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Cheap flights from Hartford to Chicago from $152

1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Hartford to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
12:26 pm - 7:47 pmBDL  Hartford Bradley Intl-MDW Chicago Midway
8h 21m1 stop Orlando
Frontier Logo
8:42 pm - 11:31 amMDW  Chicago Midway-BDL Hartford Bradley Intl
13h 49m1 stop Orlando
$303Frontier
Fri, Nov 20 - Sat, Nov 21
Southwest Logo
6:25 pm - 7:55 pmBDL  Hartford Bradley Intl-MDW Chicago Midway
2h 30mnonstop
Southwest Logo
7:50 am - 3:10 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
6h 20m1 stop Nashville Intl
$307Southwest
Thu, Dec 3 - Sat, Dec 5
Southwest Logo
12:25 pm - 7:05 pmBDL  Hartford Bradley Intl-MDW Chicago Midway
7h 40m1 stop Nashville Intl
Southwest Logo
3:40 pm - 6:40 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
2h 00mnonstop
$307Southwest
Tue, Dec 8 - Sat, Dec 12
Southwest Logo
3:50 pm - 5:20 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
Sat, Dec 5 - Mon, Dec 7
Southwest Logo
5:50 am - 10:00 amBDL  Hartford Bradley Intl-MDW Chicago Midway
5h 10m1 stop Baltimore/Washington
Southwest Logo
7:10 pm - 10:15 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
2h 05mnonstop
$307Southwest
Thu, Oct 29 - Thu, Nov 5
Southwest Logo
7:45 am - 9:15 amBDL  Hartford Bradley Intl-MDW Chicago Midway
2h 30mnonstop
Southwest Logo
5:05 am - 12:05 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
6h 00m1 stop Baltimore/Washington
$307Southwest
Tue, Nov 10 - Thu, Nov 12
Southwest Logo
11:30 am - 4:05 pmBDL  Hartford Bradley Intl-MDW Chicago Midway
5h 35m1 stop Baltimore/Washington
Southwest Logo
6:05 pm - 9:15 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
2h 10mnonstop
$307Southwest
Tue, Oct 27 - Wed, Oct 28
Southwest Logo
6:50 pm - 8:10 pmBDL  Hartford Bradley Intl-MDW Chicago Midway
2h 20mnonstop
Southwest Logo
6:00 am - 2:20 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
7h 20m1 stop Baltimore/Washington
$307Southwest
Wed, Oct 28 - Wed, Nov 4
Southwest Logo
3:15 pm - 7:40 pmBDL  Hartford Bradley Intl-MDW Chicago Midway
5h 25m1 stop Baltimore/Washington
Southwest Logo
1:20 pm - 4:25 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
2h 05mnonstop
$307Southwest
Sat, Nov 7 - Tue, Nov 10
Delta Logo
11:24 am - 4:14 pmBDL  Hartford Bradley Intl-MDW Chicago Midway
5h 50m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:04 am - 12:53 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
5h 49m1 stop Atlanta Hartsfield-Jackson
$317Delta
Thu, Oct 22 - Mon, Oct 26

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Frontier flights from Hartford to Chicago Midway Airport

Our best Frontier deals on Hartford to Chicago Midway Airport flight tickets
Frontier
Nov 20
BDL12:26 pmHartford Bradley Intl
8h 21m
1 stop
MDW7:47 pmChicago Midway
Nov 21
MDW8:42 pmChicago Midway
13h 49m
1 stop
BDL11:31 amHartford Bradley Intl
$303
Frontier
Dec 4
BDL12:56 pmHartford Bradley Intl
8h 52m
1 stop
MDW8:48 pmChicago Midway
Dec 6
MDW9:37 pmChicago Midway
13h 24m
1 stop
BDL12:01 pmHartford Bradley Intl
$336
Frontier
Nov 20
BDL12:26 pmHartford Bradley Intl
8h 21m
1 stop
MDW7:47 pmChicago Midway
Nov 22
MDW8:42 pmChicago Midway
13h 49m
1 stop
BDL11:31 amHartford Bradley Intl
$346

Delta flights from Hartford to Chicago Midway Airport

Our best Delta deals on Hartford to Chicago Midway Airport flight tickets
Delta
Oct 29
BDL11:55 amHartford Bradley Intl
5h 52m
1 stop
MDW4:47 pmChicago Midway
Oct 31
MDW9:29 amChicago Midway
6h 00m
1 stop
BDL4:29 pmHartford Bradley Intl
$317
Delta
Oct 21
BDL6:00 amHartford Bradley Intl
6h 54m
1 stop
MDW11:54 amChicago Midway
Oct 23
MDW5:31 pmChicago Midway
5h 18m
1 stop
BDL11:49 pmHartford Bradley Intl
$333
Delta
Nov 19
BDL6:00 amHartford Bradley Intl
5h 24m
1 stop
MDW10:24 amChicago Midway
Nov 23
MDW5:13 pmChicago Midway
6h 02m
1 stop
BDL12:15 amHartford Bradley Intl
$368

