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

Avelo Airlines, United Airlines, and Delta 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 51% 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 week?

1,440 flights are operational weekly from Chicago to Connecticut as of September 2026. The most popular departure day for this route is Tue, with 17% of flights per week taking off on this day.

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

As of September 2026, 205 flights take off from Chicago and land in Connecticut each day. The most common flight departure time for this route is 2:00PM, with 36% 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 September 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.

$75 Cheap Flights from Chicago to Connecticut in 2026/27

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 pmORD Chicago O'Hare Intl-HVN Tweed-New Haven

2h 22mnonstop

4:30 pm - 6:13 pmHVN Tweed-New Haven-ORD Chicago O'Hare Intl

2h 43mnonstop

$135Avelo Airlines

Fri, Oct 2 - Mon, Oct 5

7:39 pm - 10:59 pmORD Chicago O'Hare Intl-HVN Tweed-New Haven

2h 20mnonstop

4:45 pm - 6:28 pmHVN Tweed-New Haven-ORD Chicago O'Hare Intl

2h 43mnonstop

$135Avelo Airlines

Thu, Oct 15 - Mon, Oct 19

7:35 am - 8:30 pmMDW Chicago Midway-LGA New York LaGuardia

11h 55m2 stops Baltimore/Washington Lambert-St Louis

3:30 pm - 10:00 pmLGA New York LaGuardia-MDW Chicago Midway

7h 30m1 stop Kansas City

$223Southwest

Sat, Nov 7 - Mon, Nov 9

11:45 am - 8:55 pmMDW Chicago Midway-LGA New York LaGuardia

8h 10m1 stop Kansas City

7:40 am - 2:30 pmLGA New York LaGuardia-MDW Chicago Midway

7h 50m1 stop Omaha Eppley Airfield

$225Southwest

Tue, Dec 1 - Sat, Dec 5

9:38 am - 5:29 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

6h 51m1 stop Boston Logan Intl

1:00 pm - 7:14 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

7h 14m1 stop Boston Logan Intl

$229JetBlue

Wed, Oct 21 - Sat, Oct 24

6:44 am - 10:09 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 25mnonstop

5:29 pm - 11:30 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

7h 01m1 stop Washington, D.C. Reagan-National

$232American Airlines

Mon, Nov 16 - Mon, Nov 16

10:55 am - 4:31 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

4h 36m1 stop Washington, D.C. Reagan-National

10:40 am - 12:35 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 55mnonstop

$232American Airlines

Fri, Nov 13 - Mon, Nov 16

6:10 am - 9:30 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 20mnonstop

9:30 am - 11:24 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 54mnonstop

$232JetBlue

Sun, Oct 11 - Tue, Oct 13

6:00 pm - 9:40 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 40mnonstop

7:35 pm - 9:43 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

3h 08mnonstop

$232Delta

Tue, Oct 20 - Thu, Oct 22

6:00 am - 9:21 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 21mnonstop

7:35 pm - 9:43 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

3h 08mnonstop

$232Delta

Mon, Oct 5 - Tue, Oct 6

Cheap last minute flights

Enter your travel dates to find the best prices.

