What is the cheapest airline that flies from Chicago to Connecticut?

Spirit Airlines, Frontier, and Delta are the most popular carriers operating from Chicago to Connecticut

How many flights depart from Chicago to Connecticut on average per week?

1,358 flights are operational weekly from Chicago to Connecticut as of March 2026. The most popular departure day for this route is Fri, with 17% of flights per week taking off on this day.

What airlines fly to Connecticut?

United Airlines, American Airlines and Avelo Airlines are the top three most popular airlines that fly to Connecticut from Chicago according to our data. United Airlines is the first choice among our users, with 46% of people opting to fly with this airline when traveling to Connecticut. Keep in mind that there are 4 different airlines that fly to Connecticut on a routine basis, so you have a few additional options to choose from.

How many flights depart from Chicago to Connecticut on average per day?

As of March 2026, 194 flights take off from Chicago and land in Connecticut each day. The most common flight departure time for this route is 7:00PM, with 43% of daily flights taking off at noon.

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

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

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

The number of operators available for flights from Chicago to Connecticut is 7 as of March 2026.

How old do you have to be to fly from Chicago to Connecticut?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Connecticut.

What documentation or ID do you need to fly to Connecticut?

The travel and health documents required for your trip to Connecticut 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 Connecticut. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$52 Cheap Flights from Chicago to Connecticut in 2026

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Find the cheapest flights from Chicago to Connecticut