momondo Fare Finder

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

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Depart

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Price

Cheapest round-trip

HartfordChicago

BDL Hartford Bradley Intl - MDW Chicago Midway

BDLMDW

Hartford Bradley Intl

Fri 11/20

12:26 pm-7:47 pm

1 stop8h 21m

Chicago Midway

Sat 11/21

8:42 pm-11:31 am

1 stop13h 49m

$303

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

Sat 12/5

7:50 am-3:10 pm

1 stop6h 20m

$307

HartfordChicago

BDL Hartford Bradley Intl - MDW Chicago Midway

BDLMDW

Hartford Bradley Intl

Tue 12/8

12:25 pm-7:05 pm

1 stop7h 40m

Chicago Midway

Sat 12/12

3:40 pm-6:40 pm

Nonstop2h 00m

$307

HartfordChicago

BDL Hartford Bradley Intl - MDW Chicago Midway

BDLMDW

Hartford Bradley Intl

Sat 12/5

3:50 pm-5:20 pm

Nonstop2h 30m

Chicago Midway

Mon 12/7

6:00 am-2:20 pm

1 stop7h 20m

$307
Quickest round-trip

HartfordChicago

BDL Hartford Bradley Intl - MDW Chicago Midway

BDLMDW

Hartford Bradley Intl

Thu 10/29

5:50 am-10:00 am

1 stop5h 10m

Chicago Midway

Thu 11/5

7:10 pm-10:15 pm

Nonstop2h 05m

$307

HartfordChicago

BDL Hartford Bradley Intl - MDW Chicago Midway

BDLMDW

Hartford Bradley Intl

Tue 11/10

7:45 am-9:15 am

Nonstop2h 30m

Chicago Midway

Thu 11/12

5:05 am-12:05 pm

1 stop6h 00m

$307

HartfordChicago

BDL Hartford Bradley Intl - MDW Chicago Midway

BDLMDW

Hartford Bradley Intl

Tue 10/27

11:30 am-4:05 pm

1 stop5h 35m

Chicago Midway

Wed 10/28

6:05 pm-9:15 pm

Nonstop2h 10m

$307

HartfordChicago

BDL Hartford Bradley Intl - MDW Chicago Midway

BDLMDW

Hartford Bradley Intl

Wed 10/28

6:50 pm-8:10 pm

Nonstop2h 20m

Chicago Midway

Wed 11/4

6:00 am-2:20 pm

1 stop7h 20m

$307

HartfordChicago

BDL Hartford Bradley Intl - MDW Chicago Midway

BDLMDW

Hartford Bradley Intl

Sat 11/7

3:15 pm-7:40 pm

1 stop5h 25m

Chicago Midway

Tue 11/10

1:20 pm-4:25 pm

Nonstop2h 05m

$307

HartfordChicago

BDL Hartford Bradley Intl - MDW Chicago Midway

BDLMDW

Hartford Bradley Intl

Thu 10/22

11:24 am-4:14 pm

1 stop5h 50m

Chicago Midway

Mon 10/26

6:04 am-12:53 pm

1 stop5h 49m

$317

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 Hartford 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 typical price of a round-trip flight between Hartford and Chicago Midway Airport?

Prices are currently low for flights on this route.

Typical prices usually range from $380 to $539.
The lowest price recently found on this route was $303.

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 Hartford, with most prices found around $176. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Hartford during the month November is also very affordable. Most momondo users find prices during this month for around $394.

What is the cheapest Hartford Bradley Intl to Chicago Midway flight route?

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

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

There is only 1 cabin class available to choose from on Hartford 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.

How have Hartford to Chicago Midway Airport flight prices changed over time?

As of October 2026, prices for Hartford to Chicago Midway Airport flights are approximately 26% more expensive when compared to flights at the same time last year.

When to book flights from Hartford to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Hartford to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Hartford to Chicago Midway Airport (BDL to MDW) flight deals and tips

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

Best Price Found

$152

Fastest flight time

2h 20m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Hartford in the past 72 hours is $152. The best round-trip flight deal from Hartford to Chicago Midway Airport found on momondo in the last 72 hours is $303.
The fastest flight from Hartford to Chicago Midway Airport takes 2h 20m
Direct flights go from Hartford to Chicago Midway Airport every day.
Search flight deals

Frequently asked questions about flying from Hartford to Chicago Midway Airport

  • How far is Hartford Bradley Intl to Chicago Midway by plane?

    A flight from Hartford Bradley Intl to Chicago Midway will travel around 774.9 mi. 2h 20m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Hartford Bradley Intl Airport to Chicago Midway Airport?

    Prices for flights from Hartford Bradley Intl Airport to Chicago Midway Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Hartford Bradley Intl Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Hartford Bradley Intl Airport to Chicago Midway Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Hartford Bradley Intl Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Hartford to Chicago Midway Airport?

  • What is the most popular airline from Hartford to Chicago Midway Airport?

Best airlines flying from Hartford to Chicago Midway Airport

Compare and see reviews for airlines that fly from Hartford to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $293Free CancellationRating
7.9
4,215 reviews
Search Southwest flights

  • Southwest Flights From Hartford to Chicago Midway Airport

    Southwest flies from Hartford to Chicago Midway Airport around 9 times per week, with 4,215 momondo users rating the airline 7.9/10. The cheapest Southwest deal from Hartford to Chicago Midway Airport in the last 72 hours was $293 (round-trip), much lower than the average airfare cost of $433 for Southwest flights on this route.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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New Buffalo
Hammond
Portage
Benton Harbor
Saint Joseph
Lansing
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 Hartford to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Hartford to Chicago. momondo saves you time and could save you money on your trip.

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

All flight searches from Hartford to Chicago on momondo can be filtered to show those which offer flexible booking policies.

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

momondo helps you find the best flight between Hartford and Chicago 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 Hartford to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Hartford to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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