What is the cheapest airline that flies from Connecticut to Chicago O'Hare Intl?

Avelo Airlines, Frontier, and Delta are the most popular carriers operating from Connecticut to Chicago O'Hare Intl

How many flights depart from Connecticut to Chicago O'Hare Intl Airport on average per week?

The number of flights available between Connecticut and Chicago O'Hare Intl Airport is 1,039 per week as of November 2025. The most frequent departure day is Fri, with 17% of weekly flights leaving on this day.

How long does it take to fly to Chicago O'Hare Intl Airport?

On average, it takes 2h 30m to fly from Connecticut to Chicago O'Hare Intl Airport if you fly out of New Haven (the most popular airport in Connecticut) and into Chicago O'Hare Intl Airport (the most popular airport in Chicago O'Hare Intl Airport). If you’re flying out of Hartford and into Chicago O'Hare Intl Airport, then the flight time is around 2h 33m.

What airlines fly to Chicago O'Hare Intl Airport?

American Airlines, United Airlines and Frontier are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from Connecticut according to our data. American Airlines is the first choice among our users, with 59% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 3 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.

How many flights depart from Connecticut to Chicago O'Hare Intl Airport on average per day?

The number of flights available between Connecticut and Chicago O'Hare Intl Airport is 148 per day as of November 2025. The most frequent departure time is 12:00PM, with 50% of daily flights leaving in the afternoon.

How many operators does momondo search for flights from Connecticut to Chicago O'Hare Intl Airport?

There are 6 operators available for flights from Connecticut to Chicago O'Hare Intl Airport as of November 2025.

How old do you have to be to fly from Connecticut to Chicago O'Hare Intl Airport?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Connecticut to Chicago O'Hare Intl Airport.

What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

The necessary travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$45 Cheap Flights from Connecticut to Chicago O'Hare Intl Airport in 2025/26

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Find the cheapest flights from Connecticut to Chicago

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One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

11:05 am - 12:35 pmHVN-ORD

2h 30mnonstop

1:20 pm - 4:25 pmORD-HVN

2h 05mnonstop

$84Avelo Airlines

Find Deal

Fri, Nov 28 - Mon, Dec 1

1:00 pm - 2:57 pmJFK-ORD

2h 57mnonstop

11:44 am - 12:59 amORD-JFK

12h 15m1 stop

$95Frontier

Find Deal

Fri, Dec 12 - Mon, Dec 15

6:20 am - 5:27 pmLGA-ORD

12h 07m1 stop

4:38 pm - 7:42 pmORD-LGA

2h 04mnonstop

$95Multiple Airlines

Find Deal

Thu, Dec 4 - Sat, Dec 6

12:59 pm - 2:31 pmLGA-ORD

2h 32mnonstop

10:59 am - 2:04 pmORD-LGA

2h 05mnonstop

$96Spirit Airlines

Find Deal

Tue, Dec 2 - Wed, Dec 3

7:30 am - 9:01 amLGA-ORD

2h 31mnonstop

4:38 pm - 7:42 pmORD-LGA

2h 04mnonstop

$97Spirit Airlines

Find Deal

Mon, Nov 24 - Thu, Dec 4

6:20 am - 11:54 amLGA-ORD

6h 34m1 stop

4:38 pm - 7:42 pmORD-LGA

2h 04mnonstop

$101Multiple Airlines

Find Deal

Sat, Dec 6 - Mon, Dec 8

7:00 pm - 8:58 pmJFK-ORD

2h 58mnonstop

10:06 am - 1:29 pmORD-JFK

2h 23mnonstop

$117American Airlines

Find Deal

Sat, Dec 6 - Mon, Dec 8

7:00 am - 8:47 amLGA-ORD

2h 47mnonstop

4:45 pm - 7:58 pmORD-LGA

2h 13mnonstop

$117American Airlines

Find Deal

Sat, Dec 6 - Mon, Dec 8

9:01 am - 10:45 amEWR-ORD

2h 44mnonstop

4:25 pm - 7:48 pmORD-EWR

2h 23mnonstop

$126United Airlines

Find Deal

Mon, Nov 24 - Wed, Dec 3

9:57 pm - 11:32 pmEWR-ORD

2h 35mnonstop

7:40 pm - 11:02 pmORD-EWR

2h 22mnonstop

$137United Airlines

Find Deal

Thu, Dec 11 - Sat, Dec 13

American Airlines flights from Connecticut to Chicago O'Hare Intl Airport

Our best American Airlines deals on Connecticut to Chicago O'Hare Intl Airport flight tickets

American Airlines

Dec 6

JFK7:00 pmNew York John F Kennedy Intl

2h 58m

ORD8:58 pmChicago O'Hare Intl

Dec 8

ORD10:06 amChicago O'Hare Intl

2h 23m

JFK1:29 pmNew York John F Kennedy Intl

$117

Find similar

American Airlines

Dec 6

EWR7:07 amNewark

2h 58m

ORD9:05 amChicago O'Hare Intl

Dec 8

ORD7:27 pmChicago O'Hare Intl

2h 14m

EWR10:41 pmNewark

$138

Find similar

American Airlines

Dec 6

EWR7:07 amNewark

2h 58m

ORD9:05 amChicago O'Hare Intl

Dec 8

ORD7:27 pmChicago O'Hare Intl

2h 14m

EWR10:41 pmNewark

$139

Find similar

JetBlue flights from Connecticut to Chicago O'Hare Intl Airport

Our best JetBlue deals on Connecticut to Chicago O'Hare Intl Airport flight tickets

