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Cheap flights from Connecticut to Chicago Midway Airport from $49

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 Midway Airport departing on 1/7. 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 Connecticut to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Connecticut to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Connecticut to Chicago.

Cheap last minute flights

Planning a quick getaway from Connecticut to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Connecticut to Chicago

Find recent round-trip train or bus tickets from Connecticut to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
10:59 am - 4:16 pmLGA-MDW
6h 17m1 stop
6:45 am - 5:00 pmMDW-LGA
9h 15m1 stop
$118Frontier
Find Deal
Tue, Jan 28 - Fri, Jan 31
11:00 am - 4:16 pmJFK-MDW
6h 16m1 stop
12:43 pm - 6:30 amMDW-JFK
16h 47m1 stop
$119Frontier
Find Deal
Tue, Jan 28 - Thu, Jan 30
6:00 am - 7:35 amLGA-MDW
2h 35mnonstop
8:05 pm - 11:10 pmMDW-LGA
2h 05mnonstop
$148Southwest
Find Deal
Fri, Jan 17 - Fri, Jan 24
10:05 am - 10:04 pmEWR-MDW
12h 59m1 stop
8:07 am - 9:10 pmMDW-EWR
12h 03m1 stop
Sat, Feb 22 - Tue, Feb 25
1:00 pm - 6:14 pmEWR-MDW
6h 14m1 stop
6:00 am - 12:15 pmMDW-EWR
5h 15m1 stop
$158Delta
Find Deal
Tue, Jan 7 - Wed, Jan 8
1:00 pm - 6:14 pmEWR-MDW
6h 14m1 stop
9:34 am - 5:05 pmMDW-EWR
6h 31m1 stop
$162Delta
Find Deal
Thu, Jan 23 - Sat, Jan 25
9:35 pm - 11:05 pmLGA-MDW
2h 30mnonstop
12:45 pm - 3:50 pmMDW-LGA
2h 05mnonstop
$168Southwest
Find Deal
Thu, Jan 23 - Sat, Jan 25
10:00 pm - 1:09 pmEWR-MDW
16h 09m2 stops
5:24 pm - 9:10 pmMDW-EWR
26h 46m1 stop
Mon, Dec 23 - Tue, Jan 14
6:40 am - 12:10 pmEWR-MDW
6h 30m1 stop
1:05 pm - 9:15 pmMDW-EWR
7h 10m1 stop
$450Porter Airlines
Find Deal
Thu, Jan 16 - Mon, Jan 20
6:50 am - 12:10 pmEWR-MDW
6h 20m1 stop
1:05 pm - 9:15 pmMDW-EWR
7h 10m1 stop
$458Porter Airlines
Find Deal
Fri, Jan 10 - Mon, Jan 13
11:00 am - 4:14 pmJFK-MDW
6h 14m1 stop
$49Frontier
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Tue, Jan 7
10:59 am - 4:14 pmLGA-MDW
6h 15m1 stop
$49Frontier
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Tue, Jan 14
9:30 pm - 11:00 pmLGA-MDW
2h 30mnonstop
$74Southwest
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Thu, Jan 16
9:37 am - 1:08 pmEWR-MDW
4h 31m1 stop
$83Delta
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Thu, Jan 9
9:05 am - 10:45 amLGA-MDW
2h 40mnonstop
$94Southwest
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Sat, Jan 18
9:18 pm - 1:24 pmEWR-MDW
17h 06m1 stop
Tue, Dec 17
11:55 am - 9:55 amEWR-MDW
23h 00m2 stops
Tue, Dec 17
6:00 am - 8:50 amEWR-MDW
3h 50m1 stop
$104Delta
Find Deal
Fri, Dec 27
7:40 am - 4:40 pmEWR-MDW
10h 00m2 stops
$237Porter Airlines
