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

As of May 2026, there are 10 flights per day flying from Chicago Midway Airport to Connecticut. The most common time of day flights depart is 7:00AM, with 40% of flights taking off in the afternoon.

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

70 flights are operational weekly from Chicago Midway Airport to Connecticut as of May 2026. The most popular departure day for this route is Mon, with 20% of flights per week taking off on this day.

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

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

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

There are 3 operators available for flights from Chicago Midway Airport to Connecticut as of May 2026.

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

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 Chicago Midway Airport to Connecticut.

What documentation or ID do you need to fly to Connecticut?

The required travel and health documents for your Connecticut trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Connecticut. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$89 Cheap Flights from Chicago Midway Airport to Connecticut in 2026

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Find the cheapest flights from Chicago Midway Airport to Connecticut

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:45 pm - 10:55 pm

MDW

LGA

2h 10mnonstop

7:25 am - 8:50 am

LGA

MDW

2h 25mnonstop

$177Southwest

Thu, Jul 2 - Tue, Jul 7

5:15 am - 8:15 am

MDW

LGA

2h 00mnonstop

6:00 am - 7:20 am

LGA

MDW

2h 20mnonstop

$182Southwest

Thu, Jul 2 - Sun, Jul 5

5:15 am - 8:15 am

MDW

LGA

2h 00mnonstop

6:00 am - 7:20 am

LGA

MDW

2h 20mnonstop

$186Southwest

Wed, Jun 3 - Sat, Jun 6

7:45 pm - 10:55 pm

MDW

LGA

2h 10mnonstop

6:00 am - 7:20 am

LGA

MDW

2h 20mnonstop

$187Southwest

Thu, Jul 2 - Sun, Jul 5

1:27 pm - 7:25 pm

MDW

EWR

4h 58m

1 stop

3:20 pm - 10:36 pm

EWR

MDW

8h 16m

1 stop

$197Delta

Thu, Aug 13 - Tue, Aug 18

1:27 pm - 7:25 pm

MDW

EWR

4h 58m

1 stop

9:39 am - 12:39 pm

EWR

MDW

4h 00m

1 stop

$202Delta

Sun, Aug 9 - Wed, Aug 12

1:27 pm - 7:25 pm

MDW

EWR

4h 58m

1 stop

8:30 am - 3:27 pm

EWR

MDW

7h 57m

1 stop

$207Delta

Thu, Aug 6 - Wed, Sep 9

12:04 pm - 1:05 am

MDW

EWR

12h 01m

1 stop

5:55 am - 11:07 am

EWR

MDW

6h 12m

1 stop

$218Frontier

Wed, Jun 24 - Wed, Aug 12

12:04 pm - 9:29 pm

MDW

EWR

8h 25m

1 stop

5:55 am - 10:02 pm

EWR

MDW

17h 07m

1 stop

$219Frontier

Wed, May 27 - Fri, May 29

12:11 pm - 1:03 am

MDW

EWR

11h 52m

1 stop

5:55 am - 11:07 am

EWR

MDW

6h 12m

1 stop

$225Frontier

Wed, Aug 5 - Wed, Aug 12

Delta flights from Chicago Midway Airport to Connecticut

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

Delta

Aug 13

MDW1:27 pmChicago Midway

4h 58m

1 stop

EWR7:25 pmNewark

Aug 18

EWR3:20 pmNewark

8h 16m

1 stop

MDW10:36 pmChicago Midway

$197

Delta

Aug 9

MDW1:27 pmChicago Midway

4h 58m

1 stop

EWR7:25 pmNewark

Aug 12

EWR9:39 amNewark

4h 00m

1 stop

MDW12:39 pmChicago Midway

$202

Delta

Aug 6

MDW1:27 pmChicago Midway

4h 58m

1 stop

EWR7:25 pmNewark

Sep 9

EWR8:30 amNewark

7h 57m

1 stop

MDW3:27 pmChicago Midway

$207

Frontier flights from Chicago Midway Airport to Connecticut

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

Frontier

Sep 16

MDW12:03 pmChicago Midway

11h 56m

1 stop

EWR12:59 amNewark

Sep 22

EWR5:55 amNewark

6h 03m

1 stop

MDW10:58 amChicago Midway

$218

Frontier

Oct 26

MDW12:03 pmChicago Midway

8h 25m

1 stop

EWR9:28 pmNewark

Oct 31

EWR5:55 amNewark

6h 03m

1 stop

MDW10:58 amChicago Midway

$219

Frontier

Aug 18

MDW12:27 pmChicago Midway

8h 02m

1 stop

EWR9:29 pmNewark

Aug 22

EWR5:55 amNewark

6h 09m

1 stop

MDW11:04 amChicago Midway

$220

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Thu 7/2

7:45 pm-10:55 pm

Nonstop2h 10m

New York LaGuardia

Tue 7/7

7:25 am-8:50 am

Nonstop2h 25m

$177

Quickest round-trip

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Thu 7/2

5:15 am-8:15 am

Nonstop2h 00m

New York LaGuardia

Sun 7/5

6:00 am-7:20 am

Nonstop2h 20m

$182

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 6/3

5:15 am-8:15 am

Nonstop2h 00m

New York LaGuardia

Sat 6/6

6:00 am-7:20 am

Nonstop2h 20m

$186

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Thu 7/2

7:45 pm-10:55 pm

Nonstop2h 10m

New York LaGuardia

Sun 7/5

6:00 am-7:20 am

Nonstop2h 20m

$187

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Thu 8/13

1:27 pm-7:25 pm

1 stop4h 58m

Newark

Tue 8/18

3:20 pm-10:36 pm

