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Cheap flights from Hartford to Chicago from $80

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Hartford to Chicago departing on 5/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
1:12 pm - 7:47 pm
BDL
-
MDW
7h 35m
1 stop
Multiple Airlines Logo
9:51 pm - 6:11 pm
MDW
-
BDL
19h 20m
2 stops
$291Multiple Airlines
Thu, Mar 12 - Mon, Mar 16
Southwest Logo
6:10 pm - 7:40 pm
BDL
-
MDW
2h 30mnonstop
Southwest Logo
6:10 pm - 9:10 pm
MDW
-
BDL
2h 00mnonstop
$293Southwest
Tue, Mar 10 - Wed, Mar 11
Frontier Logo
1:07 pm - 7:31 pm
BDL
-
MDW
7h 24m
1 stop
Frontier Logo
9:14 am - 4:05 am
MDW
-
BDL
17h 51m
2 stops
$294Frontier
Thu, Apr 30 - Sun, May 3
Frontier Logo
2:27 pm - 7:59 pm
BDL
-
MDW
6h 32m
1 stop
Frontier Logo
6:15 am - 7:13 pm
MDW
-
BDL
11h 58m
1 stop
$295Frontier
Sun, Mar 1 - Sat, Mar 7
Multiple Airlines Logo
8:08 pm - 1:02 pm
BDL
-
MDW
17h 54m
2 stops
Multiple Airlines Logo
9:10 am - 7:13 pm
MDW
-
BDL
9h 03m
1 stop
$296Multiple Airlines
Mon, Mar 23 - Thu, Mar 26
Frontier Logo
1:07 pm - 7:31 pm
BDL
-
MDW
7h 24m
1 stop
Frontier Logo
6:00 am - 7:17 pm
MDW
-
BDL
12h 17m
2 stops
$297Frontier
Fri, May 1 - Mon, May 4
Multiple Airlines Logo
1:07 pm - 7:31 pm
BDL
-
MDW
7h 24m
1 stop
Multiple Airlines Logo
9:14 am - 11:16 pm
MDW
-
BDL
13h 02m
2 stops
$298Multiple Airlines
Fri, May 1 - Mon, May 4
Delta Logo
5:30 am - 8:47 am
BDL
-
MDW
4h 17m
1 stop
Delta Logo
6:00 am - 1:16 pm
MDW
-
BDL
6h 16m
1 stop
$299Delta
Sat, Apr 18 - Thu, Apr 23
Frontier Logo
1:07 pm - 10:19 pm
BDL
-
MDW
10h 12m
1 stop
Frontier Logo
9:14 am - 7:17 pm
MDW
-
BDL
9h 03m
1 stop
$300Frontier
Sun, Apr 19 - Thu, Apr 23
Frontier Logo
1:07 pm - 7:31 pm
BDL
-
MDW
7h 24m
1 stop
Frontier Logo
2:20 pm - 12:15 pm
MDW
-
BDL
20h 55m
1 stop
$302Frontier
Thu, Apr 16 - Sun, Apr 19

Southwest flights from Hartford to Chicago Midway Airport

Our best Southwest deals on Hartford to Chicago Midway Airport flight tickets
Southwest
Mar 10
BDL6:10 pmHartford Bradley Intl
2h 30m
MDW7:40 pmChicago Midway
Mar 11
MDW6:10 pmChicago Midway
2h 00m
BDL9:10 pmHartford Bradley Intl
$293
Southwest
Mar 10
BDL2:35 pmHartford Bradley Intl
6h 00m
1 stop
MDW7:35 pmChicago Midway
Mar 11
MDW6:10 pmChicago Midway
2h 00m
BDL9:10 pmHartford Bradley Intl
$303
Southwest
Mar 10
BDL2:35 pmHartford Bradley Intl
5h 55m
2 stops
MDW7:30 pmChicago Midway
Mar 11
MDW7:40 amChicago Midway
2h 00m
BDL10:40 amHartford Bradley Intl
$308

