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Cheap flights from Hartford to Chicago from $141

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 10/26. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Hartford to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
6:20 pm - 7:40 pmBDL  Hartford Bradley Intl-MDW Chicago Midway
2h 20mnonstop
Southwest Logo
6:30 am - 12:10 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
4h 40m1 stop Baltimore/Washington
$277Southwest
Thu, Sep 10 - Tue, Sep 15
Southwest Logo
12:45 pm - 8:05 pmBDL  Hartford Bradley Intl-MDW Chicago Midway
8h 20m2 stops Baltimore/Washington Charlotte Douglas
Southwest Logo
1:15 pm - 7:40 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
5h 25m2 stops Richmond Byrd Intl Baltimore/Washington
$279Southwest
Mon, Nov 2 - Wed, Nov 4
Southwest Logo
12:30 pm - 7:05 pmBDL  Hartford Bradley Intl-MDW Chicago Midway
7h 35m2 stops Baltimore/Washington Nashville Intl
Southwest Logo
1:15 pm - 10:05 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
7h 50m2 stops Richmond Byrd Intl Baltimore/Washington
$279Southwest
Mon, Nov 16 - Wed, Nov 18
Southwest Logo
6:00 am - 12:55 pmBDL  Hartford Bradley Intl-MDW Chicago Midway
7h 55m2 stops Baltimore/Washington Atlanta Hartsfield-Jackson
Southwest Logo
7:45 am - 5:35 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
8h 50m2 stops Norfolk Baltimore/Washington
$279Southwest
Thu, Jan 28 - Sat, Jan 30
Frontier Logo
5:31 pm - 7:02 pmBDL  Hartford Bradley Intl-MDW Chicago Midway
26h 31m1 stop Orlando
Frontier Logo
8:07 pm - 4:36 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
19h 29m1 stop Orlando
$281Frontier
Thu, Dec 3 - Sun, Dec 6
Delta Logo
5:55 pm - 10:44 pmBDL  Hartford Bradley Intl-MDW Chicago Midway
5h 49m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:10 pm - 11:59 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
5h 49m1 stop Atlanta Hartsfield-Jackson
$282Delta
Fri, Sep 11 - Mon, Sep 14
Delta Logo
5:30 am - 9:07 amBDL  Hartford Bradley Intl-MDW Chicago Midway
4h 37m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:29 am - 4:28 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
5h 59m1 stop Detroit Metropolitan Wayne County
$286Delta
Tue, Sep 22 - Wed, Sep 30
Delta Logo
7:00 am - 1:20 pmBDL  Hartford Bradley Intl-MDW Chicago Midway
7h 20m1 stop Minneapolis St Paul
Delta Logo
9:29 am - 4:28 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
5h 59m1 stop Detroit Metropolitan Wayne County
$286Delta
Sat, Sep 26 - Wed, Sep 30
Frontier Logo
5:31 pm - 7:02 pmBDL  Hartford Bradley Intl-MDW Chicago Midway
26h 31m1 stop Orlando
Frontier Logo
8:07 pm - 4:36 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
19h 29m1 stop Orlando
$320Frontier
Thu, Dec 10 - Sun, Dec 13
Frontier Logo
5:31 pm - 7:02 pmBDL  Hartford Bradley Intl-MDW Chicago Midway
26h 31m1 stop Orlando
Frontier Logo
8:07 pm - 4:36 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
19h 29m1 stop Orlando
$352Frontier
Thu, Dec 17 - Sun, Dec 20

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Southwest flights from Hartford to Chicago Midway Airport

Our best Southwest deals on Hartford to Chicago Midway Airport flight tickets
Southwest
Sep 10
BDL6:20 pmHartford Bradley Intl
2h 20m
MDW7:40 pmChicago Midway
Sep 15
MDW6:30 amChicago Midway
4h 40m
1 stop
BDL12:10 pmHartford Bradley Intl
$277
Southwest
Oct 5
BDL5:50 amHartford Bradley Intl
10h 05m
2 stops
MDW2:55 pmChicago Midway
Oct 6
MDW7:55 amChicago Midway
6h 45m
2 stops
BDL3:40 pmHartford Bradley Intl
$279
Southwest
Aug 31
BDL6:20 pmHartford Bradley Intl
2h 20m
MDW7:40 pmChicago Midway
Sep 5
MDW7:50 amChicago Midway
2h 15m
BDL11:05 amHartford Bradley Intl
$282

