Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Connecticut to Chicago from $149

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.
Frontier Logo
1:12 pm - 7:42 pmBDL  Hartford Bradley Intl-MDW Chicago Midway
7h 30m1 stop Orlando
Frontier Logo
8:47 pm - 12:17 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
14h 30m1 stop Orlando
$300Frontier
Fri, Feb 5 - Sun, Feb 7
Frontier Logo
2:29 pm - 2:41 pmBDL  Hartford Bradley Intl-MDW Chicago Midway
25h 12m1 stop Orlando
Frontier Logo
8:37 pm - 12:51 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
15h 14m1 stop Orlando
$300Frontier
Thu, Dec 3 - Sun, Dec 6
Frontier Logo
7:19 pm - 7:42 pmBDL  Hartford Bradley Intl-MDW Chicago Midway
25h 23m1 stop Orlando
Frontier Logo
8:47 pm - 12:17 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
14h 30m1 stop Orlando
$300Frontier
Thu, Feb 25 - Sun, Feb 28
Frontier Logo
1:12 pm - 7:42 pmBDL  Hartford Bradley Intl-MDW Chicago Midway
7h 30m1 stop Orlando
Frontier Logo
8:47 pm - 12:17 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
14h 30m1 stop Orlando
$300Frontier
Thu, Jan 21 - Sun, Jan 24
Frontier Logo
1:12 pm - 7:42 pmBDL  Hartford Bradley Intl-MDW Chicago Midway
7h 30m1 stop Orlando
Frontier Logo
8:47 pm - 12:17 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
14h 30m1 stop Orlando
$300Frontier
Thu, Jan 28 - Sun, Jan 31
Southwest Logo
6:25 pm - 7:55 pmBDL  Hartford Bradley Intl-MDW Chicago Midway
2h 30mnonstop
Southwest Logo
6:00 am - 11:50 amMDW  Chicago Midway-BDL Hartford Bradley Intl
4h 50m1 stop Baltimore/Washington
$307Southwest
Tue, Dec 1 - Tue, Dec 8
Southwest Logo
1:20 pm - 2:50 pmBDL  Hartford Bradley Intl-MDW Chicago Midway
2h 30mnonstop
Southwest Logo
5:10 pm - 10:40 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
4h 30m1 stop Baltimore/Washington
$307Southwest
Thu, Jan 7 - Sat, Jan 9
Southwest Logo
5:40 am - 9:00 amBDL  Hartford Bradley Intl-MDW Chicago Midway
4h 20m1 stop Baltimore/Washington
Southwest Logo
6:20 pm - 9:25 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
2h 05mnonstop
$307Southwest
Mon, Dec 14 - Mon, Dec 14
Southwest Logo
6:25 pm - 7:55 pmBDL  Hartford Bradley Intl-MDW Chicago Midway
2h 30mnonstop
Southwest Logo
6:00 am - 11:50 amMDW  Chicago Midway-BDL Hartford Bradley Intl
4h 50m1 stop Baltimore/Washington
$307Southwest
Thu, Dec 3 - Mon, Dec 7
Southwest Logo
6:25 pm - 7:55 pmBDL  Hartford Bradley Intl-MDW Chicago Midway
2h 30mnonstop
Southwest Logo
6:00 am - 2:20 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
7h 20m1 stop Baltimore/Washington
$307Southwest
Thu, Dec 3 - Thu, Dec 10

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Frontier flights from Connecticut to Chicago Midway Airport

Our best Frontier deals on Connecticut to Chicago Midway Airport flight tickets
Frontier
Dec 3
BDL2:29 pmHartford Bradley Intl
25h 12m
1 stop
MDW2:41 pmChicago Midway
Dec 6
MDW8:37 pmChicago Midway
15h 14m
1 stop
BDL12:51 pmHartford Bradley Intl
$300
Frontier
Dec 21
BDL9:44 pmHartford Bradley Intl
22h 46m
1 stop
MDW7:30 pmChicago Midway
Dec 28
MDW8:35 pmChicago Midway
14h 42m
1 stop
BDL12:17 pmHartford Bradley Intl
$309
Frontier
Feb 25
BDL7:19 pmHartford Bradley Intl
25h 23m
1 stop
MDW7:42 pmChicago Midway
Feb 27
MDW8:47 pmChicago Midway
14h 30m
1 stop
BDL12:17 pmHartford Bradley Intl
$320

