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

As of August 2025, 149 flights take off from Chicago and land in Connecticut each day. The most common flight departure time for this route is 6:00PM, with 44% of daily flights taking off in the evening.

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

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

What airlines fly to Connecticut?

American Airlines, United Airlines and Southwest are the top three most popular airlines that fly to Connecticut from Chicago according to our data. American Airlines is the first choice among our users, with 53% 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?

1,048 flights are operational weekly from Chicago to Connecticut as of August 2025. The most popular departure day for this route is Sat, with 19% 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 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.

$25 Cheap Flights from Chicago to Connecticut in 2025

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Find the cheapest flights from Chicago to Connecticut

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

4:35 pm - 7:41 pmORD-LGA

2h 06mnonstop

3:13 pm - 4:51 pmLGA-ORD

2h 38mnonstop

$56Spirit Airlines

Find Deal

Sat, Sep 6 - Wed, Sep 10

4:35 pm - 7:41 pmORD-LGA

2h 06mnonstop

3:13 pm - 4:51 pmLGA-ORD

2h 38mnonstop

$60Spirit Airlines

Find Deal

Sat, Sep 6 - Wed, Sep 10

5:56 pm - 9:00 pmMDW-EWR

2h 04mnonstop

10:00 pm - 11:25 pmEWR-MDW

2h 25mnonstop

$97Frontier

Find Deal

Tue, Oct 7 - Tue, Oct 14

6:40 am - 10:03 amORD-JFK

2h 23mnonstop

11:00 am - 12:45 pmJFK-ORD

2h 45mnonstop

$99Frontier

Find Deal

Wed, Oct 8 - Sat, Oct 18

8:48 am - 12:20 pmORD-BDL

2h 32mnonstop

6:10 am - 7:53 amBDL-ORD

2h 43mnonstop

$137United Airlines

Find Deal

Thu, Sep 4 - Sun, Sep 7

1:45 pm - 4:50 pmMDW-BDL

2h 05mnonstop

5:35 am - 6:55 amBDL-MDW

2h 20mnonstop

$137Southwest

Find Deal

Thu, Sep 4 - Sun, Sep 7

8:02 am - 11:24 amORD-BDL

2h 22mnonstop

5:44 pm - 7:25 pmBDL-ORD

2h 41mnonstop

$138American Airlines

Find Deal

Tue, Sep 2 - Tue, Sep 2

7:05 pm - 10:15 pmMDW-LGA

2h 10mnonstop

7:30 am - 8:50 amLGA-MDW

2h 20mnonstop

$142Southwest

Find Deal

Wed, Sep 3 - Sat, Sep 6

1:59 pm - 5:17 pmORD-JFK

2h 18mnonstop

11:00 am - 12:41 pmJFK-ORD

2h 41mnonstop

$149American Airlines

Find Deal

Sat, Sep 13 - Sat, Sep 20

10:35 am - 1:52 pmORD-EWR

2h 17mnonstop

9:44 pm - 11:25 pmEWR-ORD

2h 41mnonstop

$157United Airlines

Find Deal

Sat, Sep 6 - Mon, Sep 8

JetBlue flights from Chicago to Connecticut

Our best JetBlue deals on Chicago to Connecticut flight tickets

JetBlue

Aug 26

ORD6:15 amChicago O'Hare Intl

2h 12m

JFK9:27 amNew York John F Kennedy Intl

Sep 6

JFK4:30 pmNew York John F Kennedy Intl

2h 53m

ORD6:23 pmChicago O'Hare Intl

$152

Find similar

JetBlue

Sep 6

ORD8:34 amChicago O'Hare Intl

2h 26m

JFK12:00 pmNew York John F Kennedy Intl

Sep 9

JFK10:30 amNew York John F Kennedy Intl

2h 40m

ORD12:10 pmChicago O'Hare Intl

$154

Find similar

JetBlue

Sep 6

ORD8:34 amChicago O'Hare Intl

2h 26m

JFK12:00 pmNew York John F Kennedy Intl

Sep 8

JFK10:31 amNew York John F Kennedy Intl

2h 50m

ORD12:21 pmChicago O'Hare Intl

$156

Find similar

American Airlines flights from Chicago to Connecticut

Our best American Airlines deals on Chicago to Connecticut flight tickets

American Airlines

Sep 2

ORD8:02 amChicago O'Hare Intl

2h 22m

BDL11:24 amHartford Bradley Intl

Sep 2

BDL5:44 pmHartford Bradley Intl

2h 41m

ORD7:25 pmChicago O'Hare Intl

$138

Find similar

American Airlines

Sep 13

ORD1:59 pmChicago O'Hare Intl

2h 18m

JFK5:17 pmNew York John F Kennedy Intl

Sep 20

JFK11:00 amNew York John F Kennedy Intl

2h 41m

ORD12:41 pmChicago O'Hare Intl

$149

Find similar

American Airlines

Oct 10

ORD1:43 pmChicago O'Hare Intl

2h 22m

JFK5:05 pmNew York John F Kennedy Intl

Oct 15

JFK11:00 amNew York John F Kennedy Intl

2h 40m

ORD12:40 pmChicago O'Hare Intl

$158

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Sat 9/6

4:35 pm-7:41 pm

Nonstop2h 06m

New York LaGuardia

Wed 9/10

3:13 pm-4:51 pm

Nonstop2h 38m

$56

ChicagoNew York

