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$94+ 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 7/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BDL
Aug 10 — Aug 171
Mon 8/10
Mon 8/17
1 adult, Economy
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Cheap 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 11, 2026.

This Southwest deal was found by Cheapflights users on 7/6. 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.
Fri 10/305:10 pm
MDW
-
LGA
Nonstop2h 05m
Southwest
Tue 11/37:00 am
LGA
-
MDW
1 stop6h 55m
Southwest
Deal found 7/6$184
This Southwest deal was found by Cheapflights users on 7/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/58:50 am
MDW
-
LGA
2 stops7h 15m
Southwest
Sat 9/197:00 am
LGA
-
MDW
2 stops7h 20m
Southwest
Deal found 7/8$185
This Cheapflightsfares deal was found by Cheapflights users on 7/7. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/259:40 am
ORD
-
JFK
Nonstop2h 19m
JetBlue
Wed 9/23:40 pm
JFK
-
ORD
Nonstop2h 55m
JetBlue
Deal found 7/7$185
This American Airlines deal was found by Cheapflights users on 7/10. 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 7/306:00 am
ORD
-
LGA
Nonstop2h 17m
American Airlines
Tue 8/116:10 am
LGA
-
ORD
Nonstop2h 49m
American Airlines
Deal found 7/10$186
This Southwest deal was found by Cheapflights users on 7/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:15 am
MDW
-
LGA
1 stop5h 40m
Southwest
Sat 8/228:20 am
LGA
-
MDW
1 stop6h 45m
Southwest
Deal found 7/9$186
This JetBlue deal was found by Cheapflights users on 7/10. 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.
Wed 8/196:30 pm
ORD
-
JFK
Nonstop2h 36m
JetBlue
Fri 8/218:00 pm
JFK
-
ORD
Nonstop2h 58m
JetBlue
Deal found 7/10$186
This United Airlines deal was found by Cheapflights users on 7/6. 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.
Tue 8/117:00 am
ORD
-
LGA
Nonstop2h 17m
United Airlines
Sat 8/159:27 pm
LGA
-
ORD
Nonstop2h 32m
United Airlines
Deal found 7/6$187
This Southwest deal was found by Cheapflights users on 7/10. 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.
Sat 8/87:45 am
MDW
-
LGA
1 stop8h 20m
Southwest
Mon 8/106:00 am
LGA
-
MDW
Nonstop2h 15m
Southwest
Deal found 7/10$187
This Delta deal was found by Cheapflights users on 7/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/46:00 am
ORD
-
JFK
Nonstop2h 24m
Delta
Tue 8/117:35 pm
JFK
-
ORD
Nonstop3h 17m
Delta
Deal found 7/7$187
This United Airlines deal was found by Cheapflights users on 7/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/97:45 pm
ORD
-
LGA
Nonstop2h 25m
United Airlines
Sat 10/178:27 pm
LGA
-
ORD
Nonstop2h 44m
United Airlines
Deal found 7/8$188
This Southwest deal was found by Cheapflights users on 7/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/65:00 am
MDW
-
LGA
Nonstop2h 00m
Southwest
Mon 8/108:35 am
LGA
-
MDW
1 stop7h 50m
Southwest
Deal found 7/8$188
This Super.com deal was found by Cheapflights users on 7/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/109:42 am
ORD
-
JFK
Nonstop2h 17m
JetBlue
Wed 8/128:00 pm
JFK
-
ORD
Nonstop2h 58m
JetBlue
Deal found 7/9$188

Find 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 11, 2026.

Round-trip from

$184
(Southwest)

One-way from

$94
(United Airlines)

Popular in

April

Cheapest in

October

Average price

$457

Good round-trip deal

$155 or less

Good one-way deal

$117 or less
From Chicago (CHI) to Connecticut
Search Deals
One-way flight from Chicago (CHI) to Connecticut
Search Deals
Highest demand for flights based on searches. 20% potential increase in price ($101 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Connecticut.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Connecticut.
Search Deals

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 11, 2026.
Use the filters below to find and compare flights from Chicago to Connecticut that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Tue 8/18

