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Cheap flights from Connecticut to Chicago from $59

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 departing on 4/25. 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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0 bags

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Find the cheapest flights from Connecticut to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
11:30 am - 1:00 pm
EWR
-
MDW
2h 30mnonstop
Frontier Logo
2:15 pm - 1:16 am
MDW
-
EWR
10h 01m
1 stop
$134Frontier
Sat, May 2 - Mon, May 4
Frontier Logo
5:55 am - 11:09 am
EWR
-
MDW
6h 14m
1 stop
Frontier Logo
12:04 pm - 1:18 am
MDW
-
EWR
12h 14m
1 stop
$135Frontier
Wed, May 27 - Wed, Jun 3
Frontier Logo
11:30 am - 1:00 pm
EWR
-
MDW
2h 30mnonstop
Frontier Logo
2:15 pm - 9:29 pm
MDW
-
EWR
6h 14m
1 stop
$136Frontier
Sat, May 2 - Mon, May 4
Frontier Logo
11:30 am - 1:00 pm
EWR
-
MDW
2h 30mnonstop
Frontier Logo
7:30 am - 10:38 am
MDW
-
EWR
2h 08mnonstop
$137Frontier
Sun, Apr 26 - Mon, Apr 27
Frontier Logo
10:29 pm - 7:31 pm
EWR
-
MDW
22h 02m
1 stop
Frontier Logo
7:30 am - 10:38 am
MDW
-
EWR
2h 08mnonstop
$138Frontier
Mon, Apr 27 - Thu, Apr 30
Multiple Airlines Logo
11:30 am - 1:00 pm
EWR
-
MDW
2h 30mnonstop
Multiple Airlines Logo
2:15 pm - 11:36 am
MDW
-
EWR
20h 21m
1 stop
$142Multiple Airlines
Sat, May 2 - Sun, May 3
Multiple Airlines Logo
8:00 am - 4:13 pm
LGA
-
MDW
9h 13m
1 stop
Multiple Airlines Logo
11:59 am - 7:29 pm
MDW
-
LGA
6h 30m
1 stop
$175Multiple Airlines
Sat, May 2 - Sat, May 9
Southwest Logo
12:45 pm - 2:20 pm
PVD
-
MDW
2h 35mnonstop
Southwest Logo
11:40 am - 9:30 pm
MDW
-
PVD
8h 50m
1 stop
$284Southwest
Wed, May 6 - Sat, May 9
Southwest Logo
11:45 am - 5:05 pm
PVD
-
MDW
6h 20m
2 stops
Southwest Logo
4:15 pm - 7:25 pm
MDW
-
PVD
2h 10mnonstop
$289Southwest
Wed, May 6 - Sat, May 9
Delta Logo
5:46 am - 8:43 am
PVD
-
MDW
3h 57m
1 stop
Delta Logo
6:36 pm - 11:28 pm
MDW
-
PVD
3h 52m
1 stop
$294Delta
Thu, May 7 - Tue, May 12

Frontier flights from Connecticut to Chicago Midway Airport

Our best Frontier deals on Connecticut to Chicago Midway Airport flight tickets
Frontier
Apr 22
EWR11:30 amNewark
2h 30m
MDW1:00 pmChicago Midway
May 1
MDW7:30 amChicago Midway
2h 08m
EWR10:38 amNewark
$132
Frontier
May 2
EWR11:30 amNewark
2h 30m
MDW1:00 pmChicago Midway
May 4
MDW2:15 pmChicago Midway
6h 14m
1 stop
EWR9:29 pmNewark
$134
Frontier
Apr 24
EWR11:30 amNewark
2h 30m
MDW1:00 pmChicago Midway
May 2
MDW7:30 amChicago Midway
2h 08m
EWR10:38 amNewark
$135

