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

115 flights are operational weekly from Chicago to Connecticut as of November 2026. The most popular departure day for this route is Mon, with 19% of flights per week taking off on this day.

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

Avelo Airlines, United Airlines, and American Airlines 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 50% 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 November 2026, 16 flights take off from Chicago and land in Connecticut each day. The most common flight departure time for this route is 6:00PM, 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 4 as of November 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.

$104 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.

7:07 pm - 10:30 pmORD Chicago O'Hare Intl-HVN Tweed-New Haven

2h 23mnonstop

4:35 pm - 6:28 pmHVN Tweed-New Haven-ORD Chicago O'Hare Intl

2h 53mnonstop

$172Avelo Airlines

Thu, Dec 10 - Sun, Jan 10

7:07 pm - 10:30 pmORD Chicago O'Hare Intl-HVN Tweed-New Haven

2h 23mnonstop

4:25 pm - 6:18 pmHVN Tweed-New Haven-ORD Chicago O'Hare Intl

2h 53mnonstop

$204Avelo Airlines

Thu, Dec 3 - Thu, Dec 10

7:03 pm - 10:26 pmORD Chicago O'Hare Intl-HVN Tweed-New Haven

2h 23mnonstop

9:37 am - 6:03 pmHVN Tweed-New Haven-ORD Chicago O'Hare Intl

9h 26m2 stops Raleigh-Durham Atlanta Hartsfield-Jackson

$285Multiple Airlines

Tue, Dec 1 - Fri, Dec 4

10:29 pm - 12:25 pmORD Chicago O'Hare Intl-HVN Tweed-New Haven

12h 56m1 stop Atlanta Hartsfield-Jackson

4:25 pm - 6:18 pmHVN Tweed-New Haven-ORD Chicago O'Hare Intl

2h 53mnonstop

$293Multiple Airlines

Thu, Dec 3 - Thu, Dec 10

1:15 pm - 7:45 pmMDW Chicago Midway-BDL Hartford Bradley Intl

5h 30m2 stops Richmond Byrd Intl Baltimore/Washington

8:25 am - 1:40 pmBDL Hartford Bradley Intl-MDW Chicago Midway

6h 15m1 stop Baltimore/Washington

$322Southwest

Tue, Dec 15 - Thu, Dec 17

1:55 pm - 9:20 pmMDW Chicago Midway-BDL Hartford Bradley Intl

6h 25m1 stop Orlando

3:30 pm - 12:20 amBDL Hartford Bradley Intl-MDW Chicago Midway

9h 50m2 stops Baltimore/Washington Nashville Intl

$322Southwest

Sat, Jan 9 - Mon, Jan 18

9:42 am - 5:38 pmORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

6h 56m1 stop Washington, D.C. Reagan-National

9:12 am - 11:05 amBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

2h 53mnonstop

$323American Airlines

Thu, Dec 24 - Mon, Jan 4

8:50 am - 2:06 pmORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

4h 16m1 stop Washington, D.C. Reagan-National

3:27 pm - 5:29 pmBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

3h 02mnonstop

$323American Airlines

Wed, Jan 13 - Mon, Jan 18

11:00 am - 2:18 pmORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

2h 18mnonstop

6:00 am - 7:51 amBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

2h 51mnonstop

$344United Airlines

Mon, Nov 23 - Sat, Nov 28

8:50 am - 2:02 pmORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

4h 12m1 stop Washington, D.C. Dulles Intl

6:00 am - 7:51 amBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

2h 51mnonstop

$354United Airlines

Mon, Nov 23 - Sat, Nov 28

Cheap last minute 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

4:45 pm - 6:24 pmHVN Tweed-New Haven-ORD Chicago O'Hare Intl

2h 39mnonstop

$212Avelo Airlines

Mon, Nov 9 - Thu, Nov 12

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

2h 22mnonstop

4:45 pm - 6:24 pmHVN Tweed-New Haven-ORD Chicago O'Hare Intl

2h 39mnonstop

$214Avelo Airlines

Fri, Nov 6 - Sun, Nov 8

7:09 pm - 10:29 pmORD Chicago O'Hare Intl-HVN Tweed-New Haven

2h 20mnonstop

4:45 pm - 6:24 pmHVN Tweed-New Haven-ORD Chicago O'Hare Intl

2h 39mnonstop

$214Avelo Airlines

Thu, Nov 5 - Sun, Nov 8

