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

The number of flights available between Connecticut and Chicago Midway Airport is 64 per week as of August 2025. The most frequent departure day is Mon, with 20% of weekly flights leaving on this day.

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

As of August 2025, there are 9 flights per day flying from Connecticut to Chicago Midway Airport. The most common time of day flights depart is 7:00AM, with 40% of flights taking off at noon.

How long does it take to fly to Chicago Midway Airport?

On average, it takes 2h 20m to fly from Connecticut to Chicago Midway 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 Midway Airport). If you’re flying out of Hartford and into Chicago O'Hare Intl Airport, then the flight time is around 2h 33m.

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

Frontier and Southwest are the most popular carriers operating from Connecticut to Chicago Midway

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

Prices for flights from Connecticut to Chicago Midway Airport were last updated today.

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

There are 4 operators available for flights from Connecticut to Chicago Midway Airport as of August 2025.

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

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 Midway Airport.

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

The travel and health documents required for your trip to Chicago Midway Airport 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 Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$58 Cheap Flights from Connecticut to Chicago Midway Airport 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

10:00 pm - 11:25 pmEWR-MDW

2h 25mnonstop

5:56 pm - 9:00 pmMDW-EWR

2h 04mnonstop

$97Frontier

Find Deal

mar., oct. 7 - mar., oct. 14

10:00 pm - 11:25 pmEWR-MDW

2h 25mnonstop

5:56 pm - 9:00 pmMDW-EWR

2h 04mnonstop

$107Frontier

Find Deal

jue., oct. 9 - mar., oct. 14

10:00 pm - 11:25 pmEWR-MDW

2h 25mnonstop

5:56 pm - 9:00 pmMDW-EWR

2h 04mnonstop

$114Frontier

Find Deal

dom., oct. 12 - mar., oct. 14

10:00 pm - 11:25 pmEWR-MDW

2h 25mnonstop

5:56 pm - 9:00 pmMDW-EWR

2h 04mnonstop

$117Frontier

Find Deal

jue., oct. 30 - dom., nov. 2

10:00 pm - 11:25 pmEWR-MDW

2h 25mnonstop

5:56 pm - 9:00 pmMDW-EWR

2h 04mnonstop

$118Frontier

Find Deal

mar., oct. 14 - jue., oct. 16

3:35 pm - 5:05 pmLGA-MDW

2h 30mnonstop

10:40 am - 1:45 pmMDW-LGA

2h 05mnonstop

$119Southwest

Find Deal

mar., sep. 2 - mié., sep. 3

11:25 am - 12:50 pmLGA-MDW

2h 25mnonstop

2:35 pm - 5:40 pmMDW-LGA

2h 05mnonstop

$122Southwest

Find Deal

mié., sep. 3 - sáb., sep. 6

6:15 am - 10:30 amEWR-MDW

5h 15m1 stop

1:08 pm - 7:23 pmMDW-EWR

5h 15m1 stop

$179Delta

Find Deal

sáb., oct. 25 - mar., oct. 28

12:27 pm - 5:37 pmEWR-MDW

6h 10m1 stop

6:00 am - 12:11 pmMDW-EWR

5h 11m1 stop

$183Delta

Find Deal

mié., sep. 3 - mié., sep. 10

5:15 am - 3:58 pmEWR-MDW

11h 43m1 stop

6:20 am - 9:01 pmMDW-EWR

13h 41m2 stops

$201

Find Deal

mar., sep. 9 - jue., sep. 11

