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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 4/23. 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
3:34 pm - 10:26 pm
BDL
-
MDW
7h 52m
1 stop
Frontier Logo
6:00 am - 2:49 pm
MDW
-
BDL
7h 49m
1 stop
$335Frontier
Fri, Apr 17 - Sun, Apr 19
Delta Logo
5:30 am - 8:47 am
BDL
-
MDW
4h 17m
1 stop
Delta Logo
5:21 pm - 11:59 pm
MDW
-
BDL
5h 38m
1 stop
$336Delta
Wed, Apr 29 - Fri, May 1
Frontier Logo
3:50 pm - 7:59 am
BDL
-
MDW
17h 09m
2 stops
Frontier Logo
6:00 am - 2:49 pm
MDW
-
BDL
7h 49m
1 stop
$337Frontier
Thu, Apr 16 - Sun, Apr 19
Frontier Logo
8:50 pm - 7:31 pm
BDL
-
MDW
23h 41m
2 stops
Frontier Logo
6:00 am - 2:49 pm
MDW
-
BDL
7h 49m
1 stop
$339Frontier
Mon, Apr 20 - Thu, Apr 23
Southwest Logo
3:00 pm - 6:15 pm
BDL
-
MDW
4h 15m
1 stop
Southwest Logo
3:45 pm - 6:45 pm
MDW
-
BDL
2h 00mnonstop
$343Southwest
Sat, Apr 25 - Sat, May 2
Southwest Logo
11:40 am - 1:05 pm
BDL
-
MDW
2h 25mnonstop
Southwest Logo
6:00 pm - 9:05 pm
MDW
-
BDL
2h 05mnonstop
$344Southwest
Thu, Apr 23 - Tue, Apr 28
Southwest Logo
8:45 am - 3:05 pm
BDL
-
MDW
7h 20m
1 stop
Southwest Logo
7:40 am - 10:40 am
MDW
-
BDL
2h 00mnonstop
$347Southwest
Thu, May 21 - Tue, May 26
Southwest Logo
11:40 am - 1:05 pm
BDL
-
MDW
2h 25mnonstop
Southwest Logo
2:15 pm - 10:55 pm
MDW
-
BDL
7h 40m
2 stops
$348Southwest
Thu, May 28 - Sat, May 30
Multiple Airlines Logo
8:05 am - 1:00 pm
BDL
-
MDW
29h 55m
2 stops
Multiple Airlines Logo
6:00 am - 2:49 pm
MDW
-
BDL
7h 49m
1 stop
$349Multiple Airlines
Tue, Apr 14 - Thu, Apr 16
Delta Logo
5:54 pm - 10:28 pm
BDL
-
MDW
5h 34m
1 stop
Delta Logo
5:21 pm - 11:59 pm
MDW
-
BDL
5h 38m
1 stop
$351Delta
Sat, May 2 - Mon, May 4

Frontier flights from Hartford to Chicago Midway Airport

Our best Frontier deals on Hartford to Chicago Midway Airport flight tickets
Frontier
Apr 5
BDL2:55 pmHartford Bradley Intl
6h 12m
1 stop
MDW8:07 pmChicago Midway
Apr 6
MDW5:30 amChicago Midway
7h 23m
1 stop
BDL1:53 pmHartford Bradley Intl
$335
Frontier
Apr 16
BDL3:50 pmHartford Bradley Intl
17h 09m
2 stops
MDW7:59 amChicago Midway
Apr 19
MDW6:00 amChicago Midway
7h 49m
1 stop
BDL2:49 pmHartford Bradley Intl
$337
Frontier
Apr 20
BDL8:50 pmHartford Bradley Intl
23h 41m
2 stops
MDW7:31 pmChicago Midway
Apr 23
MDW6:00 amChicago Midway
7h 49m
1 stop
BDL2:49 pmHartford Bradley Intl
$339

Delta flights from Hartford to Chicago Midway Airport

Our best Delta deals on Hartford to Chicago Midway Airport flight tickets
Delta
Apr 29
BDL5:30 amHartford Bradley Intl
4h 17m
1 stop
MDW8:47 amChicago Midway
May 1
MDW5:21 pmChicago Midway
5h 38m
1 stop
BDL11:59 pmHartford Bradley Intl
$336
Delta
May 2
BDL5:54 pmHartford Bradley Intl
5h 34m
1 stop
MDW10:28 pmChicago Midway
May 4
MDW5:21 pmChicago Midway
5h 38m
1 stop
BDL11:59 pmHartford Bradley Intl
$351
Delta
May 13
BDL2:07 pmHartford Bradley Intl
8h 02m
1 stop
MDW9:09 pmChicago Midway
May 16
MDW6:36 pmChicago Midway
3h 59m
1 stop
BDL11:35 pmHartford Bradley Intl
$353

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 March 30, 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

Cheapest round-trip

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Fri 4/17

3:34 pm-10:26 pm

1 stop7h 52m

Chicago Midway

Sun 4/19

6:00 am-2:49 pm

1 stop7h 49m

$335

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Wed 4/29

5:30 am-8:47 am

1 stop4h 17m

Chicago Midway

Fri 5/1

5:21 pm-11:59 pm

1 stop5h 38m

$336

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 4/16

3:50 pm-7:59 am

2 stops17h 09m

Chicago Midway

Sun 4/19

6:00 am-2:49 pm

1 stop7h 49m

$337

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Mon 4/20

8:50 pm-7:31 pm

2 stops23h 41m

Chicago Midway

Thu 4/23

6:00 am-2:49 pm

1 stop7h 49m

$339

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sat 4/25

3:00 pm-6:15 pm

1 stop4h 15m

Chicago Midway

Sat 5/2

3:45 pm-6:45 pm

Nonstop2h 00m

$343
Quickest round-trip

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 4/23

11:40 am-1:05 pm

Nonstop2h 25m

Chicago Midway

Tue 4/28

6:00 pm-9:05 pm

Nonstop2h 05m

$344

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 5/21

8:45 am-3:05 pm

1 stop7h 20m

Chicago Midway

Tue 5/26

7:40 am-10:40 am

Nonstop2h 00m

$347

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 5/28

11:40 am-1:05 pm

Nonstop2h 25m

Chicago Midway

Sat 5/30

2:15 pm-10:55 pm

2 stops7h 40m

$348

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 4/14

8:05 am-1:00 pm

2 stops29h 55m

Chicago Midway

Thu 4/16

6:00 am-2:49 pm

1 stop7h 49m

$349

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sat 5/2

5:54 pm-10:28 pm

1 stop5h 34m

Chicago Midway

Mon 5/4

5:21 pm-11:59 pm

1 stop5h 38m

$351

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?

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 49% 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 March 2026, prices for Hartford to Chicago Midway Airport flights are approximately 139% 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

$221

Fastest flight time

2h 15m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Hartford in the past 72 hours is $221. The best round-trip flight deal from Hartford to Chicago Midway Airport found on momondo in the last 72 hours is $428.
The fastest flight from Hartford to Chicago Midway Airport takes 2h 15m
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 15m 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
8,361 reviews
Search Delta flights
SouthwestPriceFrom $177Free CancellationRating
8.0
4,329 reviews
Search Southwest flights

  • Southwest Flights From Hartford to Chicago Midway Airport

    Southwest flies from Hartford to Chicago Midway Airport around 13 times per week, with 4,329 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 $390 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
Saint Joseph
Benton Harbor
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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