7:09 pm - 10:29 pmORD Chicago O'Hare Intl-HVN Tweed-New Haven

2h 20mnonstop

11:15 am - 12:21 amHVN Tweed-New Haven-ORD Chicago O'Hare Intl

14h 06m2 stops Raleigh-Durham Denver Intl

$335Multiple Airlines

Thu, Nov 5 - Sat, Nov 7

4:00 pm - 2:20 pmORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

21h 20m1 stop Orlando

3:15 pm - 5:07 pmBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

26h 52m1 stop Orlando

$362Frontier

Sat, Nov 7 - Mon, Nov 9

9:51 am - 2:20 pmORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

27h 29m1 stop Orlando

3:15 pm - 5:07 pmBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

26h 52m1 stop Orlando

$366Frontier

Thu, Nov 5 - Mon, Nov 9

7:25 am - 10:43 amORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

2h 18mnonstop

12:37 pm - 2:29 pmBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

2h 52mnonstop

$466United Airlines

Thu, Nov 5 - Thu, Nov 5

11:00 am - 2:18 pmORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

2h 18mnonstop

5:02 pm - 6:50 pmBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

2h 48mnonstop

$466United Airlines

Fri, Nov 6 - Fri, Nov 6

7:10 pm - 10:15 pmMDW Chicago Midway-BDL Hartford Bradley Intl

2h 05mnonstop

7:25 am - 8:55 amBDL Hartford Bradley Intl-MDW Chicago Midway

2h 30mnonstop

$471Southwest

Mon, Nov 9 - Fri, Nov 13

8:00 am - 11:10 amMDW Chicago Midway-BDL Hartford Bradley Intl

2h 10mnonstop

12:55 pm - 2:25 pmBDL Hartford Bradley Intl-MDW Chicago Midway

2h 30mnonstop

$471Southwest

Sun, Nov 8 - Mon, Nov 9

Cheap direct flights

Enter your travel dates to find the best prices.

7:07 pm - 10:30 pmORD Chicago O'Hare Intl-HVN Tweed-New Haven

2h 23mnonstop

4:35 pm - 6:28 pmHVN Tweed-New Haven-ORD Chicago O'Hare Intl

2h 53mnonstop

$172Avelo Airlines

Thu, Dec 10 - Sun, Jan 10

7:07 pm - 10:30 pmORD Chicago O'Hare Intl-HVN Tweed-New Haven

2h 23mnonstop

4:25 pm - 6:18 pmHVN Tweed-New Haven-ORD Chicago O'Hare Intl

2h 53mnonstop

$204Avelo Airlines

Thu, Dec 3 - Thu, Dec 10

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

2h 22mnonstop

4:35 pm - 6:28 pmHVN Tweed-New Haven-ORD Chicago O'Hare Intl

2h 53mnonstop

$214Avelo Airlines

Mon, Nov 16 - Thu, Nov 19

7:10 pm - 10:20 pmMDW Chicago Midway-BDL Hartford Bradley Intl

2h 10mnonstop

6:40 pm - 8:05 pmBDL Hartford Bradley Intl-MDW Chicago Midway

2h 25mnonstop

$323Southwest

Wed, Dec 23 - Mon, Jan 4

7:50 am - 10:50 amMDW Chicago Midway-BDL Hartford Bradley Intl

2h 00mnonstop

6:25 pm - 7:55 pmBDL Hartford Bradley Intl-MDW Chicago Midway

2h 30mnonstop

$323Southwest

Tue, Dec 29 - Thu, Dec 31

11:00 am - 2:18 pmORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

2h 18mnonstop

6:00 am - 7:51 amBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

2h 51mnonstop

$344United Airlines

Mon, Nov 23 - Sat, Nov 28

2:35 pm - 5:51 pmORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

2h 16mnonstop

9:29 am - 11:25 amBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

2h 56mnonstop

$357United Airlines

Thu, Feb 18 - Sun, Feb 21

7:36 pm - 10:56 pmORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

2h 20mnonstop

7:00 am - 9:07 amBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

3h 07mnonstop

$357American Airlines

Fri, Dec 18 - Tue, Dec 29

8:30 pm - 11:52 pmORD Chicago O'Hare Intl-BDL Hartford Bradley Intl

2h 22mnonstop

7:00 am - 9:07 amBDL Hartford Bradley Intl-ORD Chicago O'Hare Intl

3h 07mnonstop

$357American Airlines

Thu, Dec 10 - Wed, Dec 23

8:00 am - 11:10 amMDW Chicago Midway-BDL Hartford Bradley Intl

2h 10mnonstop

7:25 am - 8:55 amBDL Hartford Bradley Intl-MDW Chicago Midway

2h 30mnonstop

$357Southwest

Mon, Nov 23 - Fri, Nov 27

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Frontier flights from Chicago to Connecticut

