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$65+ 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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — ORD
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$120
(Cheapflightsfares)

One-way from

$65
(Kiwi.com)

Good round-trip deal

$366 or less

Good one-way deal

$173 or less
Provider with most accurate pricing for Springfield (SFY)-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Springfield (SFY)-Chicago (CHI) flights.
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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 May 1, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/295:39 pmEWR - ORD
1 stop7h 26mSpirit Airlines
Tue 6/39:08 pmORD - EWR
Nonstop2h 21mSpirit Airlines
Deal found 4/29$120
This Expedia deal was found by Cheapflights users on 4/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/246:30 pmLGA - ORD
Nonstop2h 37mSpirit Airlines
Mon 6/97:35 pmORD - LGA
1 stop13h 25mSpirit Airlines
Deal found 4/30$141
This United Airlines deal was found by Cheapflights users on 4/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/248:30 pmEWR - ORD
Nonstop2h 42mUnited Airlines
Sun 5/256:00 amORD - EWR
Nonstop2h 13mUnited Airlines
Deal found 4/28$147
This American Airlines deal was found by Cheapflights users on 4/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/203:55 pmJFK - ORD
Nonstop2h 39mAmerican Airlines
Thu 5/224:44 pmORD - JFK
Nonstop2h 16mAmerican Airlines
Deal found 4/29$153
This JetBlue deal was found by Cheapflights users on 4/29. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/281:20 pmJFK - ORD
Nonstop2h 44mJetBlue
Sat 5/314:03 pmORD - JFK
Nonstop2h 26mJetBlue
Deal found 4/29$157
This United Airlines deal was found by Cheapflights users on 4/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/148:25 amLGA - ORD
Nonstop2h 41mUnited Airlines
Sat 5/178:00 pmORD - LGA
Nonstop2h 18mUnited Airlines
Deal found 4/30$157
This Southwest deal was found by Cheapflights users on 4/30. 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.
Fri 5/309:45 pmLGA - MDW
Nonstop2h 15mSouthwest
Tue 7/17:20 pmMDW - LGA
Nonstop2h 10mSouthwest
Deal found 4/30$157
This American Airlines deal was found by Cheapflights users on 4/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/125:49 pmEWR - ORD
Nonstop2h 38mAmerican Airlines
Sat 8/168:30 pmORD - EWR
Nonstop2h 29mAmerican Airlines
Deal found 4/29$159
This Orbitz deal was found by Cheapflights users on 4/29. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/66:30 amLGA - ORD
1 stop11h 11mMultiple Airlines
Tue 5/135:51 amORD - LGA
Nonstop2h 09mMultiple Airlines
Deal found 4/29$171
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/168:00 amJFK - ORD
Nonstop2h 57mDelta
Thu 7/247:00 amORD - JFK
Nonstop2h 23mDelta
Deal found 4/29$177
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/165:05 pmLGA - ORD
Nonstop3h 06mDelta
Thu 7/246:59 pmORD - LGA
Nonstop2h 31mDelta
Deal found 4/29$177
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/43:55 pmEWR - MDW
1 stop6h 32mDelta
Tue 6/106:00 amMDW - EWR
1 stop5h 39mDelta
Deal found 4/30$179

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 May 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

NewarkChicago

EWR - ORD

EWRORD

Newark

Thu 5/29

5:55 am-7:27 am

Nonstop2h 32m

Chicago O'Hare Intl

Thu 5/29

7:35 pm-9:07 am

1 stop12h 32m

$120

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 5/24

6:30 pm-8:07 pm

Nonstop2h 37m

Chicago O'Hare Intl

Mon 6/9

7:35 pm-10:00 am

1 stop13h 25m

$141

NewarkChicago

EWR - ORD

EWRORD

Newark

Sat 5/24

8:30 pm-10:12 pm

Nonstop2h 42m

Chicago O'Hare Intl

Sun 5/25

6:00 am-9:13 am

Nonstop2h 13m

$147

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Tue 5/20

3:55 pm-5:34 pm

Nonstop2h 39m

Chicago O'Hare Intl

Thu 5/22

4:44 pm-8:00 pm

Nonstop2h 16m

$153

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Wed 5/28

1:20 pm-3:04 pm

Nonstop2h 44m

Chicago O'Hare Intl

Sat 5/31

4:03 pm-7:29 pm

Nonstop2h 26m

$157

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 5/30

9:45 pm-11:00 pm

Nonstop2h 15m

Chicago Midway

Tue 7/1

7:20 pm-10:30 pm

Nonstop2h 10m

$157

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 5/14

8:25 am-10:06 am

Nonstop2h 41m

Chicago O'Hare Intl

Sat 5/17

8:00 pm-11:18 pm

Nonstop2h 18m

$157

NewarkChicago

EWR - ORD

EWRORD

Newark

Tue 8/12

5:49 pm-7:27 pm

Nonstop2h 38m

Chicago O'Hare Intl

Sat 8/16

8:30 pm-11:59 pm

Nonstop2h 29m

$159

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 5/6

6:30 am-4:41 pm

1 stop11h 11m

Chicago O'Hare Intl

Tue 5/13

5:51 am-9:00 am

Nonstop2h 09m

$171

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Wed 7/16

8:00 am-9:57 am

Nonstop2h 57m

Chicago O'Hare Intl

Thu 7/24

7:00 am-10:23 am

Nonstop2h 23m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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, 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 May 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 May 1, 2025.

The most flights from USCT to USIL are scheduled on a Wednesday (17 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (2 on average).

Rainfall in Illinois by month

Plan your trip to Illinois by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Illinois ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Illinois when rainfall is around 1.7 in.

Temperature in Illinois by month

Plan your trip to Illinois by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Illinois, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 May 1, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest and Delta from Connecticut to Illinois by reading reviews from past customers. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,972 reviews

Boarding

8.1

Crew

8.5

Overall

8.0

Food

7.1

Entertainment

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,972 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Boarding

8.1

Crew

8.5

Overall

8.0

Food

7.1

Entertainment

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,294 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Boarding

8.1

Crew

8.5

Overall

8.0

Food

7.1

Entertainment

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,934 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Boarding

8.1

Crew

8.5

Overall

8.0

Food

7.1

Entertainment

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,696 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Boarding

8.1

Crew

8.5

Overall

8.0

Food

7.1

Entertainment

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
JetBlue
7.3
Good
2,924 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Boarding

8.1

Crew

8.5

Overall

8.0

Food

7.1

Entertainment

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 $65 on Spirit Airlines. Other airlines that offer cheap prices include JetBlue from $69 and Delta 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, 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

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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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$77Average$178FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$108Average$207FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$116Average$231FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$125Average$416FlexibilityNo cancel feeOn-time69%
DeltaCheapest$176Average$346FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$198Average$396FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$232Average$385FlexibilityNo cancel feeOn-time63%

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