Southwest flights from Connecticut to Chicago Midway Airport

Our best Southwest deals on Connecticut to Chicago Midway Airport flight tickets
Southwest
Dec 3
BDL6:25 pmHartford Bradley Intl
2h 30m
MDW7:55 pmChicago Midway
Dec 10
MDW6:00 amChicago Midway
7h 20m
1 stop
BDL2:20 pmHartford Bradley Intl
$307
Southwest
Dec 1
BDL6:25 pmHartford Bradley Intl
2h 30m
MDW7:55 pmChicago Midway
Dec 8
MDW1:15 pmChicago Midway
5h 30m
2 stops
BDL7:45 pmHartford Bradley Intl
$312
Southwest
Dec 2
BDL7:45 amHartford Bradley Intl
2h 30m
MDW9:15 amChicago Midway
Dec 2
MDW6:20 pmChicago Midway
2h 05m
BDL9:25 pmHartford Bradley Intl
$319

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

Fly to

Route

Depart

Return

Price

Cheapest round-trip

HartfordChicago

BDL Hartford Bradley Intl - MDW Chicago Midway

BDLMDW

Hartford Bradley Intl

Fri 2/5

1:12 pm-7:42 pm

1 stop7h 30m

Chicago Midway

Sun 2/7

8:47 pm-12:17 pm

1 stop14h 30m

$300

HartfordChicago

BDL Hartford Bradley Intl - MDW Chicago Midway

BDLMDW

Hartford Bradley Intl

Thu 12/3

2:29 pm-2:41 pm

1 stop25h 12m

Chicago Midway

Sun 12/6

8:37 pm-12:51 pm

1 stop15h 14m

$300

HartfordChicago

BDL Hartford Bradley Intl - MDW Chicago Midway

BDLMDW

Hartford Bradley Intl

Thu 2/25

7:19 pm-7:42 pm

1 stop25h 23m

Chicago Midway

Sun 2/28

8:47 pm-12:17 pm

1 stop14h 30m

$300

HartfordChicago

BDL Hartford Bradley Intl - MDW Chicago Midway

BDLMDW

Hartford Bradley Intl

Thu 1/21

1:12 pm-7:42 pm

1 stop7h 30m

Chicago Midway

Sun 1/24

8:47 pm-12:17 pm

1 stop14h 30m

$300

HartfordChicago

BDL Hartford Bradley Intl - MDW Chicago Midway

BDLMDW

Hartford Bradley Intl

Thu 1/28

1:12 pm-7:42 pm

1 stop7h 30m

Chicago Midway

Sun 1/31

8:47 pm-12:17 pm

1 stop14h 30m

$300

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

Tue 12/8

6:00 am-11:50 am

1 stop4h 50m

$307

HartfordChicago

BDL Hartford Bradley Intl - MDW Chicago Midway

BDLMDW

Hartford Bradley Intl

Thu 1/7

1:20 pm-2:50 pm

Nonstop2h 30m

Chicago Midway

Sat 1/9

5:10 pm-10:40 pm

1 stop4h 30m

$307
Quickest round-trip

HartfordChicago

BDL Hartford Bradley Intl - MDW Chicago Midway

BDLMDW

Hartford Bradley Intl

Mon 12/14

5:40 am-9:00 am

1 stop4h 20m

Chicago Midway

Mon 12/14

6:20 pm-9:25 pm

Nonstop2h 05m

$307

HartfordChicago

BDL Hartford Bradley Intl - MDW Chicago Midway

BDLMDW

Hartford Bradley Intl

Thu 12/3

6:25 pm-7:55 pm

Nonstop2h 30m

Chicago Midway

Mon 12/7

6:00 am-11:50 am

1 stop4h 50m

$307

HartfordChicago

BDL Hartford Bradley Intl - MDW Chicago Midway

BDLMDW

Hartford Bradley Intl

Thu 12/3

6:25 pm-7:55 pm

Nonstop2h 30m

Chicago Midway

Thu 12/10

6:00 am-2:20 pm

1 stop7h 20m

$307

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 September is also very affordable. Most momondo users find prices during this month for around $396.

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?

No. A direct flight is the cheapest option for a flight between Connecticut to Chicago Midway Airport.

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

$149

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 $149. The best round-trip flight deal from Connecticut to Chicago Midway Airport found on momondo in the last 72 hours is $300.
The fastest flight from Connecticut to Chicago Midway Airport takes 2h 25m
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 $303Free CancellationRating
8.0
4,219 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
Lansing
Benton Harbor
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.

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Thu 12/10
Thu 12/17
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago