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 64 per week as of September 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?

On average, it takes 2h 21m 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.

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

As of September 2025, there are 9 flights per day flying from Connecticut to Chicago Midway Airport. The most common time of day flights depart is 5:00PM, with 59% of flights taking off in the afternoon.

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 5 operators available for flights from Connecticut to Chicago Midway Airport as of September 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.

$72 Cheap Flights from Connecticut to Chicago Midway Airport in 2025/26

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Find the cheapest flights from Connecticut to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

12:30 pm - 6:39 pmLGA-MDW

7h 09m1 stop

12:30 pm - 10:00 pmMDW-LGA

8h 30m1 stop

$135Frontier

Find Deal

Thu, Oct 30 - Thu, Nov 6

6:29 am - 11:38 amLGA-MDW

6h 09m1 stop

1:56 pm - 10:21 pmMDW-LGA

7h 25m1 stop

$138Frontier

Find Deal

Tue, Oct 28 - Tue, Oct 28

11:30 am - 10:47 pmLGA-MDW

12h 17m1 stop

12:03 pm - 10:44 pmMDW-LGA

9h 41m1 stop

$142Frontier

Find Deal

Sat, Oct 25 - Mon, Oct 27

11:30 am - 10:47 pmLGA-MDW

12h 17m1 stop

12:03 pm - 10:44 pmMDW-LGA

9h 41m1 stop

$143Frontier

Find Deal

Sat, Oct 25 - Mon, Oct 27

6:05 am - 7:30 amLGA-MDW

2h 25mnonstop

5:50 pm - 8:55 pmMDW-LGA

2h 05mnonstop

$157Southwest

Find Deal

Wed, Oct 22 - Sat, Oct 25

8:15 am - 9:40 amLGA-MDW

2h 25mnonstop

8:20 pm - 11:25 pmMDW-LGA

2h 05mnonstop

$158Southwest

Find Deal

Sat, Oct 25 - Mon, Oct 27

10:00 pm - 11:25 pmEWR-MDW

2h 25mnonstop

5:28 pm - 9:58 amMDW-EWR

15h 30m2 stops

$171Multiple Airlines

Find Deal

Tue, Oct 14 - Mon, Oct 20

10:30 pm - 11:55 pmEWR-MDW

2h 25mnonstop

6:06 pm - 9:00 amMDW-EWR

37h 54m2 stops

$177Multiple Airlines

Find Deal

Thu, Nov 6 - Sun, Nov 9

10:41 am - 4:09 pmEWR-MDW

6h 28m1 stop

6:00 am - 12:18 pmMDW-EWR

5h 18m1 stop

$179Delta

Find Deal

Tue, Oct 21 - Tue, Oct 28

8:15 am - 3:26 pmEWR-MDW

8h 11m1 stop

6:00 am - 12:24 pmMDW-EWR

5h 24m1 stop

$188Delta

Find Deal

Sat, Oct 18 - Wed, Oct 22

Frontier flights from Connecticut to Chicago Midway Airport

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

Frontier

Oct 30

LGA12:30 pmNew York LaGuardia

7h 09m

1 stop

MDW6:39 pmChicago Midway

Nov 6

MDW12:30 pmChicago Midway

8h 30m

1 stop

LGA10:00 pmNew York LaGuardia

$135

Find similar

Frontier

Oct 28

LGA6:29 amNew York LaGuardia

6h 09m

1 stop

MDW11:38 amChicago Midway

Oct 28

MDW1:56 pmChicago Midway

7h 25m

1 stop

LGA10:21 pmNew York LaGuardia

$138

Find similar

Frontier

Oct 25

LGA11:30 amNew York LaGuardia

12h 17m

1 stop

MDW10:47 pmChicago Midway

Oct 27

MDW12:03 pmChicago Midway

9h 41m

1 stop

LGA10:44 pmNew York LaGuardia

$142

Find similar

Southwest flights from Connecticut to Chicago Midway Airport

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

Southwest

Oct 22

LGA6:05 amNew York LaGuardia

2h 25m

MDW7:30 amChicago Midway

Oct 25

MDW5:50 pmChicago Midway

2h 05m

LGA8:55 pmNew York LaGuardia

$157

Find similar

Southwest

Oct 25

LGA8:15 amNew York LaGuardia

2h 25m

MDW9:40 amChicago Midway

Oct 27

MDW8:20 pmChicago Midway

2h 05m

LGA11:25 pmNew York LaGuardia

$158

Find similar

Southwest

Nov 13

LGA9:00 amNew York LaGuardia

2h 25m

MDW10:25 amChicago Midway

Nov 17

MDW8:25 amChicago Midway

2h 05m

LGA11:30 amNew York LaGuardia

$159

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

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 10/30

12:30 pm-6:39 pm

1 stop7h 09m

Chicago Midway

Thu 11/6

12:30 pm-10:00 pm

