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Cheap flights from Hartford to Chicago from $70

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 2/7. 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.
Frontier Logo
2:27 pm - 7:59 pm
BDL
-
MDW
6h 32m1 stop
Frontier Logo
9:22 pm - 9:23 am
MDW
-
BDL
11h 01m1 stop
$197Frontier
Sun, Mar 1 - Mon, Mar 2
Frontier Logo
10:52 am - 8:27 pm
BDL
-
MDW
10h 35m1 stop
Frontier Logo
7:30 am - 5:05 pm
MDW
-
BDL
8h 35m1 stop
$234Frontier
Mon, Feb 23 - Thu, Feb 26
Delta Logo
6:03 am - 11:05 am
BDL
-
MDW
6h 02m1 stop
Delta Logo
4:30 pm - 10:32 pm
MDW
-
BDL
5h 02m1 stop
$245Delta
Sat, Jan 17 - Sat, Jan 24
Frontier Logo
1:07 pm - 7:47 pm
BDL
-
MDW
7h 40m1 stop
Frontier Logo
6:15 am - 7:13 pm
MDW
-
BDL
11h 58m1 stop
$250Frontier
Sun, Mar 8 - Mon, Mar 9
Southwest Logo
5:30 am - 7:05 am
BDL
-
MDW
2h 35mnonstop
Southwest Logo
1:25 pm - 4:20 pm
MDW
-
BDL
1h 55mnonstop
$259Southwest
Sun, Jan 18 - Thu, Jan 22
Frontier Logo
2:27 pm - 10:29 pm
BDL
-
MDW
9h 02m1 stop
Frontier Logo
7:53 pm - 11:04 am
MDW
-
BDL
14h 11m2 stops
$261Frontier
Thu, Feb 26 - Fri, Feb 27
Frontier Logo
10:52 am - 8:27 pm
BDL
-
MDW
10h 35m1 stop
Frontier Logo
7:30 am - 5:05 pm
MDW
-
BDL
8h 35m1 stop
$264Frontier
Mon, Feb 23 - Thu, Feb 26
Multiple Airlines Logo
7:45 am - 10:19 pm
BDL
-
MDW
15h 34m2 stops
Multiple Airlines Logo
1:00 pm - 7:06 pm
MDW
-
BDL
29h 06m1 stop
$265Multiple Airlines
Mon, Jan 19 - Fri, Jan 23
Southwest Logo
5:30 am - 7:05 am
BDL
-
MDW
2h 35mnonstop
Southwest Logo
6:00 am - 2:50 pm
MDW
-
BDL
7h 50m1 stop
$269Southwest
Sun, Jan 18 - Thu, Jan 22
Frontier Logo
8:08 pm - 6:13 pm
BDL
-
MDW
23h 05m1 stop
Frontier Logo
11:00 am - 7:13 pm
MDW
-
BDL
7h 13m1 stop
$272Frontier
Mon, Mar 9 - Thu, Mar 12

Frontier flights from Hartford to Chicago Midway Airport

Our best Frontier deals on Hartford to Chicago Midway Airport flight tickets
Frontier
Mar 1
BDL2:27 pmHartford Bradley Intl
6h 32m
1 stop
MDW7:59 pmChicago Midway
Mar 2
MDW9:22 pmChicago Midway
11h 01m
1 stop
BDL9:23 amHartford Bradley Intl
$197
Find similar
Frontier
Feb 23
BDL10:52 amHartford Bradley Intl
10h 35m
1 stop
MDW8:27 pmChicago Midway
Feb 26
MDW7:30 amChicago Midway
8h 35m
1 stop
BDL5:05 pmHartford Bradley Intl
$234
Find similar
Frontier
Mar 8
BDL1:07 pmHartford Bradley Intl
7h 40m
1 stop
MDW7:47 pmChicago Midway
Mar 9
MDW6:15 amChicago Midway
11h 58m
1 stop
BDL7:13 pmHartford Bradley Intl
$250
Find similar