6:00 am-9:24 am

Nonstop2h 24m

New York John F Kennedy Intl

Tue 8/25

7:33 am-9:27 am

Nonstop2h 54m

$187

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Sun 9/13

5:25 am-8:25 am

Nonstop2h 00m

New York LaGuardia

Wed 9/16

6:55 am-1:30 pm

1 stop7h 35m

$188

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Thu 8/6

5:00 am-8:00 am

Nonstop2h 00m

New York LaGuardia

Mon 8/10

8:35 am-3:25 pm

1 stop7h 50m

$188

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Sat 9/5

7:45 pm-11:10 pm

Nonstop2h 25m

New York LaGuardia

Mon 9/7

8:05 am-9:45 am

Nonstop2h 40m

$189

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Fri 8/21

8:12 pm-11:44 pm

Nonstop2h 32m

New York LaGuardia

Mon 9/7

6:00 am-7:29 am

Nonstop2h 29m

$189

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Sat 8/1

4:22 pm-12:10 am

1 stop6h 48m

Newark

Wed 8/26

6:00 am-9:17 am

1 stop4h 17m

$192

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Sat 8/22

7:05 am-10:19 am

Nonstop2h 14m

New York LaGuardia

Thu 8/27

6:00 am-7:29 am

Nonstop2h 29m

$197

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Sat 8/29

7:05 am-10:19 am

Nonstop2h 14m

New York LaGuardia

Sun 8/30

5:00 pm-7:12 pm

Nonstop3h 12m

$201

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Fri 8/28

5:27 pm-9:00 pm

Nonstop2h 33m

New York John F Kennedy Intl

Mon 8/31

2:29 pm-4:17 pm

Nonstop2h 48m

$207

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Fri 8/14

12:00 pm-3:17 pm

Nonstop2h 17m

New York LaGuardia

Fri 8/21

3:29 pm-5:14 pm

Nonstop2h 45m

$207

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/10

Showing 1-10 of 60 resultsSorted by cheapest first
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2
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6

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, September is the cheapest month in which you can book a flight from Chicago to Connecticut (average of $23). Flying from Chicago to Connecticut in March is currently the most expensive (average of $158). 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 11, 2026.

It’s typically best to fly out from Chicago to Connecticut in the morning. Doing so could potentially save you 21% on the flight price compared to flying at noon, which is usually more expensive.

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 11, 2026.

The most flights from CHI to USCT are scheduled on a Monday (22 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (19 on average).

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

How far ahead should I book a flight from Chicago to Connecticut?

The price you pay for your flight from Chicago to Connecticut may vary depending on when you book. For the best chance of a lower fare, look to book 67 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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 July 11, 2026.

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

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 11, 2026.
Get a feel of what it's like to fly with Southwest,Avelo Airlines, andUnited 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
7.9
Good
4,251 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.
Southwest
7.9
Good
4,251 reviews
Southwest
7.9
Good
4,251 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.
Avelo Airlines
7.5
Good
Southwest
7.9
Good
4,251 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.
United Airlines
7.4
Good
9,981 reviews
Southwest
7.9
Good
4,251 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.
American Airlines
7.1
Good
11,805 reviews
Southwest
7.9
Good
4,251 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.

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?

    Delta, Southwest, and United Airlines can get you from Chicago to Connecticut in just under 2h. 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?

    $68 is the cheapest one-way deal found within the past few days, from Avelo Airlines. You may also be able to find cheap deals on Frontier and American Airlines, with prices starting from $88 and $108, 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 (94%), United Airlines (84%) or Envoy Air (83%) 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 $379, our data shows the cheapest flight currently is $180. When looking at the most popular route, (Chicago O'Hare Intl - New York John F Kennedy Intl), you can expect to pay $128 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, September is the cheapest month in which you can book a flight from Chicago to Connecticut (average of $23). Flying from Chicago to Connecticut in March is currently the most expensive (average of $158). 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 5 airlines flying from Chicago to Connecticut

Discover the top 5 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 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$84Average$150FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$177Average$417FlexibilityNo cancel feeOn-time71%
FrontierCheapest$185Average$230FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$201Average$435FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$248Average$373FlexibilityNo cancel feeOn-time63%

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