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Cheap flights from Chicago Midway Airport to Connecticut from $73

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Connecticut departing on 10/20. 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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Find the cheapest flights from Chicago Midway Airport to Connecticut

Cheap round-trip flights

Southwest Logo
8:15 pm - 11:25 pmMDW-LGA
2h 10mnonstop
Southwest Logo
9:35 pm - 10:55 pmLGA-MDW
2h 20mnonstop
$142Southwest
Find Deal
Fri, Sep 5 - Wed, Sep 10
Frontier Logo
5:15 pm - 11:57 pmMDW-LGA
5h 42m1 stop
Frontier Logo
11:30 am - 4:00 pmLGA-MDW
5h 30m1 stop
$143Frontier
Find Deal
Mon, Sep 8 - Fri, Sep 12
Frontier Logo
5:15 pm - 11:57 pmMDW-LGA
5h 42m1 stop
Frontier Logo
6:30 am - 4:00 pmLGA-MDW
10h 30m1 stop
$144Frontier
Find Deal
Fri, Sep 19 - Mon, Sep 22
Frontier Logo
6:21 am - 10:01 amMDW-JFK
26h 40m1 stop
Frontier Logo
11:00 am - 12:44 pmJFK-MDW
26h 44m1 stop
$145Frontier
Find Deal
Mon, Sep 15 - Sun, Sep 21
Southwest Logo
6:00 am - 9:00 amMDW-LGA
2h 00mnonstop
Southwest Logo
9:35 pm - 10:55 pmLGA-MDW
2h 20mnonstop
$147Southwest
Find Deal
Tue, Sep 16 - Tue, Sep 23
Frontier Logo
5:15 pm - 1:08 amMDW-JFK
6h 53m1 stop
Frontier Logo
9:00 am - 4:00 pmJFK-MDW
8h 00m1 stop
$147Frontier
Find Deal
Mon, Sep 8 - Fri, Sep 12
Frontier Logo
4:56 pm - 1:08 amMDW-JFK
7h 12m1 stop
Frontier Logo
1:01 pm - 11:17 pmJFK-MDW
11h 16m1 stop
$148Frontier
Find Deal
Thu, Sep 4 - Sat, Sep 6
Frontier Logo
5:15 pm - 1:08 amMDW-JFK
6h 53m1 stop
Frontier Logo
6:15 am - 4:00 pmJFK-MDW
10h 45m1 stop
$149Frontier
Find Deal
Fri, Sep 19 - Mon, Sep 22
Delta Logo
9:35 am - 3:58 pmMDW-EWR
5h 23m1 stop
Delta Logo
6:15 am - 1:08 pmEWR-MDW
7h 53m1 stop
$179Delta
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Tue, Oct 21 - Sat, Oct 25
Delta Logo
6:17 pm - 11:12 pmMDW-EWR
3h 55m1 stop
Delta Logo
3:29 pm - 9:12 pmEWR-MDW
6h 43m1 stop
$182Delta
Find Deal
Wed, Sep 3 - Sat, Sep 6

Frontier flights from Chicago Midway Airport to Connecticut

Our best Frontier deals on Chicago Midway Airport to Connecticut flight tickets
Frontier
Sep 8
MDW5:15 pmChicago Midway
5h 42m
1 stop
LGA11:57 pmNew York LaGuardia
Sep 12
LGA11:30 amNew York LaGuardia
5h 30m
1 stop
MDW4:00 pmChicago Midway
$143
Find similar
Frontier
Sep 19
MDW5:15 pmChicago Midway
5h 42m
1 stop
LGA11:57 pmNew York LaGuardia
Sep 22
LGA6:30 amNew York LaGuardia
10h 30m
1 stop
MDW4:00 pmChicago Midway
$144
Find similar
Frontier
Sep 15
MDW6:21 amChicago Midway
26h 40m
1 stop
JFK10:01 amNew York John F Kennedy Intl
Sep 21
JFK11:00 amNew York John F Kennedy Intl
26h 44m
1 stop
MDW12:44 pmChicago Midway
$145
Find similar