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

2:09 pm - 5:20 pm

ORD

LGA

2h 11mnonstop

6:15 pm - 7:57 pm

LGA

ORD

2h 42mnonstop

$93Spirit Airlines

Thu, Apr 30 - Thu, May 7

7:31 pm - 10:36 pm

ORD

LGA

2h 05mnonstop

6:30 am - 8:01 am

LGA

ORD

2h 31mnonstop

$94Spirit Airlines

Tue, Apr 7 - Thu, Apr 9

7:30 am - 10:38 am

MDW

EWR

2h 08mnonstop

11:30 am - 1:00 pm

EWR

MDW

2h 30mnonstop

$103Frontier

Thu, Apr 30 - Sun, May 3

7:30 am - 10:38 am

MDW

EWR

2h 08mnonstop

11:30 am - 1:00 pm

EWR

MDW

2h 30mnonstop

$104Frontier

Thu, Apr 16 - Mon, Apr 20

8:10 am - 11:15 am

MDW

LGA

2h 05mnonstop

9:30 pm - 11:00 pm

LGA

MDW

2h 30mnonstop

$177Southwest

Fri, Apr 10 - Wed, Jun 3

1:55 pm - 11:00 pm

MDW

LGA

8h 05m

1 stop

6:00 am - 7:25 am

LGA

MDW

2h 25mnonstop

$187Southwest

Wed, Apr 15 - Thu, Apr 16

7:06 pm - 10:30 pm

ORD

PVD

2h 24mnonstop

7:00 am - 8:52 am

PVD

ORD

2h 52mnonstop

$257American Airlines

Wed, May 13 - Tue, May 26

7:06 pm - 10:30 pm

ORD

PVD

2h 24mnonstop

7:00 am - 8:52 am

PVD

ORD

2h 52mnonstop

$259American Airlines

Wed, May 20 - Tue, May 26

5:56 pm - 9:28 pm

ORD

PVD

2h 32mnonstop

7:36 pm - 11:43 pm

PVD

ORD

5h 07m

1 stop

$267United Airlines

Tue, Apr 14 - Tue, Apr 21

4:20 pm - 11:54 pm

ORD

PVD

6h 34m

1 stop

7:36 pm - 11:43 pm

PVD

ORD

5h 07m

1 stop

$277United Airlines

Tue, Apr 14 - Tue, Apr 21

JetBlue flights from Chicago to Connecticut

Our best JetBlue deals on Chicago to Connecticut flight tickets

JetBlue

May 2

ORD8:31 amChicago O'Hare Intl

2h 18m

JFK11:49 amNew York John F Kennedy Intl

May 4

JFK6:00 amNew York John F Kennedy Intl

2h 41m

ORD7:41 amChicago O'Hare Intl

$172

JetBlue

Apr 16

ORD8:31 amChicago O'Hare Intl

2h 19m

JFK11:50 amNew York John F Kennedy Intl

Apr 20

JFK6:00 amNew York John F Kennedy Intl

2h 41m

ORD7:41 amChicago O'Hare Intl

$173

JetBlue

May 6

ORD8:31 amChicago O'Hare Intl

2h 18m

JFK11:49 amNew York John F Kennedy Intl

May 13

JFK6:00 amNew York John F Kennedy Intl

2h 41m

ORD7:41 amChicago O'Hare Intl

$174

Delta flights from Chicago to Connecticut

Our best Delta deals on Chicago to Connecticut flight tickets

Delta

Apr 24

ORD6:21 pmChicago O'Hare Intl

2h 39m

JFK10:00 pmNew York John F Kennedy Intl

Apr 27

JFK3:24 pmNew York John F Kennedy Intl

3h 17m

ORD5:41 pmChicago O'Hare Intl

$196

Delta

Apr 17

ORD6:04 amChicago O'Hare Intl

2h 25m

JFK9:29 amNew York John F Kennedy Intl

Apr 21

JFK7:36 pmNew York John F Kennedy Intl

3h 21m

ORD9:57 pmChicago O'Hare Intl

$197

Delta

Apr 16

ORD6:04 amChicago O'Hare Intl

2h 25m

JFK9:29 amNew York John F Kennedy Intl

Apr 20

JFK7:36 pmNew York John F Kennedy Intl

3h 21m

ORD9:57 pmChicago O'Hare Intl

$198

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Thu 4/30

2:09 pm-5:20 pm

Nonstop2h 11m

New York LaGuardia

Thu 5/7

6:15 pm-7:57 pm

Nonstop2h 42m

$93

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Tue 4/7

7:31 pm-10:36 pm

Nonstop2h 05m

New York LaGuardia

Thu 4/9

6:30 am-8:01 am

Nonstop2h 31m

$94

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Thu 4/30

7:30 am-10:38 am

Nonstop2h 08m

Newark

Sun 5/3

11:30 am-1:00 pm

Nonstop2h 30m

$103

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Thu 4/16

7:30 am-10:38 am

Nonstop2h 08m

Newark

Mon 4/20

11:30 am-1:00 pm

Nonstop2h 30m

$104

Quickest round-trip

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Fri 4/10

8:10 am-11:15 am

Nonstop2h 05m

New York LaGuardia

Wed 6/3

9:30 pm-11:00 pm

Nonstop2h 30m

$177

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 4/15

1:55 pm-11:00 pm

1 stop8h 05m

New York LaGuardia

Thu 4/16

6:00 am-7:25 am

Nonstop2h 25m

$187

ChicagoProvidence

ORD - PVD

ORDPVD

Chicago O'Hare Intl

Wed 5/13

7:06 pm-10:30 pm

Nonstop2h 24m

Providence-TFGreen

Tue 5/26

7:00 am-8:52 am

Nonstop2h 52m

$257

ChicagoProvidence

ORD - PVD

ORDPVD

Chicago O'Hare Intl

Wed 5/20

7:06 pm-10:30 pm

Nonstop2h 24m

Providence-TFGreen

Tue 5/26

7:00 am-8:52 am

Nonstop2h 52m

$259

ChicagoProvidence

ORD - PVD

ORDPVD

Chicago O'Hare Intl

Tue 4/14

5:56 pm-9:28 pm

Nonstop2h 32m

Providence-TFGreen

Tue 4/21

7:36 pm-11:43 pm

1 stop5h 07m

$267

ChicagoProvidence

ORD - PVD

ORDPVD

Chicago O'Hare Intl

Tue 4/14

4:20 pm-11:54 pm

1 stop6h 34m

Providence-TFGreen

Tue 4/21

7:36 pm-11:43 pm

1 stop5h 07m

$277

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago to Connecticut

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

Prices

Airlines

Other information

What is the cheapest month to fly to Connecticut?

In general, August is the cheapest month to fly from Chicago to Connecticut. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $249. If you aren’t able to travel to Connecticut during the month of August, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $288.

What is the cheapest Chicago to Connecticut flight route?

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

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

There are 4 cabin classes available to choose from on Chicago to Connecticut 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 Chicago to Connecticut flights?

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

Cheap Chicago to Connecticut flight deals and tips

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

Best Price Found	$130
Fastest flight time	1h 55m
Direct flights	Every day
Airports in Connecticut	90 airports

The best one-way flight to Connecticut from Chicago in the past 72 hours is $130. The best round-trip flight deal from Chicago to Connecticut found on momondo in the last 72 hours is $142.

The fastest flight from Chicago to Connecticut takes 1h 55m

Direct flights go from Chicago to Connecticut every day.

There are 90 airports in Connecticut. From Chicago there are direct flights to Newark (EWR), New York LaGuardia (LGA), Hartford Bradley Intl (BDL).

Search flight deals

When did momondo last update prices for flights from Chicago to Connecticut?
Prices for flights from Chicago to Connecticut were last updated today.
How many operators does momondo search for flights from Chicago to Connecticut?
The number of operators available for flights from Chicago to Connecticut is 7 as of March 2026.
How old do you have to be to fly from Chicago to Connecticut?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Connecticut.
What documentation or ID do you need to fly to Connecticut?
The travel and health documents required for your trip to Connecticut 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 Connecticut. 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 Chicago to Connecticut?
Based on momondo bookings for flights between Chicago and Connecticut, the leading plane model is Boeing 737-800, making up 32.66% of the total bookings. Other popular models include Embraer 175 with 19.09%, Embraer 175 (Enhanced Winglets) with 7.85%, and Airbus A320-100/200 with 7.07%.

Best airlines flying from Chicago to Connecticut

Compare and see reviews for airlines that fly from Chicago to Connecticut with momondo

Airline	Rating	Free Cancellation	Price
Avelo Airlines	PriceFrom $78	Free Cancellation	Rating 7.6 88 reviews	Search Avelo Airlines flights
American Airlines	PriceFrom $177	Free Cancellation	Rating 7.1 11,483 reviews	Search American Airlines flights
United Airlines	PriceFrom $185	Free Cancellation	Rating 7.4 9,454 reviews	Search United Airlines flights
Southwest	PriceFrom $240	Free Cancellation	Rating 8.0 4,324 reviews	Search Southwest flights

Why use momondo?

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

Finding the right flight to Connecticut from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Connecticut quick and easy, saving you time and money.

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

momondo does allow users to show only those flights to Connecticut from Chicago which offer a flexible booking policy as well as other useful filters and features.

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

Once all potential Chicago to Connecticut 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 Chicago to Connecticut right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to Connecticut flights. All you need is a valid email address and we will do the rest; it is that quick and easy.