6:10 pm - 9:42 pmORD Chicago O'Hare Intl-HVN Tweed-New Haven

2h 32mnonstop

3:25 pm - 5:18 pmHVN Tweed-New Haven-ORD Chicago O'Hare Intl

2h 53mnonstop

$151Avelo Airlines

Wed, Sep 23 - Wed, Sep 30

6:10 pm - 9:42 pmORD Chicago O'Hare Intl-HVN Tweed-New Haven

2h 32mnonstop

3:25 pm - 5:18 pmHVN Tweed-New Haven-ORD Chicago O'Hare Intl

2h 53mnonstop

$158Avelo Airlines

Wed, Sep 23 - Wed, Sep 30

3:50 pm - 1:01 amORD Chicago O'Hare Intl-EWR Newark

8h 11m1 stop Orlando

10:29 pm - 9:20 amEWR Newark-ORD Chicago O'Hare Intl

11h 51m1 stop Atlanta Hartsfield-Jackson

$241Frontier

Tue, Sep 22 - Thu, Sep 24

3:50 pm - 1:01 amORD Chicago O'Hare Intl-EWR Newark

8h 11m1 stop Orlando

10:29 pm - 9:20 amEWR Newark-ORD Chicago O'Hare Intl

11h 51m1 stop Atlanta Hartsfield-Jackson

$244Frontier

Wed, Sep 23 - Thu, Sep 24

7:00 am - 10:27 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 27mnonstop

9:30 am - 11:24 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 54mnonstop

$245JetBlue

Sat, Sep 19 - Tue, Oct 20

7:00 am - 10:27 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 27mnonstop

9:30 am - 11:24 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 54mnonstop

$252JetBlue

Sun, Sep 20 - Tue, Oct 20

6:59 am - 10:10 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 11mnonstop

8:07 pm - 10:00 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 53mnonstop

$254American Airlines

Wed, Sep 23 - Sat, Oct 10

6:59 am - 10:10 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 11mnonstop

6:00 am - 7:49 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 49mnonstop

$254American Airlines

Sun, Sep 20 - Tue, Oct 20

5:25 am - 8:25 amMDW Chicago Midway-LGA New York LaGuardia

2h 00mnonstop

9:05 pm - 10:30 pmLGA New York LaGuardia-MDW Chicago Midway

2h 25mnonstop

$254Southwest

Sun, Sep 20 - Tue, Oct 20

9:35 am - 12:40 pmMDW Chicago Midway-LGA New York LaGuardia

2h 05mnonstop

3:25 pm - 4:45 pmLGA New York LaGuardia-MDW Chicago Midway

2h 20mnonstop

$254Southwest

Sat, Sep 19 - Tue, Oct 20

Cheap direct flights

Enter your travel dates to find the best prices.

7:17 pm - 10:39 pmORD Chicago O'Hare Intl-HVN Tweed-New Haven

2h 22mnonstop

4:30 pm - 6:13 pmHVN Tweed-New Haven-ORD Chicago O'Hare Intl

2h 43mnonstop

$135Avelo Airlines

Fri, Oct 2 - Mon, Oct 5

7:39 pm - 10:59 pmORD Chicago O'Hare Intl-HVN Tweed-New Haven

2h 20mnonstop

4:45 pm - 6:28 pmHVN Tweed-New Haven-ORD Chicago O'Hare Intl

2h 43mnonstop

$135Avelo Airlines

Thu, Oct 15 - Mon, Oct 19

6:00 am - 9:12 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 12mnonstop

8:35 pm - 10:17 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 42mnonstop

$232Delta

Thu, Oct 15 - Fri, Oct 16

6:00 pm - 9:40 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 40mnonstop

7:35 pm - 9:43 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

3h 08mnonstop

$232Delta

Tue, Oct 20 - Thu, Oct 22

6:10 am - 9:30 amORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 20mnonstop

9:30 am - 11:24 amJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 54mnonstop

$232JetBlue

Sun, Oct 11 - Tue, Oct 13

12:38 pm - 4:00 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 22mnonstop

8:15 pm - 10:10 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 55mnonstop

$232JetBlue

Fri, Oct 23 - Fri, Oct 23

2:00 pm - 5:25 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 25mnonstop

6:00 am - 7:39 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 39mnonstop

$233United Airlines

Thu, Oct 15 - Thu, Oct 22

6:00 am - 9:15 amORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 15mnonstop

8:10 am - 9:47 amLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 37mnonstop

$234United Airlines

Thu, Oct 15 - Thu, Oct 22

6:29 pm - 9:57 pmORD Chicago O'Hare Intl-LGA New York LaGuardia

2h 28mnonstop

2:10 pm - 4:05 pmLGA New York LaGuardia-ORD Chicago O'Hare Intl

2h 55mnonstop

$234American Airlines

Fri, Oct 30 - Fri, Nov 6

1:31 pm - 5:00 pmORD Chicago O'Hare Intl-JFK New York John F Kennedy Intl

2h 29mnonstop

2:59 pm - 4:55 pmJFK New York John F Kennedy Intl-ORD Chicago O'Hare Intl

2h 56mnonstop

$234American Airlines

Fri, Oct 30 - Fri, Nov 6

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JetBlue flights from Chicago to Connecticut

