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Cheap flights from Connecticut to Chicago from $139

1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Connecticut to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
7:45 am - 9:15 amBDL  Hartford Bradley Intl-MDW Chicago Midway
2h 30mnonstop
Southwest Logo
6:45 pm - 9:50 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
2h 05mnonstop
$297Southwest
Thu, Nov 19 - Sat, Nov 21
Southwest Logo
6:25 pm - 7:55 pmBDL  Hartford Bradley Intl-MDW Chicago Midway
2h 30mnonstop
Southwest Logo
6:20 pm - 9:25 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
2h 05mnonstop
$297Southwest
Mon, Nov 16 - Thu, Nov 19
Southwest Logo
6:40 pm - 8:05 pmBDL  Hartford Bradley Intl-MDW Chicago Midway
2h 25mnonstop
Southwest Logo
1:20 pm - 4:25 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
2h 05mnonstop
$297Southwest
Mon, Nov 2 - Wed, Nov 4
Southwest Logo
6:25 pm - 7:55 pmBDL  Hartford Bradley Intl-MDW Chicago Midway
2h 30mnonstop
Southwest Logo
6:20 pm - 9:25 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
2h 05mnonstop
$297Southwest
Tue, Dec 1 - Thu, Dec 3
Southwest Logo
1:25 pm - 2:45 pmBDL  Hartford Bradley Intl-MDW Chicago Midway
2h 20mnonstop
Southwest Logo
8:00 am - 11:10 amMDW  Chicago Midway-BDL Hartford Bradley Intl
2h 10mnonstop
$297Southwest
Wed, Oct 21 - Sat, Oct 24
Southwest Logo
8:10 am - 9:30 amBDL  Hartford Bradley Intl-MDW Chicago Midway
2h 20mnonstop
Southwest Logo
1:20 pm - 4:25 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
2h 05mnonstop
$297Southwest
Sat, Oct 31 - Tue, Nov 3
Southwest Logo
1:00 pm - 2:45 pmBDL  Hartford Bradley Intl-MDW Chicago Midway
2h 45mnonstop
Southwest Logo
5:40 pm - 8:40 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
2h 00mnonstop
$297Southwest
Wed, Feb 24 - Sat, Feb 27
Southwest Logo
6:40 am - 8:20 amBDL  Hartford Bradley Intl-MDW Chicago Midway
2h 40mnonstop
Southwest Logo
12:55 pm - 3:55 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
2h 00mnonstop
$297Southwest
Thu, Feb 25 - Sat, Feb 27
Delta Logo
5:23 am - 9:32 amBDL  Hartford Bradley Intl-MDW Chicago Midway
5h 09m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:44 pm - 11:41 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
3h 57m1 stop Detroit Metropolitan Wayne County
$317Delta
Thu, Nov 5 - Mon, Nov 9
Delta Logo
5:40 pm - 10:10 pmBDL  Hartford Bradley Intl-MDW Chicago Midway
5h 30m1 stop Atlanta Hartsfield-Jackson
Delta Logo
10:35 am - 4:44 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
5h 09m1 stop Atlanta Hartsfield-Jackson
$317Delta
Wed, Jan 13 - Sat, Jan 16

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Frontier flights from Connecticut to Chicago Midway Airport

Our best Frontier deals on Connecticut to Chicago Midway Airport flight tickets
Frontier
Jan 7
BDL1:12 pmHartford Bradley Intl
7h 30m
1 stop
MDW7:42 pmChicago Midway
Jan 10
MDW8:47 pmChicago Midway
14h 30m
1 stop
BDL12:17 pmHartford Bradley Intl
$353
Frontier
Nov 24
BDL12:26 pmHartford Bradley Intl
8h 21m
1 stop
MDW7:47 pmChicago Midway
Nov 29
MDW8:42 pmChicago Midway
13h 49m
1 stop
BDL11:31 amHartford Bradley Intl
$375

