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$70+ Cheap flights from Connecticut to Illinois

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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — ORD
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Connecticut to Illinois

Keep the following information in mind while searching for Connecticut to Illinois flight deals. Data was last updated September 15, 2025.

Round-trip from

$127
(Kiwi.com)

One-way from

$70
(American Airlines)

Popular in

April

Cheapest in

August

Average price

$317

Good round-trip deal

$178 or less

Good one-way deal

$77 or less
From Connecticut to Illinois
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One-way flight from Connecticut to Illinois
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Highest demand for flights based on searches. 5% potential increase in price ($18 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Connecticut to Illinois.
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Price to beat on a one-way flight from Connecticut to Illinois.
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Find flight deals from Connecticut to Illinois

Cheapest flights from Connecticut to Illinois
Explore the most affordable flight options available from Connecticut to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Tue 10/711:59 amLGA - ORD
1 stop7h 39mSpirit Airlines
Wed 10/1511:13 amORD - LGA
Nonstop1h 55mSpirit Airlines
Deal found 9/15$127
This Trip.com deal was found by Cheapflights users on 9/15. 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.
Wed 10/19:00 amJFK - ORD
1 stop9h 39mFrontier
Wed 10/86:40 amORD - JFK
Nonstop2h 23mFrontier
Deal found 9/15$128
This Priceline deal was found by Cheapflights users on 9/15. 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 10/89:59 amLGA - ORD
1 stop8h 54mMultiple Airlines
Thu 10/96:00 amORD - LGA
1 stop9h 29mMultiple Airlines
Deal found 9/15$128
This Frontier deal was found by Cheapflights users on 9/15. 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.
Wed 10/1511:00 amJFK - ORD
Nonstop2h 45mFrontier
Fri 10/1712:28 pmORD - JFK
1 stop11h 05mFrontier
Deal found 9/15$129
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Fri 9/2612:56 pmLGA - ORD
1 stop7h 48mMultiple Airlines
Thu 10/212:05 pmORD - LGA
1 stop7h 24mMultiple Airlines
Deal found 9/15$129
This Booking.com deal was found by Cheapflights users on 9/15. 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 10/811:00 amJFK - ORD
Nonstop2h 45mFrontier
Thu 10/99:24 amORD - JFK
1 stop24h 00mFrontier
Deal found 9/15$130
This Priceline deal was found by Cheapflights users on 9/15. 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 9/2612:56 pmLGA - ORD
1 stop7h 48mMultiple Airlines
Mon 9/2910:27 amORD - LGA
1 stop11h 36mMultiple Airlines
Deal found 9/15$130
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 10/13:13 pmLGA - ORD
Nonstop2h 38mSpirit Airlines
Thu 10/910:27 amORD - LGA
1 stop11h 14mSpirit Airlines
Deal found 9/15$131
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Fri 12/1211:00 amJFK - ORD
Nonstop2h 45mFrontier
Wed 12/176:40 amORD - JFK
Nonstop2h 23mFrontier
Deal found 9/14$132
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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.
Mon 10/203:29 pmLGA - ORD
Nonstop2h 44mSpirit Airlines
Wed 10/2211:13 amORD - LGA
Nonstop1h 55mSpirit Airlines
Deal found 9/13$132
This JetBlue deal was found by Cheapflights users on 9/12. 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.
Sat 12/138:00 pmJFK - ORD
Nonstop2h 48mJetBlue
Tue 12/167:00 amORD - JFK
Nonstop2h 13mJetBlue
Deal found 9/12$133
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 11/112:59 pmLGA - ORD
Nonstop2h 46mMultiple Airlines
Sun 11/25:11 amORD - LGA
1 stop5h 18mMultiple Airlines
Deal found 9/14$133

Cheapflights Fare Finder

 
Customize your flight search to find flights from Connecticut to Illinois 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 September 15, 2025.
Use the filters below to find and compare flights from Connecticut to Illinois that are best for you.

Fly from

Connecticut

Fly to

Illinois

Route

Depart

Return

Price

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Tue 10/21

10:30 am-12:22 pm

Nonstop2h 52m

Chicago O'Hare Intl

Wed 10/29

6:45 am-9:59 am

Nonstop2h 14m

$134

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Tue 10/14

9:00 am-10:35 am

Nonstop2h 35m

Chicago Midway

Tue 10/21

6:10 am-9:15 am

Nonstop2h 05m

$137

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Thu 2/19

7:40 pm-9:33 pm

Nonstop2h 53m

Chicago O'Hare Intl

Sat 2/21

7:00 am-10:23 am

Nonstop2h 23m

$139

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Thu 1/8

4:41 pm-6:34 pm

Nonstop2h 53m

Chicago O'Hare Intl

Mon 1/12

9:00 am-12:17 pm

Nonstop2h 17m

$139

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 10/1

10:59 am-10:48 pm

1 stop12h 49m

Chicago O'Hare Intl

Sun 10/5

6:58 pm-9:00 am

1 stop13h 02m

$142

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Mon 10/20

9:35 pm-11:05 pm

Nonstop2h 30m

Chicago Midway

Wed 10/22

6:10 am-9:15 am

Nonstop2h 05m

$142

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 11/13

9:55 pm-11:20 pm

Nonstop2h 25m

Chicago Midway

Sun 11/16

6:10 am-9:15 am

Nonstop2h 05m

$147

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Mon 9/29

7:00 pm-8:49 pm

Nonstop2h 49m

Chicago O'Hare Intl

Wed 10/8

1:20 pm-4:44 pm

Nonstop2h 24m

$147

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Mon 11/10

9:55 pm-11:20 pm

Nonstop2h 25m

Chicago Midway

Thu 11/13

8:25 pm-11:25 pm

Nonstop2h 00m

$147

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Tue 10/21

10:30 am-12:22 pm

Nonstop2h 52m

Chicago O'Hare Intl

Fri 10/24

6:45 am-9:59 am

Nonstop2h 14m

$147

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 60 results
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Best time to book a flight from Connecticut to Illinois

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

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

Currently, August is the cheapest month in which you can book a flight from Connecticut to Illinois (average of $245). Flying from Connecticut to Illinois in March is currently the most expensive (average of $321). 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 CT to IL?

Find hourly flight availability from Connecticut to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

When flying from Connecticut to Illinois, 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 Connecticut to Illinois

Explore weekly flight availability from Connecticut to Illinois. 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 September 15, 2025.

The most flights from USCT to USIL are scheduled on a Monday (20 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (15 on average).

Reviews of airlines servicing Illinois

Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated September 15, 2025.
Get a feel of what it's like to fly with Southwest, Avelo Airlines, and United Airlines from Connecticut to Illinois by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

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
4,242 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

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
8,929 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

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
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

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
3,172 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

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 Connecticut to Illinois. 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 Connecticut to Illinois?

    There are many flights that can get you from Connecticut to Illinois in 2h 35m. Fly via JetBlue, Southwest, or Spirit Airlines to get the fastest option. The distance between Connecticut and Illinois is about 722 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    One-way options have recently been found by users for as low as $70 on JetBlue. Other airlines that offer cheap prices include United Airlines from $70 and Southwest from $70 one-way.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Connecticut to Illinois (average of $245). Flying from Connecticut to Illinois in March is currently the most expensive (average of $321). 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Connecticut to Illinois

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Connecticut to Illinois

Discover the top 4 airlines that operate flights from Connecticut to Illinois. 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$115Average$207FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$177Average$384FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$185Average$400FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$231Average$391FlexibilityNo cancel feeOn-time69%

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