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

As of October 2025, 88 flights take off from Chicago and land in Connecticut each day. The most common flight departure time for this route is 6:00PM, with 38% of daily flights taking off at noon.

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

622 flights are operational weekly from Chicago to Connecticut as of October 2025. The most popular departure day for this route is Thu, with 36% of flights per week taking off on this day.

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

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

What airlines fly to Connecticut?

American Airlines, United Airlines and Southwest are the top three most popular airlines that fly to Connecticut from Chicago according to our data. American Airlines is the first choice among our users, with 47% 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.

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 October 2025.

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.

$60 Cheap Flights from Chicago to Connecticut in 2025/26

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One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

4:57 pm - 8:00 pmORD-LGA

2h 03mnonstop

7:30 am - 9:01 amLGA-ORD

2h 31mnonstop

$86Spirit Airlines

Find Deal

Tue, Nov 18 - Tue, Nov 25

6:40 am - 10:03 amORD-JFK

2h 23mnonstop

1:00 pm - 12:59 amJFK-ORD

12h 59m1 stop

$86Frontier

Find Deal

Tue, Nov 18 - Tue, Nov 18

7:34 pm - 10:42 pmORD-LGA

2h 08mnonstop

12:30 pm - 12:11 amLGA-ORD

12h 41m1 stop

$92Multiple Airlines

Find Deal

Sat, Nov 15 - Mon, Nov 17

7:34 pm - 10:42 pmORD-LGA

2h 08mnonstop

5:30 pm - 12:08 amLGA-ORD

7h 38m1 stop

$93Multiple Airlines

Find Deal

Wed, Nov 12 - Thu, Nov 20

7:15 pm - 10:20 pmMDW-LGA

2h 05mnonstop

9:45 pm - 11:15 pmLGA-MDW

2h 30mnonstop

$139Southwest

Find Deal

Wed, Jan 7 - Thu, Jan 8

10:52 am - 2:08 pmORD-EWR

2h 16mnonstop

2:20 pm - 4:06 pmEWR-ORD

2h 46mnonstop

$147United Airlines

Find Deal

Sat, Jan 10 - Wed, Jan 14

5:55 pm - 9:00 pmMDW-LGA

2h 05mnonstop

9:45 pm - 11:15 pmLGA-MDW

2h 30mnonstop

$148Southwest

Find Deal

Wed, Jan 14 - Sun, Jan 18

7:15 am - 10:24 amORD-EWR

2h 09mnonstop

7:29 pm - 9:15 pmEWR-ORD

2h 46mnonstop

$149United Airlines

Find Deal

Sat, Nov 8 - Sat, Nov 8

7:49 pm - 10:59 pmORD-EWR

2h 10mnonstop

11:53 am - 1:37 pmEWR-ORD

2h 44mnonstop

$162American Airlines

Find Deal

Wed, Jan 14 - Fri, Jan 16

8:00 am - 4:08 pmORD-BDL

7h 08m1 stop

12:16 pm - 2:15 pmBDL-ORD

2h 59mnonstop

$235American Airlines

Find Deal

Sat, Jan 31 - Sun, Feb 1

Frontier flights from Chicago to Connecticut

Our best Frontier deals on Chicago to Connecticut flight tickets

Frontier

Nov 13

ORD6:40 amChicago O'Hare Intl

2h 23m

JFK10:03 amNew York John F Kennedy Intl

Nov 13

JFK1:05 pmNew York John F Kennedy Intl

12h 54m

1 stop

ORD12:59 amChicago O'Hare Intl

$86

Find similar

Frontier

Nov 11

ORD6:40 amChicago O'Hare Intl

2h 23m

JFK10:03 amNew York John F Kennedy Intl

Nov 20

JFK7:00 amNew York John F Kennedy Intl

11h 13m

1 stop

ORD5:13 pmChicago O'Hare Intl

$87

Find similar

Frontier

Nov 12

ORD6:40 amChicago O'Hare Intl

2h 23m

JFK10:03 amNew York John F Kennedy Intl

Dec 10

JFK6:15 amNew York John F Kennedy Intl

9h 16m

1 stop

ORD2:31 pmChicago O'Hare Intl

$88

Find similar

JetBlue flights from Chicago to Connecticut

Our best JetBlue deals on Chicago to Connecticut flight tickets

JetBlue

Nov 15

ORD6:45 amChicago O'Hare Intl

2h 14m

JFK9:59 amNew York John F Kennedy Intl

Dec 9

JFK8:00 pmNew York John F Kennedy Intl

2h 52m

ORD9:52 pmChicago O'Hare Intl

$132

Find similar

JetBlue

Nov 15

ORD10:00 amChicago O'Hare Intl

5h 54m

1 stop

JFK4:54 pmNew York John F Kennedy Intl

Nov 15

JFK7:00 pmNew York John F Kennedy Intl

2h 52m

ORD8:52 pmChicago O'Hare Intl

$135

Find similar

JetBlue

Nov 11

ORD6:45 amChicago O'Hare Intl

2h 14m

JFK9:59 amNew York John F Kennedy Intl

Nov 11

JFK7:00 pmNew York John F Kennedy Intl

2h 52m

ORD8:52 pmChicago O'Hare Intl

$137

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Tue 11/18

4:57 pm-8:00 pm

Nonstop2h 03m

New York LaGuardia

Tue 11/25

7:30 am-9:01 am

Nonstop2h 31m

$86

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Tue 11/18

6:40 am-10:03 am

Nonstop2h 23m

New York John F Kennedy Intl

Tue 11/18

1:00 pm-12:59 am

1 stop12h 59m

$86

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Sat 11/15

7:34 pm-10:42 pm

Nonstop2h 08m

New York LaGuardia

Mon 11/17

12:30 pm-12:11 am

1 stop12h 41m

$92

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Wed 11/12

7:34 pm-10:42 pm

Nonstop2h 08m

New York LaGuardia

Thu 11/20

5:30 pm-12:08 am

1 stop7h 38m

$93

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 1/7

7:15 pm-10:20 pm

Nonstop2h 05m

New York LaGuardia

Thu 1/8

9:45 pm-11:15 pm

Nonstop2h 30m

$139

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Sat 1/10

10:52 am-2:08 pm

Nonstop2h 16m

Newark

Wed 1/14

2:20 pm-4:06 pm

Nonstop2h 46m

$147

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 1/14