JetBlue

Dec 6

JFK8:00 pmNew York John F Kennedy Intl

2h 52m

ORD9:52 pmChicago O'Hare Intl

Dec 8

ORD7:00 amChicago O'Hare Intl

2h 17m

JFK10:17 amNew York John F Kennedy Intl

$133

Find similar

JetBlue

Dec 2

JFK8:00 pmNew York John F Kennedy Intl

2h 52m

ORD9:52 pmChicago O'Hare Intl

Dec 16

ORD7:00 amChicago O'Hare Intl

2h 17m

JFK10:17 amNew York John F Kennedy Intl

$134

Find similar

JetBlue

Nov 22

JFK8:30 pmNew York John F Kennedy Intl

2h 51m

ORD10:21 pmChicago O'Hare Intl

Nov 27

ORD8:20 amChicago O'Hare Intl

2h 15m

JFK11:35 amNew York John F Kennedy Intl

$141

Find similar

momondo Fare Finder

Use the filters below to find and compare flights from Connecticut to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

New HavenChicago

HVN - ORD

HVNORD

Tweed-New Haven

Fri 11/28

11:05 am-12:35 pm

Nonstop2h 30m

Chicago O'Hare Intl

Mon 12/1

1:20 pm-4:25 pm

Nonstop2h 05m

$84

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Fri 12/12

1:00 pm-2:57 pm

Nonstop2h 57m

Chicago O'Hare Intl

Mon 12/15

11:44 am-12:59 am

1 stop12h 15m

$95

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Thu 12/4

6:20 am-5:27 pm

1 stop12h 07m

Chicago O'Hare Intl

Sat 12/6

4:38 pm-7:42 pm

Nonstop2h 04m

$95

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Tue 12/2

12:59 pm-2:31 pm

Nonstop2h 32m

Chicago O'Hare Intl

Wed 12/3

10:59 am-2:04 pm

Nonstop2h 05m

$96

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Mon 11/24

7:30 am-9:01 am

Nonstop2h 31m

Chicago O'Hare Intl

Thu 12/4

4:38 pm-7:42 pm

Nonstop2h 04m

$97

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 12/6

6:20 am-11:54 am

1 stop6h 34m

Chicago O'Hare Intl

Mon 12/8

4:38 pm-7:42 pm

Nonstop2h 04m

$101

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sat 12/6

7:00 pm-8:58 pm

Nonstop2h 58m

Chicago O'Hare Intl

Mon 12/8

10:06 am-1:29 pm

Nonstop2h 23m

$117

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 12/6

7:00 am-8:47 am

Nonstop2h 47m

Chicago O'Hare Intl

Mon 12/8

4:45 pm-7:58 pm

Nonstop2h 13m

$117

NewarkChicago

EWR - ORD

EWRORD

Newark

Mon 11/24

9:01 am-10:45 am

Nonstop2h 44m

Chicago O'Hare Intl

Wed 12/3

4:25 pm-7:48 pm

Nonstop2h 23m

$126

NewarkChicago

EWR - ORD

EWRORD

Newark

Thu 12/11

9:57 pm-11:32 pm

Nonstop2h 35m

Chicago O'Hare Intl

Sat 12/13

7:40 pm-11:02 pm

Nonstop2h 22m

$137

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 Connecticut to Chicago O'Hare Intl Airport

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 Chicago O'Hare Intl Airport?

The month of September is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Connecticut averaging around $307.

What is the cheapest Connecticut to Chicago O'Hare Intl flight route?

Fly from Tweed-New Haven to Chicago O'Hare Intl for the best Connecticut - Chicago O'Hare Intl flight prices

What cabin class options are available on Connecticut to Chicago O'Hare Intl flights?

There are 4 cabin classes available to choose from on Connecticut to Chicago O'Hare Intl 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 Connecticut to Chicago O'Hare Intl Airport flights?

No. A direct flight is the cheapest option for a flight between Connecticut to Chicago O'Hare Intl Airport.

Cheap Connecticut to Chicago O'Hare Intl Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Connecticut to Chicago O'Hare Intl Airport

Best Price Found	$49
Fastest flight time	2h 21m
Direct flights	Every day

The best one-way flight to Chicago O'Hare Intl Airport from Connecticut in the past 72 hours is $49. The best round-trip flight deal from Connecticut to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $347.

The fastest flight from Connecticut to Chicago O'Hare Intl Airport takes 2h 21m

Direct flights go from Connecticut to Chicago O'Hare Intl Airport every day.