1 stop8h 16m

$197

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Sun 8/9

1:27 pm-7:25 pm

1 stop4h 58m

Newark

Wed 8/12

9:39 am-12:39 pm

1 stop4h 00m

$202

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Thu 8/6

1:27 pm-7:25 pm

1 stop4h 58m

Newark

Wed 9/9

8:30 am-3:27 pm

1 stop7h 57m

$207

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Wed 6/24

12:04 pm-1:05 am

1 stop12h 01m

Newark

Wed 8/12

5:55 am-11:07 am

1 stop6h 12m

$218

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Wed 5/27

12:04 pm-9:29 pm

1 stop8h 25m

Newark

Fri 5/29

5:55 am-10:02 pm

1 stop17h 07m

$219

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Wed 8/5

12:11 pm-1:03 am

1 stop11h 52m

Newark

Wed 8/12

5:55 am-11:07 am

1 stop6h 12m

$225

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 Chicago Midway Airport to Connecticut

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 Connecticut?

In general, November is the cheapest month to fly from Chicago Midway Airport to Connecticut. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $0. If you aren’t able to travel to Connecticut during the month of November, then flying in February is also cheap. Prices for this month can be found on momondo for an average of $0.

What is the cheapest Chicago Midway to Connecticut flight route?

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

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

There is only 1 cabin class available to choose from on Chicago Midway Airport to Connecticut 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 Chicago Midway Airport to Connecticut flights?

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

Cheap Chicago Midway Airport to Connecticut flight deals and tips

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

Best Price Found	$166
Fastest flight time	2h 00m
Direct flights	Every day
Airports in Connecticut	90 airports

The best one-way flight to Connecticut from Chicago Midway Airport in the past 72 hours is $166. The best round-trip flight deal from Chicago Midway Airport to Connecticut found on momondo in the last 72 hours is $355.

The fastest flight from Chicago Midway Airport to Connecticut takes 2h 00m

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

There are 90 airports in Connecticut. From Chicago Midway Airport there are direct flights to New York LaGuardia (LGA), Hartford Bradley Intl (BDL), Providence-TFGreen (PVD).

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Frequently asked questions about flying from Chicago Midway Airport to Connecticut

When did momondo last update prices for flights from Chicago Midway Airport to Connecticut?
Prices for flights from Chicago Midway Airport to Connecticut refresh daily.
How many operators does momondo search for flights from Chicago Midway Airport to Connecticut?
There are 3 operators available for flights from Chicago Midway Airport to Connecticut as of May 2026.
How old do you have to be to fly from Chicago Midway Airport to Connecticut?
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 Chicago Midway Airport to Connecticut.
What documentation or ID do you need to fly to Connecticut?
The required travel and health documents for your Connecticut trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Connecticut. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Chicago Midway Airport to Connecticut?
Based on momondo bookings for flights between Chicago Midway Airport and Connecticut, the leading plane model is Boeing 737-800, making up 28.57% of the total bookings. Other popular models include Boeing 737 MAX 8 with 12.00%, Embraer 175 with 11.43%, and Boeing 737-800 Passenger/BBJ2 (winglets) with 10.29%.

Best airlines flying from Chicago Midway Airport to Connecticut

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

Airline	Rating	Free Cancellation	Price
Southwest	PriceFrom $240	Free Cancellation	Rating 7.9 4,284 reviews		Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Connecticut?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Connecticut for you.

Can I find flights from Chicago to Connecticut with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Chicago to Connecticut flights to just show those with flexible booking policies.

How can momondo help me find flights from Chicago to Connecticut?

momondo helps you find the best flight between Chicago and Connecticut by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Chicago to Connecticut right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to Connecticut flights. All you need is a valid email address and we will do the rest; it is that quick and easy.