Cheap flights from Connecticut to Illinois from $90

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Connecticut to Illinois departing on 7/28. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
6:34 am - 8:20 am
LGA
-
ORD
2h 46mnonstop
American Airlines Logo
7:59 pm - 11:21 pm
ORD
-
LGA
2h 22mnonstop
$179American Airlines
Sat, Jul 11 - Mon, Jul 13
American Airlines Logo
7:59 am - 10:02 am
JFK
-
ORD
3h 03mnonstop
American Airlines Logo
4:48 pm - 8:24 pm
ORD
-
JFK
2h 36mnonstop
$180American Airlines
Wed, Jul 15 - Sat, Jul 18
JetBlue Logo
7:05 am - 8:50 am
JFK
-
ORD
2h 45mnonstop
JetBlue Logo
5:27 pm - 9:00 pm
ORD
-
JFK
2h 33mnonstop
$181JetBlue
Mon, Jul 6 - Sat, Jul 11
Southwest Logo
9:30 pm - 10:55 pm
LGA
-
MDW
2h 25mnonstop
Southwest Logo
5:15 am - 8:15 am
MDW
-
LGA
2h 00mnonstop
$182Southwest
Fri, Jul 3 - Tue, Jul 7
JetBlue Logo
7:30 pm - 9:30 pm
JFK
-
ORD
3h 00mnonstop
JetBlue Logo
5:22 pm - 9:00 pm
ORD
-
JFK
2h 38mnonstop
$182JetBlue
Fri, Jul 3 - Sat, Jul 4
Delta Logo
9:00 pm - 10:48 pm
LGA
-
ORD
2h 48mnonstop
Delta Logo
8:10 pm - 11:44 pm
ORD
-
LGA
2h 34mnonstop
$182Delta
Fri, Jul 3 - Tue, Jul 7
Southwest Logo
6:00 am - 7:20 am
LGA
-
MDW
2h 20mnonstop
Southwest Logo
12:25 pm - 3:30 pm
MDW
-
LGA
2h 05mnonstop
$184Southwest
Sun, Aug 2 - Tue, Aug 11
Delta Logo
7:30 am - 9:09 am
LGA
-
ORD
2h 39mnonstop
Delta Logo
7:00 am - 10:17 am
ORD
-
LGA
2h 17mnonstop
$186Delta
Tue, Sep 8 - Sat, Sep 12
United Airlines Logo
7:29 am - 9:00 am
LGA
-
ORD
2h 31mnonstop
United Airlines Logo
6:00 am - 9:11 am
ORD
-
LGA
2h 11mnonstop
$187United Airlines
Sat, Jun 27 - Mon, Jun 29
United Airlines Logo
8:05 am - 9:44 am
LGA
-
ORD
2h 39mnonstop
United Airlines Logo
4:00 pm - 7:22 pm
ORD
-
LGA
2h 22mnonstop
$192United Airlines
Wed, Jun 17 - Sat, Jun 20

American Airlines flights from Connecticut to Illinois

Our best American Airlines deals on Connecticut to Illinois flight tickets
American Airlines
Jul 11
LGA6:34 amNew York LaGuardia
2h 46m
ORD8:20 amChicago O'Hare Intl
Jul 13
ORD7:59 pmChicago O'Hare Intl
2h 22m
LGA11:21 pmNew York LaGuardia
$179
American Airlines
Jul 15
JFK7:59 amNew York John F Kennedy Intl
3h 03m
ORD10:02 amChicago O'Hare Intl
Jul 18
ORD4:48 pmChicago O'Hare Intl
2h 36m
JFK8:24 pmNew York John F Kennedy Intl
$180
American Airlines
Jul 17
LGA9:29 pmNew York LaGuardia
3h 01m
ORD11:30 pmChicago O'Hare Intl
Jul 18
ORD6:00 amChicago O'Hare Intl
2h 16m
LGA9:16 amNew York LaGuardia
$183

JetBlue flights from Connecticut to Illinois

Our best JetBlue deals on Connecticut to Illinois flight tickets
JetBlue
Jul 6
JFK7:05 amNew York John F Kennedy Intl
2h 45m
ORD8:50 amChicago O'Hare Intl
Jul 11
ORD5:27 pmChicago O'Hare Intl
2h 33m
JFK9:00 pmNew York John F Kennedy Intl
$181
JetBlue
Jul 3
JFK7:30 pmNew York John F Kennedy Intl
3h 00m
ORD9:30 pmChicago O'Hare Intl
Jul 4
ORD5:22 pmChicago O'Hare Intl
2h 38m
JFK9:00 pmNew York John F Kennedy Intl
$182
JetBlue
Jun 29
JFK7:30 pmNew York John F Kennedy Intl
3h 00m
ORD9:30 pmChicago O'Hare Intl
Jul 4
ORD5:22 pmChicago O'Hare Intl
2h 38m
JFK9:00 pmNew York John F Kennedy Intl
$183

momondo 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, momondo users made 832,500 searches. Data last updated June 1, 2026.
Use the filters below to find and compare flights from Connecticut to Illinois that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 7/11