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Mon, Dec 16
7:40 am - 4:40 pmEWR-MDW
10h 00m2 stops
$240Porter Airlines
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Sun, Dec 15
6:00 am - 8:50 amEWR-MDW
3h 50m1 stop
9:30 am - 4:27 pmMDW-EWR
5h 57m1 stop
$336Delta
Find Deal
Tue, Nov 26 - Sat, Dec 7
5:59 pm - 1:10 pmLGA-MDW
20h 11m1 stop
9:48 pm - 5:00 pmMDW-LGA
18h 12m1 stop
$356Frontier
Find Deal
Tue, Nov 26 - Wed, Nov 27
10:59 pm - 7:41 amLGA-MDW
9h 42m1 stop
7:42 am - 8:29 pmMDW-LGA
35h 47m2 stops
Thu, Nov 28 - Mon, Dec 2
6:55 pm - 8:25 pmLGA-MDW
2h 30mnonstop
6:00 am - 9:05 amMDW-LGA
2h 05mnonstop
$373Southwest
Find Deal
Fri, Nov 29 - Sun, Dec 8
6:00 am - 12:15 pmLGA-MDW
7h 15m1 stop
6:00 am - 9:05 amMDW-LGA
2h 05mnonstop
$380Southwest
Find Deal
Fri, Nov 29 - Sun, Dec 8
6:30 am - 8:00 amLGA-MDW
2h 30mnonstop
7:55 pm - 11:00 pmMDW-LGA
2h 05mnonstop
$383Southwest
Find Deal
Tue, Nov 26 - Wed, Dec 4
5:59 pm - 1:10 pmLGA-MDW
20h 11m1 stop
7:42 am - 8:29 pmMDW-LGA
35h 47m2 stops
Wed, Nov 27 - Mon, Dec 2
10:55 am - 5:26 pmEWR-MDW
7h 31m1 stop
8:15 pm - 10:05 amMDW-EWR
12h 50m1 stop
$771Allegiant Air
Find Deal
Wed, Nov 27 - Sun, Dec 1
6:50 am - 4:40 pmEWR-MDW
10h 50m1 stop
12:05 pm - 9:15 pmMDW-EWR
8h 10m1 stop
$910Porter Airlines
Find Deal
Thu, Nov 28 - Fri, Dec 6
12:15 pm - 4:40 pmEWR-MDW
5h 25m1 stop
11:15 am - 5:55 pmMDW-EWR
5h 40m1 stop
$978Porter Airlines
Find Deal
Fri, Nov 29 - Sun, Dec 8
6:00 am - 7:35 amLGA-MDW
2h 35mnonstop
8:05 pm - 11:10 pmMDW-LGA
2h 05mnonstop
$148Southwest
Find Deal
Fri, Jan 17 - Fri, Jan 24
9:35 pm - 11:05 pmLGA-MDW
2h 30mnonstop
8:05 pm - 11:10 pmMDW-LGA
2h 05mnonstop
$153Southwest
Find Deal
Tue, Jan 7 - Wed, Feb 19
9:35 pm - 11:05 pmLGA-MDW
2h 30mnonstop
12:45 pm - 3:50 pmMDW-LGA
2h 05mnonstop
$168Southwest
Find Deal
Thu, Jan 23 - Sat, Jan 25
6:00 am - 7:35 amLGA-MDW
2h 35mnonstop
5:50 am - 9:00 amMDW-LGA
2h 10mnonstop
$169Southwest
Find Deal
Mon, Feb 24 - Fri, Feb 28
6:30 am - 8:00 amLGA-MDW
2h 30mnonstop
8:20 pm - 11:25 pmMDW-LGA
2h 05mnonstop
$190Southwest
Find Deal
Sun, Dec 29 - Sun, Jan 5
9:55 pm - 11:20 pmLGA-MDW
2h 25mnonstop
6:00 am - 9:05 amMDW-LGA
2h 05mnonstop
$193Southwest
Find Deal
Mon, Dec 16 - Wed, Dec 18
9:55 pm - 11:20 pmLGA-MDW
2h 25mnonstop
7:55 pm - 11:00 pmMDW-LGA
2h 05mnonstop
$198Southwest
Find Deal
Thu, Dec 5 - Fri, Dec 6
6:30 am - 8:00 amLGA-MDW
2h 30mnonstop
8:05 pm - 11:10 pmMDW-LGA
2h 05mnonstop
$207Southwest
Find Deal
Thu, Jan 2 - Thu, Jan 23
6:30 am - 8:00 amLGA-MDW
2h 30mnonstop
2:25 pm - 5:25 pmMDW-LGA
2h 00mnonstop
$210Southwest
Find Deal
Thu, Feb 13 - Mon, Feb 17
7:15 am - 8:45 amLGA-MDW
2h 30mnonstop
6:00 am - 9:05 amMDW-LGA
2h 05mnonstop
$214Southwest
Find Deal
Fri, Dec 13 - Mon, Dec 16

