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$56+ Cheap flights from Illinois 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 5/16. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BDL
Apr 24 — May 11
Fri 4/24
Fri 5/1
1 adult, Economy
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Cheap flight deals from Illinois to Connecticut

Cheapest flights from Illinois to Connecticut
Explore the most affordable flight options available from Illinois to Connecticut. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 25, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 3/20. 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 5/122:09 pm
ORD
-
LGA
Nonstop2h 11m
Spirit Airlines
Wed 5/136:15 pm
LGA
-
ORD
Nonstop2h 42m
Spirit Airlines
Deal found 3/20$94
This Cheapflightsfares deal was found by Cheapflights users on 3/24. 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 4/87:31 pm
ORD
-
LGA
Nonstop2h 05m
Spirit Airlines
Mon 4/136:30 am
LGA
-
ORD
Nonstop2h 31m
Spirit Airlines
Deal found 3/24$101
This Cheapflightsfares deal was found by Cheapflights users on 3/25. 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 4/212:09 pm
ORD
-
LGA
Nonstop2h 11m
Spirit Airlines
Tue 4/286:15 pm
LGA
-
ORD
Nonstop2h 42m
Spirit Airlines
Deal found 3/25$102
This Cheapflightsfares deal was found by Cheapflights users on 3/21. 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 5/82:09 pm
ORD
-
LGA
Nonstop2h 11m
Spirit Airlines
Mon 5/116:15 pm
LGA
-
ORD
Nonstop2h 42m
Spirit Airlines
Deal found 3/21$103
This Priceline deal was found by Cheapflights users on 3/20. 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.
Tue 4/142:15 pm
MDW
-
EWR
1 stop10h 01m
Frontier
Tue 4/2111:30 am
EWR
-
MDW
Nonstop2h 30m
Frontier
Deal found 3/20$103
This Cheapflightsfares deal was found by Cheapflights users on 3/22. 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 3/316:01 pm
ORD
-
EWR
Nonstop2h 08m
Spirit Airlines
Fri 4/1010:54 pm
EWR
-
ORD
Nonstop2h 28m
Spirit Airlines
Deal found 3/22$103
This Mytrip deal was found by Cheapflights users on 3/21. 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.
Thu 4/167:30 am
MDW
-
EWR
Nonstop2h 08m
Frontier
Sun 4/1911:30 am
EWR
-
MDW
Nonstop2h 30m
Frontier
Deal found 3/21$104
This CheapOair deal was found by Cheapflights users on 3/24. 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 4/86:01 pm
ORD
-
EWR
Nonstop2h 08m
Spirit Airlines
Sat 4/1110:54 pm
EWR
-
ORD
Nonstop2h 28m
Spirit Airlines
Deal found 3/24$104
This Kiwi.com deal was found by Cheapflights users on 3/21. 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.
Thu 4/167:30 am
MDW
-
EWR
Nonstop2h 08m
Frontier
Fri 4/2411:30 am
EWR
-
MDW
Nonstop2h 30m
Frontier
Deal found 3/21$105
This Super.com deal was found by Cheapflights users on 3/21. 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.
Sat 4/47:31 pm
ORD
-
LGA
Nonstop2h 05m
Spirit Airlines
Fri 4/106:30 am
LGA
-
ORD
Nonstop2h 31m
Spirit Airlines
Deal found 3/21$106
This Kiwi.com deal was found by Cheapflights users on 3/24. 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.
Thu 4/167:30 am
MDW
-
EWR
Nonstop2h 08m
Frontier
Thu 4/2311:30 am
EWR
-
MDW
Nonstop2h 30m
Frontier
Deal found 3/24$107
This Frontier deal was found by Cheapflights users on 3/21. 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.
Sat 4/187:30 am
MDW
-
EWR
Nonstop2h 08m
Frontier
Fri 4/2411:30 am
EWR
-
MDW
Nonstop2h 30m
Frontier
Deal found 3/21$108

Find flight deals from Illinois to Connecticut

Keep the following information in mind while searching for Illinois to Connecticut flight deals. Data was last updated March 25, 2026.