Search flight deals

When did momondo last update prices for flights from Connecticut to Chicago O'Hare Intl Airport?
Prices for flights from Connecticut to Chicago O'Hare Intl Airport refresh daily.
How many operators does momondo search for flights from Connecticut to Chicago O'Hare Intl Airport?
There are 6 operators available for flights from Connecticut to Chicago O'Hare Intl Airport as of November 2025.
How old do you have to be to fly from Connecticut to Chicago O'Hare Intl Airport?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Connecticut to Chicago O'Hare Intl Airport.
What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?
The necessary travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Connecticut to Chicago O'Hare Intl Airport?
Based on momondo bookings for flights between Connecticut and Chicago O'Hare Intl Airport, the leading plane model is Boeing 737-800, making up 31.31% of the total bookings. Other popular models include Embraer 175 with 16.10%, Airbus A320-100/200 with 12.30%, and Embraer 175 (Enhanced Winglets) with 9.26%.

Best airlines flying from Connecticut to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Connecticut to Chicago O'Hare Intl Airport with momondo

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $97	Free Cancellation	Rating 5.8 3,111 reviews	Search Frontier flights
American Airlines	PriceFrom $185	Free Cancellation	Rating 7.2 11,046 reviews	Search American Airlines flights
United Airlines	PriceFrom $224	Free Cancellation	Rating 7.4 9,014 reviews	Search United Airlines flights

Lake Geneva

South Haven

Schaumburg

Rockford

Merrillville

Gurnee

Naperville

Rosemont

Kenosha

New Buffalo

Joliet

Oak Brook

Orland Park

Racine

Hammond

Tinley Park

Janesville

Aurora

Elgin

Benton Harbor

Why use momondo?

Why should I use momondo to find a flight deal from Connecticut to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Connecticut to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from Connecticut to Chicago with flexible booking policies on momondo?

Flights from Connecticut to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Connecticut to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Connecticut.

I’m not ready to book a flight from Connecticut to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Connecticut to Chicago 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 Chicago O'Hare Intl Airport trip

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Cheap flights from Connecticut to Chicago from $45

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Connecticut to Chicago departing on 12/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Big names and deals

Filter for what you want

Filter for what you want

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Find the cheapest flights from Connecticut to Chicago

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American Airlines flights from Connecticut to Chicago O'Hare Intl Airport

Our best American Airlines deals on Connecticut to Chicago O'Hare Intl Airport flight tickets

JetBlue flights from Connecticut to Chicago O'Hare Intl Airport

Our best JetBlue deals on Connecticut to Chicago O'Hare Intl Airport flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Connecticut to Chicago O'Hare Intl Airport that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from Connecticut to Chicago O'Hare Intl Airport

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 month to fly to Chicago O'Hare Intl Airport?

The month of September is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Connecticut averaging around $307.

What is the cheapest Connecticut to Chicago O'Hare Intl flight route?

Fly from Tweed-New Haven to Chicago O'Hare Intl for the best Connecticut - Chicago O'Hare Intl flight prices

What cabin class options are available on Connecticut to Chicago O'Hare Intl flights?

There are 4 cabin classes available to choose from on Connecticut to Chicago O'Hare Intl 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 Connecticut to Chicago O'Hare Intl Airport flights?

No. A direct flight is the cheapest option for a flight between Connecticut to Chicago O'Hare Intl Airport.

What is the cheapest airline that flies from Connecticut to Chicago O'Hare Intl?

Avelo Airlines, Frontier, and Delta are the most popular carriers operating from Connecticut to Chicago O'Hare Intl

What airlines fly to Chicago O'Hare Intl Airport?

How many flights depart from Connecticut to Chicago O'Hare Intl Airport on average per day?

The number of flights available between Connecticut and Chicago O'Hare Intl Airport is 148 per day as of November 2025. The most frequent departure time is 12:00PM, with 50% of daily flights leaving in the afternoon.

How many flights depart from Connecticut to Chicago O'Hare Intl Airport on average per week?

The number of flights available between Connecticut and Chicago O'Hare Intl Airport is 1,039 per week as of November 2025. The most frequent departure day is Fri, with 17% of weekly flights leaving on this day.

How long does it take to fly to Chicago O'Hare Intl Airport?

Cheap Connecticut to Chicago O'Hare Intl Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Connecticut to Chicago O'Hare Intl Airport

Best Price Found

Fastest flight time

Direct flights

When did momondo last update prices for flights from Connecticut to Chicago O'Hare Intl Airport?

How many operators does momondo search for flights from Connecticut to Chicago O'Hare Intl Airport?

How old do you have to be to fly from Connecticut to Chicago O'Hare Intl Airport?

What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

What is the most popular plane model from Connecticut to Chicago O'Hare Intl Airport?

Best airlines flying from Connecticut to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Connecticut to Chicago O'Hare Intl Airport with momondo

Traveling to a place near Chicago?

Why use momondo?

Why should I use momondo to find a flight deal from Connecticut to Chicago?

Can I find flights from Connecticut to Chicago with flexible booking policies on momondo?

How can momondo help me find flights from Connecticut to Chicago?

I’m not ready to book a flight from Connecticut to Chicago right now. Can momondo alert me if prices change?

An easier way to manage your Chicago O'Hare Intl Airport 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 Chicago

Popular cities in the United States

Popular flights according to clicks in the last 7 days on momondo