ORD - LGA

ORDLGA

Chicago O'Hare Intl

Sat 9/6

4:35 pm-7:41 pm

Nonstop2h 06m

New York LaGuardia

Wed 9/10

3:13 pm-4:51 pm

Nonstop2h 38m

$60

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Tue 10/7

5:56 pm-9:00 pm

Nonstop2h 04m

Newark

Tue 10/14

10:00 pm-11:25 pm

Nonstop2h 25m

$97

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Wed 10/8

6:40 am-10:03 am

Nonstop2h 23m

New York John F Kennedy Intl

Sat 10/18

11:00 am-12:45 pm

Nonstop2h 45m

$99

ChicagoHartford

ORD - BDL

ORDBDL

Chicago O'Hare Intl

Thu 9/4

8:48 am-12:20 pm

Nonstop2h 32m

Hartford Bradley Intl

Sun 9/7

6:10 am-7:53 am

Nonstop2h 43m

$137

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Thu 9/4

1:45 pm-4:50 pm

Nonstop2h 05m

Hartford Bradley Intl

Sun 9/7

5:35 am-6:55 am

Nonstop2h 20m

$137

ChicagoHartford

ORD - BDL

ORDBDL

Chicago O'Hare Intl

Tue 9/2

8:02 am-11:24 am

Nonstop2h 22m

Hartford Bradley Intl

Tue 9/2

5:44 pm-7:25 pm

Nonstop2h 41m

$138

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 9/3

7:05 pm-10:15 pm

Nonstop2h 10m

New York LaGuardia

Sat 9/6

7:30 am-8:50 am

Nonstop2h 20m

$142

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Sat 9/13

1:59 pm-5:17 pm

Nonstop2h 18m

New York John F Kennedy Intl

Sat 9/20

11:00 am-12:41 pm

Nonstop2h 41m

$149

ChicagoNewark

ORD - EWR

ORDEWR

Chicago O'Hare Intl

Sat 9/6

10:35 am-1:52 pm

Nonstop2h 17m

Newark

Mon 9/8

9:44 pm-11:25 pm

Nonstop2h 41m

$157

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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 Chicago to Connecticut flight route?

Fly from Chicago Midway to Hartford Bradley Intl 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.

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 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 29.80% of the total bookings. Other popular models include Embraer 175 (Enhanced Winglets) with 13.31%, Airbus A320-100/200 with 12.19%, and Embraer 170 with 10.32%.

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 $95	Free Cancellation	Rating 7.5 78 reviews	Search Avelo Airlines flights
American Airlines	PriceFrom $178	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Southwest	PriceFrom $197	Free Cancellation	Rating 8.0 4,246 reviews	Search Southwest flights
United Airlines	PriceFrom $226	Free Cancellation	Rating 7.4 8,905 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.

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 $48

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Flights to Orlandofrom $54

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Flights to San Franciscofrom $61

Flights to Washington, D.C.from $48

Flights to Bostonfrom $67

Flights to Atlantafrom $39

Flights to Dallasfrom $55

Flights to Seattlefrom $94

Cheap flights from Chicago to Connecticut from $25

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 9/6. 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

Cheap one-way flights

Cheap last minute flights

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JetBlue flights from Chicago to Connecticut

Our best JetBlue deals on Chicago to Connecticut flight tickets

American Airlines flights from Chicago to Connecticut

Our best American Airlines 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

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

What is the cheapest Chicago to Connecticut flight route?

Fly from Chicago Midway to Hartford Bradley Intl 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.

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

Spirit Airlines and Frontier 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 August 2025, 149 flights take off from Chicago and land in Connecticut each day. The most common flight departure time for this route is 6:00PM, with 44% of daily flights taking off in the evening.

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

1,048 flights are operational weekly from Chicago to Connecticut as of August 2025. The most popular departure day for this route is Sat, with 19% of flights per week taking off on this day.

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