How many flights depart from Chicago Midway Airport to Connecticut on average per week?

3 flights are operational weekly from Chicago Midway Airport to Connecticut as of September 2026. The most popular departure day for this route is Mon, with 100% of flights per week taking off on this day.

What is the cheapest airline that flies from Chicago Midway to Connecticut?

Delta and Southwest are the most popular carriers operating from Chicago Midway to Connecticut

How many operators does momondo search for flights from Chicago Midway Airport to Connecticut?

There is 1 operator available for flights from Chicago Midway Airport to Connecticut as of September 2026.

How old do you have to be to fly from Chicago Midway Airport to Connecticut?

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 Chicago Midway Airport to Connecticut.

What documentation or ID do you need to fly to Connecticut?

The required travel and health documents for your Connecticut trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Connecticut. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$159 Cheap Flights from Chicago Midway Airport to Connecticut in 2026/27

Find the cheapest flights from Chicago Midway Airport to Connecticut

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:20 pm - 9:25 pmMDW Chicago Midway-BDL Hartford Bradley Intl

2h 05mnonstop

7:45 am - 9:15 amBDL Hartford Bradley Intl-MDW Chicago Midway

2h 30mnonstop

$297Southwest

Mon, Nov 16 - Wed, Nov 18

1:20 pm - 4:25 pmMDW Chicago Midway-BDL Hartford Bradley Intl

2h 05mnonstop

5:05 pm - 6:45 pmBDL Hartford Bradley Intl-MDW Chicago Midway

2h 40mnonstop

$297Southwest

Tue, Jan 5 - Tue, Jan 12

8:00 am - 11:10 amMDW Chicago Midway-BDL Hartford Bradley Intl

2h 10mnonstop

7:30 am - 9:00 amBDL Hartford Bradley Intl-MDW Chicago Midway

2h 30mnonstop

$297Southwest

Mon, Nov 23 - Thu, Nov 26

8:00 am - 11:10 amMDW Chicago Midway-BDL Hartford Bradley Intl

2h 10mnonstop

1:35 pm - 2:55 pmBDL Hartford Bradley Intl-MDW Chicago Midway

2h 20mnonstop

$297Southwest

Sat, Oct 24 - Sat, Oct 31

8:35 am - 11:45 amMDW Chicago Midway-BDL Hartford Bradley Intl

2h 10mnonstop

7:45 am - 9:15 amBDL Hartford Bradley Intl-MDW Chicago Midway

2h 30mnonstop

$297Southwest

Sat, Oct 31 - Tue, Nov 3

6:20 pm - 9:20 pmMDW Chicago Midway-BDL Hartford Bradley Intl

2h 00mnonstop

7:45 am - 9:15 amBDL Hartford Bradley Intl-MDW Chicago Midway

2h 30mnonstop

$297Southwest

Thu, Dec 10 - Mon, Dec 14

6:20 pm - 9:20 pmMDW Chicago Midway-BDL Hartford Bradley Intl

2h 00mnonstop

6:25 pm - 7:55 pmBDL Hartford Bradley Intl-MDW Chicago Midway

2h 30mnonstop

$297Southwest

Tue, Nov 3 - Wed, Nov 4

7:45 am - 10:55 amMDW Chicago Midway-BDL Hartford Bradley Intl

2h 10mnonstop

1:25 pm - 2:45 pmBDL Hartford Bradley Intl-MDW Chicago Midway

2h 20mnonstop

$297Southwest

Tue, Oct 27 - Tue, Oct 27

8:42 pm - 11:31 amMDW Chicago Midway-BDL Hartford Bradley Intl

13h 49m1 stop Orlando

12:26 pm - 7:47 pmBDL Hartford Bradley Intl-MDW Chicago Midway

8h 21m1 stop Orlando

$303Frontier

Fri, Nov 20 - Mon, Nov 23

9:29 am - 4:29 pmMDW Chicago Midway-BDL Hartford Bradley Intl

6h 00m1 stop Detroit Metropolitan Wayne County

7:00 am - 11:54 amBDL Hartford Bradley Intl-MDW Chicago Midway

5h 54m1 stop Atlanta Hartsfield-Jackson

$317Delta

Wed, Oct 21 - Thu, Oct 29

Cheap last minute flights

Enter your travel dates to find the best prices.