5:55 pm-9:00 pm

Nonstop2h 05m

New York LaGuardia

Sun 1/18

9:45 pm-11:15 pm

Nonstop2h 30m

$148

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Sat 11/8

7:15 am-10:24 am

Nonstop2h 09m

Newark

Sat 11/8

7:29 pm-9:15 pm

Nonstop2h 46m

$149

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Wed 1/14

7:49 pm-10:59 pm

Nonstop2h 10m

Newark

Fri 1/16

11:53 am-1:37 pm

Nonstop2h 44m

$162

ChicagoHartford

ORD - BDL

ORDBDL

Chicago O'Hare Intl

Sat 1/31

8:00 am-4:08 pm

1 stop7h 08m

Hartford Bradley Intl

Sun 2/1

12:16 pm-2:15 pm

Nonstop2h 59m

$235

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 $292.

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	$206
Fastest flight time	1h 55m
Direct flights	Every day
Airports in Connecticut	2 airports

The best one-way flight to Connecticut from Chicago in the past 72 hours is $206. The best round-trip flight deal from Chicago to Connecticut found on momondo in the last 72 hours is $108.

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

Direct flights go from Chicago to Connecticut every day.

There are 2 airports near Connecticut: 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 October 2025.
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 29.64% of the total bookings. Other popular models include Embraer 175 with 16.29%, Airbus A320-100/200 with 11.67%, and Embraer 175 (Enhanced Winglets) with 11.02%.

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 $85	Free Cancellation	Rating 7.5 82 reviews	Search Avelo Airlines flights
American Airlines	PriceFrom $188	Free Cancellation	Rating 7.2 11,034 reviews	Search American Airlines flights
Southwest	PriceFrom $197	Free Cancellation	Rating 8.0 4,243 reviews	Search Southwest flights
United Airlines	PriceFrom $212	Free Cancellation	Rating 7.4 8,998 reviews	Search United Airlines 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.

An easier way to manage your Connecticut trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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Sat 11/29

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Find better results for your trip to Connecticut

Popular cities in Connecticut

Flights to New Yorkfrom $49

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Flights to Chicagofrom $49

Flights to Orlandofrom $47

Flights to Las Vegasfrom $39

Flights to San Franciscofrom $39

Flights to Washington, D.C.from $40

Flights to Bostonfrom $60

Flights to Atlantafrom $47

Flights to Dallasfrom $49

Flights to Seattlefrom $53

Cheap flights from Chicago to Connecticut from $60

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Connecticut departing on 11/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

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Find the cheapest flights from Chicago to Connecticut

Cheap round-trip flights

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Cheap last minute flights

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Frontier flights from Chicago to Connecticut

Our best Frontier deals on Chicago to Connecticut flight tickets

JetBlue flights from Chicago to Connecticut

Our best JetBlue deals on Chicago to Connecticut flight tickets

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

See travel insights to Connecticut from

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

What is the cheapest month to fly to Connecticut?

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.

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

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

What airlines fly to Connecticut?

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

As of October 2025, 88 flights take off from Chicago and land in Connecticut each day. The most common flight departure time for this route is 6:00PM, with 38% of daily flights taking off at noon.

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

622 flights are operational weekly from Chicago to Connecticut as of October 2025. The most popular departure day for this route is Thu, with 36% of flights per week taking off on this day.

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

Fastest flight time

Direct flights

Airports in Connecticut

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

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

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

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

What is the most popular plane model from Chicago to Connecticut?

Best airlines flying from Chicago to Connecticut

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

Why use momondo?

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

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

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

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

An easier way to manage your Connecticut trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Connecticut

Popular cities in Connecticut

Popular flights according to clicks in the last 7 days on momondo