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

As of November 2025, there are 8 flights per day flying from Connecticut to Chicago Midway Airport. The most common time of day flights depart is 5:00AM, with 45% 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 62 per week as of November 2025. The most frequent departure day is Thu, with 18% of weekly flights leaving on this day.

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

On average, it takes 2h 30m 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 6 operators available for flights from Connecticut to Chicago Midway Airport as of November 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.

$59 Cheap Flights from Connecticut to Chicago Midway Airport in 2025/26

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One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

1:00 pm - 6:08 pmJFK-MDW

6h 08m1 stop

2:59 pm - 12:07 amMDW-JFK

8h 08m1 stop

$109Frontier

Find Deal

Thu, Dec 4 - Sat, Dec 6

6:20 am - 1:59 pmLGA-MDW

8h 39m1 stop

12:18 pm - 10:00 pmMDW-LGA

8h 42m1 stop

$109Frontier

Find Deal

Sat, Dec 6 - Mon, Dec 8

6:25 am - 1:59 pmJFK-MDW

8h 34m1 stop

8:42 pm - 9:01 amMDW-JFK

11h 19m1 stop

$110Frontier

Find Deal

Sat, Dec 6 - Mon, Dec 8

6:20 am - 6:08 pmLGA-MDW

12h 48m1 stop

12:35 pm - 9:13 pmMDW-LGA

7h 38m1 stop

$110Frontier

Find Deal

Thu, Dec 4 - Mon, Dec 8

11:30 am - 1:01 pmEWR-MDW

2h 31mnonstop

2:59 pm - 11:59 pmMDW-EWR

8h 00m1 stop

$122Multiple Airlines

Find Deal

Thu, Dec 11 - Sat, Dec 13

5:10 am - 6:45 amBDL-MDW

2h 35mnonstop

6:05 pm - 9:05 pmMDW-BDL

2h 00mnonstop

$225Southwest

Find Deal

Sun, Feb 22 - Sat, Feb 28

7:25 am - 1:00 pmBDL-MDW

6h 35m2 stops

12:55 pm - 8:05 pmMDW-BDL

6h 10m1 stop

$227Southwest

Find Deal

Thu, Dec 11 - Tue, Dec 16

5:42 pm - 4:57 pmBDL-MDW

24h 15m1 stop

7:44 am - 1:42 pmMDW-BDL

28h 58m2 stops

$234Multiple Airlines

Find Deal

Tue, Nov 25 - Tue, Dec 2

5:30 am - 8:54 amBDL-MDW

4h 24m1 stop

12:46 pm - 9:32 pmMDW-BDL

7h 46m1 stop

$245Delta

Find Deal

Tue, Mar 3 - Wed, Mar 4

5:40 am - 8:54 amPVD-MDW

4h 14m1 stop

6:00 am - 12:09 pmMDW-PVD

5h 09m1 stop

$309Delta

Find Deal

Thu, Nov 27 - Tue, Dec 2

Southwest flights from Connecticut to Chicago Midway Airport

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

Southwest

Dec 11

LGA6:00 amNew York LaGuardia

2h 30m

MDW7:30 amChicago Midway

Dec 15

MDW7:15 pmChicago Midway

2h 05m

LGA10:20 pmNew York LaGuardia

$137

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Southwest

Dec 5

LGA6:00 amNew York LaGuardia

2h 30m

MDW7:30 amChicago Midway

Dec 8

MDW7:15 pmChicago Midway

2h 05m

LGA10:20 pmNew York LaGuardia

$143

Find similar

Southwest

Jan 9

LGA9:45 pmNew York LaGuardia

2h 30m

MDW11:15 pmChicago Midway

Jan 12

MDW5:55 pmChicago Midway

2h 05m

LGA9:00 pmNew York LaGuardia

$148

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Frontier flights from Connecticut to Chicago Midway Airport

