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$69+ 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 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BDL
Nov 9 — Nov 161
Sun 11/9
Sun 11/16
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 October 10, 2025.

Round-trip from

$104
(Cheapflightsfares)

One-way from

$69
(United Airlines)

Popular in

December

Cheapest in

August

Average price

$348

Good round-trip deal

$104 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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Highest demand for flights based on searches. 12% potential increase in price ($52 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 October 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 October 10, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 10/9. 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 10/2311:13 amORD - LGA
Nonstop1h 55mSpirit Airlines
Wed 10/299:59 amLGA - ORD
1 stop12h 34mSpirit Airlines
Deal found 10/9$104
This Cheapflightsfares deal was found by Cheapflights users on 10/9. 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 11/46:40 amORD - JFK
Nonstop2h 23mFrontier
Tue 11/116:20 amJFK - ORD
1 stop5h 54mFrontier
Deal found 10/9$104
This Cheapflightsfares deal was found by Cheapflights users on 10/9. 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 10/2111:13 amORD - LGA
Nonstop1h 55mSpirit Airlines
Fri 10/243:29 pmLGA - ORD
Nonstop2h 44mSpirit Airlines
Deal found 10/9$105
This Frontier deal was found by Cheapflights users on 10/9. 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 10/286:40 amORD - JFK
Nonstop2h 23mFrontier
Fri 10/319:00 amJFK - ORD
1 stop8h 56mFrontier
Deal found 10/9$105
This Cheapflightsfares deal was found by Cheapflights users on 10/9. 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 11/87:34 pmORD - LGA
Nonstop2h 08mSpirit Airlines
Sat 11/156:00 pmLGA - ORD
1 stop7h 27mSpirit Airlines
Deal found 10/9$106
This Gotogate deal was found by Cheapflights users on 10/8. 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.
Sat 11/86:40 amORD - JFK
Nonstop2h 23mFrontier
Mon 11/101:08 pmJFK - ORD
1 stop12h 51mFrontier
Deal found 10/8$106
This Trip.com deal was found by Cheapflights users on 10/7. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/811:35 amORD - LGA
Nonstop2h 01mSpirit Airlines
Tue 11/1110:59 amLGA - ORD
1 stop14h 28mSpirit Airlines
Deal found 10/7$108
This Frontier deal was found by Cheapflights users on 10/9. 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 11/612:30 pmMDW - LGA
1 stop8h 30mFrontier
Wed 11/126:24 amLGA - MDW
1 stop7h 17mFrontier
Deal found 10/9$108
This Gotogate deal was found by Cheapflights users on 10/9. 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.
Thu 11/61:37 pmMDW - JFK
1 stop9h 56mFrontier
Thu 11/131:05 pmJFK - MDW
1 stop8h 39mFrontier
Deal found 10/9$108
This Mytrip deal was found by Cheapflights users on 10/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/255:45 pmORD - JFK
1 stop5h 48mFrontier
Mon 10/271:00 pmJFK - ORD
1 stop12h 59mFrontier
Deal found 10/9$108
This Kiwi.com deal was found by Cheapflights users on 10/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2511:12 amORD - LGA
Nonstop1h 55mSpirit Airlines
Wed 10/2912:59 pmLGA - ORD
Nonstop2h 46mSpirit Airlines
Deal found 10/8$109
This Booking.com deal was found by Cheapflights users on 10/9. 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.
Sat 11/82:05 pmMDW - JFK
1 stop10h 10mFrontier
Sat 11/1510:00 amJFK - MDW
1 stop9h 39mFrontier
Deal found 10/9$109

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 October 10, 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

Wed 10/22

11:00 am-2:19 pm

Nonstop2h 19m

New York LaGuardia

Wed 10/29

7:15 am-8:57 am

Nonstop2h 42m

$137

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Sat 11/15

5:40 pm-8:45 pm

Nonstop2h 05m

New York LaGuardia

Mon 11/17

9:55 pm-11:20 pm

Nonstop2h 25m

$137

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Wed 11/5

1:00 pm-4:11 pm

Nonstop2h 11m

New York LaGuardia

Wed 11/5

8:15 pm-9:57 pm

Nonstop2h 42m

$137

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Wed 10/29

12:00 pm-3:11 pm

Nonstop2h 11m

New York LaGuardia

Wed 10/29

9:15 pm-10:57 pm

Nonstop2h 42m

$137

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Fri 10/31

6:45 am-9:59 am

Nonstop2h 14m

New York John F Kennedy Intl

Mon 11/10

7:00 pm-8:52 pm

Nonstop2h 52m

$138

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Mon 11/17

6:00 am-9:00 am

Nonstop2h 00m

New York LaGuardia

Fri 11/21

9:00 am-10:25 am

Nonstop2h 25m

$138

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Tue 10/28

7:00 am-10:15 am

Nonstop2h 15m

New York John F Kennedy Intl

Tue 10/28

7:00 pm-8:52 pm

Nonstop2h 52m

$139

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 12/9

7:15 pm-10:20 pm

Nonstop2h 05m

New York LaGuardia

Thu 12/11

9:55 pm-11:20 pm

Nonstop2h 25m

$139

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Thu 11/27

8:20 am-11:35 am

Nonstop2h 15m

New York John F Kennedy Intl

Tue 12/2

8:00 pm-9:52 pm

Nonstop2h 52m

$139

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Wed 12/10

1:00 pm-4:11 pm

Nonstop2h 11m

New York LaGuardia

Wed 12/10

8:15 pm-9:57 pm

Nonstop2h 42m

$139

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/7

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 $120). Flying from Chicago to Connecticut in February is currently the most expensive (average of $257). 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 October 10, 2025.

It’s typically best to fly out from Chicago to Connecticut in the morning. Doing so could potentially save you 33% on the flight price compared to flying at noon, which is usually more expensive.

What is the cheapest day to fly from Chicago to Connecticut?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Connecticut. Price data was last updated on October 5, 2025.

Travelers seeking maximum savings on their Chicago to Connecticut flight should consider departing on Wednesday evenings when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 October 10, 2025.

The most flights from CHI to USCT are scheduled on a Monday (24 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (12 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 October 10, 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
4,236 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,236 reviews
Southwest
8.0
Very good
4,236 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Avelo Airlines
7.5
Good
Southwest
8.0
Very good
4,236 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,966 reviews
Southwest
8.0
Very good
4,236 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,043 reviews
Southwest
8.0
Very good
4,236 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,143 reviews
Southwest
8.0
Very good
4,236 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • How long is the flight from Chicago to Connecticut?

    United Airlines, Southwest, and JetBlue can get you from Chicago to Connecticut in just under 2h 05m. Your travel time will be generally consistent. There are 722 mi between Chicago and Connecticut. Most flights are nonstop.

  • What are the cheapest airlines to fly from Chicago to Connecticut one-way?

    $69 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on Southwest and JetBlue, with prices starting from $69 and $70, respectively.

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

    While some choose either Chicago O'Hare Intl - Newark or Chicago O'Hare Intl - New York LaGuardia, 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 (90%) or Envoy Air (87%) 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 $268, our data shows the cheapest flight currently is $88. When looking at the most popular route, (Chicago O'Hare Intl - New York John F Kennedy Intl), you can expect to pay $58 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 $120). Flying from Chicago to Connecticut in February is currently the most expensive (average of $257). 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.
O'Hare Intl to John F Kennedy Intl flights
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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 October 10, 2025.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$85Average$138FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$177Average$371FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$197Average$330FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$204Average$407FlexibilityNo cancel feeOn-time69%

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