Frontier flights from Hartford to Chicago Midway Airport

Our best Frontier deals on Hartford to Chicago Midway Airport flight tickets
Frontier
Apr 30
BDL1:07 pmHartford Bradley Intl
7h 24m
1 stop
MDW7:31 pmChicago Midway
May 3
MDW9:14 amChicago Midway
17h 51m
2 stops
BDL4:05 amHartford Bradley Intl
$294
Frontier
Mar 1
BDL2:27 pmHartford Bradley Intl
6h 32m
1 stop
MDW7:59 pmChicago Midway
Mar 7
MDW6:15 amChicago Midway
11h 58m
1 stop
BDL7:13 pmHartford Bradley Intl
$295
Frontier
May 1
BDL1:07 pmHartford Bradley Intl
7h 24m
1 stop
MDW7:31 pmChicago Midway
May 4
MDW6:00 amChicago Midway
12h 17m
2 stops
BDL7:17 pmHartford Bradley Intl
$297

momondo Fare Finder

 
Customize your flight search to find flights from Hartford 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 February 16, 2026.
Use the filters below to find and compare flights from Hartford to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 3/12

1:12 pm-7:47 pm

1 stop7h 35m

Chicago Midway

Mon 3/16

9:51 pm-6:11 pm

2 stops19h 20m

$291

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 3/10

6:10 pm-7:40 pm

Nonstop2h 30m

Chicago Midway

Wed 3/11

6:10 pm-9:10 pm

Nonstop2h 00m

$293

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 4/30

1:07 pm-7:31 pm

1 stop7h 24m

Chicago Midway

Sun 5/3

9:14 am-4:05 am

2 stops17h 51m

$294

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sun 3/1

2:27 pm-7:59 pm

1 stop6h 32m

Chicago Midway

Sat 3/7

6:15 am-7:13 pm

1 stop11h 58m

$295

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Mon 3/23

8:08 pm-1:02 pm

2 stops17h 54m

Chicago Midway

Thu 3/26

9:10 am-7:13 pm

1 stop9h 03m

$296

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Fri 5/1

1:07 pm-7:31 pm

1 stop7h 24m

Chicago Midway

Mon 5/4

6:00 am-7:17 pm

2 stops12h 17m

$297

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Fri 5/1

1:07 pm-7:31 pm

1 stop7h 24m

Chicago Midway

Mon 5/4

9:14 am-11:16 pm

2 stops13h 02m

$298

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sat 4/18

5:30 am-8:47 am

1 stop4h 17m

Chicago Midway

Thu 4/23

6:00 am-1:16 pm

1 stop6h 16m

$299

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sun 4/19

1:07 pm-10:19 pm

1 stop10h 12m

Chicago Midway

Thu 4/23

9:14 am-7:17 pm

1 stop9h 03m

$300

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 4/16

1:07 pm-7:31 pm

1 stop7h 24m

Chicago Midway

Sun 4/19

2:20 pm-12:15 pm

1 stop20h 55m

$302

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 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 August is also very affordable. Most momondo users find prices during this month for around $234.

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 Bradley Intl to Chicago Midway flights?

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

You could potentially save up to 52% on your flight if you consider stops on a Hartford to Chicago Midway Airport flight.

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

As of February 2026, prices for Hartford to Chicago Midway Airport flights are approximately 4% cheaper 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

$206

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 $206. The best round-trip flight deal from Hartford to Chicago Midway Airport found on momondo in the last 72 hours is $413.
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

  • 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
DeltaPriceFrom $176Free CancellationRating
7.9
8,205 reviews
Search Delta flights
SouthwestPriceFrom $177Free CancellationRating
8.0
4,289 reviews
Search Southwest flights
United AirlinesPriceFrom $299Free CancellationRating
7.4
9,308 reviews
Search United Airlines flights

  • Southwest Flights From Hartford to Chicago Midway Airport

    Southwest flies from Hartford to Chicago Midway Airport around 11 times per week, with 4,289 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Hartford to Chicago Midway Airport in the last 72 hours was $177 (round-trip), much lower than the average airfare cost of $381 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
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
Chesterton
Monticello
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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