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Cheap flights from Connecticut to Chicago from $91

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 8/28. 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.
Southwest Logo
9:30 pm - 10:55 pm
LGA
-
MDW
2h 25mnonstop
Southwest Logo
5:15 am - 8:15 am
MDW
-
LGA
2h 00mnonstop
$182Southwest
Fri, Jul 3 - Tue, Jul 7
Southwest Logo
6:00 am - 7:20 am
LGA
-
MDW
2h 20mnonstop
Southwest Logo
12:25 pm - 3:30 pm
MDW
-
LGA
2h 05mnonstop
$184Southwest
Sun, Aug 2 - Tue, Aug 11
Southwest Logo
7:35 am - 8:55 am
LGA
-
MDW
2h 20mnonstop
Southwest Logo
5:20 pm - 11:00 pm
MDW
-
LGA
4h 40m
1 stop
$186Southwest
Sat, Aug 15 - Wed, Aug 19
Southwest Logo
7:25 am - 8:50 am
LGA
-
MDW
2h 25mnonstop
Southwest Logo
5:50 pm - 8:55 pm
MDW
-
LGA
2h 05mnonstop
$187Southwest
Wed, Jun 24 - Wed, Jun 24
Delta Logo
8:30 am - 3:38 pm
EWR
-
MDW
8h 08m
1 stop
Delta Logo
6:05 am - 2:14 pm
MDW
-
EWR
7h 09m
1 stop
$197Delta
Sat, Aug 29 - Tue, Sep 1
Delta Logo
6:00 am - 9:59 am
EWR
-
MDW
4h 59m
1 stop
Delta Logo
5:45 pm - 11:25 pm
MDW
-
EWR
4h 40m
1 stop
$202Delta
Sun, Aug 30 - Tue, Sep 1
Delta Logo
6:00 am - 9:17 am
EWR
-
MDW
4h 17m
1 stop
Delta Logo
5:59 pm - 11:01 pm
MDW
-
EWR
4h 02m
1 stop
$207Delta
Fri, Sep 4 - Tue, Sep 8
Frontier Logo
5:55 am - 11:12 am
EWR
-
MDW
6h 17m
1 stop
Frontier Logo
12:27 pm - 1:05 am
MDW
-
EWR
11h 38m
1 stop
$240Frontier
Tue, Aug 25 - Tue, Sep 1
Frontier Logo
5:55 am - 11:07 am
EWR
-
MDW
6h 12m
1 stop
Frontier Logo
12:11 pm - 9:28 pm
MDW
-
EWR
8h 17m
1 stop
$241Frontier
Wed, Jul 8 - Tue, Jul 21
Frontier Logo
5:58 am - 11:09 am
EWR
-
MDW
6h 11m
1 stop
Frontier Logo
12:04 pm - 1:05 am
MDW
-
EWR
12h 01m
1 stop
$242Frontier
Wed, Jun 17 - Wed, Jun 24

Delta flights from Connecticut to Chicago Midway Airport

Our best Delta deals on Connecticut to Chicago Midway Airport flight tickets
Delta
Aug 26
EWR10:30 amNewark
6h 45m
1 stop
MDW4:15 pmChicago Midway
Sep 2
MDW6:05 amChicago Midway
7h 09m
1 stop
EWR2:14 pmNewark
$197
Delta
Aug 30
EWR6:00 amNewark
4h 59m
1 stop
MDW9:59 amChicago Midway
Sep 1
MDW5:45 pmChicago Midway
4h 40m
1 stop
EWR11:25 pmNewark
$202
Delta
Sep 4
EWR6:00 amNewark
4h 17m
1 stop
MDW9:17 amChicago Midway
Sep 8
MDW5:59 pmChicago Midway
4h 02m
1 stop
EWR11:01 pmNewark
$207

Frontier flights from Connecticut to Chicago Midway Airport

Our best Frontier deals on Connecticut to Chicago Midway Airport flight tickets
Frontier
Aug 11
EWR5:55 amNewark
6h 12m
1 stop
MDW11:07 amChicago Midway
Aug 12
MDW12:11 pmChicago Midway
11h 52m
1 stop
EWR1:03 amNewark
$208
Frontier
Aug 23
EWR5:55 amNewark
6h 17m
1 stop
MDW11:12 amChicago Midway
Sep 1
MDW12:27 pmChicago Midway
8h 02m
1 stop
EWR9:29 pmNewark
$209
Frontier
Jun 30
EWR5:58 amNewark
6h 14m
1 stop
MDW11:12 amChicago Midway
Jul 7
MDW12:11 pmChicago Midway
11h 52m
1 stop
EWR1:03 amNewark
$240

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 June 2, 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
Quickest round-trip

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 7/3

9:30 pm-10:55 pm

Nonstop2h 25m

Chicago Midway

Tue 7/7

5:15 am-8:15 am

Nonstop2h 00m

$182

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sun 8/2

6:00 am-7:20 am

Nonstop2h 20m

Chicago Midway

Tue 8/11

12:25 pm-3:30 pm

Nonstop2h 05m

$184

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 8/15

7:35 am-8:55 am

Nonstop2h 20m

Chicago Midway

Wed 8/19

5:20 pm-11:00 pm

1 stop4h 40m

$186

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 6/24

7:25 am-8:50 am

Nonstop2h 25m

Chicago Midway

Wed 6/24

5:50 pm-8:55 pm

Nonstop2h 05m

$187

NewarkChicago

EWR - MDW

EWRMDW

Newark

Sat 8/29

8:30 am-3:38 pm

1 stop8h 08m

Chicago Midway

Tue 9/1

6:05 am-2:14 pm

1 stop7h 09m

$197

NewarkChicago

EWR - MDW

EWRMDW

Newark

Sun 8/30

6:00 am-9:59 am

1 stop4h 59m

Chicago Midway

Tue 9/1

5:45 pm-11:25 pm

1 stop4h 40m

$202

NewarkChicago

EWR - MDW

EWRMDW

Newark

Fri 9/4

6:00 am-9:17 am

1 stop4h 17m

Chicago Midway

Tue 9/8

5:59 pm-11:01 pm

1 stop4h 02m

$207

NewarkChicago

EWR - MDW

EWRMDW

Newark

Tue 8/25

5:55 am-11:12 am

1 stop6h 17m

Chicago Midway

Tue 9/1

12:27 pm-1:05 am

1 stop11h 38m

$240

NewarkChicago

EWR - MDW

EWRMDW

Newark

Wed 7/8

5:55 am-11:07 am

1 stop6h 12m

Chicago Midway

Tue 7/21

12:11 pm-9:28 pm

1 stop8h 17m

$241

NewarkChicago

EWR - MDW

EWRMDW

Newark

Wed 6/17

5:58 am-11:09 am

1 stop6h 11m

Chicago Midway

Wed 6/24

12:04 pm-1:05 am

1 stop12h 01m

$242

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 August is, on average, the cheapest month to fly to Chicago Midway Airport from Connecticut, with most prices found around $137. If you are unable to visit Chicago Midway Airport during the month of August, then departing from Connecticut during the month September is also very affordable. Most momondo users find prices during this month for around $152.

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 Airport flights?

There is only 1 cabin class available to choose from on Connecticut to Chicago Midway Airport 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 3% 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

$238

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 $238. The best round-trip flight deal from Connecticut to Chicago Midway Airport found on momondo in the last 72 hours is $433.
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
SouthwestPriceFrom $184Free CancellationRating
8.0
4,255 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
Portage
Benton Harbor
Lansing
Valparaiso
Schererville
Munster
Crown Point
Monticello
Chesterton
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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