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 49% of people opting to fly with this airline when traveling to Connecticut. Keep in mind that there are 5 different airlines that fly to Connecticut on a routine basis, so you have a few additional options to choose from.

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

Avelo Airlines, Delta, and Southwest are the most popular carriers operating from Chicago to Connecticut

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

As of August 2026, 171 flights take off from Chicago and land in Connecticut each day. The most common flight departure time for this route is 6:00PM, with 37% of daily flights taking off in the evening.

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

1,200 flights are operational weekly from Chicago to Connecticut as of August 2026. The most popular departure day for this route is Fri, with 18% 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 August 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.

$53 Cheap Flights from Chicago to Connecticut in 2026

Discover deals from 900+ travel sites with momondo.

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.

7:17 pm - 10:39 pm

ORD

HVN

2h 22mnonstop

4:30 pm - 6:13 pm

HVN

ORD

2h 43mnonstop

$103Avelo Airlines

Mon, Sep 14 - Mon, Sep 21

6:10 pm - 9:42 pm

ORD

HVN

2h 32mnonstop

3:25 pm - 5:18 pm

HVN

ORD

2h 53mnonstop

$103Avelo Airlines

Wed, Sep 16 - Wed, Sep 23

6:07 pm - 9:29 pm

ORD

HVN

2h 22mnonstop

1:00 pm - 6:39 pm

HVN

ORD

6h 39m

1 stop

$162Multiple Airlines

Thu, Sep 3 - Sun, Sep 6

6:07 pm - 9:29 pm

ORD

HVN

2h 22mnonstop

1:00 pm - 6:39 pm

HVN

ORD

6h 39m

1 stop

$163Multiple Airlines

Thu, Sep 3 - Sun, Sep 6

6:00 am - 9:17 am

ORD

JFK

2h 17mnonstop

3:40 pm - 5:35 pm

JFK

ORD

2h 55mnonstop

$195JetBlue

Sat, Aug 22 - Wed, Aug 26

5:00 am - 8:14 am

ORD

EWR

2h 14mnonstop

11:35 am - 6:23 pm

EWR

ORD

7h 48m

1 stop

$195Frontier

Wed, Sep 2 - Wed, Sep 9

10:26 am - 9:24 pm

ORD

EWR

9h 58m

1 stop

5:55 am - 10:59 pm

EWR

ORD

18h 04m

1 stop

$195Frontier

Thu, Sep 24 - Sun, Sep 27

10:09 am - 1:30 pm

ORD

EWR

2h 21mnonstop

5:19 pm - 7:20 pm

EWR

ORD

3h 01mnonstop

$201American Airlines

Tue, Sep 1 - Tue, Sep 1

7:00 am - 10:10 am

ORD

LGA

2h 10mnonstop

12:11 pm - 1:59 pm

LGA

ORD

2h 48mnonstop

$202American Airlines

Wed, Sep 2 - Wed, Sep 2

6:00 am - 9:17 am

ORD

JFK

2h 17mnonstop

3:40 pm - 5:35 pm

JFK

ORD

2h 55mnonstop

$205JetBlue

Sat, Aug 22 - Wed, Aug 26

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Delta flights from Chicago to Connecticut

