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

As of January 2026, there are 10 flights per day flying from Connecticut to Chicago Midway Airport. The most common time of day flights depart is 5:00AM, with 100% of flights taking off in the morning.

What airlines fly to Chicago Midway Airport?

Southwest, United Airlines and Delta are the top three most popular airlines that fly to Chicago Midway Airport from Connecticut according to our data. Southwest is the first choice among our users, with 85% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 3 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.

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

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

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 73 per week as of January 2026. The most frequent departure day is Fri, with 26% of weekly flights leaving on this day.

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

On average, it takes 2h 33m to fly from Connecticut to Chicago Midway Airport if you fly out of Hartford (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 New Haven and into Chicago O'Hare Intl Airport, then the flight time is around 2h 45m.

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 January 2026.

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.

$56 Cheap Flights from Connecticut to Chicago Midway Airport in 2026

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Cheap round-trip flights

Enter your travel dates to find the best prices.

11:30 am - 1:02 pm

EWR

MDW

2h 32mnonstop

7:30 am - 10:30 am

MDW

EWR

2h 00mnonstop

$100Frontier

Tue, Mar 10 - Tue, Mar 17

11:30 am - 1:02 pm

EWR

MDW

2h 32mnonstop

9:30 am - 12:30 pm

MDW

EWR

2h 00mnonstop

$106Frontier

Thu, Mar 26 - Tue, Mar 31

11:30 am - 1:02 pm

EWR

MDW

2h 32mnonstop

7:30 am - 10:30 am

MDW

EWR

2h 00mnonstop

$108Frontier

Sun, Mar 8 - Tue, Mar 10

11:30 am - 1:02 pm

EWR

MDW

2h 32mnonstop

7:30 am - 10:30 am

MDW

EWR

2h 00mnonstop

$110Frontier

Tue, Mar 10 - Thu, Mar 12

11:30 am - 1:02 pm

EWR

MDW

2h 32mnonstop

7:30 am - 10:30 am

MDW

EWR

2h 00mnonstop

$115Frontier

Thu, Mar 19 - Sun, Mar 22

10:30 pm - 2:26 pm

EWR

MDW

16h 56m

1 stop

7:30 am - 10:30 am

MDW

EWR

2h 00mnonstop

$124Frontier

Wed, Mar 4 - Sun, Mar 8

6:15 am - 7:50 am

LGA

MDW

2h 35mnonstop

6:05 pm - 9:10 pm

MDW

LGA

2h 05mnonstop

$137Southwest

Fri, Feb 27 - Mon, Mar 2

9:05 am - 10:45 am

LGA

MDW

2h 40mnonstop

2:00 pm - 5:00 pm

MDW

LGA

2h 00mnonstop

$143Southwest

Thu, Feb 26 - Sat, Feb 28

6:00 am - 7:40 am

LGA

MDW

2h 40mnonstop

8:20 pm - 11:20 pm

MDW

LGA

2h 00mnonstop

$147Southwest

Tue, Mar 3 - Fri, Mar 6

7:00 am - 7:58 pm

BDL

MDW

13h 58m

2 stops

1:00 pm - 11:24 am

MDW

BDL

21h 24m

1 stop

$226Multiple Airlines

Mon, Feb 2 - Mon, Feb 9

Southwest flights from Connecticut to Chicago Midway Airport

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

Southwest

Feb 27

LGA6:15 amNew York LaGuardia

2h 35m

MDW7:50 amChicago Midway

Mar 4

MDW6:05 amChicago Midway

2h 05m

LGA9:10 amNew York LaGuardia

$137

Southwest

Feb 26

LGA9:05 amNew York LaGuardia

2h 40m

MDW10:45 amChicago Midway

Feb 28

MDW2:00 pmChicago Midway

2h 00m

LGA5:00 pmNew York LaGuardia

$143

Southwest

Mar 4

LGA6:00 amNew York LaGuardia

2h 40m

MDW7:40 amChicago Midway

Mar 8

MDW6:00 amChicago Midway

2h 05m

LGA9:05 amNew York LaGuardia

$147

Frontier flights from Connecticut to Chicago Midway Airport

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

Frontier

Mar 10

EWR11:30 amNewark

2h 32m

MDW1:02 pmChicago Midway

Mar 17

MDW7:30 amChicago Midway

2h 00m

EWR10:30 amNewark

$100

Frontier

Mar 12

EWR11:30 amNewark

2h 32m

MDW1:02 pmChicago Midway

Mar 17

MDW7:30 amChicago Midway

2h 00m

EWR10:30 amNewark

$106

Frontier

Mar 8

EWR11:30 amNewark

2h 32m

MDW1:02 pmChicago Midway

Mar 10

MDW7:30 amChicago Midway

2h 00m

EWR10:30 amNewark

$108

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

Tue 3/10

11:30 am-1:02 pm

Nonstop2h 32m

Chicago Midway

Tue 3/17

7:30 am-10:30 am

Nonstop2h 00m

$100

NewarkChicago

