:45 pm

Nonstop2h 45m

$122

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Sat 9/6

11:57 am-9:05 pm

1 stop8h 08m

New York LaGuardia

Mon 9/15

3:13 pm-4:51 pm

Nonstop2h 38m

$123

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Tue 9/9

10:27 am-11:03 pm

1 stop11h 36m

New York LaGuardia

Mon 9/15

3:13 pm-4:51 pm

Nonstop2h 38m

$123

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Wed 10/22

11:13 am-2:08 pm

Nonstop1h 55m

New York LaGuardia

Sun 10/26

8:29 am-10:13 am

Nonstop2h 44m

$123

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Wed 9/10

5:05 am-3:59 pm

1 stop9h 54m

New York LaGuardia

Mon 9/15

3:13 pm-4:51 pm

Nonstop2h 38m

$123

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/16

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 August 18, 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 August 18, 2025.

The most flights from CHI to USCT are scheduled on a Friday (24 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (9 on average).

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 August 18, 2025.
Get a feel of what it's like to fly with Southwest, Avelo Airlines, 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
4,246 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Avelo Airlines
7.5
Good
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
8,925 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Frontier
5.8
Fair
3,212 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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?

    $73 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on United Airlines and JetBlue, with prices starting from $74 and $78, 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 (95%), United Airlines (87%) or Envoy Air (85%) 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 $68. When looking at the most popular route, (Chicago O'Hare Intl - New York John F Kennedy Intl), you can expect to pay $75 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.

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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 August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$88Average$136FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$154Average$367FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$197Average$350FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$232Average$418FlexibilityNo cancel feeOn-time69%

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