Southwest flights from Connecticut to Chicago Midway Airport

Our best Southwest deals on Connecticut to Chicago Midway Airport flight tickets

Southwest

Sep 2

LGA3:35 pmNew York LaGuardia

2h 30m

MDW5:05 pmChicago Midway

Sep 3

MDW10:40 amChicago Midway

2h 05m

LGA1:45 pmNew York LaGuardia

$119

Find similar

Southwest

Sep 3

LGA11:25 amNew York LaGuardia

2h 25m

MDW12:50 pmChicago Midway

Sep 6

MDW2:35 pmChicago Midway

2h 05m

LGA5:40 pmNew York LaGuardia

$122

Find similar

Southwest

Sep 6

BDL5:00 pmHartford Bradley Intl

2h 20m

MDW6:20 pmChicago Midway

Sep 8

MDW6:50 pmChicago Midway

2h 05m

BDL9:55 pmHartford Bradley Intl

$125

Find similar

Frontier flights from Connecticut to Chicago Midway Airport

Our best Frontier deals on Connecticut to Chicago Midway Airport flight tickets

Frontier

Oct 7

EWR10:00 pmNewark

2h 25m

MDW11:25 pmChicago Midway

Oct 14

MDW5:56 pmChicago Midway

2h 04m

EWR9:00 pmNewark

$97

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Frontier

Oct 9

EWR10:00 pmNewark

2h 25m

MDW11:25 pmChicago Midway

Oct 14

MDW5:56 pmChicago Midway

2h 04m

EWR9:00 pmNewark

$107

Find similar

Frontier

Oct 12

EWR10:00 pmNewark

2h 25m

MDW11:25 pmChicago Midway

Oct 14

MDW5:56 pmChicago Midway

2h 04m

EWR9:00 pmNewark

$114

Find similar

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

NewarkChicago

EWR - MDW

EWRMDW

Newark

mar. 10/7

10:00 pm-11:25 pm

Nonstop2h 25m

Chicago Midway

mar. 10/14

5:56 pm-9:00 pm

Nonstop2h 04m

$97

NewarkChicago

EWR - MDW

EWRMDW

Newark

jue. 10/9

10:00 pm-11:25 pm

Nonstop2h 25m

Chicago Midway

mar. 10/14

5:56 pm-9:00 pm

Nonstop2h 04m

$107

NewarkChicago

EWR - MDW

EWRMDW

Newark

dom. 10/12

10:00 pm-11:25 pm

Nonstop2h 25m

Chicago Midway

mar. 10/14

5:56 pm-9:00 pm

Nonstop2h 04m

$114

NewarkChicago

EWR - MDW

EWRMDW

Newark

jue. 10/30

10:00 pm-11:25 pm

Nonstop2h 25m

Chicago Midway

dom. 11/2

5:56 pm-9:00 pm

Nonstop2h 04m

$117

NewarkChicago

EWR - MDW

EWRMDW

Newark

mar. 10/14

10:00 pm-11:25 pm

Nonstop2h 25m

Chicago Midway

jue. 10/16

5:56 pm-9:00 pm

Nonstop2h 04m

$118

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

mar. 9/2

3:35 pm-5:05 pm

Nonstop2h 30m

Chicago Midway

mié. 9/3

10:40 am-1:45 pm

Nonstop2h 05m

$119

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

mié. 9/3

11:25 am-12:50 pm

Nonstop2h 25m

Chicago Midway

sáb. 9/6

2:35 pm-5:40 pm

Nonstop2h 05m

$122

NewarkChicago

EWR - MDW

EWRMDW

Newark

sáb. 10/25

6:15 am-10:30 am

1 stop5h 15m

Chicago Midway

mar. 10/28

1:08 pm-7:23 pm

1 stop5h 15m

$179

NewarkChicago

EWR - MDW

EWRMDW

Newark

mié. 9/3

12:27 pm-5:37 pm

1 stop6h 10m

Chicago Midway

mié. 9/10

6:00 am-12:11 pm

1 stop5h 11m

$183

NewarkChicago

EWR - MDW

EWRMDW

Newark

mar. 9/9

5:15 am-3:58 pm

1 stop11h 43m

Chicago Midway

jue. 9/11

6:20 am-9:01 pm

2 stops13h 41m

$201

Flights are sorted by cheapest round-trip flights first.

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How to get the cheapest flight ticket from Connecticut to Chicago Midway 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 Midway Airport?