EWR - MDW

EWRMDW

Newark

Thu 3/26

11:30 am-1:02 pm

Nonstop2h 32m

Chicago Midway

Tue 3/31

9:30 am-12:30 pm

Nonstop2h 00m

$106

NewarkChicago

EWR - MDW

EWRMDW

Newark

Sun 3/8

11:30 am-1:02 pm

Nonstop2h 32m

Chicago Midway

Tue 3/10

7:30 am-10:30 am

Nonstop2h 00m

$108

NewarkChicago

EWR - MDW

EWRMDW

Newark

Tue 3/10

11:30 am-1:02 pm

Nonstop2h 32m

Chicago Midway

Thu 3/12

7:30 am-10:30 am

Nonstop2h 00m

$110

NewarkChicago

EWR - MDW

EWRMDW

Newark

Thu 3/19

11:30 am-1:02 pm

Nonstop2h 32m

Chicago Midway

Sun 3/22

7:30 am-10:30 am

Nonstop2h 00m

$115

NewarkChicago

EWR - MDW

EWRMDW

Newark

Wed 3/4

10:30 pm-2:26 pm

1 stop16h 56m

Chicago Midway

Sun 3/8

7:30 am-10:30 am

Nonstop2h 00m

$124

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 2/27

6:15 am-7:50 am

Nonstop2h 35m

Chicago Midway

Mon 3/2

6:05 pm-9:10 pm

Nonstop2h 05m

$137

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 2/26

9:05 am-10:45 am

Nonstop2h 40m

Chicago Midway

Sat 2/28

2:00 pm-5:00 pm

Nonstop2h 00m

$143

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Tue 3/3

6:00 am-7:40 am

Nonstop2h 40m

Chicago Midway

Fri 3/6

8:20 pm-11:20 pm

Nonstop2h 00m

$147

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Mon 2/2

7:00 am-7:58 pm

2 stops13h 58m

Chicago Midway

Mon 2/9

1:00 pm-11:24 am

1 stop21h 24m

$226

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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 August is, on average, the cheapest month to fly to Chicago Midway Airport from Connecticut, with most prices found around $237. If you are unable to visit Chicago Midway Airport during the month of August, then departing from Connecticut during the month September is also very affordable. Most momondo users find prices during this month for around $311.

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 is only 1 cabin class 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?

You could potentially save up to 52% on your flight if you consider stops on a Connecticut to Chicago Midway Airport flight.

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	$223
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 $223. The best round-trip flight deal from Connecticut to Chicago Midway Airport found on momondo in the last 72 hours is $392.

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 January 2026.
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 19.57% of all bookings. The subsequent popular models are Airbus A220-300 at 16.82%, Boeing 737 MAX 8 at 11.01%, and Boeing 737-800 Passenger/BBJ2 (winglets) at 10.40%.

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
Delta	PriceFrom $176	Free Cancellation	Rating 7.9 8,037 reviews	Search Delta flights
Southwest	PriceFrom $177	Free Cancellation	Rating 8.0 4,255 reviews	Search Southwest flights
United Airlines	PriceFrom $299	Free Cancellation	Rating 7.4 9,144 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?

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

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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 3/19. 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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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

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 is only 1 cabin class 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?

You could potentially save up to 52% on your flight if you consider stops on a Connecticut to Chicago Midway Airport flight.

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

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

What airlines fly to Chicago Midway Airport?

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

As of January 2026, there are 10 flights per day flying from Connecticut to Chicago Midway Airport. The most common time of day flights depart is 5:00AM, with 100% of flights taking off in the morning.

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 73 per week as of January 2026. The most frequent departure day is Fri, with 26% 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