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

Frontier

Dec 4

JFK1:00 pmNew York John F Kennedy Intl

6h 08m

1 stop

MDW6:08 pmChicago Midway

Dec 6

MDW2:59 pmChicago Midway

8h 08m

1 stop

JFK12:07 amNew York John F Kennedy Intl

$109

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Frontier

Dec 6

JFK6:25 amNew York John F Kennedy Intl

8h 34m

1 stop

MDW1:59 pmChicago Midway

Dec 8

MDW8:42 pmChicago Midway

11h 19m

1 stop

JFK9:01 amNew York John F Kennedy Intl

$110

Find similar

Frontier

Dec 6

JFK6:00 amNew York John F Kennedy Intl

17h 30m

1 stop

MDW10:30 pmChicago Midway

Dec 9

MDW2:49 pmChicago Midway

9h 10m

1 stop

JFK12:59 amNew York John F Kennedy Intl

$111

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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

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Thu 12/4

1:00 pm-6:08 pm

1 stop6h 08m

Chicago Midway

Sat 12/6

2:59 pm-12:07 am

1 stop8h 08m

$109

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 12/6

6:20 am-1:59 pm

1 stop8h 39m

Chicago Midway

Mon 12/8

12:18 pm-10:00 pm

1 stop8h 42m

$109

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Sat 12/6

6:25 am-1:59 pm

1 stop8h 34m

Chicago Midway

Mon 12/8

8:42 pm-9:01 am

1 stop11h 19m

$110

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 12/4

6:20 am-6:08 pm

1 stop12h 48m

Chicago Midway

Mon 12/8

12:35 pm-9:13 pm

1 stop7h 38m

$110

NewarkChicago

EWR - MDW

EWRMDW

Newark

Thu 12/11

11:30 am-1:01 pm

Nonstop2h 31m

Chicago Midway

Sat 12/13

2:59 pm-11:59 pm

1 stop8h 00m

$122

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sun 2/22

5:10 am-6:45 am

Nonstop2h 35m

Chicago Midway

Sat 2/28

6:05 pm-9:05 pm

Nonstop2h 00m

$225

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 12/11

7:25 am-1:00 pm

2 stops6h 35m

Chicago Midway

Tue 12/16

12:55 pm-8:05 pm

1 stop6h 10m

$227

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 11/25

5:42 pm-4:57 pm

1 stop24h 15m

Chicago Midway

Tue 12/2

7:44 am-1:42 pm

2 stops28h 58m

$234

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 3/3

5:30 am-8:54 am

1 stop4h 24m

Chicago Midway

Wed 3/4

12:46 pm-9:32 pm

1 stop7h 46m

$245

ProvidenceChicago

PVD - MDW

PVDMDW

Providence-TFGreen

Thu 11/27

5:40 am-8:54 am

1 stop4h 14m

Chicago Midway

Tue 12/2

6:00 am-12:09 pm

1 stop5h 09m

$309

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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

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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 3% 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	$198
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 $198. The best round-trip flight deal from Connecticut to Chicago Midway Airport found on momondo in the last 72 hours is $361.

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 6 operators available for flights from Connecticut to Chicago Midway Airport as of November 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 23.63% of all bookings. The subsequent popular models are Boeing 737-800 Passenger/BBJ2 (winglets) at 10.96%, Airbus A320-100/200 at 10.39%, and Embraer 175 at 10.27%.

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
Southwest	PriceFrom $177	Free Cancellation	Rating 8.0 4,236 reviews		Search Southwest flights
United Airlines	PriceFrom $299	Free Cancellation	Rating 7.4 9,015 reviews		Search United Airlines flights

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Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

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

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Cheap flights from Connecticut to Chicago from $60

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 12/13. 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

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Filter for what you want

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Find the cheapest flights from Connecticut to Chicago

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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

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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 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 3% 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 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 November 2025, there are 8 flights per day flying from Connecticut to Chicago Midway Airport. The most common time of day flights depart is 5:00AM, with 45% 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 62 per week as of November 2025. The most frequent departure day is Thu, with 18% 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