The month of September is, on average, the cheapest month to fly to Chicago Midway Airport from Connecticut, with most prices found around $319. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Connecticut during the month August is also very affordable. Most momondo users find prices during this month for around $331.

What is the cheapest Connecticut to Chicago Midway flight route?

Fly from Hartford Bradley Intl to Chicago Midway for the best Connecticut - Chicago Midway flight prices

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

There are 1 cabin classes available to choose from on Connecticut to Chicago Midway 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 Midway Airport flights?

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

Cheap Connecticut to Chicago Midway Airport flight deals and tips

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

Best Price Found	$58
Fastest flight time	2h 20m
Direct flights	Every day

The best one-way flight to Chicago Midway Airport from Connecticut in the past 72 hours is $58. The best round-trip flight deal from Connecticut to Chicago Midway Airport found on momondo in the last 72 hours is $97.

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

Direct flights go from Connecticut to Chicago Midway Airport every day.

Search flight deals

When did momondo last update prices for flights from Connecticut to Chicago Midway Airport?
Prices for flights from Connecticut to Chicago Midway Airport were last updated today.
How many operators does momondo search for flights from Connecticut to Chicago Midway Airport?
There are 4 operators available for flights from Connecticut to Chicago Midway Airport as of August 2025.
How old do you have to be to fly from Connecticut to Chicago Midway Airport?
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 Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents required for your trip to Chicago Midway Airport 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 Chicago Midway Airport. 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 Connecticut to Chicago Midway Airport?
momondo data reveals that the most frequently booked plane model on the route from Connecticut to Chicago Midway Airport is Boeing 737-800, representing 25.55% of all bookings. The subsequent popular models are Boeing 737-700 Passenger/BBJ1 (winglets) at 11.91%, Embraer 175 (Enhanced Winglets) at 10.32%, and Airbus A320-100/200 at 10.17%.

Best airlines flying from Connecticut to Chicago Midway Airport

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

Airline	Rating	Free Cancellation	Price
Avelo Airlines	PriceFrom $77	Free Cancellation	Rating 7.5 78 reviews		Search Avelo Airlines flights
Southwest	PriceFrom $177	Free Cancellation	Rating 8.0 4,247 reviews		Search Southwest flights

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Lansing

Portage

Schererville

Valparaiso

Crown Point

Munster

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?

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 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 simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Connecticut and alert you when they change.

An easier way to manage your Chicago Midway 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.

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Cheap flights from Connecticut to Chicago from $58

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 10/7. 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

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Find the cheapest flights from Connecticut to Chicago

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

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Southwest flights from Connecticut to Chicago Midway Airport

Our best Southwest deals on Connecticut to Chicago Midway Airport flight tickets

Frontier flights from Connecticut to Chicago Midway Airport

Our best Frontier deals on Connecticut to Chicago Midway Airport flight tickets

momondo Fare Finder

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

See travel insights to Chicago from

How to get the cheapest flight ticket from Connecticut to Chicago Midway 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 Midway Airport?

What is the cheapest Connecticut to Chicago Midway flight route?

Fly from Hartford Bradley Intl to Chicago Midway for the best Connecticut - Chicago Midway flight prices

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

There are 1 cabin classes available to choose from on Connecticut to Chicago Midway 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 Midway Airport flights?

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

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

Frontier and Southwest are the most popular carriers operating from Connecticut to Chicago Midway

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

As of August 2025, there are 9 flights per day flying from Connecticut to Chicago Midway Airport. The most common time of day flights depart is 7:00AM, with 40% of flights taking off at noon.

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

The number of flights available between Connecticut and Chicago Midway Airport is 64 per week as of August 2025. The most frequent departure day is Mon, with 20% of weekly flights leaving on this day.

How long does it take to fly to Chicago Midway Airport?

Cheap Connecticut to Chicago Midway Airport flight deals and tips

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

Best Price Found

Fastest flight time

Direct flights

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

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

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

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

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

Best airlines flying from Connecticut to Chicago Midway Airport

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