Our best Delta deals on Chicago to Connecticut flight tickets

Delta

Sep 2

ORD6:00 amChicago O'Hare Intl

2h 24m

JFK9:24 amNew York John F Kennedy Intl

Sep 2

JFK2:59 pmNew York John F Kennedy Intl

3h 02m

ORD5:01 pmChicago O'Hare Intl

$207

Delta

Aug 22

ORD6:00 amChicago O'Hare Intl

2h 24m

JFK9:24 amNew York John F Kennedy Intl

Aug 23

JFK7:33 amNew York John F Kennedy Intl

2h 54m

ORD9:27 amChicago O'Hare Intl

$222

Delta

Aug 22

ORD6:00 amChicago O'Hare Intl

2h 24m

JFK9:24 amNew York John F Kennedy Intl

Aug 23

JFK7:33 amNew York John F Kennedy Intl

2h 54m

ORD9:27 amChicago O'Hare Intl

$224

JetBlue flights from Chicago to Connecticut

Our best JetBlue deals on Chicago to Connecticut flight tickets

JetBlue

Aug 22

ORD6:00 amChicago O'Hare Intl

2h 17m

JFK9:17 amNew York John F Kennedy Intl

Aug 26

JFK3:40 pmNew York John F Kennedy Intl

2h 55m

ORD5:35 pmChicago O'Hare Intl

$195

JetBlue

Aug 22

ORD6:00 amChicago O'Hare Intl

2h 17m

JFK9:17 amNew York John F Kennedy Intl

Aug 25

JFK8:00 pmNew York John F Kennedy Intl

2h 58m

ORD9:58 pmChicago O'Hare Intl

$205

JetBlue

Aug 25

ORD6:00 amChicago O'Hare Intl

2h 17m

JFK9:17 amNew York John F Kennedy Intl

Aug 29

JFK2:29 pmNew York John F Kennedy Intl

2h 48m

ORD4:17 pmChicago O'Hare Intl

$210

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoNew Haven

ORD - HVN

ORDHVN

Chicago O'Hare Intl

Mon 9/14

7:17 pm-10:39 pm

Nonstop2h 22m

Tweed-New Haven

Mon 9/21

4:30 pm-6:13 pm

Nonstop2h 43m

$103

ChicagoNew Haven

ORD - HVN

ORDHVN

Chicago O'Hare Intl

Wed 9/16

6:10 pm-9:42 pm

Nonstop2h 32m

Tweed-New Haven

Wed 9/23

3:25 pm-5:18 pm

Nonstop2h 53m

$103

ChicagoNew Haven

ORD - HVN

ORDHVN

Chicago O'Hare Intl

Thu 9/3

6:07 pm-9:29 pm

Nonstop2h 22m

Tweed-New Haven

Sun 9/6

1:00 pm-6:39 pm

1 stop6h 39m

$162

ChicagoNew Haven

ORD - HVN

ORDHVN

Chicago O'Hare Intl

Thu 9/3

6:07 pm-9:29 pm

Nonstop2h 22m

Tweed-New Haven

Sun 9/6

1:00 pm-6:39 pm

1 stop6h 39m

$163

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Sat 8/22

6:00 am-9:17 am

Nonstop2h 17m

New York John F Kennedy Intl

Wed 8/26

3:40 pm-5:35 pm

Nonstop2h 55m

$195

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Wed 9/2

5:00 am-8:14 am

Nonstop2h 14m

Newark

Wed 9/9

11:35 am-6:23 pm

1 stop7h 48m

$195

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Thu 9/24

10:26 am-9:24 pm

1 stop9h 58m

Newark

Sun 9/27

5:55 am-10:59 pm

1 stop18h 04m

$195

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Tue 9/1

10:09 am-1:30 pm

Nonstop2h 21m

Newark

Tue 9/1

5:19 pm-7:20 pm

Nonstop3h 01m

$201

Quickest round-trip

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Wed 9/2

7:00 am-10:10 am

Nonstop2h 10m

New York LaGuardia

Wed 9/2

12:11 pm-1:59 pm

Nonstop2h 48m

$202

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Sat 8/22

6:00 am-9:17 am

Nonstop2h 17m

New York John F Kennedy Intl

Wed 8/26

3:40 pm-5:35 pm

Nonstop2h 55m

$205

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, September 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 $282. If you aren’t able to travel to Connecticut during the month of September, then flying in October is also cheap. Prices for this month can be found on momondo for an average of $296.

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	$88
Fastest flight time	2h 00m
Direct flights	Every day
Airports in Connecticut	90 airports

The best one-way flight to Connecticut from Chicago in the past 72 hours is $88. The best round-trip flight deal from Chicago to Connecticut found on momondo in the last 72 hours is $127.

The fastest flight from Chicago to Connecticut takes 2h 00m

Direct flights go from Chicago to Connecticut every day.

There are 90 airports in Connecticut. From Chicago there are direct flights to New York LaGuardia (LGA).

Search flight deals

Frequently asked questions about flying from Chicago to Connecticut

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 August 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 31.86% of the total bookings. Other popular models include Embraer 175 with 14.80%, Boeing 737-900 with 11.29%, and Embraer 175 (Enhanced Winglets) with 11.18%.

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 $84	Free Cancellation	Rating 7.5 84 reviews	Search Avelo Airlines flights
Frontier	PriceFrom $185	Free Cancellation	Rating 5.6 2,735 reviews	Search Frontier flights
United Airlines	PriceFrom $202	Free Cancellation	Rating 7.4 10,060 reviews	Search United Airlines flights
American Airlines	PriceFrom $204	Free Cancellation	Rating 7.1 11,844 reviews	Search American Airlines flights
Southwest	PriceFrom $248	Free Cancellation	Rating 8.0 4,221 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.