Southwest flights from Connecticut to Chicago Midway Airport

Our best Southwest deals on Connecticut to Chicago Midway Airport flight tickets
Southwest
Apr 25
LGA7:35 amNew York LaGuardia
2h 25m
MDW9:00 amChicago Midway
May 2
MDW6:10 pmChicago Midway
2h 05m
LGA9:15 pmNew York LaGuardia
$168
Southwest
May 2
LGA3:35 pmNew York LaGuardia
2h 40m
MDW5:15 pmChicago Midway
May 4
MDW5:15 amChicago Midway
2h 00m
LGA8:15 amNew York LaGuardia
$172
Southwest
Jun 11
LGA9:30 pmNew York LaGuardia
2h 25m
MDW10:55 pmChicago Midway
Jun 16
MDW7:45 pmChicago Midway
2h 10m
LGA10:55 pmNew York LaGuardia
$177

momondo Fare Finder

 
Customize your flight search to find flights from Connecticut to Chicago Midway Airport 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 April 17, 2026.
Use the filters below to find and compare flights from Connecticut to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

NewarkChicago

EWR - MDW

EWRMDW

Newark

Sat 5/2

11:30 am-1:00 pm

Nonstop2h 30m

Chicago Midway

Mon 5/4

2:15 pm-1:16 am

1 stop10h 01m

$134

NewarkChicago

EWR - MDW

EWRMDW

Newark

Wed 5/27

5:55 am-11:09 am

1 stop6h 14m

Chicago Midway

Wed 6/3

12:04 pm-1:18 am

1 stop12h 14m

$135

NewarkChicago

EWR - MDW

EWRMDW

Newark

Sat 5/2

11:30 am-1:00 pm

Nonstop2h 30m

Chicago Midway

Mon 5/4

2:15 pm-9:29 pm

1 stop6h 14m

$136
Quickest round-trip

NewarkChicago

EWR - MDW

EWRMDW

Newark

Sun 4/26

11:30 am-1:00 pm

Nonstop2h 30m

Chicago Midway

Mon 4/27

7:30 am-10:38 am

Nonstop2h 08m

$137

NewarkChicago

EWR - MDW

EWRMDW

Newark

Mon 4/27

10:29 pm-7:31 pm

1 stop22h 02m

Chicago Midway

Thu 4/30

7:30 am-10:38 am

Nonstop2h 08m

$138

NewarkChicago

EWR - MDW

EWRMDW

Newark

Sat 5/2

11:30 am-1:00 pm

Nonstop2h 30m

Chicago Midway

Sun 5/3

2:15 pm-11:36 am

1 stop20h 21m

$142

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 5/2

8:00 am-4:13 pm

1 stop9h 13m

Chicago Midway

Sat 5/9

11:59 am-7:29 pm

1 stop6h 30m

$175

ProvidenceChicago

PVD - MDW

PVDMDW

Providence-TFGreen

Wed 5/6

12:45 pm-2:20 pm

Nonstop2h 35m

Chicago Midway

Sat 5/9

11:40 am-9:30 pm

1 stop8h 50m

$284

ProvidenceChicago

PVD - MDW

PVDMDW

Providence-TFGreen

Wed 5/6

11:45 am-5:05 pm

2 stops6h 20m

Chicago Midway

Sat 5/9

4:15 pm-7:25 pm

Nonstop2h 10m

$289

ProvidenceChicago

PVD - MDW

PVDMDW

Providence-TFGreen

Thu 5/7

5:46 am-8:43 am

1 stop3h 57m

Chicago Midway

Tue 5/12

6:36 pm-11:28 pm

1 stop3h 52m

$294

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 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 month to fly to Chicago Midway Airport?

The month of January is, on average, the cheapest month to fly to Chicago Midway Airport from Connecticut, with most prices found around $176. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Connecticut during the month August is also very affordable. Most momondo users find prices during this month for around $232.

What is the cheapest Connecticut to Chicago Midway flight route?

Fly from Hartford Bradley Intl to Chicago Midway for the best Connecticut - Chicago Midway flight prices

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

There is only 1 cabin class 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 49% 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

$207

Fastest flight time

2h 15m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Connecticut in the past 72 hours is $207. The best round-trip flight deal from Connecticut to Chicago Midway Airport found on momondo in the last 72 hours is $418.
The fastest flight from Connecticut to Chicago Midway Airport takes 2h 15m
Direct flights go from Connecticut to Chicago Midway Airport every day.
Search flight deals

Frequently asked questions about flying from Connecticut to Chicago Midway Airport

  • 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
DeltaPriceFrom $176Free CancellationRating
7.9
8,406 reviews
Search Delta flights
SouthwestPriceFrom $177Free CancellationRating
8.0
4,328 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

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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