6:34 am-8:20 am

Nonstop2h 46m

Chicago O'Hare Intl

Mon 7/13

7:59 pm-11:21 pm

Nonstop2h 22m

$179

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Wed 7/15

7:59 am-10:02 am

Nonstop3h 03m

Chicago O'Hare Intl

Sat 7/18

4:48 pm-8:24 pm

Nonstop2h 36m

$180

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Mon 7/6

7:05 am-8:50 am

Nonstop2h 45m

Chicago O'Hare Intl

Sat 7/11

5:27 pm-9:00 pm

Nonstop2h 33m

$181
Quickest round-trip

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 7/3

9:30 pm-10:55 pm

Nonstop2h 25m

Chicago Midway

Tue 7/7

5:15 am-8:15 am

Nonstop2h 00m

$182

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Fri 7/3

7:30 pm-9:30 pm

Nonstop3h 00m

Chicago O'Hare Intl

Sat 7/4

5:22 pm-9:00 pm

Nonstop2h 38m

$182

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Fri 7/3

9:00 pm-10:48 pm

Nonstop2h 48m

Chicago O'Hare Intl

Tue 7/7

8:10 pm-11:44 pm

Nonstop2h 34m

$182

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sun 8/2

6:00 am-7:20 am

Nonstop2h 20m

Chicago Midway

Tue 8/11

12:25 pm-3:30 pm

Nonstop2h 05m

$184

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 9/8

7:30 am-9:09 am

Nonstop2h 39m

Chicago O'Hare Intl

Sat 9/12

7:00 am-10:17 am

Nonstop2h 17m

$186

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 6/27

7:29 am-9:00 am

Nonstop2h 31m

Chicago O'Hare Intl

Mon 6/29

6:00 am-9:11 am

Nonstop2h 11m

$187

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 6/17

8:05 am-9:44 am

Nonstop2h 39m

Chicago O'Hare Intl

Sat 6/20

4:00 pm-7:22 pm

Nonstop2h 22m

$192

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Illinois from

How to get the cheapest flight ticket from Connecticut to Illinois

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Illinois?

The cheapest month to fly to Illinois from Connecticut is in September. Flight prices, which tend to average around $51, are often lower during this time because this is during the off-season. If you aren’t able to travel to Illinois during the month of September, then flying in November is also cheap. Prices for this month can be found on momondo for an average of $55.

What is the cheapest day to depart on your flight to Illinois?

The cheapest day to depart from Connecticut to Illinois is on a Wednesday when prices can be found for as low as $444. Flights from Connecticut to Illinois on a Sunday will generally be more expensive and average around $563. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Illinois?

Our most recent data shows that the best time of day to fly to Illinois is in the evening. Flights from Connecticut to Illinois during this time can be as low as $420. Flights at noon are often more expensive with an average ticket price of $500.

What is the cheapest Connecticut to Illinois flight route?

Fly from Tweed-New Haven to Chicago O'Hare Intl for the best Connecticut - Illinois flight prices

What cabin class options are available on Connecticut to Illinois flights?

There are 4 cabin classes available to choose from on Connecticut to Illinois flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Connecticut to Illinois flights?

No. A direct flight is the cheapest option for a flight between Connecticut to Illinois.

Cheap Connecticut to Illinois flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Connecticut to Illinois

Best Price Found

$231

Fastest flight time

2h 15m

Direct flights

Every day

Airports in Illinois

98 airports
The best one-way flight to Illinois from Connecticut in the past 72 hours is $231. The best round-trip flight deal from Connecticut to Illinois found on momondo in the last 72 hours is $178.
The fastest flight from Connecticut to Illinois takes 2h 15m
Direct flights go from Connecticut to Illinois every day.
There are 98 airports in Illinois. From Connecticut there are direct flights to Chicago Midway (MDW), Lambert-St Louis (STL).

Frequently asked questions about flying from Connecticut to Illinois

  • When did momondo last update prices for flights from Connecticut to Illinois?

    Prices for flights from Connecticut to Illinois were last updated today.

  • How many operators does momondo search for flights from Connecticut to Illinois?

  • How old do you have to be to fly from Connecticut to Illinois?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Connecticut to Illinois.

  • What documentation or ID do you need to fly to Illinois?

    The travel and health documents required for your trip to Illinois can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Illinois. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Connecticut to Illinois?

Best airlines flying from Connecticut to Illinois

Compare and see reviews for airlines that fly from Connecticut to Illinois with momondo
Airline
Rating
Free Cancellation
Price
Avelo AirlinesPriceFrom $77Free CancellationRating
7.6
88 reviews
Search Avelo Airlines flights
JetBluePriceFrom $112Free CancellationRating
7.1
2,984 reviews
Search JetBlue flights
DeltaPriceFrom $176Free CancellationRating
7.9
8,400 reviews
Search Delta flights
American AirlinesPriceFrom $177Free CancellationRating
7.1
11,644 reviews
Search American Airlines flights
SouthwestPriceFrom $184Free CancellationRating
8.0
4,260 reviews
Search Southwest flights
United AirlinesPriceFrom $222Free CancellationRating
7.4
9,775 reviews
Search United Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Connecticut to Illinois?

It is quick and easy to find Connecticut to Illinois flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Illinois that suits you.

Can I find flights from Connecticut to Illinois with flexible booking policies on momondo?

All flight searches from Connecticut to Illinois on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Connecticut to Illinois?

Once all potential Connecticut to Illinois flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Connecticut to Illinois right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Illinois, momondo offers a useful price alert feature which will track prices for flights to Illinois from Connecticut and alert you when they change.

An easier way to manage your Illinois trip

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1 adult
Wed 7/1
Wed 7/8

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