Delta flights from Chicago Midway Airport to Connecticut

Our best Delta deals on Chicago Midway Airport to Connecticut flight tickets
Delta
Oct 21
MDW9:35 amChicago Midway
5h 23m
1 stop
EWR3:58 pmNewark
Oct 25
EWR6:15 amNewark
7h 53m
1 stop
MDW1:08 pmChicago Midway
$179
Find similar
Delta
Sep 3
MDW6:17 pmChicago Midway
3h 55m
1 stop
EWR11:12 pmNewark
Sep 6
EWR3:29 pmNewark
6h 43m
1 stop
MDW9:12 pmChicago Midway
$182
Find similar
Delta
Sep 10
MDW9:30 amChicago Midway
5h 27m
1 stop
EWR3:57 pmNewark
Sep 17
EWR6:00 amNewark
3h 40m
1 stop
MDW8:40 amChicago Midway
$183
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Connecticut that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated August 18, 2025.
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

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Fri 9/5

8:15 pm-11:25 pm

Nonstop2h 10m

New York LaGuardia

Wed 9/10

9:35 pm-10:55 pm

Nonstop2h 20m

$142

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Mon 9/8

5:15 pm-11:57 pm

1 stop5h 42m

New York LaGuardia

Fri 9/12

11:30 am-4:00 pm

1 stop5h 30m

$143

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Fri 9/19

5:15 pm-11:57 pm

1 stop5h 42m

New York LaGuardia

Mon 9/22

6:30 am-4:00 pm

1 stop10h 30m

$144

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Mon 9/15

6:21 am-10:01 am

1 stop26h 40m

New York John F Kennedy Intl

Sun 9/21

11:00 am-12:44 pm

1 stop26h 44m

$145

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 9/16

6:00 am-9:00 am

Nonstop2h 00m

New York LaGuardia

Tue 9/23

9:35 pm-10:55 pm

Nonstop2h 20m

$147

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Mon 9/8

5:15 pm-1:08 am

1 stop6h 53m

New York John F Kennedy Intl

Fri 9/12

9:00 am-4:00 pm

1 stop8h 00m

$147

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Thu 9/4

4:56 pm-1:08 am

1 stop7h 12m

New York John F Kennedy Intl

Sat 9/6

1:01 pm-11:17 pm

1 stop11h 16m

$148

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Fri 9/19

5:15 pm-1:08 am

1 stop6h 53m

New York John F Kennedy Intl

Mon 9/22

6:15 am-4:00 pm

1 stop10h 45m

$149

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Tue 10/21

9:35 am-3:58 pm

1 stop5h 23m

Newark

Sat 10/25

6:15 am-1:08 pm

1 stop7h 53m

$179

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Wed 9/3

6:17 pm-11:12 pm

1 stop3h 55m

Newark

Sat 9/6

3:29 pm-9:12 pm

1 stop6h 43m

$182

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Connecticut from

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

What is the cheapest month to fly to Connecticut?

In general, September 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 $276. If you aren’t able to travel to Connecticut during the month of September, then flying in March is also cheap. Prices for this month can be found on momondo for an average of $297.

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 to Connecticut flights?

There are 1 cabin classes available to choose from on Chicago Midway 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

$73

Fastest flight time

2h 00m

Direct flights

Every day

Airports in Connecticut

5 airports
The best one-way flight to Connecticut from Chicago Midway Airport in the past 72 hours is $73. The best round-trip flight deal from Chicago Midway Airport to Connecticut found on momondo in the last 72 hours is $142.
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 5 airports near Connecticut: Newark (EWR), New York LaGuardia (LGA), Hartford Bradley Intl (BDL), New York John F Kennedy Intl (JFK), Providence-TFGreen (PVD)
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  • 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?

  • 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?

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
SouthwestPriceFrom $197Free CancellationRating
8.0
4,246 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.

An easier way to manage your Connecticut 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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