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$55+ 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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — ORD
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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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 October 30, 2025.

This Frontier deal was found by Cheapflights users on 10/30. 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 11/141:08 pmJFK - ORD
1 stop12h 51mFrontier
Mon 11/176:40 amORD - JFK
Nonstop2h 23mFrontier
Deal found 10/30$101
This Kiwi.com deal was found by Cheapflights users on 10/30. 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.
Sun 11/237:30 amLGA - ORD
Nonstop2h 31mSpirit Airlines
Tue 12/23:53 pmORD - LGA
Nonstop2h 07mSpirit Airlines
Deal found 10/30$101
This Booking.com deal was found by Cheapflights users on 10/30. 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.
Mon 11/176:20 amJFK - ORD
1 stop11h 36mFrontier
Tue 11/186:40 amORD - JFK
Nonstop2h 23mFrontier
Deal found 10/30$102
This Priceline deal was found by Cheapflights users on 10/29. 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 11/1412:59 pmLGA - ORD
Nonstop2h 32mSpirit Airlines
Tue 11/1810:52 amORD - LGA
1 stop7h 08mSpirit Airlines
Deal found 10/29$102
This Priceline deal was found by Cheapflights users on 10/28. 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.
Thu 11/1311:00 amJFK - ORD
Nonstop2h 45mFrontier
Sat 11/156:40 amORD - JFK
Nonstop2h 23mFrontier
Deal found 10/28$103
This Cheapflightsfares deal was found by Cheapflights users on 10/30. 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 11/88:59 amLGA - ORD
Nonstop2h 31mSpirit Airlines
Sat 11/227:21 pmORD - LGA
Nonstop2h 08mSpirit Airlines
Deal found 10/30$103
This Frontier deal was found by Cheapflights users on 10/28. 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 11/1311:00 amJFK - ORD
Nonstop2h 45mFrontier
Thu 11/206:45 pmORD - JFK
1 stop10h 16mFrontier
Deal found 10/28$104
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/612:59 pmLGA - ORD
Nonstop2h 32mSpirit Airlines
Mon 11/107:34 pmORD - LGA
Nonstop2h 08mSpirit Airlines
Deal found 10/29$104
This Priceline deal was found by Cheapflights users on 10/28. 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 12/121:00 pmJFK - ORD
Nonstop2h 57mFrontier
Sat 12/138:36 amORD - JFK
Nonstop2h 24mFrontier
Deal found 10/28$105
This Cheapflightsfares deal was found by Cheapflights users on 10/28. 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 11/2212:59 pmLGA - ORD
Nonstop2h 32mSpirit Airlines
Sat 12/612:09 pmORD - LGA
1 stop6h 51mSpirit Airlines
Deal found 10/28$105
This Mytrip deal was found by Cheapflights users on 10/28. 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.
Fri 11/711:00 amJFK - ORD
Nonstop2h 45mFrontier
Mon 11/106:40 amORD - JFK
Nonstop2h 23mFrontier
Deal found 10/28$106
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 11/2112:59 pmLGA - ORD
Nonstop2h 32mSpirit Airlines
Thu 11/273:53 pmORD - LGA
Nonstop2h 07mSpirit Airlines
Deal found 10/28$106

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 October 30, 2025.

Round-trip from

$100
(Cheapflightsfares)

One-way from

$55
(Priceline)

Popular in

December

Cheapest in

September

Average price

$319

Good round-trip deal

$351 or less

Good one-way deal

$49 or less
From Connecticut to Illinois
Search Deals
One-way flight from Connecticut to Illinois
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($14 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 October 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 October 30, 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 - MDW

JFKMDW

New York John F Kennedy Intl

Thu 11/20

1:00 pm-12:13 am

1 stop12h 13m

Chicago Midway

Thu 12/4

2:16 pm-12:07 am

1 stop8h 51m

$110

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Wed 11/19

10:50 am-12:39 pm

Nonstop2h 49m

Chicago O'Hare Intl

Wed 11/19

6:33 pm-10:05 pm

Nonstop2h 32m

$137

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 11/15

11:30 am-1:17 pm

Nonstop2h 47m

Chicago O'Hare Intl

Mon 11/17

9:30 am-12:41 pm

Nonstop2h 11m

$137

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 11/13

6:15 am-7:55 am

Nonstop2h 40m

Chicago O'Hare Intl

Wed 11/19

7:00 am-10:15 am

Nonstop2h 15m

$137

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 11/11

10:59 am-12:27 am

1 stop14h 28m

Chicago O'Hare Intl

Wed 11/12

10:52 am-11:21 pm

1 stop11h 29m

$138

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 1/15

7:30 am-9:27 am

Nonstop2h 57m

Chicago O'Hare Intl

Sun 1/18

10:45 am-1:58 pm

Nonstop2h 13m

$138

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sat 2/7

7:00 pm-8:53 pm

Nonstop2h 53m

Chicago O'Hare Intl

Sat 2/14

7:30 am-10:56 am

Nonstop2h 26m

$139

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Fri 11/14

8:50 pm-10:35 pm

Nonstop2h 45m

Chicago O'Hare Intl

Mon 11/17

5:50 pm-9:01 pm

Nonstop2h 11m

$143

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Tue 12/2

8:01 am-9:56 am

Nonstop2h 55m

Chicago O'Hare Intl

Sat 12/13

6:30 pm-10:04 pm

Nonstop2h 34m

$148

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Mon 12/8

8:01 am-9:56 am

Nonstop2h 55m

Chicago O'Hare Intl

Tue 12/9

10:36 am-1:59 pm

Nonstop2h 23m

$148

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

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 February is currently the most expensive (average of $269). 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 October 30, 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 30% 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 October 30, 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
4,243 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

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
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

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
4,243 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

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
8,999 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

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
11,034 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

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
3,123 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

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 49m. Fly via Frontier, Delta, or Spirit Airlines to get the fastest option. The distance between Connecticut and Illinois is about 738 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 $65 on Frontier. Other airlines that offer cheap prices include United Airlines from $69 and Delta 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, 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 February is currently the most expensive (average of $269). 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$97Average$182FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$177Average$382FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$191Average$376FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$225Average$392FlexibilityNo cancel feeOn-time69%

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