1 stop8h 30m

$135

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Tue 10/28

6:29 am-11:38 am

1 stop6h 09m

Chicago Midway

Tue 10/28

1:56 pm-10:21 pm

1 stop7h 25m

$138

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 10/25

11:30 am-10:47 pm

1 stop12h 17m

Chicago Midway

Mon 10/27

12:03 pm-10:44 pm

1 stop9h 41m

$142

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 10/25

11:30 am-10:47 pm

1 stop12h 17m

Chicago Midway

Mon 10/27

12:03 pm-10:44 pm

1 stop9h 41m

$143

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 10/22

6:05 am-7:30 am

Nonstop2h 25m

Chicago Midway

Sat 10/25

5:50 pm-8:55 pm

Nonstop2h 05m

$157

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 10/25

8:15 am-9:40 am

Nonstop2h 25m

Chicago Midway

Mon 10/27

8:20 pm-11:25 pm

Nonstop2h 05m

$158

NewarkChicago

EWR - MDW

EWRMDW

Newark

Tue 10/14

10:00 pm-11:25 pm

Nonstop2h 25m

Chicago Midway

Mon 10/20

5:28 pm-9:58 am

2 stops15h 30m

$171

NewarkChicago

EWR - MDW

EWRMDW

Newark

Thu 11/6

10:30 pm-11:55 pm

Nonstop2h 25m

Chicago Midway

Sun 11/9

6:06 pm-9:00 am

2 stops37h 54m

$177

NewarkChicago

EWR - MDW

EWRMDW

Newark

Tue 10/21

10:41 am-4:09 pm

1 stop6h 28m

Chicago Midway

Tue 10/28

6:00 am-12:18 pm

1 stop5h 18m

$179

NewarkChicago

EWR - MDW

EWRMDW

Newark

Sat 10/18

8:15 am-3:26 pm

1 stop8h 11m

Chicago Midway

Wed 10/22

6:00 am-12:24 pm

1 stop5h 24m

$188

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 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 $346.

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?

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	$179
Fastest flight time	2h 20m
Direct flights	Mon, Tue, Wed, Thu, Fri and Sat

The best one-way flight to Chicago Midway Airport from Connecticut in the past 72 hours is $179. The best round-trip flight deal from Connecticut to Chicago Midway Airport found on momondo in the last 72 hours is $337.

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

Direct flights go from Connecticut to Chicago Midway Airport on Monday, Tuesday, Wednesday, Thursday, Friday and Saturday. There are no airlines offering direct flights.

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 5 operators available for flights from Connecticut to Chicago Midway Airport as of September 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 24.98% of all bookings. The subsequent popular models are Airbus A320-100/200 at 11.31%, Boeing 737-700 Passenger/BBJ1 (winglets) at 9.90%, and Embraer 175 (Enhanced Winglets) at 9.46%.

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 4,244 reviews		Search Southwest flights

Merrillville

New Buffalo

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

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 $72

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 10/31. 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

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Cheap last minute flights

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Frontier flights from Connecticut to Chicago Midway Airport

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

Southwest flights from Connecticut to Chicago Midway Airport

Our best Southwest 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 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?

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, 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 day?

As of September 2025, there are 9 flights per day flying from Connecticut to Chicago Midway Airport. The most common time of day flights depart is 5:00PM, with 59% of flights taking off in the afternoon.

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 September 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