4:15 pm - 7:20 pmMDW Chicago Midway-BDL Hartford Bradley Intl

2h 05mnonstop

8:10 am - 9:30 amBDL Hartford Bradley Intl-MDW Chicago Midway

2h 20mnonstop

$412Southwest

Sat, Oct 3 - Sat, Oct 17

4:50 pm - 9:45 pmMDW Chicago Midway-BDL Hartford Bradley Intl

3h 55m1 stop Baltimore/Washington

8:10 am - 9:30 amBDL Hartford Bradley Intl-MDW Chicago Midway

2h 20mnonstop

$422Southwest

Sat, Oct 3 - Sat, Oct 17

8:10 am - 4:40 pmMDW Chicago Midway-BDL Hartford Bradley Intl

7h 30m2 stops Greater Rochester Intl Baltimore/Washington

8:10 am - 9:30 amBDL Hartford Bradley Intl-MDW Chicago Midway

2h 20mnonstop

$427Southwest

Sat, Oct 3 - Sat, Oct 17

8:10 am - 4:40 pmMDW Chicago Midway-BDL Hartford Bradley Intl

7h 30m2 stops Greater Rochester Intl Baltimore/Washington

1:10 pm - 6:45 pmBDL Hartford Bradley Intl-MDW Chicago Midway

6h 35m1 stop Baltimore/Washington

$437Southwest

Sat, Oct 3 - Sat, Oct 17

8:10 am - 3:00 pmMDW Chicago Midway-BDL Hartford Bradley Intl

5h 50m2 stops Greater Rochester Intl Baltimore/Washington

5:40 am - 5:25 pmBDL Hartford Bradley Intl-MDW Chicago Midway

12h 45m2 stops Baltimore/Washington Louisville Intl

$448Southwest

Sat, Oct 3 - Sat, Oct 17

1:00 pm - 4:05 pmMDW Chicago Midway-BDL Hartford Bradley Intl

2h 05mnonstop

5:55 pm - 7:15 pmBDL Hartford Bradley Intl-MDW Chicago Midway

2h 20mnonstop

$527Southwest

Tue, Sep 29 - Tue, Sep 29

8:45 am - 12:00 pmMDW Chicago Midway-BDL Hartford Bradley Intl

2h 15mnonstop

3:05 pm - 6:45 pmBDL Hartford Bradley Intl-MDW Chicago Midway

4h 40m1 stop Baltimore/Washington

$537Southwest

Tue, Sep 29 - Tue, Sep 29

1:00 pm - 4:05 pmMDW Chicago Midway-BDL Hartford Bradley Intl

2h 05mnonstop

7:35 am - 8:55 amBDL Hartford Bradley Intl-MDW Chicago Midway

2h 20mnonstop

$539Southwest

Wed, Sep 30 - Sun, Oct 4

1:00 pm - 9:08 pmMDW Chicago Midway-BDL Hartford Bradley Intl

7h 08m1 stop Atlanta Hartsfield-Jackson

11:51 am - 6:19 pmBDL Hartford Bradley Intl-MDW Chicago Midway

7h 28m1 stop Minneapolis St Paul

$540Delta

Tue, Sep 29 - Wed, Sep 30

6:40 pm - 11:12 pmMDW Chicago Midway-BDL Hartford Bradley Intl

3h 32m1 stop Detroit Metropolitan Wayne County

9:43 am - 12:47 pmBDL Hartford Bradley Intl-MDW Chicago Midway

4h 04m1 stop Detroit Metropolitan Wayne County

$547Delta

Sat, Oct 3 - Wed, Oct 7

Cheap direct flights

Enter your travel dates to find the best prices.