Frontier flights from Connecticut to Chicago Midway Airport

Our best Frontier deals on Connecticut to Chicago Midway Airport flight tickets
Frontier
Jan 28
LGA10:59 amNew York LaGuardia
6h 17m
1 stop
MDW4:16 pmChicago Midway
Jan 31
MDW6:45 amChicago Midway
9h 15m
1 stop
LGA5:00 pmNew York LaGuardia
Frontier
Jan 28
JFK11:00 amNew York John F Kennedy Intl
6h 16m
1 stop
MDW4:16 pmChicago Midway
Jan 30
MDW12:43 pmChicago Midway
16h 47m
1 stop
JFK6:30 amNew York John F Kennedy Intl
Frontier
Jan 7
JFK11:00 amNew York John F Kennedy Intl
6h 14m
1 stop
MDW4:14 pmChicago Midway
Jan 9
MDW12:43 pmChicago Midway
16h 47m
1 stop
JFK6:30 amNew York John F Kennedy Intl

Southwest flights from Connecticut to Chicago Midway Airport

Our best Southwest deals on Connecticut to Chicago Midway Airport flight tickets
Southwest
Jan 17
LGA6:00 amNew York LaGuardia
2h 35m
MDW7:35 amChicago Midway
Jan 24
MDW8:05 pmChicago Midway
2h 05m
LGA11:10 pmNew York LaGuardia
Southwest
Jan 23
LGA9:35 pmNew York LaGuardia
2h 30m
MDW11:05 pmChicago Midway
Jan 25
MDW12:45 pmChicago Midway
2h 05m
LGA3:50 pmNew York LaGuardia
Southwest
Jan 6
LGA6:30 amNew York LaGuardia
2h 30m
MDW8:00 amChicago Midway
Jan 9
MDW8:05 pmChicago Midway
2h 05m
LGA11:10 pmNew York LaGuardia

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 Connecticut to Chicago Midway flight route?

Fly from Tweed-New Haven to Chicago Midway for the best Connecticut - Chicago Midway flight prices

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

There are 1 cabin classes 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?

You could potentially save up to 33% on your flight if you consider stops on a Connecticut to Chicago Midway Airport flight.

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

$49

Fastest flight time

2h 20m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Connecticut in the past 72 hours is $49. The best round-trip flight deal from Connecticut to Chicago Midway Airport found on momondo in the last 72 hours is $118.
The fastest flight from Connecticut to Chicago Midway Airport takes 2h 20m
Direct flights go from Connecticut to Chicago Midway Airport every day.

  • 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?

  • 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?


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
Avelo AirlinesPriceFrom $77Free CancellationRating
7.5
74 reviews
Search Avelo Airlines flights
FrontierPriceFrom $108Free CancellationRating
6.1
3,526 reviews
Search Frontier flights
DeltaPriceFrom $176Free CancellationRating
8.0
8,734 reviews
Search Delta flights
SouthwestPriceFrom $190Free CancellationRating
8.1
4,984 reviews
Search Southwest flights

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

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