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Cheap flights from Connecticut to Chicago Midway Airport from $53

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 11/13. 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.
11:00 am - 8:25 pmJFK-MDW
10h 25m1 stop
7:42 am - 10:00 amMDW-JFK
25h 18m1 stop
$103Frontier
Find Deal
Thu, Nov 14 - Mon, Nov 18
12:29 pm - 6:16 pmLGA-MDW
30h 47m1 stop
8:20 pm - 4:29 pmMDW-LGA
19h 09m1 stop
$103Frontier
Find Deal
Thu, Nov 14 - Mon, Nov 18
9:55 pm - 11:20 pmLGA-MDW
2h 25mnonstop
6:00 am - 9:05 amMDW-LGA
2h 05mnonstop
$118Southwest
Find Deal
Tue, Nov 12 - Wed, Nov 13
9:50 pm - 11:15 pmLGA-MDW
2h 25mnonstop
6:15 am - 9:25 amMDW-LGA
2h 10mnonstop
$133Southwest
Find Deal
Fri, Nov 15 - Sat, Nov 16
9:40 am - 12:33 pmEWR-MDW
3h 53m1 stop
11:20 am - 5:46 pmMDW-EWR
5h 26m1 stop
$166Delta
Find Deal
Wed, Jan 8 - Fri, Jan 10
10:14 am - 11:29 pmEWR-MDW
14h 15m1 stop
6:17 pm - 9:19 amMDW-EWR
14h 02m1 stop
Sat, Dec 7 - Mon, Dec 9
6:00 am - 8:50 amEWR-MDW
3h 50m1 stop
6:49 pm - 12:59 amMDW-EWR
5h 10m1 stop
$171Delta
Find Deal
Tue, Nov 12 - Wed, Nov 20
7:00 am - 3:50 pmPVD-MDW
33h 50m2 stops
6:00 am - 12:57 pmMDW-PVD
29h 57m2 stops
Tue, Nov 12 - Thu, Nov 14
10:00 am - 4:40 pmEWR-MDW
7h 40m1 stop
11:15 am - 7:50 pmMDW-EWR
7h 35m1 stop
$455Porter Airlines
Find Deal
Fri, Dec 6 - Sun, Dec 8
11:15 am - 4:40 pmEWR-MDW
6h 25m1 stop
11:25 am - 6:00 pmMDW-EWR
5h 35m1 stop
$457Porter Airlines
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Thu, Nov 28 - Thu, Dec 5
1:22 pm - 7:55 amJFK-MDW
19h 33m1 stop
$53Frontier
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Wed, Nov 13
10:59 am - 5:08 pmLGA-MDW
7h 09m1 stop
$53Frontier
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Thu, Nov 14
9:55 pm - 11:20 pmLGA-MDW
2h 25mnonstop
$59Southwest
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Wed, Nov 13
9:50 pm - 11:15 pmLGA-MDW
2h 25mnonstop
$74Southwest
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Fri, Nov 15
9:40 am - 12:33 pmEWR-MDW
3h 53m1 stop
$83Delta
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Wed, Jan 8
5:42 pm - 5:18 pmEWR-MDW
24h 36m1 stop
Wed, Dec 4
12:30 pm - 6:32 pmEWR-MDW
7h 02m1 stop
$88Delta
Find Deal
Wed, Nov 13
12:35 pm - 11:08 pmEWR-MDW
11h 33m1 stop
Mon, Nov 25
10:55 am - 8:04 pmEWR-MDW
10h 09m1 stop
$183Allegiant Air
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Thu, Nov 14
11:55 am - 7:25 pmEWR-MDW
8h 30m1 stop
$591Allegiant Air
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Sun, Dec 1
10:59 pm - 10:23 amLGA-MDW
12h 24m1 stop
1:47 pm - 8:59 pmMDW-LGA
6h 12m1 stop
$160Frontier
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Mon, Nov 4 - Sat, Nov 9
12:38 pm - 2:55 pmBDL-MDW
27h 17m1 stop
1:58 pm - 6:11 pmMDW-BDL
27h 13m1 stop
$168Frontier
Find Deal
Sat, Nov 2 - Thu, Nov 14
9:55 pm - 11:20 pmLGA-MDW
2h 25mnonstop
1:00 pm - 4:00 pmMDW-LGA
2h 00mnonstop
$243Southwest
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Mon, Nov 4 - Sat, Nov 9
9:15 am - 10:50 amLGA-MDW
2h 35mnonstop
7:55 pm - 11:00 pmMDW-LGA
2h 05mnonstop
$253Southwest
Find Deal
Mon, Nov 4 - Mon, Nov 4
8:59 am - 8:20 amLGA-MDW
24h 21m1 stop
6:00 pm - 11:29 pmMDW-LGA
28h 29m2 stops
Sun, Nov 3 - Mon, Nov 25
9:29 pm - 11:34 pmLGA-MDW
27h 05m2 stops
6:00 pm - 11:29 pmMDW-LGA
28h 29m2 stops
Sun, Nov 3 - Mon, Nov 25
1:00 pm - 5:03 pmEWR-MDW
5h 03m1 stop
6:00 am - 12:10 pmMDW-EWR
5h 10m1 stop
$316Delta
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Sat, Nov 2 - Tue, Nov 5
5:42 pm - 9:38 pmEWR-MDW
4h 56m1 stop
6:00 am - 12:10 pmMDW-EWR
5h 10m1 stop
$326Delta
Find Deal
Fri, Nov 1 - Tue, Nov 5
12:15 pm - 4:40 pmEWR-MDW
5h 25m1 stop
11:15 am - 6:00 pmMDW-EWR
5h 45m1 stop
$1,122Porter Airlines
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Thu, Oct 31 - Fri, Nov 1
10:00 am - 4:40 pmEWR-MDW
7h 40m1 stop
11:15 am - 6:00 pmMDW-EWR
5h 45m1 stop
$1,154Porter Airlines
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Thu, Oct 31 - Fri, Nov 1
9:55 pm - 11:20 pmLGA-MDW
2h 25mnonstop
6:00 am - 9:05 amMDW-LGA
2h 05mnonstop
$118Southwest
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Tue, Nov 12 - Wed, Nov 13
9:50 pm - 11:15 pmLGA-MDW
2h 25mnonstop
6:15 am - 9:25 amMDW-LGA
2h 10mnonstop
$133Southwest
Find Deal
Fri, Nov 15 - Sat, Nov 16
7:15 am - 8:45 amLGA-MDW
2h 30mnonstop
7:55 pm - 11:00 pmMDW-LGA
2h 05mnonstop
$138Southwest
Find Deal
Thu, Nov 14 - Tue, Nov 19
9:55 pm - 11:20 pmLGA-MDW
2h 25mnonstop
7:55 pm - 11:00 pmMDW-LGA
2h 05mnonstop
$148Southwest
Find Deal
Fri, Dec 6 - Sun, Dec 8
9:20 am - 10:55 amLGA-MDW
2h 35mnonstop
1:10 pm - 4:10 pmMDW-LGA
2h 00mnonstop
$153Southwest
Find Deal
Thu, Nov 14 - Thu, Nov 14
6:30 am - 8:00 amLGA-MDW
2h 30mnonstop
7:55 pm - 11:00 pmMDW-LGA
2h 05mnonstop
$158Southwest
Find Deal
Tue, Nov 5 - Tue, Nov 5
6:30 am - 8:00 amLGA-MDW
2h 30mnonstop
6:15 am - 9:25 amMDW-LGA
2h 10mnonstop
$165Southwest
Find Deal
Sat, Nov 9 - Sat, Nov 16
7:15 am - 8:45 amLGA-MDW
2h 30mnonstop
7:55 pm - 11:00 pmMDW-LGA
2h 05mnonstop
$168Southwest
Find Deal
Fri, Nov 15 - Fri, Nov 15
6:00 am - 7:30 amLGA-MDW
2h 30mnonstop
8:20 pm - 11:25 pmMDW-LGA
2h 05mnonstop
$169Southwest
Find Deal
Sat, Jan 4 - Sun, Jan 5
11:15 am - 12:45 pmLGA-MDW
2h 30mnonstop
2:25 pm - 5:25 pmMDW-LGA
2h 00mnonstop
$173Southwest
Find Deal
Fri, Nov 22 - Mon, Nov 25