Our best JetBlue deals on Chicago to Connecticut flight tickets

JetBlue

Oct 21

ORD9:38 amChicago O'Hare Intl

6h 51m

1 stop

JFK5:29 pmNew York John F Kennedy Intl

Oct 24

JFK1:00 pmNew York John F Kennedy Intl

7h 14m

1 stop

ORD7:14 pmChicago O'Hare Intl

$229

JetBlue

Oct 11

ORD6:10 amChicago O'Hare Intl

2h 20m

JFK9:30 amNew York John F Kennedy Intl

Oct 13

JFK9:30 amNew York John F Kennedy Intl

2h 54m

ORD11:24 amChicago O'Hare Intl

$233

JetBlue

Oct 3

ORD10:59 amChicago O'Hare Intl

2h 21m

JFK2:20 pmNew York John F Kennedy Intl

Oct 6

JFK8:10 amNew York John F Kennedy Intl

2h 49m

ORD9:59 amChicago O'Hare Intl

$234

Delta flights from Chicago to Connecticut

Our best Delta deals on Chicago to Connecticut flight tickets

Delta

Oct 15

ORD6:00 amChicago O'Hare Intl

2h 12m

LGA9:12 amNew York LaGuardia

Oct 16

LGA8:35 pmNew York LaGuardia

2h 42m

ORD10:17 pmChicago O'Hare Intl

$232

Delta

Nov 1

ORD6:15 amChicago O'Hare Intl

2h 12m

LGA9:27 amNew York LaGuardia

Nov 4

LGA7:20 amNew York LaGuardia

2h 42m

ORD9:02 amChicago O'Hare Intl

$235

Delta

Oct 3

ORD7:00 amChicago O'Hare Intl

2h 15m

LGA10:15 amNew York LaGuardia

Oct 6

LGA6:00 amNew York LaGuardia

2h 36m

ORD7:36 amChicago O'Hare Intl

$240

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoNew Haven

ORD Chicago O'Hare Intl - HVN Tweed-New Haven

ORDHVN

Chicago O'Hare Intl

Fri 10/2

7:17 pm-10:39 pm

Nonstop2h 22m

Tweed-New Haven

Mon 10/5

4:30 pm-6:13 pm

Nonstop2h 43m

$135

Quickest round-trip

ChicagoNew Haven

ORD Chicago O'Hare Intl - HVN Tweed-New Haven

ORDHVN

Chicago O'Hare Intl

Thu 10/15

7:39 pm-10:59 pm

Nonstop2h 20m

Tweed-New Haven

Mon 10/19

4:45 pm-6:28 pm

Nonstop2h 43m

$135

ChicagoNew York

MDW Chicago Midway - LGA New York LaGuardia

MDWLGA

Chicago Midway

Sat 11/7

7:35 am-8:30 pm

2 stops11h 55m

New York LaGuardia

Mon 11/9

3:30 pm-10:00 pm

1 stop7h 30m

$223

ChicagoNew York

MDW Chicago Midway - LGA New York LaGuardia

MDWLGA

Chicago Midway

Tue 12/1

11:45 am-8:55 pm

1 stop8h 10m

New York LaGuardia

Sat 12/5

7:40 am-2:30 pm

1 stop7h 50m

$225

ChicagoNew York

ORD Chicago O'Hare Intl - JFK New York John F Kennedy Intl

ORDJFK

Chicago O'Hare Intl

Wed 10/21

9:38 am-5:29 pm

1 stop6h 51m

New York John F Kennedy Intl

Sat 10/24

1:00 pm-7:14 pm

1 stop7h 14m

$229

ChicagoNew York

ORD Chicago O'Hare Intl - JFK New York John F Kennedy Intl

ORDJFK

Chicago O'Hare Intl

Mon 11/16

6:44 am-10:09 am

Nonstop2h 25m

New York John F Kennedy Intl

Mon 11/16

5:29 pm-11:30 pm

1 stop7h 01m

$232

ChicagoNew York

ORD Chicago O'Hare Intl - JFK New York John F Kennedy Intl

ORDJFK

Chicago O'Hare Intl

Fri 11/13

10:55 am-4:31 pm

1 stop4h 36m

New York John F Kennedy Intl

Mon 11/16

10:40 am-12:35 pm

Nonstop2h 55m

$232

ChicagoNew York

ORD Chicago O'Hare Intl - JFK New York John F Kennedy Intl

ORDJFK

Chicago O'Hare Intl

Sun 10/11

6:10 am-9:30 am

Nonstop2h 20m

New York John F Kennedy Intl

Tue 10/13

9:30 am-11:24 am

Nonstop2h 54m

$232

ChicagoNew York

ORD Chicago O'Hare Intl - JFK New York John F Kennedy Intl

ORDJFK

Chicago O'Hare Intl

Tue 10/20

6:00 pm-9:40 pm

Nonstop2h 40m

New York John F Kennedy Intl

Thu 10/22

7:35 pm-9:43 pm

Nonstop3h 08m

$232

ChicagoNew York

ORD Chicago O'Hare Intl - JFK New York John F Kennedy Intl

ORDJFK

Chicago O'Hare Intl

Mon 10/5

6:00 am-9:21 am

Nonstop2h 21m

New York John F Kennedy Intl

Tue 10/6

7:35 pm-9:43 pm

Nonstop3h 08m

$232

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, December 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 $318. If you aren’t able to travel to Connecticut during the month of December, then flying in October is also cheap. Prices for this month can be found on momondo for an average of $325.

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	$75
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 $75. The best round-trip flight deal from Chicago to Connecticut found on momondo in the last 72 hours is $135.

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 Newark (EWR), New York LaGuardia (LGA), Hartford Bradley Intl (BDL).

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 September 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 29.65% of the total bookings. Other popular models include Embraer 175 with 13.65%, Boeing 737 MAX 8 with 12.99%, and Boeing 737-900 with 8.56%.

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 $88	Free Cancellation	Rating 7.5 85 reviews	Search Avelo Airlines flights
United Airlines	PriceFrom $225	Free Cancellation	Rating 7.4 10,224 reviews	Search United Airlines flights
American Airlines	PriceFrom $232	Free Cancellation	Rating 7.1 12,080 reviews	Search American Airlines flights
Southwest	PriceFrom $248	Free Cancellation	Rating 8.0 4,189 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.