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$51+ 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 2/20. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — ORD
Jan 15 — Jan 221
Thu 1/15
Thu 1/22
1 adult, Economy
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Cheap 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 December 16, 2025.

This Super.com deal was found by Cheapflights users on 12/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:37 pmLGA - ORD
Nonstop2h 30mSpirit Airlines
Tue 1/64:38 pmORD - LGA
Nonstop2h 04mSpirit Airlines
Deal found 12/15$84
This Cheapflightsfares deal was found by Cheapflights users on 12/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:37 pmLGA - ORD
Nonstop2h 30mSpirit Airlines
Mon 1/54:38 pmORD - LGA
Nonstop2h 04mSpirit Airlines
Deal found 12/14$102
This Kiwi.com deal was found by Cheapflights users on 12/15. 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.
Wed 12/316:55 amEWR - ORD
Nonstop2h 36mSpirit Airlines
Tue 1/69:34 amORD - EWR
Nonstop2h 16mSpirit Airlines
Deal found 12/15$111
This Kiwi.com deal was found by Cheapflights users on 12/15. 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.
Thu 12/256:55 amEWR - ORD
Nonstop2h 36mSpirit Airlines
Mon 1/59:34 amORD - EWR
Nonstop2h 16mSpirit Airlines
Deal found 12/15$116
This Super.com deal was found by Cheapflights users on 12/13. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/276:55 amEWR - ORD
Nonstop2h 36mSpirit Airlines
Sat 1/104:38 pmORD - EWR
Nonstop2h 08mSpirit Airlines
Deal found 12/13$120
This Super.com deal was found by Cheapflights users on 12/14. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3111:00 amJFK - ORD
Nonstop2h 57mFrontier
Mon 1/56:40 amORD - JFK
Nonstop2h 24mFrontier
Deal found 12/14$121
This Priceline deal was found by Cheapflights users on 12/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/286:55 amEWR - ORD
Nonstop2h 36mSpirit Airlines
Thu 1/84:38 pmORD - EWR
Nonstop2h 08mSpirit Airlines
Deal found 12/14$121
This Kiwi.com deal was found by Cheapflights users on 12/15. 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.
Wed 12/316:55 amEWR - ORD
Nonstop2h 36mSpirit Airlines
Thu 1/88:43 pmORD - EWR
1 stop13h 59mSpirit Airlines
Deal found 12/15$123
This Cheapflightsfares deal was found by Cheapflights users on 12/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:55 amEWR - ORD
Nonstop2h 36mSpirit Airlines
Sat 1/39:34 amORD - EWR
Nonstop2h 16mSpirit Airlines
Deal found 12/14$124
This Super.com deal was found by Cheapflights users on 12/14. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3111:00 amJFK - ORD
Nonstop2h 57mFrontier
Sat 1/36:40 amORD - JFK
Nonstop2h 24mFrontier
Deal found 12/14$127
This Frontier deal was found by Cheapflights users on 12/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/2611:00 amJFK - ORD
Nonstop2h 57mFrontier
Sat 1/108:35 amORD - JFK
Nonstop2h 24mFrontier
Deal found 12/14$128
This CheapOair deal was found by Cheapflights users on 12/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/236:00 amLGA - ORD
1 stop13h 39mSpirit Airlines
Sun 1/115:53 pmORD - LGA
Nonstop2h 06mSpirit Airlines
Deal found 12/15$130

Find flight deals from Connecticut to Illinois

Keep the following information in mind while searching for Connecticut to Illinois flight deals. Data was last updated December 16, 2025.

Round-trip from

$83
(Frontier)

One-way from

$51
(CheapOair)

Popular in

May

Cheapest in

October

Average price

$367

Good round-trip deal

$95 or less

Good one-way deal

$45 or less
From Connecticut to Illinois
Search Deals
One-way flight from Connecticut to Illinois
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($42 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Connecticut to Illinois.
Search Deals
Price to beat on a one-way flight from Connecticut to Illinois.
Search Deals

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 December 16, 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

NewarkChicago

EWR - ORD

EWRORD

Newark

Sun 1/18

9:05 pm-10:42 pm

Nonstop2h 37m

Chicago O'Hare Intl

Tue 1/20

10:48 am-11:27 pm

1 stop11h 39m

$107

NewarkChicago

EWR - ORD

EWRORD

Newark

Tue 1/20

1:00 pm-11:46 pm

1 stop11h 46m

Chicago O'Hare Intl

Thu 1/22

8:43 pm-11:42 am

1 stop13h 59m

$119

NewarkChicago

EWR - ORD

EWRORD

Newark

Wed 5/13

9:05 pm-10:43 pm

Nonstop2h 38m

Chicago O'Hare Intl

Sun 5/17

4:47 pm-7:55 pm

Nonstop2h 08m

$120

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Mon 3/2

6:00 am-6:52 pm

1 stop13h 52m

Chicago O'Hare Intl

Wed 3/4

12:44 pm-10:38 pm

1 stop8h 54m

$124

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 2/19

9:55 am-7:45 pm

1 stop10h 50m

Chicago O'Hare Intl

Fri 2/20

5:58 pm-8:59 pm

Nonstop2h 01m

$127

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Fri 5/8

8:48 pm-9:12 am

1 stop13h 24m

Chicago O'Hare Intl

Mon 5/11

9:04 am-12:04 pm

Nonstop2h 00m

$137

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sat 1/17

7:00 pm-8:53 pm

Nonstop2h 53m

Chicago O'Hare Intl

Thu 1/22

7:01 am-10:30 am

Nonstop2h 29m

$139

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 1/15

6:00 am-7:40 am

Nonstop2h 40m

Chicago Midway

Sun 1/18

7:15 pm-10:20 pm

Nonstop2h 05m

$139

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sun 1/18

7:50 am-9:49 am

Nonstop2h 59m

Chicago O'Hare Intl

Tue 1/20

1:57 pm-5:30 pm

Nonstop2h 33m

$139

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Mon 1/19

7:50 am-9:49 am

Nonstop2h 59m

Chicago O'Hare Intl

Wed 1/21

6:25 pm-9:59 pm

Nonstop2h 34m

$139

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/14

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, September is the cheapest month in which you can book a flight from Connecticut to Illinois (average of $115). Flying from Connecticut to Illinois in December is currently the most expensive (average of $234). 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 December 16, 2025.

One of the essential ways to save on airfare from Connecticut to Illinois is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 28% on airfare.

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

Use this chart to determine the cheapest time to fly round-trip from Connecticut to Illinois. Price data was last updated on December 16, 2024.

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

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 December 16, 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
7.9
Good
4,250 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

7.9

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

7.9

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Avelo Airlines
7.5
Good
Southwest
7.9
Good
4,250 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

7.9

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,094 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

7.9

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,048 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

7.9

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.8
Fair
3,082 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

7.9

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 37m. Fly via Spirit Airlines, Delta, or Southwest to get the fastest option. The distance between Connecticut and Illinois is about 716 mi. Most flights are nonstop.

  • 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 $39 on Avelo Airlines. Other airlines that offer cheap prices include Southwest from $68 and Frontier from $69 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, September is the cheapest month in which you can book a flight from Connecticut to Illinois (average of $115). Flying from Connecticut to Illinois in December is currently the most expensive (average of $234). 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 6 airlines flying from Connecticut to Illinois

Discover the top 6 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 December 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$97Average$232FlexibilityNo cancel feeOn-time62%
Avelo AirlinesCheapest$104Average$199FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$176Average$287FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$177Average$374FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$177Average$372FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$218Average$391FlexibilityNo cancel feeOn-time69%

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