Connecticut

$105+ Cheap flights from Illinois to Connecticut

ORD — BDL
Oct 10 — Oct 171
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Cheap flight deals from Illinois to Connecticut

Cheapest flights from Illinois to Connecticut

Fri 10/306:44 pm -
1 stop14h 52m
Tue 11/310:14 pm -
1 stop20h 26m
Deal found 9/6$159
Wed 10/72:29 pm -
1 stop5h 55m
Tue 10/1310:29 pm -
1 stop20h 11m
Deal found 9/4$172
Fri 10/236:35 pm -
1 stop14h 58m
Tue 10/2710:14 pm -
1 stop20h 26m
Deal found 9/7$181
Mon 10/126:35 pm -
1 stop14h 58m
Wed 10/2111:30 am -
1 stop7h 10m
Deal found 9/6$186
Mon 10/266:35 pm -
1 stop15h 01m
Wed 10/2811:35 am -
1 stop7h 05m
Deal found 9/6$188
Wed 10/72:29 pm -
1 stop5h 55m
Wed 10/1411:30 am -
1 stop7h 10m
Deal found 9/4$197
Tue 9/226:20 am -
1 stop8h 40m
Wed 9/236:15 am -
1 stop6h 36m
Deal found 9/5$222
Tue 9/296:25 am -
1 stop8h 35m
Wed 9/306:15 am -
1 stop12h 36m
Deal found 9/5$222
Sat 9/263:50 pm -
1 stop8h 11m
Wed 9/3010:29 pm -
1 stop11h 51m
Deal found 9/5$222
Wed 9/303:50 pm -
1 stop8h 11m
Thu 10/11:30 pm -
1 stop12h 15m
Deal found 9/5$225
Wed 9/303:50 pm -
1 stop8h 11m
Wed 10/710:29 pm -
1 stop11h 52m
Deal found 9/7$226
Tue 9/293:50 pm -
1 stop8h 11m
Sat 10/311:35 am -
1 stop7h 48m
Deal found 9/7$227

Find flight deals from Illinois to Connecticut

Round-trip from

$159
(Kiwi.com)

One-way from

$105
(Super.com)

Popular in

April

Cheapest in

October

Average price

$315

Good round-trip deal

$114 or less

Good one-way deal

$91 or less
From Illinois to Connecticut
One-way flight from Illinois to Connecticut
Highest demand for flights based on searches. 18% potential increase in price ($91 potential increase over avg. RT price).
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Average for round-trip flights in September 2026
Price to beat on a round-trip flight from Illinois to Connecticut.
Price to beat on a one-way flight from Illinois to Connecticut.

Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Illinois to Connecticut that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoNew York

ORD Chicago O'Hare Intl - LGA New York LaGuardia

ORDLGA

Chicago O'Hare Intl

Tue 10/20

9:00 am-12:23 pm

Nonstop2h 23m

New York LaGuardia

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$134

ChicagoNew York

ORD Chicago O'Hare Intl - LGA New York LaGuardia

ORDLGA

Chicago O'Hare Intl

Tue 10/27

7:20 pm-10:49 pm

Nonstop2h 29m

New York LaGuardia

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$134
Quickest round-trip

ChicagoNew York

MDW Chicago Midway - LGA New York LaGuardia

MDWLGA

Chicago Midway

Sun 11/15

5:00 am-8:05 am

Nonstop2h 05m

New York LaGuardia

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$134

ChicagoNew York

ORD Chicago O'Hare Intl - LGA New York LaGuardia

ORDLGA

Chicago O'Hare Intl

Sat 10/17

6:29 pm-9:54 pm

Nonstop2h 25m

New York LaGuardia

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$134

ChicagoNew York

ORD Chicago O'Hare Intl - LGA New York LaGuardia

ORDLGA

Chicago O'Hare Intl

Wed 12/9

8:50 am-12:05 pm

Nonstop2h 15m

New York LaGuardia

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$134

ChicagoNew York

MDW Chicago Midway - LGA New York LaGuardia

MDWLGA

Chicago Midway

Fri 12/4

1:55 pm-5:00 pm

Nonstop2h 05m

New York LaGuardia

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$134

ChicagoNew York

ORD Chicago O'Hare Intl - LGA New York LaGuardia

ORDLGA

Chicago O'Hare Intl

Tue 10/20

11:30 am-2:49 pm

Nonstop2h 19m

New York LaGuardia

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$134

ChicagoNew York

MDW Chicago Midway - LGA New York LaGuardia

MDWLGA

Chicago Midway

Tue 10/20

8:15 am-11:20 am

Nonstop2h 05m

New York LaGuardia

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$134

ChicagoNewark

ORD Chicago O'Hare Intl - EWR Newark

ORDEWR

Chicago O'Hare Intl

Thu 10/22

5:00 am-8:12 am

Nonstop2h 12m

Newark

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$134

ChicagoNew York

MDW Chicago Midway - LGA New York LaGuardia

MDWLGA

Chicago Midway

Sat 10/24

4:25 pm-7:35 pm

Nonstop2h 10m

New York LaGuardia

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$134

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Illinois to Connecticut

Have a flexible travel schedule? Discover the best time to fly to Connecticut from Illinois with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

Everything you need to know about your flight from Illinois to Connecticut

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

Currently, December is the cheapest month in which you can book a flight from Illinois to Connecticut (average of $319). Flying from Illinois to Connecticut in July is currently the most expensive (average of $501). 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 IL to CT?

One of the essential ways to save on airfare from Illinois to Connecticut is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the morning could potentially save you up to 21% on airfare.

Weekly flight availability from Illinois to Connecticut

The most flights from USIL to USCT are scheduled on a Tuesday (19 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (5 on average).

How much does it cost to fly round-trip from Illinois to Connecticut?

Airfare is below average for this route at the moment.
Illinois to Connecticut flights typically cost between $300 and $492 in September.
The cheapest round-trip price found within the last 5 days was $279 on Multiple Airlines (Sep 30-Oct 3).

How far ahead should I book a flight from Illinois to Connecticut?

The price you pay for your flight from Illinois to Connecticut may vary depending on when you book. For the best chance of a lower fare, look to book 69 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

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

Reviews of airlines servicing Connecticut

Read reviews from past customers who have flown Southwest,Delta, andAvelo Airlines from Illinois to Connecticut. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.

Food

7.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.

Food

7.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.

Food

7.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.
Avelo Airlines
7.5
Good

Food

7.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.

Food

7.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.

Food

7.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.

Related info for your journey

  • How long is the flight from Illinois to Connecticut?

    A quick flight from Illinois to Connecticut can take about 2h 09m. United Airlines provides one of the quickest options available for as low as $267. The distance from Illinois to Connecticut is about 731 mi. Generally, flights for this route are nonstop.

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

    To fly one-way, consider booking your trip with Avelo Airlines, which is currently one of the cheapest options available, starting at $37. Frontier flights start at $88 while deals on American Airlines start at $103 one-way.

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

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

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

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

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

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

    Currently, December is the cheapest month in which you can book a flight from Illinois to Connecticut (average of $319). Flying from Illinois to Connecticut in July is currently the most expensive (average of $501). 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

Alternative routes for Illinois to Connecticut

Top 5 airlines flying from Illinois to Connecticut

AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$88Average$144FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$225Average$372FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$240Average$458FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$248Average$423FlexibilityNo cancel feeOn-time63%
DeltaCheapest$308Average$530FlexibilityNo cancel feeOn-timeN/A

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