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

As of May 2026, 176 flights take off from Chicago and land in Connecticut each day. The most common flight departure time for this route is 7:00PM, with 35% of daily flights taking off in the evening.

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

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

1,238 flights are operational weekly from Chicago to Connecticut as of May 2026. The most popular departure day for this route is Tue, with 19% 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 45% 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.

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 8 as of May 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.

$70 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.

6:35 pm - 10:07 pm

ORD

HVN

2h 32mnonstop

4:20 pm - 6:13 pm

HVN

ORD

2h 53mnonstop

$114Avelo Airlines

Thu, Jun 11 - Mon, Jun 15

6:35 pm - 10:07 pm

ORD

HVN

2h 32mnonstop

4:20 pm - 6:13 pm

HVN

ORD

2h 53mnonstop

$116Avelo Airlines

Thu, Jun 11 - Mon, Jun 15

7:07 pm - 10:39 pm

ORD

HVN

2h 32mnonstop

4:20 pm - 6:13 pm

HVN

ORD

2h 53mnonstop

$122Avelo Airlines

Fri, Jun 5 - Mon, Jun 8

1:49 pm - 5:00 pm

ORD

LGA

2h 11mnonstop

8:47 pm - 10:25 pm

LGA

ORD

2h 38mnonstop

$128Spirit Airlines

Thu, Jun 4 - Wed, Jun 10

1:49 pm - 5:00 pm

ORD

LGA

2h 11mnonstop

8:42 pm - 10:20 pm

LGA

ORD

2h 38mnonstop

$129Spirit Airlines

Wed, Jun 3 - Wed, Jun 10

5:15 am - 8:15 am

MDW

LGA

2h 00mnonstop

6:00 am - 7:20 am

LGA

MDW

2h 20mnonstop

$177Southwest

Thu, Jun 11 - Wed, Jun 17

5:15 pm - 8:20 pm

MDW

LGA

2h 05mnonstop

8:55 am - 1:45 pm

LGA

MDW

5h 50m

1 stop

$187Southwest

Thu, Jun 11 - Mon, Jun 15

1:40 pm - 5:11 pm

ORD

PVD

2h 31mnonstop

5:41 pm - 7:50 pm

PVD

ORD

3h 09mnonstop

$257American Airlines

Tue, Jun 16 - Tue, Jun 23

7:10 pm - 10:35 pm

ORD

PVD

2h 25mnonstop

7:22 pm - 12:34 am

PVD

ORD

6h 12m

1 stop

$267American Airlines

Tue, Jun 16 - Tue, Jun 23

10:45 am - 2:25 pm

ORD

PVD

2h 40mnonstop

6:00 am - 8:00 am

PVD

ORD

3h 00mnonstop

$274United Airlines

Wed, Jun 3 - Sat, Jun 6

Frontier flights from Chicago to Connecticut

Our best Frontier deals on Chicago to Connecticut flight tickets

Frontier

Jun 2

ORD1:29 pmChicago O'Hare Intl

21h 10m

1 stop

JFK11:39 amNew York John F Kennedy Intl

Jun 16

JFK1:05 pmNew York John F Kennedy Intl

7h 45m

1 stop

ORD7:50 pmChicago O'Hare Intl

$148

Frontier

Jun 2

MDW6:00 amChicago Midway

28h 39m

1 stop

JFK11:39 amNew York John F Kennedy Intl

Jun 16

JFK1:05 pmNew York John F Kennedy Intl

10h 06m

1 stop

MDW10:11 pmChicago Midway

$151

Frontier

Jun 2

MDW6:00 amChicago Midway

13h 56m

1 stop

LGA8:56 pmNew York LaGuardia

Jun 4

LGA6:29 amNew York LaGuardia

16h 33m

1 stop

MDW10:02 pmChicago Midway

$160

JetBlue flights from Chicago to Connecticut

Our best JetBlue deals on Chicago to Connecticut flight tickets

JetBlue

Jun 13

ORD6:00 amChicago O'Hare Intl

2h 20m

JFK9:20 amNew York John F Kennedy Intl

Jun 14

JFK7:00 amNew York John F Kennedy Intl

2h 45m

ORD8:45 amChicago O'Hare Intl

$155

JetBlue

Jun 27

ORD6:00 amChicago O'Hare Intl

2h 20m

JFK9:20 amNew York John F Kennedy Intl

Jun 29

JFK7:00 amNew York John F Kennedy Intl

2h 45m

ORD8:45 amChicago O'Hare Intl

$161

JetBlue

Jun 20

ORD5:22 pmChicago O'Hare Intl

2h 38m

JFK9:00 pmNew York John F Kennedy Intl

Jun 22

JFK7:00 amNew York John F Kennedy Intl

2h 45m

ORD8:45 amChicago O'Hare Intl

$166

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoNew Haven

ORD - HVN

ORDHVN

Chicago O'Hare Intl

Thu 6/11

6:35 pm-10:07 pm

Nonstop2h 32m

Tweed-New Haven

Mon 6/15

4:20 pm-6:13 pm

Nonstop2h 53m

$114

ChicagoNew Haven

ORD - HVN

ORDHVN

Chicago O'Hare Intl

Thu 6/11

6:35 pm-10:07 pm

Nonstop2h 32m

Tweed-New Haven

Mon 6/15

4:20 pm-6:13 pm

Nonstop2h 53m

$116

ChicagoNew Haven

ORD - HVN

ORDHVN

Chicago O'Hare Intl

Fri 6/5

7:07 pm-10:39 pm

Nonstop2h 32m

Tweed-New Haven

Mon 6/8

4:20 pm-6:13 pm

Nonstop2h 53m

$122

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Thu 6/4

1:49 pm-5:00 pm

Nonstop2h 11m

New York LaGuardia

Wed 6/10

8:47 pm-10:25 pm

Nonstop2h 38m

$128

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Wed 6/3

1:49 pm-5:00 pm

Nonstop2h 11m

New York LaGuardia

Wed 6/10

8:42 pm-10:20 pm

Nonstop2h 38m

$129

Quickest round-trip

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Thu 6/11

5:15 am-8:15 am

Nonstop2h 00m

New York LaGuardia

Wed 6/17

6:00 am-7:20 am

Nonstop2h 20m

$177

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Thu 6/11

5:15 pm-8:20 pm

Nonstop2h 05m

New York LaGuardia

Mon 6/15

8:55 am-1:45 pm

1 stop5h 50m

$187

ChicagoProvidence

ORD - PVD

ORDPVD

Chicago O'Hare Intl

Tue 6/16

1:40 pm-5:11 pm

Nonstop2h 31m

Providence-TFGreen

Tue 6/23

5:41 pm-7:50 pm

Nonstop3h 09m

$257

ChicagoProvidence

ORD - PVD

ORDPVD

Chicago O'Hare Intl

Tue 6/16

7:10 pm-10:35 pm

Nonstop2h 25m

Providence-TFGreen

Tue 6/23

7:22 pm-12:34 am

1 stop6h 12m

$267

ChicagoProvidence

ORD - PVD

ORDPVD

Chicago O'Hare Intl

Wed 6/3

10:45 am-2:25 pm

Nonstop2h 40m

Providence-TFGreen

Sat 6/6

6:00 am-8:00 am

Nonstop3h 00m

$274

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 $23. 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 $41.

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

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	$100
Fastest flight time	1h 45m
Direct flights	Every day
Airports in Connecticut	90 airports

The best one-way flight to Connecticut from Chicago in the past 72 hours is $100. The best round-trip flight deal from Chicago to Connecticut found on momondo in the last 72 hours is $106.

The fastest flight from Chicago to Connecticut takes 1h 45m

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), Providence-TFGreen (PVD).

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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 8 as of May 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 35.31% of the total bookings. Other popular models include Embraer 175 with 16.81%, Embraer 175 (Enhanced Winglets) with 11.53%, and Boeing 737-900 with 11.47%.

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 7.6 88 reviews	Search Avelo Airlines flights
Frontier	PriceFrom $109	Free Cancellation	Rating 5.6 2,965 reviews	Search Frontier flights
American Airlines	PriceFrom $177	Free Cancellation	Rating 7.1 11,672 reviews	Search American Airlines flights
United Airlines	PriceFrom $199	Free Cancellation	Rating 7.4 9,684 reviews	Search United Airlines flights
Southwest	PriceFrom $240	Free Cancellation	Rating 7.9 4,305 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.