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

As of July 2025, 145 flights take off from Connecticut and land in Chicago each day. The most common flight departure time for this route is 6:00PM, with 46% of daily flights taking off at noon.

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 55% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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

1,021 flights are operational weekly from Connecticut to Chicago as of July 2025. The most popular departure day for this route is Thu, with 22% of flights per week taking off on this day.

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

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

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 New Haven to Chicago O'Hare Intl Airport is 2h 20m on average, while flying from Hartford to Chicago O'Hare Intl Airport is 2h 37m on average. Chicago O'Hare Intl Airport is the most popular airport in 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 July 2025, 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.

$28 Cheap Flights from Connecticut to Chicago in 2025

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Find the cheapest flights from Connecticut to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

11:00 am - 12:45 pmJFK-ORD

2h 45mnonstop

6:40 am - 10:03 amORD-JFK

2h 23mnonstop

$67Frontier

Find Deal

Wed, Oct 8 - Sat, Oct 11

10:00 pm - 11:25 pmEWR-MDW

2h 25mnonstop

5:56 pm - 9:00 pmMDW-EWR

2h 04mnonstop

$67Frontier

Find Deal

Tue, Oct 7 - Tue, Oct 14

10:59 am - 11:59 pmLGA-ORD

14h 00m1 stop

4:35 pm - 7:41 pmORD-LGA

2h 06mnonstop

$67Spirit Airlines

Find Deal

Sat, Aug 30 - Sat, Sep 6

3:12 pm - 4:50 pmLGA-ORD

2h 38mnonstop

11:13 am - 2:18 pmORD-LGA

2h 05mnonstop

$69Spirit Airlines

Find Deal

Sat, Sep 6 - Mon, Sep 8

8:30 pm - 10:28 pmJFK-ORD

2h 58mnonstop

6:10 am - 9:29 amORD-JFK

2h 19mnonstop

$137JetBlue

Find Deal

Sat, Aug 30 - Wed, Sep 3

12:40 pm - 2:00 pmBDL-MDW

2h 20mnonstop

6:50 pm - 9:55 pmMDW-BDL

2h 05mnonstop

$137Southwest

Find Deal

Thu, Aug 28 - Thu, Sep 4

6:00 am - 7:20 amLGA-MDW

2h 20mnonstop

7:05 pm - 10:15 pmMDW-LGA

2h 10mnonstop

$137Southwest

Find Deal

Wed, Sep 3 - Wed, Sep 3

6:00 am - 7:43 amBDL-ORD

2h 43mnonstop

7:32 am - 10:51 amORD-BDL

2h 19mnonstop

$137United Airlines

Find Deal

Thu, Sep 25 - Sun, Sep 28

4:30 pm - 6:23 pmJFK-ORD

2h 53mnonstop

6:45 am - 9:59 amORD-JFK

2h 14mnonstop

$141JetBlue

Find Deal

Sat, Sep 6 - Mon, Sep 8

7:00 am - 8:38 amEWR-ORD

2h 38mnonstop

1:12 pm - 4:30 pmORD-EWR

2h 18mnonstop

$142United Airlines

Find Deal

Wed, Sep 3 - Wed, Sep 3

Frontier flights from Connecticut to Chicago

Our best Frontier deals on Connecticut to Chicago flight tickets

Frontier

Oct 8

JFK11:00 amNew York John F Kennedy Intl

2h 45m

ORD12:45 pmChicago O'Hare Intl

Oct 11

ORD6:40 amChicago O'Hare Intl

2h 23m

JFK10:03 amNew York John F Kennedy Intl

$67

Find similar

Frontier

Nov 1

JFK11:00 amNew York John F Kennedy Intl

2h 45m

ORD12:45 pmChicago O'Hare Intl

Nov 5

ORD6:40 amChicago O'Hare Intl

2h 23m

JFK10:03 amNew York John F Kennedy Intl

$78

Find similar

Frontier

Oct 23

EWR10:00 pmNewark

2h 25m

MDW11:25 pmChicago Midway

Oct 28

MDW5:56 pmChicago Midway

2h 04m

EWR9:00 pmNewark

$85

Find similar

Delta flights from Connecticut to Chicago

Our best Delta deals on Connecticut to Chicago flight tickets

Delta

Sep 13

JFK10:30 amNew York John F Kennedy Intl

2h 46m

ORD12:16 pmChicago O'Hare Intl

Sep 16

ORD6:28 pmChicago O'Hare Intl

2h 40m

JFK10:08 pmNew York John F Kennedy Intl

$147

Find similar

Delta

Sep 6

JFK8:00 amNew York John F Kennedy Intl

2h 55m

ORD9:55 amChicago O'Hare Intl

Sep 8

ORD7:00 amChicago O'Hare Intl

2h 23m

JFK10:23 amNew York John F Kennedy Intl

$157

Find similar

Delta

Sep 6

JFK3:29 pmNew York John F Kennedy Intl

3h 08m

ORD5:37 pmChicago O'Hare Intl

Sep 8

ORD7:00 amChicago O'Hare Intl

2h 23m

JFK10:23 amNew York John F Kennedy Intl

$158

Find similar

Fly from

Fly to

Route

Depart

Return

Price

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Wed 10/8

11:00 am-12:45 pm

Nonstop2h 45m

Chicago O'Hare Intl

Sat 10/11

6:40 am-10:03 am

Nonstop2h 23m

$67

NewarkChicago

EWR - MDW

EWRMDW

Newark

Tue 10/7

10:00 pm-11:25 pm

Nonstop2h 25m

Chicago Midway

Tue 10/14

5:56 pm-9:00 pm