Round-trip from

$94
(Cheapflightsfares)

One-way from

$56
(Mytrip)

Popular in

March

Cheapest in

August

Average price

$453

Good round-trip deal

$142 or less

Good one-way deal

$114 or less
From Illinois to Connecticut
Search Deals
One-way flight from Illinois to Connecticut
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($74 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals
Price to beat on a round-trip flight from Illinois to Connecticut.
Search Deals
Price to beat on a one-way flight from Illinois to Connecticut.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois 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 25, 2026.
Use the filters below to find and compare flights from Illinois to Connecticut that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Sat 4/18

5:30 am-8:30 am

Nonstop2h 00m

New York LaGuardia

Wed 4/22

7:25 am-8:50 am

Nonstop2h 25m

$161

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Sat 5/16

10:10 pm-1:30 am

Nonstop2h 20m

Newark

Tue 5/19

7:52 pm-9:40 pm

Nonstop2h 48m

$169

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Tue 6/16

2:09 pm-5:20 pm

Nonstop2h 11m

New York LaGuardia

Sat 6/20

6:01 pm-7:32 pm

Nonstop2h 31m

$174

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Thu 4/16

6:04 am-9:29 am

Nonstop2h 25m

New York John F Kennedy Intl

Mon 4/20

7:36 pm-9:57 pm

Nonstop3h 21m

$177

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Wed 4/22

12:50 pm-4:08 pm

Nonstop2h 18m

New York LaGuardia

Sun 4/26

7:10 am-8:49 am

Nonstop2h 39m

$178

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Mon 6/1

7:50 pm-10:55 pm

Nonstop2h 05m

New York LaGuardia

Wed 6/3

12:35 pm-8:10 pm

2 stops8h 35m

$186

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Thu 5/28

7:10 am-10:30 am

Nonstop2h 20m

Newark

Sun 5/31

6:00 am-7:42 am

Nonstop2h 42m

$188

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Mon 4/27

7:50 pm-10:55 pm

Nonstop2h 05m

New York LaGuardia

Fri 5/1

6:00 am-7:25 am

Nonstop2h 25m

$189

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Tue 4/21

12:00 pm-3:15 pm

Nonstop2h 15m

New York LaGuardia

Tue 4/21

8:25 pm-10:15 pm

Nonstop2h 50m

$197

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Fri 5/1

7:44 pm-10:59 pm

Nonstop2h 15m

New York LaGuardia

Sun 5/10

7:30 am-9:11 am

Nonstop2h 41m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/24

Showing 1-10 of 60 resultsSorted by cheapest first
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6

Best time to book a flight from Illinois to Connecticut

Have a flexible travel schedule? Discover the best time to fly to Connecticut from Illinois 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 Illinois to Connecticut

What is the cheapest month to book a flight from Illinois to Connecticut?

Currently, September is the cheapest month in which you can book a flight from Illinois to Connecticut (average of $23). Flying from Illinois to Connecticut in March is currently the most expensive (average of $314). 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 IL to CT?

Find hourly flight availability from Illinois 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 25, 2026.

One of the essential ways to save on airfare from Illinois to Connecticut is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 24% on airfare.

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

Use this chart to determine the cheapest time to fly round-trip from Illinois to Connecticut. Price data was last updated on March 23, 2026.

Travelers seeking maximum savings on their Illinois 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.

Weekly flight availability from Illinois to Connecticut

Explore weekly flight availability from Illinois 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 25, 2026.

The most flights from USIL to USCT are scheduled on a Monday (18 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (4 on average).

How much does it cost to fly round-trip from Illinois 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 March 25, 2026.
Read reviews from past customers who have flown Southwest,Avelo Airlines, andUnited Airlines from Illinois to Connecticut. 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
4,332 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,332 reviews
Southwest
8.0
Very good
4,332 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Avelo Airlines
7.6
Good
Southwest
8.0
Very good
4,332 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,476 reviews
Southwest
8.0
Very good
4,332 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,493 reviews
Southwest
8.0
Very good
4,332 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Related info for your journey

Find useful and relevant information for your journey from Illinois 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 Illinois to Connecticut?

    A quick flight from Illinois to Connecticut can take about 2h. Southwest provides one of the quickest options available for as low as $161. The distance from Illinois to Connecticut is about 722 mi. Generally, flights for this route are nonstop.

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

    To fly one-way, consider booking your trip with Avelo Airlines, which is currently one of the cheapest options available, starting at $37. Frontier flights start at $52 while deals on Southwest start at $68 one-way.

  • Can I find deals for flights from Illinois to Connecticut that include hotel bookings?

    Yes. In addition to deals on Illinois to Connecticut flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Illinois to Connecticut?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Illinois to Connecticut.

  • Can I find deals for business class flights from Illinois to Connecticut?

    Yes. Cheapflights offers flight deals from Illinois 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 Illinois to Connecticut?

    Currently, September is the cheapest month in which you can book a flight from Illinois to Connecticut (average of $23). Flying from Illinois to Connecticut in March is currently the most expensive (average of $314). 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 Illinois 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 Illinois to Connecticut

Discover the top 4 airlines that operate flights from Illinois 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 25, 2026.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$78Average$141FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$177Average$352FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$199Average$359FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$240Average$350FlexibilityNo cancel feeOn-time63%

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