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

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

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 44% 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 December 2025, 112 flights take off from Chicago and land in Connecticut each day. The most common flight departure time for this route is 6:00PM, with 49% of daily flights taking off in the evening.

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

784 flights are operational weekly from Chicago to Connecticut as of December 2025. The most popular departure day for this route is Thu, with 27% of flights per week taking off on this day.

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 December 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.

$47 Cheap Flights from Chicago to Connecticut in 2025/26

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Find the cheapest flights from Chicago to Connecticut

Round-trip

One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

4:38 pm - 7:42 pm

ORD

LGA

2h 04mnonstop

7:30 am - 9:12 am

LGA

ORD

2h 42mnonstop

$77Spirit Airlines

Wed, Jan 7 - Tue, Jan 13

12:05 pm - 3:29 pm

ORD

JFK

2h 24mnonstop

4:29 pm - 6:29 pm

JFK

ORD

3h 00mnonstop

$77Frontier

Thu, Jan 22 - Sun, Jan 25

11:55 am - 3:19 pm

ORD

JFK

2h 24mnonstop

11:03 am - 1:03 pm

JFK

ORD

3h 00mnonstop

$78Frontier

Sun, Feb 8 - Sun, Feb 15

6:40 am - 10:04 am

ORD

JFK

2h 24mnonstop

1:00 pm - 2:57 pm

JFK

ORD

2h 57mnonstop

$79Frontier

Mon, Jan 5 - Wed, Jan 7

4:38 pm - 7:46 pm

ORD

EWR

2h 08mnonstop

11:30 am - 4:52 pm

EWR

ORD

6h 22m1 stop

$105Multiple Airlines

Sat, Jan 10 - Tue, Jan 13

4:46 pm - 1:10 am

ORD

EWR

7h 24m1 stop

9:05 pm - 10:42 pm

EWR

ORD

2h 37mnonstop

$108Multiple Airlines

Sat, Jan 10 - Fri, Jan 16

7:15 pm - 10:20 pm

MDW

LGA

2h 05mnonstop

9:00 am - 10:40 am

LGA

MDW

2h 40mnonstop

$139Southwest

Fri, Jan 23 - Sun, Jan 25

7:15 pm - 10:20 pm

MDW

LGA

2h 05mnonstop

6:00 am - 7:40 am

LGA

MDW

2h 40mnonstop

$148Southwest

Tue, Jan 13 - Tue, Jan 20

12:30 pm - 8:08 pm

ORD

BDL

6h 38m1 stop

6:04 am - 11:47 am

BDL

ORD

6h 43m1 stop

$177Delta

Sat, Jan 17 - Sun, Jan 18

11:45 am - 8:08 pm

MDW

BDL

7h 23m1 stop

5:40 am - 8:52 am

BDL

MDW

4h 12m1 stop

$177Delta

Sat, Jan 17 - Sun, Jan 18

Frontier flights from Chicago to Connecticut

Our best Frontier deals on Chicago to Connecticut flight tickets

Frontier

Jan 22

ORD12:05 pmChicago O'Hare Intl

2h 24m

JFK3:29 pmNew York John F Kennedy Intl

Jan 25

JFK4:29 pmNew York John F Kennedy Intl

3h 00m

ORD6:29 pmChicago O'Hare Intl

$77

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Frontier

Feb 8

ORD11:55 amChicago O'Hare Intl

2h 24m

JFK3:19 pmNew York John F Kennedy Intl

Feb 15

JFK11:03 amNew York John F Kennedy Intl

3h 00m

ORD1:03 pmChicago O'Hare Intl

$78

Find similar

Frontier

Jan 9

ORD8:35 amChicago O'Hare Intl

2h 24m

JFK11:59 amNew York John F Kennedy Intl

Jan 12

JFK1:00 pmNew York John F Kennedy Intl

2h 57m

ORD2:57 pmChicago O'Hare Intl

$79

Find similar

JetBlue flights from Chicago to Connecticut

Our best JetBlue deals on Chicago to Connecticut flight tickets

JetBlue

Dec 24

ORD6:45 amChicago O'Hare Intl

2h 16m

JFK10:01 amNew York John F Kennedy Intl

Dec 31

JFK1:00 pmNew York John F Kennedy Intl

6h 46m

1 stop

ORD6:46 pmChicago O'Hare Intl

$177

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JetBlue

Jan 15

ORD7:45 amChicago O'Hare Intl

14h 47m

2 stops

PVD11:32 pmProvidence-TFGreen

Jan 22

PVD6:16 amProvidence-TFGreen

12h 27m

2 stops

ORD5:43 pmChicago O'Hare Intl

$250

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Fly from

Fly to

Route

Depart

Return

Price

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Wed 1/7

4:38 pm-7:42 pm

Nonstop2h 04m

New York LaGuardia

Tue 1/13

7:30 am-9:12 am

Nonstop2h 42m