Our best Frontier deals on Chicago to Connecticut flight tickets

Frontier

Nov 19

ORD9:51 amChicago O'Hare Intl

24h 40m

1 stop

BDL11:31 amHartford Bradley Intl

Nov 23

BDL1:43 pmHartford Bradley Intl

27h 09m

1 stop

ORD3:52 pmChicago O'Hare Intl

$330

Frontier

Nov 23

MDW8:42 pmChicago Midway

13h 49m

1 stop

BDL11:31 amHartford Bradley Intl

Nov 30

BDL12:26 pmHartford Bradley Intl

8h 21m

1 stop

MDW7:47 pmChicago Midway

$334

Frontier

Nov 12

ORD9:51 amChicago O'Hare Intl

27h 29m

1 stop

BDL2:20 pmHartford Bradley Intl

Nov 16

BDL3:15 pmHartford Bradley Intl

26h 52m

1 stop

ORD5:07 pmChicago O'Hare Intl

$346

United Airlines flights from Chicago to Connecticut

Our best United Airlines deals on Chicago to Connecticut flight tickets

United Airlines

Dec 4

ORD2:15 pmChicago O'Hare Intl

2h 18m

BDL5:33 pmHartford Bradley Intl

Dec 13

BDL6:00 amHartford Bradley Intl

6h 33m

1 stop

ORD11:33 amChicago O'Hare Intl

$363

United Airlines

Nov 25

ORD7:25 amChicago O'Hare Intl

2h 18m

BDL10:43 amHartford Bradley Intl

Nov 30

BDL6:00 amHartford Bradley Intl

2h 51m

ORD7:51 amChicago O'Hare Intl

$364

United Airlines

Nov 25

ORD1:30 pmChicago O'Hare Intl

4h 12m

1 stop

BDL6:42 pmHartford Bradley Intl

Nov 27

BDL7:54 pmHartford Bradley Intl

5h 07m

1 stop

ORD12:01 amChicago O'Hare Intl

$376

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

Thu 12/10

7:07 pm-10:30 pm

Nonstop2h 23m

Tweed-New Haven

Sun 1/10

4:35 pm-6:28 pm

Nonstop2h 53m

$172

ChicagoNew Haven

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

ORDHVN

Chicago O'Hare Intl

Thu 12/3

7:07 pm-10:30 pm

Nonstop2h 23m

Tweed-New Haven

Thu 12/10

4:25 pm-6:18 pm

Nonstop2h 53m

$204

ChicagoNew Haven

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

ORDHVN

Chicago O'Hare Intl

Tue 12/1

7:03 pm-10:26 pm

Nonstop2h 23m

Tweed-New Haven

Fri 12/4

9:37 am-6:03 pm

2 stops9h 26m

$285

ChicagoNew Haven

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

ORDHVN

Chicago O'Hare Intl

Thu 12/3

10:29 pm-12:25 pm

1 stop12h 56m

Tweed-New Haven

Thu 12/10

4:25 pm-6:18 pm

Nonstop2h 53m

$293

ChicagoHartford

MDW Chicago Midway - BDL Hartford Bradley Intl

MDWBDL

Chicago Midway

Tue 12/15

1:15 pm-7:45 pm

2 stops5h 30m

Hartford Bradley Intl

Thu 12/17

8:25 am-1:40 pm

1 stop6h 15m

$322

ChicagoHartford

MDW Chicago Midway - BDL Hartford Bradley Intl

MDWBDL

Chicago Midway

Sat 1/9

1:55 pm-9:20 pm

1 stop6h 25m

Hartford Bradley Intl

Mon 1/18

3:30 pm-12:20 am

2 stops9h 50m

$322

ChicagoHartford

ORD Chicago O'Hare Intl - BDL Hartford Bradley Intl

ORDBDL

Chicago O'Hare Intl

Thu 12/24

9:42 am-5:38 pm

1 stop6h 56m

Hartford Bradley Intl

Mon 1/4

9:12 am-11:05 am

Nonstop2h 53m

$323

ChicagoHartford

ORD Chicago O'Hare Intl - BDL Hartford Bradley Intl

ORDBDL

Chicago O'Hare Intl

Wed 1/13

8:50 am-2:06 pm

1 stop4h 16m

Hartford Bradley Intl

Mon 1/18

3:27 pm-5:29 pm

Nonstop3h 02m

$323

Quickest round-trip

ChicagoHartford

ORD Chicago O'Hare Intl - BDL Hartford Bradley Intl

ORDBDL

Chicago O'Hare Intl

Mon 11/23

11:00 am-2:18 pm

Nonstop2h 18m

Hartford Bradley Intl

Sat 11/28

6:00 am-7:51 am

Nonstop2h 51m

$344

ChicagoHartford

ORD Chicago O'Hare Intl - BDL Hartford Bradley Intl

ORDBDL

Chicago O'Hare Intl

Mon 11/23

8:50 am-2:02 pm

1 stop4h 12m

Hartford Bradley Intl

Sat 11/28

6:00 am-7:51 am

Nonstop2h 51m

$354

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 $358. If you aren’t able to travel to Connecticut during the month of December, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $371.

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	$104
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 $104. The best round-trip flight deal from Chicago to Connecticut found on momondo in the last 72 hours is $172.

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 Tweed-New Haven (HVN), 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 4 as of November 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 27.13% of the total bookings. Other popular models include Boeing 737 MAX 8 with 16.58%, Airbus A319 with 10.78%, and Boeing 737-900 with 9.53%.

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 7.6 87 reviews	Search Avelo Airlines flights
Southwest	PriceFrom $248	Free Cancellation	Rating 8.0 4,215 reviews	Search Southwest flights
American Airlines	PriceFrom $252	Free Cancellation	Rating 7.0 12,233 reviews	Search American Airlines flights
United Airlines	PriceFrom $277	Free Cancellation	Rating 7.3 10,461 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.