8:00 am - 11:10 amMDW Chicago Midway-BDL Hartford Bradley Intl

2h 10mnonstop

12:55 pm - 2:25 pmBDL Hartford Bradley Intl-MDW Chicago Midway

2h 30mnonstop

$297Southwest

Thu, Nov 12 - Thu, Nov 12

8:00 am - 11:10 amMDW Chicago Midway-BDL Hartford Bradley Intl

2h 10mnonstop

6:25 pm - 7:55 pmBDL Hartford Bradley Intl-MDW Chicago Midway

2h 30mnonstop

$297Southwest

Thu, Nov 12 - Mon, Nov 16

6:20 pm - 9:25 pmMDW Chicago Midway-BDL Hartford Bradley Intl

2h 05mnonstop

7:45 am - 9:15 amBDL Hartford Bradley Intl-MDW Chicago Midway

2h 30mnonstop

$297Southwest

Mon, Nov 16 - Wed, Nov 18

1:20 pm - 4:25 pmMDW Chicago Midway-BDL Hartford Bradley Intl

2h 05mnonstop

5:05 pm - 6:45 pmBDL Hartford Bradley Intl-MDW Chicago Midway

2h 40mnonstop

$297Southwest

Tue, Jan 5 - Tue, Jan 12

8:00 am - 11:10 amMDW Chicago Midway-BDL Hartford Bradley Intl

2h 10mnonstop

7:30 am - 9:00 amBDL Hartford Bradley Intl-MDW Chicago Midway

2h 30mnonstop

$297Southwest

Mon, Nov 23 - Thu, Nov 26

8:00 am - 11:10 amMDW Chicago Midway-BDL Hartford Bradley Intl

2h 10mnonstop

1:35 pm - 2:55 pmBDL Hartford Bradley Intl-MDW Chicago Midway

2h 20mnonstop

$297Southwest

Sat, Oct 24 - Sat, Oct 31

8:35 am - 11:45 amMDW Chicago Midway-BDL Hartford Bradley Intl

2h 10mnonstop

7:45 am - 9:15 amBDL Hartford Bradley Intl-MDW Chicago Midway

2h 30mnonstop

$297Southwest

Sat, Oct 31 - Tue, Nov 3

6:20 pm - 9:20 pmMDW Chicago Midway-BDL Hartford Bradley Intl

2h 00mnonstop

7:45 am - 9:15 amBDL Hartford Bradley Intl-MDW Chicago Midway

2h 30mnonstop

$297Southwest

Thu, Dec 10 - Mon, Dec 14

6:20 pm - 9:20 pmMDW Chicago Midway-BDL Hartford Bradley Intl

2h 00mnonstop

6:25 pm - 7:55 pmBDL Hartford Bradley Intl-MDW Chicago Midway

2h 30mnonstop

$297Southwest

Tue, Nov 3 - Wed, Nov 4

7:45 am - 10:55 amMDW Chicago Midway-BDL Hartford Bradley Intl

2h 10mnonstop

1:25 pm - 2:45 pmBDL Hartford Bradley Intl-MDW Chicago Midway

2h 20mnonstop

$297Southwest

Tue, Oct 27 - Tue, Oct 27

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Delta flights from Chicago Midway Airport to Connecticut

