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

As of July 2026, there are 7 flights per day flying from Chicago Midway Airport to Connecticut. The most common time of day flights depart is 7:00AM, with 36% of flights taking off at noon.

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

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

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

55 flights are operational weekly from Chicago Midway Airport to Connecticut as of July 2026. The most popular departure day for this route is Thu, with 24% of flights per week taking off on this day.

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 July 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.

$96 Cheap Flights from Chicago Midway Airport to Connecticut in 2026

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.

5:10 am - 8:10 am

MDW

LGA

2h 00mnonstop

6:00 am - 7:15 am

LGA

MDW

2h 15mnonstop

$184Southwest

Wed, Sep 9 - Fri, Sep 11

7:50 am - 11:00 am

MDW

LGA

2h 10mnonstop

6:00 am - 7:15 am

LGA

MDW

2h 15mnonstop

$187Southwest

Sat, Aug 8 - Mon, Aug 10

5:45 pm - 8:55 pm

MDW

LGA

2h 10mnonstop

7:25 am - 8:45 am

LGA

MDW

2h 20mnonstop

$189Southwest

Tue, Aug 18 - Fri, Aug 21

4:52 pm - 11:57 pm

MDW

EWR

6h 05m

1 stop

12:00 pm - 4:16 pm

EWR

MDW

5h 16m

1 stop

$191Delta

Sat, Sep 12 - Wed, Sep 16

6:40 pm - 9:50 pm

MDW

LGA

2h 10mnonstop

6:00 am - 7:20 am

LGA

MDW

2h 20mnonstop

$194Southwest

Sat, Jul 18 - Wed, Jul 22

1:19 pm - 7:30 pm

MDW

EWR

5h 11m

1 stop

9:48 am - 12:39 pm

EWR

MDW

3h 51m

1 stop

$207Delta

Wed, Sep 30 - Thu, Oct 1

6:42 pm - 11:25 pm

MDW

EWR

3h 43m

1 stop

1:00 pm - 6:33 pm

EWR

MDW

6h 33m

1 stop

$209Delta

Tue, Aug 11 - Fri, Aug 14

6:42 pm - 11:25 pm

MDW

EWR

3h 43m

1 stop

10:29 pm - 9:51 am

EWR

MDW

12h 22m

1 stop

$236Frontier

Sat, Aug 8 - Mon, Aug 10

6:05 am - 11:50 am

MDW

JFK

28h 45m

1 stop

1:00 pm - 10:03 pm

JFK

MDW

10h 03m

1 stop

$288Frontier

Sat, Aug 8 - Wed, Aug 12

11:50 am - 11:54 am

MDW

JFK

23h 04m

1 stop

1:00 pm - 10:47 pm

JFK

MDW

10h 47m

1 stop

$311Frontier

Wed, Aug 26 - Tue, Sep 1

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Delta flights from Chicago Midway Airport to Connecticut

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

Delta

Sep 12

MDW4:52 pmChicago Midway

6h 05m

1 stop

EWR11:57 pmNewark

Sep 16

EWR12:00 pmNewark

5h 16m

1 stop

MDW4:16 pmChicago Midway

$191

Delta

Sep 30

MDW1:19 pmChicago Midway

5h 11m

1 stop

EWR7:30 pmNewark

Oct 1

EWR9:48 amNewark

3h 51m

1 stop

MDW12:39 pmChicago Midway

$207

Delta

Aug 11

MDW6:42 pmChicago Midway

3h 43m

1 stop

EWR11:25 pmNewark

Aug 14

EWR1:00 pmNewark

6h 33m

1 stop

MDW6:33 pmChicago Midway

$209

Frontier flights from Chicago Midway Airport to Connecticut

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

Frontier

Aug 8

MDW6:42 pmChicago Midway

3h 43m

1 stop

EWR11:25 pmNewark

Aug 10

EWR10:29 pmNewark

12h 22m

1 stop

MDW9:51 amChicago Midway

$236

Frontier

Aug 4

MDW12:11 pmChicago Midway

8h 17m

1 stop

EWR9:28 pmNewark

Aug 19

EWR5:55 amNewark

6h 00m

1 stop

MDW10:55 amChicago Midway

$240

Frontier

Jul 8

MDW12:11 pmChicago Midway

11h 52m

1 stop

EWR1:03 amNewark

Jul 15

EWR5:55 amNewark

6h 12m

1 stop

MDW11:07 amChicago Midway

$244

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

Quickest round-trip

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 9/9

5:10 am-8:10 am

Nonstop2h 00m

New York LaGuardia

Fri 9/11

6:00 am-7:15 am

Nonstop2h 15m

$184

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Sat 8/8

7:50 am-11:00 am

Nonstop2h 10m

New York LaGuardia

Mon 8/10

6:00 am-7:15 am

Nonstop2h 15m

$187

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 8/18

5:45 pm-8:55 pm

Nonstop2h 10m

New York LaGuardia

Fri 8/21

7:25 am-8:45 am

Nonstop2h 20m

$189

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Sat 9/12

4:52 pm-11:57 pm

1 stop6h 05m

Newark

Wed 9/16

12:00 pm-4:16 pm

1 stop5h 16m

$191

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Sat 7/18

6:40 pm-9:50 pm

Nonstop2h 10m

New York LaGuardia

Wed 7/22

6:00 am-7:20 am

Nonstop2h 20m

$194

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Wed 9/30

1:19 pm-7:30 pm

1 stop5h 11m

Newark

Thu 10/1

9:48 am-12:39 pm

1 stop3h 51m

$207

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Tue 8/11

6:42 pm-11:25 pm

1 stop3h 43m

Newark

Fri 8/14

1:00 pm-6:33 pm

1 stop6h 33m

$209

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Sat 8/8

6:42 pm-11:25 pm

1 stop3h 43m

Newark

Mon 8/10

10:29 pm-9:51 am

1 stop12h 22m

$236

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Sat 8/8

6:05 am-11:50 am

1 stop28h 45m

New York John F Kennedy Intl

Wed 8/12

1:00 pm-10:03 pm

1 stop10h 03m

$288

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Wed 8/26

11:50 am-11:54 am

1 stop23h 04m

New York John F Kennedy Intl

Tue 9/1

1:00 pm-10:47 pm

1 stop10h 47m

$311

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, February 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 February, then flying in April is also cheap. Prices for this month can be found on momondo for an average of $174.

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?

You could potentially save up to 14% on your flight if you consider stops on a Chicago Midway Airport to Connecticut flight.

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	$234
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 $234. The best round-trip flight deal from Chicago Midway Airport to Connecticut found on momondo in the last 72 hours is $405.

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).

Search flight deals

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 July 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 30.26% of the total bookings. Other popular models include Embraer 175 with 12.92%, Boeing 737-800 Passenger/BBJ2 (winglets) with 11.44%, and Boeing 737 MAX 8 with 11.07%.

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 4,249 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.