Delta flights from Hartford to Chicago Midway Airport

Our best Delta deals on Hartford to Chicago Midway Airport flight tickets
Delta
Sep 3
BDL5:30 amHartford Bradley Intl
4h 47m
1 stop
MDW9:17 amChicago Midway
Sep 6
MDW5:45 pmChicago Midway
5h 06m
1 stop
BDL11:51 pmHartford Bradley Intl
$289
Delta
Oct 23
BDL5:23 amHartford Bradley Intl
4h 54m
1 stop
MDW9:17 amChicago Midway
Oct 26
MDW5:15 pmChicago Midway
5h 44m
1 stop
BDL11:59 pmHartford Bradley Intl
$303
Delta
Sep 22
BDL5:30 amHartford Bradley Intl
4h 37m
1 stop
MDW9:07 amChicago Midway
Oct 1
MDW6:05 amChicago Midway
5h 50m
1 stop
BDL12:55 pmHartford Bradley Intl
$305

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 August 17, 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
Quickest round-trip

HartfordChicago

BDL Hartford Bradley Intl - MDW Chicago Midway

BDLMDW

Hartford Bradley Intl

Thu 9/10

6:20 pm-7:40 pm

Nonstop2h 20m

Chicago Midway

Tue 9/15

6:30 am-12:10 pm

1 stop4h 40m

$277

HartfordChicago

BDL Hartford Bradley Intl - MDW Chicago Midway

BDLMDW

Hartford Bradley Intl

Mon 11/2

12:45 pm-8:05 pm

2 stops8h 20m

Chicago Midway

Wed 11/4

1:15 pm-7:40 pm

2 stops5h 25m

$279

HartfordChicago

BDL Hartford Bradley Intl - MDW Chicago Midway

BDLMDW

Hartford Bradley Intl

Mon 11/16

12:30 pm-7:05 pm

2 stops7h 35m

Chicago Midway

Wed 11/18

1:15 pm-10:05 pm

2 stops7h 50m

$279

HartfordChicago

BDL Hartford Bradley Intl - MDW Chicago Midway

BDLMDW

Hartford Bradley Intl

Thu 1/28

6:00 am-12:55 pm

2 stops7h 55m

Chicago Midway

Sat 1/30

7:45 am-5:35 pm

2 stops8h 50m

$279

HartfordChicago

BDL Hartford Bradley Intl - MDW Chicago Midway

BDLMDW

Hartford Bradley Intl

Thu 12/3

5:31 pm-7:02 pm

1 stop26h 31m

Chicago Midway

Sun 12/6

8:07 pm-4:36 pm

1 stop19h 29m

$281

HartfordChicago

BDL Hartford Bradley Intl - MDW Chicago Midway

BDLMDW

Hartford Bradley Intl

Fri 9/11

5:55 pm-10:44 pm

1 stop5h 49m

Chicago Midway

Mon 9/14

5:10 pm-11:59 pm

1 stop5h 49m

$282

HartfordChicago

BDL Hartford Bradley Intl - MDW Chicago Midway

BDLMDW

Hartford Bradley Intl

Tue 9/22

5:30 am-9:07 am

1 stop4h 37m

Chicago Midway

Wed 9/30

9:29 am-4:28 pm

1 stop5h 59m

$286

HartfordChicago

BDL Hartford Bradley Intl - MDW Chicago Midway

BDLMDW

Hartford Bradley Intl

Sat 9/26

7:00 am-1:20 pm

1 stop7h 20m

Chicago Midway

Wed 9/30

9:29 am-4:28 pm

1 stop5h 59m

$286

HartfordChicago

BDL Hartford Bradley Intl - MDW Chicago Midway

BDLMDW

Hartford Bradley Intl

Thu 12/10

5:31 pm-7:02 pm

1 stop26h 31m

Chicago Midway

Sun 12/13

8:07 pm-4:36 pm

1 stop19h 29m

$320

HartfordChicago

BDL Hartford Bradley Intl - MDW Chicago Midway

BDLMDW

Hartford Bradley Intl

Thu 12/17

5:31 pm-7:02 pm

1 stop26h 31m

Chicago Midway

Sun 12/20

8:07 pm-4:36 pm

1 stop19h 29m

$352

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
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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 $347 to $449.
The lowest price recently found on this route was $277.

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 September is also very affordable. Most momondo users find prices during this month for around $347.

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.

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

No. A direct flight is the cheapest option for a flight between Hartford to Chicago Midway Airport.

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

As of August 2026, prices for Hartford to Chicago Midway Airport flights are approximately 30% 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

$225

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 $225. The best round-trip flight deal from Hartford to Chicago Midway Airport found on momondo in the last 72 hours is $388.
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

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 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
7.8
8,504 reviews
Search Delta flights
SouthwestPriceFrom $293Free CancellationRating
8.0
4,217 reviews
Search Southwest flights

  • Southwest Flights From Hartford to Chicago Midway Airport

    Southwest flies from Hartford to Chicago Midway Airport around 14 times per week, with 4,218 momondo users rating the airline 8.0/10. 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 $427 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
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Porter
Crown Point
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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