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

1,131 flights are operational weekly from Connecticut to Chicago as of February 2026. The most popular departure day for this route is Mon, with 18% of flights per week taking off on this day.

What airlines fly to Chicago?

American Airlines, United Airlines and Southwest are the top three most popular airlines that fly to Chicago from Connecticut according to our data. American Airlines is the first choice among our users, with 52% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

How long does it take to fly to Chicago?

Average flight duration from Connecticut to Chicago depends on which airport you fly into and out of. Flying from Hartford to Chicago O'Hare Intl Airport is 2h 33m on average, while flying from New Haven to Chicago O'Hare Intl Airport is 2h 45m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

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

As of February 2026, 161 flights take off from Connecticut and land in Chicago each day. The most common flight departure time for this route is 9:00AM, with 53% of daily flights taking off in the afternoon.

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

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

When did momondo last update prices for flights from Connecticut to Chicago?

Prices for flights from Connecticut to Chicago are updated daily.

How many operators does momondo search for flights from Connecticut to Chicago?

As of February 2026, there are 7 operators available to choose from for flights from Connecticut to Chicago.

How old do you have to be to fly from Connecticut to Chicago?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Connecticut to Chicago.

What documentation or ID do you need to fly to Chicago?

The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$50 Cheap Flights from Connecticut to Chicago in 2026

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Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