Nonstop2h 04m

$67

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 8/30

10:59 am-11:59 pm

1 stop14h 00m

Chicago O'Hare Intl

Sat 9/6

4:35 pm-7:41 pm

Nonstop2h 06m

$67

New YorkChicago

LGA - ORD

LGAORD

New York LaGuardia

Sat 9/6

3:12 pm-4:50 pm

Nonstop2h 38m

Chicago O'Hare Intl

Mon 9/8

11:13 am-2:18 pm

Nonstop2h 05m

$69

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sat 8/30

8:30 pm-10:28 pm

Nonstop2h 58m

Chicago O'Hare Intl

Wed 9/3

6:10 am-9:29 am

Nonstop2h 19m

$137

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 8/28

12:40 pm-2:00 pm

Nonstop2h 20m

Chicago Midway

Thu 9/4

6:50 pm-9:55 pm

Nonstop2h 05m

$137

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 9/3

6:00 am-7:20 am

Nonstop2h 20m

Chicago Midway

Wed 9/3

7:05 pm-10:15 pm

Nonstop2h 10m

$137

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Thu 9/25

6:00 am-7:43 am

Nonstop2h 43m

Chicago O'Hare Intl

Sun 9/28

7:32 am-10:51 am

Nonstop2h 19m

$137

New YorkChicago

JFK - ORD

JFKORD

New York John F Kennedy Intl

Sat 9/6

4:30 pm-6:23 pm

Nonstop2h 53m

Chicago O'Hare Intl

Mon 9/8

6:45 am-9:59 am

Nonstop2h 14m

$141

NewarkChicago

EWR - ORD

EWRORD

Newark

Wed 9/3

7:00 am-8:38 am

Nonstop2h 38m

Chicago O'Hare Intl

Wed 9/3

1:12 pm-4:30 pm

Nonstop2h 18m

$142

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 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	$28
Fastest flight time	2h 20m
Direct flights	Every day
Airports in Chicago	2 airports

The best one-way flight to Chicago from Connecticut in the past 72 hours is $28. The best round-trip flight deal from Connecticut to Chicago found on momondo in the last 72 hours is $67.

The fastest flight from Connecticut to Chicago takes 2h 20m

Direct flights go from Connecticut to Chicago every day.

There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), 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 July 2025, 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 29.39% of the total bookings. Other popular models include Embraer 175 (Enhanced Winglets) with 12.28%, Airbus A320-100/200 with 11.81%, and Airbus A319 with 9.27%.

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 $77	Free Cancellation	Rating 7.5 78 reviews	Search Avelo Airlines flights
Frontier	PriceFrom $116	Free Cancellation	Rating 5.9 3,239 reviews	Search Frontier flights
Delta	PriceFrom $176	Free Cancellation	Rating 8.0 7,981 reviews	Search Delta flights
Southwest	PriceFrom $177	Free Cancellation	Rating 8.0 4,246 reviews	Search Southwest flights
American Airlines	PriceFrom $184	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Spirit Airlines	PriceFrom $202	Free Cancellation	Rating 6.3 8,048 reviews	Search Spirit Airlines flights
United Airlines	PriceFrom $227	Free Cancellation	Rating 7.4 8,900 reviews	Search United Airlines flights

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Crown Point

Munster

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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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Cheap flights from Connecticut to Chicago from $28

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 11/10. 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

Trusted and free

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Price Alerts

Find the cheapest flights from Connecticut to Chicago

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Frontier flights from Connecticut to Chicago

Our best Frontier deals on Connecticut to Chicago flight tickets

Delta flights from Connecticut to Chicago

Our best Delta deals on Connecticut to Chicago flight tickets

momondo Fare Finder

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

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 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?

Frontier and Spirit Airlines 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 July 2025, 145 flights take off from Connecticut and land in Chicago each day. The most common flight departure time for this route is 6:00PM, with 46% of daily flights taking off at noon.

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

1,021 flights are operational weekly from Connecticut to Chicago as of July 2025. The most popular departure day for this route is Thu, with 22% 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