Southwest flights from Connecticut to Chicago Midway Airport

Our best Southwest deals on Connecticut to Chicago Midway Airport flight tickets
Southwest
Nov 12
LGA9:55 pmNew York LaGuardia
2h 25m
MDW11:20 pmChicago Midway
Nov 13
MDW6:00 amChicago Midway
2h 05m
LGA9:05 amNew York LaGuardia
Southwest
Nov 15
LGA9:50 pmNew York LaGuardia
2h 25m
MDW11:15 pmChicago Midway
Nov 16
MDW6:15 amChicago Midway
2h 10m
LGA9:25 amNew York LaGuardia
Southwest
Nov 14
LGA7:15 amNew York LaGuardia
2h 30m
MDW8:45 amChicago Midway
Nov 19
MDW7:55 pmChicago Midway
2h 05m
LGA11:00 pmNew York LaGuardia

Delta flights from Connecticut to Chicago Midway Airport

Our best Delta deals on Connecticut to Chicago Midway Airport flight tickets
Delta
Jan 8
EWR9:40 amNewark
3h 53m
1 stop
MDW12:33 pmChicago Midway
Jan 10
MDW11:20 amChicago Midway
5h 26m
1 stop
EWR5:46 pmNewark
Delta
Nov 12
EWR6:00 amNewark
3h 50m
1 stop
MDW8:50 amChicago Midway
Nov 20
MDW6:49 pmChicago Midway
5h 10m
1 stop
EWR12:59 amNewark
Delta
Nov 13
EWR9:33 amNewark
4h 16m
1 stop
MDW12:49 pmChicago Midway
Nov 16
MDW5:42 pmChicago Midway
4h 35m
1 stop
EWR11:17 pmNewark

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 airline that flies to Chicago Midway Airport from Connecticut?

Frontier. Frontier, Avelo Airlines, and Southwest are the most popular carriers operating from Connecticut to Chicago Midway Airport

Can stopping save me money on Connecticut to Chicago Midway Airport flights?

You could potentially save up to 10% 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

$53

Fastest flight time

2h 25m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Connecticut in the past 72 hours is $53. The best round-trip flight deal from Connecticut to Chicago Midway Airport found on momondo in the last 72 hours is $103.
The fastest flight from Connecticut to Chicago Midway Airport takes 2h 25m
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 $117Free CancellationRating
7.5
74 reviews
Search Avelo Airlines flights
FrontierPriceFrom $148Free CancellationRating
6.1
3,583 reviews
Search Frontier flights
DeltaPriceFrom $197Free CancellationRating
8.0
8,836 reviews
Search Delta flights
SouthwestPriceFrom $273Free CancellationRating
8.1
5,118 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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