11:04 am - 1:00 pm

JFK

ORD

2h 56mnonstop

6:31 am - 10:00 am

ORD

JFK

2h 29mnonstop

$87Frontier

Thu, May 14 - Mon, May 18

7:40 am - 9:22 am

LGA

ORD

2h 42mnonstop

5:58 pm - 8:59 pm

ORD

LGA

2h 01mnonstop

$87Spirit Airlines

Wed, Feb 18 - Wed, Feb 18

12:02 pm - 7:11 pm

EWR

ORD

8h 09m

1 stop

6:51 pm - 10:00 pm

ORD

EWR

2h 09mnonstop

$88Spirit Airlines

Wed, Mar 4 - Mon, Mar 9

5:59 am - 4:52 pm

EWR

ORD

11h 53m

1 stop

6:51 pm - 10:00 pm

ORD

EWR

2h 09mnonstop

$95Multiple Airlines

Wed, Mar 4 - Wed, Mar 11

6:00 am - 7:40 am

LGA

MDW

2h 40mnonstop

6:05 pm - 9:10 pm

MDW

LGA

2h 05mnonstop

$125Southwest

Sat, Feb 28 - Mon, Mar 2

6:00 am - 7:40 am

LGA

MDW

2h 40mnonstop

6:05 am - 9:10 am

MDW

LGA

2h 05mnonstop

$130Southwest

Tue, Feb 24 - Mon, Mar 2

6:30 am - 12:04 pm

PVD

ORD

6h 34m

1 stop

6:04 am - 11:38 pm

ORD

PVD

16h 34m

1 stop

$199JetBlue

Sat, Feb 28 - Sun, Mar 1

6:30 am - 12:04 pm

PVD

ORD

6h 34m

1 stop

6:04 am - 11:38 pm

ORD

PVD

16h 34m

1 stop

$202JetBlue

Sat, Feb 28 - Sun, Mar 1

5:35 pm - 11:37 pm

PVD

ORD

7h 02m

1 stop

12:05 pm - 4:37 pm

ORD

PVD

51h 32m

2 stops

$240Multiple Airlines

Mon, Mar 2 - Mon, Mar 9

6:00 am - 11:59 am

BDL

MDW

6h 59m

1 stop

6:20 pm - 11:39 pm

MDW

BDL

4h 19m

1 stop

$309Delta

Tue, Feb 24 - Tue, Feb 24

JetBlue flights from Connecticut to Chicago

Our best JetBlue deals on Connecticut to Chicago flight tickets

JetBlue

Feb 17

JFK9:25 pmNew York John F Kennedy Intl

3h 01m

ORD11:26 pmChicago O'Hare Intl

Feb 24

ORD6:04 amChicago O'Hare Intl

2h 16m

JFK9:20 amNew York John F Kennedy Intl

$161

JetBlue

Feb 17

JFK9:25 pmNew York John F Kennedy Intl

3h 01m

ORD11:26 pmChicago O'Hare Intl

Feb 23

ORD6:04 amChicago O'Hare Intl

2h 16m

JFK9:20 amNew York John F Kennedy Intl

$162

JetBlue

Feb 17

JFK9:25 pmNew York John F Kennedy Intl

3h 01m

ORD11:26 pmChicago O'Hare Intl

Feb 24

ORD10:00 amChicago O'Hare Intl

8h 00m

1 stop

JFK7:00 pmNew York John F Kennedy Intl

$167

Frontier flights from Connecticut to Chicago

Our best Frontier deals on Connecticut to Chicago flight tickets

Frontier

Apr 17

JFK11:04 amNew York John F Kennedy Intl

2h 56m

ORD1:00 pmChicago O'Hare Intl

Apr 20

ORD6:31 amChicago O'Hare Intl

2h 29m

JFK10:00 amNew York John F Kennedy Intl

$86

Frontier

Apr 19

JFK11:04 amNew York John F Kennedy Intl

2h 56m

ORD1:00 pmChicago O'Hare Intl

Apr 20

ORD6:31 amChicago O'Hare Intl

2h 29m

JFK10:00 amNew York John F Kennedy Intl

$87

Frontier

Apr 26

EWR11:30 amNewark

2h 30m

MDW1:00 pmChicago Midway

Apr 27

MDW7:30 amChicago Midway

2h 08m

EWR10:38 amNewark

$90

Fly from

Fly to

Route

Depart

Return

Price

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Thu 5/14

11:04 am-1:00 pm

Nonstop2h 56m

Chicago O'Hare Intl

Mon 5/18

6:31 am-10:00 am

Nonstop2h 29m

$87

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Wed 2/18

7:40 am-9:22 am

Nonstop2h 42m

Chicago O'Hare Intl

Wed 2/18

5:58 pm-8:59 pm

Nonstop2h 01m

$87

NewarkChicago

EWR - ORD

EWRORD

Newark

Wed 3/4

12:02 pm-7:11 pm

1 stop8h 09m

Chicago O'Hare Intl

Mon 3/9

6:51 pm-10:00 pm

Nonstop2h 09m

$88

NewarkChicago

EWR - ORD

EWRORD

Newark

Wed 3/4

5:59 am-4:52 pm

1 stop11h 53m

Chicago O'Hare Intl

Wed 3/11

6:51 pm-10:00 pm

Nonstop2h 09m

$95

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 2/28

6:00 am-7:40 am

Nonstop2h 40m

Chicago Midway

Mon 3/2

6:05 pm-9:10 pm

Nonstop2h 05m

$125

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Tue 2/24

6:00 am-7:40 am

Nonstop2h 40m

Chicago Midway

Mon 3/2

6:05 am-9:10 am

Nonstop2h 05m

$130

ProvidenceChicago

PVD - ORD

PVDORD

Providence-TFGreen

Sat 2/28

6:30 am-12:04 pm

1 stop6h 34m

Chicago O'Hare Intl

Sun 3/1

6:04 am-11:38 pm

1 stop16h 34m

$199

ProvidenceChicago

PVD - ORD

PVDORD

Providence-TFGreen

Sat 2/28

6:30 am-12:04 pm

1 stop6h 34m

Chicago O'Hare Intl

Sun 3/1

6:04 am-11:38 pm

1 stop16h 34m

$202

ProvidenceChicago

PVD - ORD

PVDORD

Providence-TFGreen

Mon 3/2

5:35 pm-11:37 pm

1 stop7h 02m

Chicago O'Hare Intl

Mon 3/9

12:05 pm-4:37 pm

2 stops51h 32m

$240

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 2/24

6:00 am-11:59 am

1 stop6h 59m

Chicago Midway

Tue 2/24

6:20 pm-11:39 pm

1 stop4h 19m

$309

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

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?

The month of October is, on average, the cheapest month to fly to Chicago from Connecticut, with most prices found around $296. If you’re not able to fly to Chicago in October, then September is your next best option. Flight prices from Connecticut to Chicago during September average around $301.

What is the cheapest Connecticut to Chicago flight route?

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

What cabin class options are available on Connecticut to Chicago flights?

There are 4 cabin classes available to choose from on Connecticut to Chicago 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 flights?

No. A direct flight is the cheapest option for a flight between Connecticut to Chicago.

