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Cheap flights from Chicago Midway Airport to Connecticut 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 Chicago Midway Airport to Connecticut departing on 11/18. 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

Enter your travel dates to find the best prices.
Frontier Logo
2:06 pm - 11:27 pmMDW-LGA
8h 21m1 stop
Frontier Logo
6:24 am - 12:41 pmLGA-MDW
7h 17m1 stop
$110Frontier
Find Deal
Wed, Nov 12 - Wed, Nov 19
Frontier Logo
2:06 pm - 12:33 amMDW-JFK
9h 27m1 stop
Frontier Logo
6:20 am - 12:41 pmJFK-MDW
7h 21m1 stop
$110Frontier
Find Deal
Wed, Nov 12 - Wed, Nov 19
Frontier Logo
1:56 pm - 11:27 pmMDW-LGA
8h 31m1 stop
Frontier Logo
12:30 pm - 6:39 pmLGA-MDW
7h 09m1 stop
$111Frontier
Find Deal
Tue, Nov 11 - Thu, Nov 13
Frontier Logo
1:56 pm - 12:33 amMDW-JFK
9h 37m1 stop
Frontier Logo
10:00 am - 6:39 pmJFK-MDW
9h 39m1 stop
$111Frontier
Find Deal
Tue, Nov 11 - Thu, Nov 13
Multiple Airlines Logo
8:42 pm - 8:31 pmMDW-EWR
22h 49m1 stop
Multiple Airlines Logo
10:30 pm - 8:46 amEWR-MDW
11h 16m1 stop
$131Multiple Airlines
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Fri, Dec 12 - Mon, Dec 15
Multiple Airlines Logo
8:42 pm - 6:59 pmMDW-EWR
21h 17m2 stops
Multiple Airlines Logo
11:30 am - 1:01 pmEWR-MDW
2h 31mnonstop
$137Multiple Airlines
Find Deal
Fri, Dec 12 - Sun, Dec 14
Southwest Logo
7:15 pm - 10:20 pmMDW-LGA
2h 05mnonstop
Southwest Logo
9:45 pm - 11:15 pmLGA-MDW
2h 30mnonstop
$139Southwest
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Wed, Jan 7 - Thu, Jan 8
Southwest Logo
5:55 pm - 9:00 pmMDW-LGA
2h 05mnonstop
Southwest Logo
9:45 pm - 11:15 pmLGA-MDW
2h 30mnonstop
$148Southwest
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Wed, Jan 14 - Sun, Jan 18
Delta Logo
6:35 pm - 11:15 pmMDW-EWR
3h 40m1 stop
Delta Logo
9:47 am - 12:48 pmEWR-MDW
4h 01m1 stop
$177Delta
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Tue, Jan 20 - Wed, Jan 21
Delta Logo
11:45 am - 8:11 pmMDW-BDL
7h 26m1 stop
Delta Logo
5:00 pm - 10:26 pmBDL-MDW
6h 26m1 stop
$177Delta
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Sat, Jan 31 - Sun, Feb 1

Frontier flights from Chicago Midway Airport to Connecticut

Our best Frontier deals on Chicago Midway Airport to Connecticut flight tickets
Frontier
Nov 12
MDW2:06 pmChicago Midway
9h 27m
1 stop
JFK12:33 amNew York John F Kennedy Intl
Nov 19
JFK6:20 amNew York John F Kennedy Intl
7h 21m
1 stop
MDW12:41 pmChicago Midway
$110
Find similar
Frontier
Nov 11
MDW1:56 pmChicago Midway
9h 37m
1 stop
JFK12:33 amNew York John F Kennedy Intl
Nov 13
JFK10:00 amNew York John F Kennedy Intl
9h 39m
1 stop
MDW6:39 pmChicago Midway
$111
Find similar
Frontier
Nov 18
MDW1:56 pmChicago Midway
8h 31m
1 stop
LGA11:27 pmNew York LaGuardia
Nov 19
LGA5:30 pmNew York LaGuardia
24h 00m
1 stop
MDW4:30 pmChicago Midway
$112
Find similar