$77

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Thu 1/22

12:05 pm-3:29 pm

Nonstop2h 24m

New York John F Kennedy Intl

Sun 1/25

4:29 pm-6:29 pm

Nonstop3h 00m

$77

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Sun 2/8

11:55 am-3:19 pm

Nonstop2h 24m

New York John F Kennedy Intl

Sun 2/15

11:03 am-1:03 pm

Nonstop3h 00m

$78

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Mon 1/5

6:40 am-10:04 am

Nonstop2h 24m

New York John F Kennedy Intl

Wed 1/7

1:00 pm-2:57 pm

Nonstop2h 57m

$79

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Sat 1/10

4:38 pm-7:46 pm

Nonstop2h 08m

Newark

Tue 1/13

11:30 am-4:52 pm

1 stop6h 22m

$105

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Sat 1/10

4:46 pm-1:10 am

1 stop7h 24m

Newark

Fri 1/16

9:05 pm-10:42 pm

Nonstop2h 37m

$108

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Fri 1/23

7:15 pm-10:20 pm

Nonstop2h 05m

New York LaGuardia

Sun 1/25

9:00 am-10:40 am

Nonstop2h 40m

$139

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 1/13

7:15 pm-10:20 pm

Nonstop2h 05m

New York LaGuardia

Tue 1/20

6:00 am-7:40 am

Nonstop2h 40m

$148

ChicagoHartford

ORD - BDL

ORDBDL

Chicago O'Hare Intl

Sat 1/17

12:30 pm-8:08 pm

1 stop6h 38m

Hartford Bradley Intl

Sun 1/18

6:04 am-11:47 am

1 stop6h 43m

$177

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Sat 1/17

11:45 am-8:08 pm

1 stop7h 23m

Hartford Bradley Intl

Sun 1/18

5:40 am-8:52 am

1 stop4h 12m

$177

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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	$37
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 $37. The best round-trip flight deal from Chicago to Connecticut found on momondo in the last 72 hours is $84.

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 December 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 26.18% of the total bookings. Other popular models include Embraer 175 with 18.73%, Embraer 175 (Enhanced Winglets) with 11.92%, and Airbus A319 with 9.40%.

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 7.5 85 reviews	Search Avelo Airlines flights
American Airlines	PriceFrom $177	Free Cancellation	Rating 7.2 11,053 reviews	Search American Airlines flights
United Airlines	PriceFrom $185	Free Cancellation	Rating 7.4 9,092 reviews	Search United Airlines flights
Southwest	PriceFrom $197	Free Cancellation	Rating 7.9 4,249 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.

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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Popular cities in Connecticut

Flights to New Yorkfrom $45

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Flights to Orlandofrom $40

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Flights to Las Vegasfrom $49

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Flights to Bostonfrom $51

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Flights to Dallasfrom $57

Flights to Seattlefrom $58

Cheap flights from Chicago to Connecticut from $47

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 12/31. 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

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Find the cheapest flights from Chicago to Connecticut

Cheap round-trip 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

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 JetBlue 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 December 2025, 112 flights take off from Chicago and land in Connecticut each day. The most common flight departure time for this route is 6:00PM, with 49% of daily flights taking off in the evening.

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

784 flights are operational weekly from Chicago to Connecticut as of December 2025. The most popular departure day for this route is Thu, with 27% 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