Delta flights from Hartford to Chicago Midway Airport

Our best Delta deals on Hartford to Chicago Midway Airport flight tickets
Delta
Jan 17
BDL6:03 amHartford Bradley Intl
6h 02m
1 stop
MDW11:05 amChicago Midway
Jan 24
MDW4:30 pmChicago Midway
5h 02m
1 stop
BDL10:32 pmHartford Bradley Intl
$245
Find similar
Delta
Feb 14
BDL5:30 amHartford Bradley Intl
4h 23m
1 stop
MDW8:53 amChicago Midway
Feb 22
MDW6:17 pmChicago Midway
4h 22m
1 stop
BDL11:39 pmHartford Bradley Intl
$305
Find similar
Delta
Jan 21
BDL6:00 amHartford Bradley Intl
6h 59m
1 stop
MDW11:59 amChicago Midway
Jan 24
MDW6:25 amChicago Midway
6h 34m
1 stop
BDL1:59 pmHartford Bradley Intl
$313
Find similar

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 December 21, 2025.
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

Sun 3/1

2:27 pm-7:59 pm

1 stop6h 32m

Chicago Midway

Mon 3/2

9:22 pm-9:23 am

1 stop11h 01m

$197

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Mon 2/23

10:52 am-8:27 pm

1 stop10h 35m

Chicago Midway

Thu 2/26

7:30 am-5:05 pm

1 stop8h 35m

$234

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sat 1/17

6:03 am-11:05 am

1 stop6h 02m

Chicago Midway

Sat 1/24

4:30 pm-10:32 pm

1 stop5h 02m

$245

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sun 3/8

1:07 pm-7:47 pm

1 stop7h 40m

Chicago Midway

Mon 3/9

6:15 am-7:13 pm

1 stop11h 58m

$250

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sun 1/18

5:30 am-7:05 am

Nonstop2h 35m

Chicago Midway

Thu 1/22

1:25 pm-4:20 pm

Nonstop1h 55m

$259

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 2/26

2:27 pm-10:29 pm

1 stop9h 02m

Chicago Midway

Fri 2/27

7:53 pm-11:04 am

2 stops14h 11m

$261

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Mon 2/23

10:52 am-8:27 pm

1 stop10h 35m

Chicago Midway

Thu 2/26

7:30 am-5:05 pm

1 stop8h 35m

$264

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Mon 1/19

7:45 am-10:19 pm

2 stops15h 34m

Chicago Midway

Fri 1/23

1:00 pm-7:06 pm

1 stop29h 06m

$265

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sun 1/18

5:30 am-7:05 am

Nonstop2h 35m

Chicago Midway

Thu 1/22

6:00 am-2:50 pm

1 stop7h 50m

$269

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Mon 3/9

8:08 pm-6:13 pm

1 stop23h 05m

Chicago Midway

Thu 3/12

11:00 am-7:13 pm

1 stop7h 13m

$272

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 August is, on average, the cheapest month to fly to Chicago Midway Airport from Hartford, with most prices found around $237. If you are unable to visit Chicago Midway Airport during the month of August, then departing from Hartford during the month September is also very affordable. Most momondo users find prices during this month for around $311.

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 2% 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?

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

$218

Fastest flight time

2h 25m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Hartford in the past 72 hours is $218. The best round-trip flight deal from Hartford to Chicago Midway Airport found on momondo in the last 72 hours is $410.
The fastest flight from Hartford to Chicago Midway Airport takes 2h 25m
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 25m 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
8,017 reviews
Search Delta flights
SouthwestPriceFrom $177Free CancellationRating
8.0
4,254 reviews
Search Southwest flights
United AirlinesPriceFrom $299Free CancellationRating
7.4
9,100 reviews
Search United Airlines flights

  • Southwest Flights From Hartford to Chicago Midway Airport

    Southwest flies from Hartford to Chicago Midway Airport around 10 times per week, with 4,254 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 $376 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
Valparaiso
Schererville
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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