Delta flights from Chicago Midway Airport to Connecticut

Our best Delta deals on Chicago Midway Airport to Connecticut flight tickets
Delta
Jan 20
MDW6:35 pmChicago Midway
3h 40m
1 stop
EWR11:15 pmNewark
Jan 21
EWR9:47 amNewark
4h 01m
1 stop
MDW12:48 pmChicago Midway
$177
Find similar
Delta
Mar 3
MDW5:25 pmChicago Midway
5h 22m
1 stop
BDL11:47 pmHartford Bradley Intl
Mar 4
BDL5:40 amHartford Bradley Intl
4h 10m
1 stop
MDW8:50 amChicago Midway
$245
Find similar
Delta
Jan 16
MDW6:30 pmChicago Midway
4h 10m
1 stop
BDL11:40 pmHartford Bradley Intl
Jan 19
BDL5:30 amHartford Bradley Intl
4h 24m
1 stop
MDW8:54 amChicago Midway
$262
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 October 30, 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

Wed 11/12

2:06 pm-11:27 pm

1 stop8h 21m

New York LaGuardia

Wed 11/19

6:24 am-12:41 pm

1 stop7h 17m

$110

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Wed 11/12

2:06 pm-12:33 am

1 stop9h 27m

New York John F Kennedy Intl

Wed 11/19

6:20 am-12:41 pm

1 stop7h 21m

$110

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 11/11

1:56 pm-11:27 pm

1 stop8h 31m

New York LaGuardia

Thu 11/13

12:30 pm-6:39 pm

1 stop7h 09m

$111

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Tue 11/11

1:56 pm-12:33 am

1 stop9h 37m

New York John F Kennedy Intl

Thu 11/13

10:00 am-6:39 pm

1 stop9h 39m

$111

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Fri 12/12

8:42 pm-8:31 pm

1 stop22h 49m

Newark

Mon 12/15

10:30 pm-8:46 am

1 stop11h 16m

$131

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Fri 12/12

8:42 pm-6:59 pm

2 stops21h 17m

Newark

Sun 12/14

11:30 am-1:01 pm

Nonstop2h 31m

$137

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 1/7

7:15 pm-10:20 pm

Nonstop2h 05m

New York LaGuardia

Thu 1/8

9:45 pm-11:15 pm

Nonstop2h 30m

$139

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 1/14

5:55 pm-9:00 pm

Nonstop2h 05m

New York LaGuardia

Sun 1/18

9:45 pm-11:15 pm

Nonstop2h 30m

$148

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Tue 1/20

6:35 pm-11:15 pm

1 stop3h 40m

Newark

Wed 1/21

9:47 am-12:48 pm

1 stop4h 01m

$177

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Sat 1/31

11:45 am-8:11 pm

1 stop7h 26m

Hartford Bradley Intl

Sun 2/1

5:00 pm-10:26 pm

1 stop6h 26m

$177

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, March 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 $297. If you aren’t able to travel to Connecticut during the month of March, then flying in January is also cheap. Prices for this month can be found on momondo for an average of $298.

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 is only 1 cabin class 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

$206

Fastest flight time

1h 55m

Direct flights

Every day

Airports in Connecticut

2 airports
The best one-way flight to Connecticut from Chicago Midway Airport in the past 72 hours is $206. The best round-trip flight deal from Chicago Midway Airport to Connecticut found on momondo in the last 72 hours is $240.
The fastest flight from Chicago Midway Airport to Connecticut takes 1h 55m
Direct flights go from Chicago Midway Airport to Connecticut every day.
There are 2 airports near Connecticut: New York LaGuardia (LGA), Hartford Bradley Intl (BDL)
Search flight deals

  • 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
4,243 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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Sat 11/29
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