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$73+ 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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — ORD
ago. 6 — ago. 131
mié. 8/6
mié. 8/13
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 agosto 1, 2025.

Round-trip from

$150
(Flysmarter)

One-way from

$73
(Cheapflightsfares)

Good round-trip deal

$104 or less

Good one-way deal

$76 or less
From Connecticut to Illinois
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One-way flight from Connecticut to Illinois
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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 agosto 1, 2025.

This Flysmarter deal was found by Cheapflights users on 7/31. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/132:30 pmJFK - ORD
Nonstop2h 51mJetBlue
lun. 9/156:45 amORD - JFK
Nonstop2h 14mJetBlue
Deal found 7/31$150
This Kiwi.com deal was found by Cheapflights users on 7/29. 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.
dom. 9/73:13 pmLGA - ORD
Nonstop2h 38mSpirit Airlines
mié. 9/1011:13 amORD - LGA
Nonstop2h 05mSpirit Airlines
Deal found 7/29$150
This Southwest deal was found by Cheapflights users on 7/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 8/316:00 amLGA - MDW
Nonstop2h 20mSouthwest
mié. 9/36:00 amMDW - LGA
Nonstop2h 00mSouthwest
Deal found 7/30$152
This Delta deal was found by Cheapflights users on 7/31. 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.
sáb. 9/68:00 amJFK - ORD
Nonstop2h 55mDelta
lun. 9/87:00 amORD - JFK
Nonstop2h 23mDelta
Deal found 7/31$157
This Delta deal was found by Cheapflights users on 7/31. 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.
sáb. 9/137:30 amLGA - ORD
Nonstop2h 32mDelta
lun. 9/156:00 amORD - LGA
Nonstop2h 08mDelta
Deal found 7/31$157
This Frontier deal was found by Cheapflights users on 7/31. 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.
sáb. 10/1111:00 amJFK - ORD
Nonstop2h 45mFrontier
lun. 10/136:16 pmORD - JFK
1 stop12h 12mFrontier
Deal found 7/31$158
This Trip.com deal was found by Cheapflights users on 7/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/610:20 amLGA - ORD
Nonstop2h 37mMultiple Airlines
lun. 9/811:13 amORD - LGA
Nonstop2h 05mMultiple Airlines
Deal found 7/30$158
This American Airlines deal was found by Cheapflights users on 7/31. 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.
mar. 9/167:30 amJFK - ORD
Nonstop2h 45mAmerican Airlines
jue. 9/181:59 pmORD - JFK
Nonstop2h 18mAmerican Airlines
Deal found 7/31$161
This United Airlines deal was found by Cheapflights users on 7/31. 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.
mié. 8/276:00 amLGA - ORD
1 stop4h 36mUnited Airlines
mié. 9/33:00 pmORD - LGA
Nonstop2h 17mUnited Airlines
Deal found 7/31$162
This American Airlines deal was found by Cheapflights users on 7/31. 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.
sáb. 9/1311:30 amLGA - ORD
Nonstop2h 45mAmerican Airlines
lun. 9/158:20 pmORD - LGA
Nonstop2h 08mAmerican Airlines
Deal found 7/31$163
This FlightHub deal was found by Cheapflights users on 7/31. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 9/285:55 amEWR - MDW
1 stop11h 03mFrontier
mar. 10/145:56 pmMDW - EWR
Nonstop2h 04mFrontier
Deal found 7/31$166
This American Airlines deal was found by Cheapflights users on 7/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/117:22 pmEWR - ORD
Nonstop2h 39mAmerican Airlines
lun. 9/158:41 pmORD - EWR
Nonstop2h 18mAmerican Airlines
Deal found 7/30$166

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 agosto 1, 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

sáb. 9/13

2:30 pm-4:21 pm

Nonstop2h 51m

Chicago O'Hare Intl

lun. 9/15

6:45 am-9:59 am

Nonstop2h 14m

$150

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

dom. 9/7

3:13 pm-4:51 pm

Nonstop2h 38m

Chicago O'Hare Intl

mié. 9/10

11:13 am-2:18 pm

Nonstop2h 05m

$150

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

mié. 9/3

8:30 pm-10:20 pm

Nonstop2h 50m

Chicago O'Hare Intl

jue. 9/11

8:20 pm-11:38 pm

Nonstop2h 18m

$152

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

dom. 8/31

6:00 am-7:20 am

Nonstop2h 20m

Chicago Midway

mié. 9/3

6:00 am-9:00 am

Nonstop2h 00m

$152

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

sáb. 9/6

3:29 pm-5:37 pm

Nonstop3h 08m

Chicago O'Hare Intl

lun. 9/8

7:00 am-10:23 am

Nonstop2h 23m

$157

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

sáb. 10/11

11:00 am-12:45 pm

Nonstop2h 45m

Chicago O'Hare Intl

lun. 10/13

6:16 pm-7:28 am

1 stop12h 12m

$158

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

sáb. 9/6

6:30 am-11:27 am

1 stop5h 57m

Chicago O'Hare Intl

sáb. 9/6

4:35 pm-7:41 pm

Nonstop2h 06m

$158

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

mar. 9/16

7:30 am-9:15 am

Nonstop2h 45m

Chicago O'Hare Intl

jue. 9/18

1:59 pm-5:17 pm

Nonstop2h 18m

$161

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

mié. 8/27

6:00 am-9:36 am

1 stop4h 36m

Chicago O'Hare Intl

mié. 9/3

3:00 pm-6:17 pm

Nonstop2h 17m

$162

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

sáb. 9/13

11:30 am-1:15 pm

Nonstop2h 45m

Chicago O'Hare Intl

lun. 9/15

8:20 pm-11:28 pm

Nonstop2h 08m

$163

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

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 agosto 1, 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 agosto 1, 2025.

The most flights from USCT to USIL are scheduled on a Thursday (20 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (8 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 agosto 1, 2025.
Get a feel of what it's like to fly with Southwest, Delta, 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
4,246 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,900 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
JetBlue
7.3
Good
2,914 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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.

  • 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 $73 on Spirit Airlines. Other airlines that offer cheap prices include Delta from $79 and American Airlines from $79 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 7 airlines flying from Connecticut to Illinois

Discover the top 7 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 agosto 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$77Average$167FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$116Average$192FlexibilityNo cancel feeOn-time62%
DeltaCheapest$176Average$276FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$177Average$362FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$184Average$394FlexibilityNo cancel feeOn-time71%
Spirit AirlinesCheapest$202Average$280FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$227Average$399FlexibilityNo cancel feeOn-time69%

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