Cheap Connecticut to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Connecticut to Chicago

Best Price Found	$37
Fastest flight time	2h 15m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Connecticut in the past 72 hours is $37. The best round-trip flight deal from Connecticut to Chicago found on momondo in the last 72 hours is $77.

The fastest flight from Connecticut to Chicago takes 2h 15m

Direct flights go from Connecticut to Chicago every day.

There are 3 airports in Chicago. From Connecticut there are direct flights to Chicago Midway (MDW).

Search flight deals

When did momondo last update prices for flights from Connecticut to Chicago?
Prices for flights from Connecticut to Chicago are updated daily.
How many operators does momondo search for flights from Connecticut to Chicago?
As of February 2026, there are 7 operators available to choose from for flights from Connecticut to Chicago.
How old do you have to be to fly from Connecticut to Chicago?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Connecticut to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Connecticut to Chicago?
Based on momondo bookings for flights between Connecticut and Chicago, the leading plane model is Boeing 737-800, making up 27.68% of the total bookings. Other popular models include Embraer 175 with 16.62%, Airbus A320-100/200 with 8.68%, and Boeing 737 MAX 8 with 8.48%.

Best airlines flying from Connecticut to Chicago

Compare and see reviews for airlines that fly from Connecticut to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Avelo Airlines	PriceFrom $76	Free Cancellation	Rating 7.6 88 reviews	Search Avelo Airlines flights
Frontier	PriceFrom $94	Free Cancellation	Rating 5.7 3,051 reviews	Search Frontier flights
American Airlines	PriceFrom $176	Free Cancellation	Rating 7.2 11,218 reviews	Search American Airlines flights
Delta	PriceFrom $176	Free Cancellation	Rating 7.9 8,142 reviews	Search Delta flights
Southwest	PriceFrom $177	Free Cancellation	Rating 8.0 4,273 reviews	Search Southwest flights
United Airlines	PriceFrom $216	Free Cancellation	Rating 7.4 9,235 reviews	Search United Airlines flights

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Munster

Crown Point

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

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

Finding the right flight to Chicago from Connecticut 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 Chicago quick and easy, saving you time and money.

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

All flight searches from Connecticut to Chicago on momondo can be filtered to show those which offer flexible booking policies.

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

Once all potential Connecticut to Chicago 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 Connecticut to Chicago right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Connecticut to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

An easier way to manage your Chicago 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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Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

Cheap flights from Connecticut to Chicago from $56

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 3/3. 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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JetBlue flights from Connecticut to Chicago

Our best JetBlue deals on Connecticut to Chicago flight tickets

Frontier flights from Connecticut to Chicago

Our best Frontier deals on Connecticut to Chicago flight tickets

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Use the filters below to find and compare flights from Connecticut to Chicago that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from Connecticut to Chicago

What is the cheapest month to fly to Chicago?

The month of October is, on average, the cheapest month to fly to Chicago from Connecticut, with most prices found around $296. If you’re not able to fly to Chicago in October, then September is your next best option. Flight prices from Connecticut to Chicago during September average around $301.

What is the cheapest Connecticut to Chicago flight route?

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

What cabin class options are available on Connecticut to Chicago flights?

There are 4 cabin classes available to choose from on Connecticut to Chicago 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 flights?

No. A direct flight is the cheapest option for a flight between Connecticut to Chicago.

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

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

What airlines fly to Chicago?

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

As of February 2026, 161 flights take off from Connecticut and land in Chicago each day. The most common flight departure time for this route is 9:00AM, with 53% of daily flights taking off in the afternoon.

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

1,131 flights are operational weekly from Connecticut to Chicago as of February 2026. The most popular departure day for this route is Mon, with 18% of flights per week taking off on this day.

How long does it take to fly to Chicago?

Cheap Connecticut to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Connecticut to Chicago

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

When did momondo last update prices for flights from Connecticut to Chicago?

How many operators does momondo search for flights from Connecticut to Chicago?

How old do you have to be to fly from Connecticut to Chicago?

What documentation or ID do you need to fly to Chicago?

What is the most popular plane model from Connecticut to Chicago?

Best airlines flying from Connecticut to Chicago

Compare and see reviews for airlines that fly from Connecticut to Chicago 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 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 the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago

Fly your favorite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

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

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According to popular flight searches on momondo this year

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