Our best Delta deals on Chicago Midway Airport to Connecticut flight tickets

Delta

Oct 29

MDW6:44 pmChicago Midway

3h 48m

1 stop

BDL11:32 pmHartford Bradley Intl

Nov 2

BDL5:35 pmHartford Bradley Intl

5h 58m

1 stop

MDW10:33 pmChicago Midway

$317

Delta

Oct 23

MDW6:44 pmChicago Midway

3h 48m

1 stop

BDL11:32 pmHartford Bradley Intl

Oct 28

BDL12:57 pmHartford Bradley Intl

6h 03m

1 stop

MDW6:00 pmChicago Midway

$333

Delta

Oct 26

MDW6:44 pmChicago Midway

3h 48m

1 stop

BDL11:32 pmHartford Bradley Intl

Oct 29

BDL5:23 amHartford Bradley Intl

5h 09m

1 stop

MDW9:32 amChicago Midway

$351

Southwest flights from Chicago Midway Airport to Connecticut

Our best Southwest deals on Chicago Midway Airport to Connecticut flight tickets

Southwest

Nov 19

MDW6:20 pmChicago Midway

2h 05m

BDL9:25 pmHartford Bradley Intl

Nov 23

BDL7:25 amHartford Bradley Intl

2h 30m

MDW8:55 amChicago Midway

$297

Southwest

Nov 19

MDW8:50 amChicago Midway

4h 30m

1 stop

BDL2:20 pmHartford Bradley Intl

Nov 23

BDL6:40 pmHartford Bradley Intl

2h 25m

MDW8:05 pmChicago Midway

$307

Southwest

Nov 19

MDW1:15 pmChicago Midway

5h 30m

2 stops

BDL7:45 pmHartford Bradley Intl

Nov 23

BDL12:55 pmHartford Bradley Intl

2h 30m

MDW2:25 pmChicago Midway

$312

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoHartford

MDW Chicago Midway - BDL Hartford Bradley Intl

MDWBDL

Chicago Midway

Mon 11/16

6:20 pm-9:25 pm

Nonstop2h 05m

Hartford Bradley Intl

Wed 11/18

7:45 am-9:15 am

Nonstop2h 30m

$297

ChicagoHartford

MDW Chicago Midway - BDL Hartford Bradley Intl

MDWBDL

Chicago Midway

Tue 1/5

1:20 pm-4:25 pm

Nonstop2h 05m

Hartford Bradley Intl

Tue 1/12

5:05 pm-6:45 pm

Nonstop2h 40m

$297

ChicagoHartford

MDW Chicago Midway - BDL Hartford Bradley Intl

MDWBDL

Chicago Midway

Mon 11/23

8:00 am-11:10 am

Nonstop2h 10m

Hartford Bradley Intl

Thu 11/26

7:30 am-9:00 am

Nonstop2h 30m

$297

Quickest round-trip

ChicagoHartford

MDW Chicago Midway - BDL Hartford Bradley Intl

MDWBDL

Chicago Midway

Sat 10/24

8:00 am-11:10 am

Nonstop2h 10m

Hartford Bradley Intl

Sat 10/31

1:35 pm-2:55 pm

Nonstop2h 20m

$297

ChicagoHartford

MDW Chicago Midway - BDL Hartford Bradley Intl

MDWBDL

Chicago Midway

Sat 10/31

8:35 am-11:45 am

Nonstop2h 10m

Hartford Bradley Intl

Tue 11/3

7:45 am-9:15 am

Nonstop2h 30m

$297

ChicagoHartford

MDW Chicago Midway - BDL Hartford Bradley Intl

MDWBDL

Chicago Midway

Thu 12/10

6:20 pm-9:20 pm

Nonstop2h 00m

Hartford Bradley Intl

Mon 12/14

7:45 am-9:15 am

Nonstop2h 30m

$297

ChicagoHartford

MDW Chicago Midway - BDL Hartford Bradley Intl

MDWBDL

Chicago Midway

Tue 11/3

6:20 pm-9:20 pm

Nonstop2h 00m

Hartford Bradley Intl

Wed 11/4

6:25 pm-7:55 pm

Nonstop2h 30m

$297

ChicagoHartford

MDW Chicago Midway - BDL Hartford Bradley Intl

MDWBDL

Chicago Midway

Tue 10/27

7:45 am-10:55 am

Nonstop2h 10m

Hartford Bradley Intl

Tue 10/27

1:25 pm-2:45 pm

Nonstop2h 20m

$297

ChicagoHartford

MDW Chicago Midway - BDL Hartford Bradley Intl

MDWBDL

Chicago Midway

Fri 11/20

8:42 pm-11:31 am

1 stop13h 49m

Hartford Bradley Intl

Mon 11/23

12:26 pm-7:47 pm

1 stop8h 21m

$303

ChicagoHartford

MDW Chicago Midway - BDL Hartford Bradley Intl

MDWBDL

Chicago Midway

Wed 10/21

9:29 am-4:29 pm

1 stop6h 00m

Hartford Bradley Intl

Thu 10/29

7:00 am-11:54 am

1 stop5h 54m

$317

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago Midway Airport to Connecticut

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

Prices

Airlines

Other information

What is the cheapest month to fly to Connecticut?

In general, February is the cheapest month to fly from Chicago Midway Airport to Connecticut. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $0. If you aren’t able to travel to Connecticut during the month of February, then flying in December is also cheap. Prices for this month can be found on momondo for an average of $318.

What is the cheapest Chicago Midway to Connecticut flight route?

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

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

There is only 1 cabin class available to choose from on Chicago Midway Airport to Connecticut 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 Chicago Midway Airport to Connecticut flights?

You could potentially save up to 2% on your flight if you consider stops on a Chicago Midway Airport to Connecticut flight.

Cheap Chicago Midway Airport to Connecticut flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Connecticut

Best Price Found	$159
Fastest flight time	2h 00m
Direct flights	Every day
Airports in Connecticut	90 airports

The best one-way flight to Connecticut from Chicago Midway Airport in the past 72 hours is $159. The best round-trip flight deal from Chicago Midway Airport to Connecticut found on momondo in the last 72 hours is $297.

The fastest flight from Chicago Midway Airport to Connecticut takes 2h 00m

Direct flights go from Chicago Midway Airport to Connecticut every day.

There are 90 airports in Connecticut. From Chicago Midway Airport there are direct flights to Hartford Bradley Intl (BDL).

Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Connecticut

When did momondo last update prices for flights from Chicago Midway Airport to Connecticut?
Prices for flights from Chicago Midway Airport to Connecticut refresh daily.
How many operators does momondo search for flights from Chicago Midway Airport to Connecticut?
There is 1 operator available for flights from Chicago Midway Airport to Connecticut as of September 2026.
How old do you have to be to fly from Chicago Midway Airport to Connecticut?
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 Chicago Midway Airport to Connecticut.
What documentation or ID do you need to fly to Connecticut?
The required travel and health documents for your Connecticut trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Connecticut. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Chicago Midway Airport to Connecticut?
Based on momondo bookings for flights between Chicago Midway Airport and Connecticut, the leading plane model is Boeing 737-800, making up 24.74% of the total bookings. Other popular models include Boeing 737 MAX 8 with 15.81%, Boeing 737-800 Passenger/BBJ2 (winglets) with 12.03%, and Embraer 175 with 11.68%.

Best airlines flying from Chicago Midway Airport to Connecticut

Compare and see reviews for airlines that fly from Chicago Midway Airport to Connecticut with momondo

Airline	Rating	Free Cancellation	Price
Southwest	PriceFrom $248	Free Cancellation	Rating 8.0 4,201 reviews		Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Connecticut?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Connecticut for you.

Can I find flights from Chicago to Connecticut with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Chicago to Connecticut flights to just show those with flexible booking policies.

How can momondo help me find flights from Chicago to Connecticut?

momondo helps you find the best flight between Chicago and Connecticut by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Chicago to Connecticut right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to Connecticut flights. All you need is a valid email address and we will do the rest; it is that quick and easy.