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Cheap flights from Hartford to Chicago from $171

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 8/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Hartford to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
6:30 pm - 8:00 pm
BDL
-
MDW
2h 30mnonstop
Southwest Logo
1:00 pm - 4:05 pm
MDW
-
BDL
2h 05mnonstop
$353Southwest
Wed, Jul 29 - Wed, Aug 5
Southwest Logo
4:00 pm - 9:35 pm
BDL
-
MDW
6h 35m
1 stop
Southwest Logo
8:45 am - 12:00 pm
MDW
-
BDL
2h 15mnonstop
$363Southwest
Wed, Jul 29 - Wed, Aug 5
Southwest Logo
1:10 pm - 2:30 pm
BDL
-
MDW
2h 20mnonstop
Southwest Logo
4:15 pm - 7:15 pm
MDW
-
BDL
2h 00mnonstop
$365Southwest
Wed, Oct 21 - Sat, Oct 24
Southwest Logo
4:00 pm - 11:10 pm
BDL
-
MDW
8h 10m
2 stops
Southwest Logo
7:50 am - 11:00 am
MDW
-
BDL
2h 10mnonstop
$368Southwest
Tue, Jun 16 - Tue, Jun 23
Delta Logo
7:35 am - 1:09 pm
BDL
-
MDW
6h 34m
1 stop
Delta Logo
6:58 pm - 11:35 pm
MDW
-
BDL
3h 37m
1 stop
$373Delta
Tue, Jun 23 - Tue, Jun 30
Southwest Logo
6:05 pm - 7:30 pm
BDL
-
MDW
2h 25mnonstop
Southwest Logo
2:30 pm - 9:45 pm
MDW
-
BDL
6h 15m
1 stop
$375Southwest
Wed, Oct 21 - Sat, Oct 24
Southwest Logo
3:50 pm - 5:15 pm
BDL
-
MDW
2h 25mnonstop
Southwest Logo
3:25 pm - 6:25 pm
MDW
-
BDL
2h 00mnonstop
$377Southwest
Sat, Sep 5 - Sat, Sep 12
Southwest Logo
2:35 pm - 10:35 pm
BDL
-
MDW
9h 00m
2 stops
Southwest Logo
7:30 am - 4:55 pm
MDW
-
BDL
8h 25m
1 stop
$378Southwest
Wed, Jul 29 - Wed, Aug 5
Southwest Logo
1:10 pm - 2:30 pm
BDL
-
MDW
2h 20mnonstop
Southwest Logo
6:30 am - 2:55 pm
MDW
-
BDL
7h 25m
2 stops
$380Southwest
Wed, Oct 21 - Sat, Oct 24
Southwest Logo
5:50 am - 12:15 pm
BDL
-
MDW
7h 25m
2 stops
Southwest Logo
12:45 pm - 9:10 pm
MDW
-
BDL
7h 25m
2 stops
$383Southwest
Wed, Jul 29 - Wed, Aug 5

Southwest flights from Hartford to Chicago Midway Airport

Our best Southwest deals on Hartford to Chicago Midway Airport flight tickets
Southwest
Jul 29
BDL6:30 pmHartford Bradley Intl
2h 30m
MDW8:00 pmChicago Midway
Aug 5
MDW1:00 pmChicago Midway
2h 05m
BDL4:05 pmHartford Bradley Intl
$353
Southwest
Jul 29
BDL4:00 pmHartford Bradley Intl
6h 35m
1 stop
MDW9:35 pmChicago Midway
Aug 5
MDW8:45 amChicago Midway
2h 15m
BDL12:00 pmHartford Bradley Intl
$363
Southwest
Oct 21
BDL1:10 pmHartford Bradley Intl
2h 20m
MDW2:30 pmChicago Midway
Oct 24
MDW4:15 pmChicago Midway
2h 00m
BDL7:15 pmHartford Bradley Intl
$365

Delta flights from Hartford to Chicago Midway Airport

Our best Delta deals on Hartford to Chicago Midway Airport flight tickets
Delta
Jun 23
BDL7:35 amHartford Bradley Intl
6h 34m
1 stop
MDW1:09 pmChicago Midway
Jun 30
MDW6:58 pmChicago Midway
3h 37m
1 stop
BDL11:35 pmHartford Bradley Intl
$373
Delta
Oct 14
BDL5:48 amHartford Bradley Intl
3h 57m
1 stop
MDW8:45 amChicago Midway
Oct 19
MDW6:45 pmChicago Midway
3h 52m
1 stop
BDL11:37 pmHartford Bradley Intl
$385
Delta
Jun 23
BDL5:30 amHartford Bradley Intl
4h 44m
1 stop
MDW9:14 amChicago Midway
Jul 4
MDW9:17 amChicago Midway
5h 56m
1 stop
BDL4:13 pmHartford Bradley Intl
$388

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 May 19, 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

Wed 7/29

6:30 pm-8:00 pm

Nonstop2h 30m

Chicago Midway

Wed 8/5

1:00 pm-4:05 pm

Nonstop2h 05m

$353

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Wed 7/29

4:00 pm-9:35 pm

1 stop6h 35m

Chicago Midway

Wed 8/5

8:45 am-12:00 pm

Nonstop2h 15m

$363
Quickest round-trip

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Wed 10/21

1:10 pm-2:30 pm

Nonstop2h 20m

Chicago Midway

Sat 10/24

4:15 pm-7:15 pm

Nonstop2h 00m

$365

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 6/16

4:00 pm-11:10 pm

2 stops8h 10m

Chicago Midway

Tue 6/23

7:50 am-11:00 am

Nonstop2h 10m

$368

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 6/23

7:35 am-1:09 pm

1 stop6h 34m

Chicago Midway

Tue 6/30

6:58 pm-11:35 pm

1 stop3h 37m

$373

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Wed 10/21

6:05 pm-7:30 pm

Nonstop2h 25m

Chicago Midway

Sat 10/24

2:30 pm-9:45 pm

1 stop6h 15m

$375

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sat 9/5

3:50 pm-5:15 pm

Nonstop2h 25m

Chicago Midway

Sat 9/12

3:25 pm-6:25 pm

Nonstop2h 00m

$377

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Wed 7/29

2:35 pm-10:35 pm

2 stops9h 00m

Chicago Midway

Wed 8/5

7:30 am-4:55 pm

1 stop8h 25m

$378

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Wed 10/21

1:10 pm-2:30 pm

Nonstop2h 20m

Chicago Midway

Sat 10/24

6:30 am-2:55 pm

2 stops7h 25m

$380

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Wed 7/29

5:50 am-12:15 pm

2 stops7h 25m

Chicago Midway

Wed 8/5

12:45 pm-9:10 pm

2 stops7h 25m

$383

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 $232.

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

Can stopping save me money on Hartford to Chicago Midway Airport flights?

You could potentially save up to 3% 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 May 2026, prices for Hartford to Chicago Midway Airport flights are approximately 104% 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

$255

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 $255. The best round-trip flight deal from Hartford to Chicago Midway Airport found on momondo in the last 72 hours is $420.
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
DeltaPriceFrom $176Free CancellationRating
7.9
8,450 reviews
Search Delta flights
SouthwestPriceFrom $177Free CancellationRating
7.9
4,284 reviews
Search Southwest flights

  • Southwest Flights From Hartford to Chicago Midway Airport

    Southwest flies from Hartford to Chicago Midway Airport around 15 times per week, with 4,284 momondo users rating the airline 7.9/10. 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 $402 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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Hammond
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Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
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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