Delta flights from Connecticut to Chicago Midway Airport

Our best Delta deals on Connecticut to Chicago Midway Airport flight tickets
Delta
Oct 22
BDL5:23 amHartford Bradley Intl
5h 09m
1 stop
MDW9:32 amChicago Midway
Oct 27
MDW5:09 pmChicago Midway
5h 50m
1 stop
BDL11:59 pmHartford Bradley Intl
$317
Delta
Oct 16
BDL11:55 amHartford Bradley Intl
5h 52m
1 stop
MDW4:47 pmChicago Midway
Oct 19
MDW6:44 pmChicago Midway
3h 48m
1 stop
BDL11:32 pmHartford Bradley Intl
$333
Delta
Nov 3
BDL5:23 amHartford Bradley Intl
5h 09m
1 stop
MDW9:32 amChicago Midway
Nov 5
MDW6:04 amChicago Midway
5h 49m
1 stop
BDL12:53 pmHartford Bradley Intl
$351

momondo Fare Finder

 
Use the filters below to find and compare flights from Connecticut to Chicago Midway Airport that are best for you.

Fly from

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Route

Depart

Return

Price

Cheapest round-trip

HartfordChicago

BDL Hartford Bradley Intl - MDW Chicago Midway

BDLMDW

Hartford Bradley Intl

Thu 11/19

7:45 am-9:15 am

Nonstop2h 30m

Chicago Midway

Sat 11/21

6:45 pm-9:50 pm

Nonstop2h 05m

$297

HartfordChicago

BDL Hartford Bradley Intl - MDW Chicago Midway

BDLMDW

Hartford Bradley Intl

Mon 11/16

6:25 pm-7:55 pm

Nonstop2h 30m

Chicago Midway

Thu 11/19

6:20 pm-9:25 pm

Nonstop2h 05m

$297

HartfordChicago

BDL Hartford Bradley Intl - MDW Chicago Midway

BDLMDW

Hartford Bradley Intl

Mon 11/2

6:40 pm-8:05 pm

Nonstop2h 25m

Chicago Midway

Wed 11/4

1:20 pm-4:25 pm

Nonstop2h 05m

$297

HartfordChicago

BDL Hartford Bradley Intl - MDW Chicago Midway

BDLMDW

Hartford Bradley Intl

Tue 12/1

6:25 pm-7:55 pm

Nonstop2h 30m

Chicago Midway

Thu 12/3

6:20 pm-9:25 pm

Nonstop2h 05m

$297

HartfordChicago

BDL Hartford Bradley Intl - MDW Chicago Midway

BDLMDW

Hartford Bradley Intl

Wed 10/21

1:25 pm-2:45 pm

Nonstop2h 20m

Chicago Midway

Sat 10/24

8:00 am-11:10 am

Nonstop2h 10m

$297
Quickest round-trip

HartfordChicago

BDL Hartford Bradley Intl - MDW Chicago Midway

BDLMDW

Hartford Bradley Intl

Sat 10/31

8:10 am-9:30 am

Nonstop2h 20m

Chicago Midway

Tue 11/3

1:20 pm-4:25 pm

Nonstop2h 05m

$297

HartfordChicago

BDL Hartford Bradley Intl - MDW Chicago Midway

BDLMDW

Hartford Bradley Intl

Wed 2/24

1:00 pm-2:45 pm

Nonstop2h 45m

Chicago Midway

Sat 2/27

5:40 pm-8:40 pm

Nonstop2h 00m

$297

HartfordChicago

BDL Hartford Bradley Intl - MDW Chicago Midway

BDLMDW

Hartford Bradley Intl

Thu 2/25

6:40 am-8:20 am

Nonstop2h 40m

Chicago Midway

Sat 2/27

12:55 pm-3:55 pm

Nonstop2h 00m

$297

HartfordChicago

BDL Hartford Bradley Intl - MDW Chicago Midway

BDLMDW

Hartford Bradley Intl

Thu 11/5

5:23 am-9:32 am

1 stop5h 09m

Chicago Midway

Mon 11/9

6:44 pm-11:41 pm

1 stop3h 57m

$317

HartfordChicago

BDL Hartford Bradley Intl - MDW Chicago Midway

BDLMDW

Hartford Bradley Intl

Wed 1/13

5:40 pm-10:10 pm

1 stop5h 30m

Chicago Midway

Sat 1/16

10:35 am-4:44 pm

1 stop5h 09m

$317

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 September is also very affordable. Most momondo users find prices during this month for around $377.

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.

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

$139

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 $139. The best round-trip flight deal from Connecticut to Chicago Midway Airport found on momondo in the last 72 hours is $297.
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 $293Free CancellationRating
8.0
4,200 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
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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.

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