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Cheap flights from Hartford to Chicago from $85

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 10/9. 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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Cheap round-trip flights

Frontier Logo
4:20 pm - 11:46 pmBDL-MDW
8h 26m1 stop
Frontier Logo
10:33 am - 6:54 pmMDW-BDL
7h 21m1 stop
$176Frontier
Find Deal
Fri, Oct 17 - Mon, Oct 20
Frontier Logo
10:30 am - 3:58 pmBDL-MDW
6h 28m1 stop
Frontier Logo
10:13 am - 7:42 pmMDW-BDL
8h 29m1 stop
$178Frontier
Find Deal
Thu, Sep 25 - Sun, Sep 28
Frontier Logo
10:30 am - 3:58 pmBDL-MDW
6h 28m1 stop
Frontier Logo
9:48 am - 7:57 pmMDW-BDL
9h 09m1 stop
$185Frontier
Find Deal
Thu, Sep 18 - Fri, Sep 19
Frontier Logo
4:20 pm - 11:46 pmBDL-MDW
8h 26m1 stop
Frontier Logo
10:33 am - 6:54 pmMDW-BDL
7h 21m1 stop
$188Frontier
Find Deal
Fri, Oct 17 - Mon, Oct 20
Delta Logo
5:25 am - 8:54 amBDL-MDW
4h 29m1 stop
Delta Logo
6:40 pm - 11:35 pmMDW-BDL
3h 55m1 stop
$197Delta
Find Deal
Tue, Dec 9 - Sun, Dec 14
Southwest Logo
8:55 am - 1:45 pmBDL-MDW
5h 50m1 stop
Southwest Logo
7:25 pm - 10:25 pmMDW-BDL
2h 00mnonstop
$212Southwest
Find Deal
Tue, Dec 9 - Sun, Dec 14
Logo
10:30 am - 3:58 pmBDL-MDW
6h 28m1 stop
Logo
10:13 am - 5:56 pmMDW-BDL
30h 43m2 stops
$221
Find Deal
Thu, Oct 2 - Sun, Oct 5
Logo
8:52 pm - 9:51 amBDL-MDW
13h 59m1 stop
Logo
8:15 am - 9:20 pmMDW-BDL
12h 05m2 stops
$222
Find Deal
Fri, Sep 26 - Mon, Sep 29
Southwest Logo
5:10 pm - 6:35 pmBDL-MDW
2h 25mnonstop
Southwest Logo
10:00 am - 1:00 pmMDW-BDL
2h 00mnonstop
$225Southwest
Find Deal
Sat, Oct 18 - Tue, Oct 21
Delta Logo
5:30 am - 8:52 amBDL-MDW
4h 22m1 stop
Delta Logo
9:32 am - 4:27 pmMDW-BDL
5h 55m1 stop
$250Delta
Find Deal
Thu, Nov 13 - Sat, Nov 15

Frontier flights from Hartford to Chicago Midway Airport

Our best Frontier deals on Hartford to Chicago Midway Airport flight tickets
Frontier
Oct 17
BDL4:20 pmHartford Bradley Intl
8h 26m
1 stop
MDW11:46 pmChicago Midway
Oct 20
MDW10:33 amChicago Midway
7h 21m
1 stop
BDL6:54 pmHartford Bradley Intl
$176
Find similar
Frontier
Sep 25
BDL10:30 amHartford Bradley Intl
6h 28m
1 stop
MDW3:58 pmChicago Midway
Sep 28
MDW10:13 amChicago Midway
8h 29m
1 stop
BDL7:42 pmHartford Bradley Intl
$178
Find similar
Frontier
Sep 18
BDL10:30 amHartford Bradley Intl
6h 28m
1 stop
MDW3:58 pmChicago Midway
Sep 19
MDW9:48 amChicago Midway
9h 09m
1 stop
BDL7:57 pmHartford Bradley Intl
$185
Find similar

Delta flights from Hartford to Chicago Midway Airport

Our best Delta deals on Hartford to Chicago Midway Airport flight tickets
Delta
Dec 9
BDL5:25 amHartford Bradley Intl
4h 29m
1 stop
MDW8:54 amChicago Midway
Dec 14
MDW6:40 pmChicago Midway
3h 55m
1 stop
BDL11:35 pmHartford Bradley Intl
$197
Find similar
Delta
Nov 13
BDL5:30 amHartford Bradley Intl
4h 22m
1 stop
MDW8:52 amChicago Midway
Nov 15
MDW9:32 amChicago Midway
5h 55m
1 stop
BDL4:27 pmHartford Bradley Intl
$250
Find similar
Delta
Oct 16
BDL5:30 amHartford Bradley Intl
4h 10m
1 stop
MDW8:40 amChicago Midway
Oct 18
MDW10:35 amChicago Midway
7h 00m
1 stop
BDL6:35 pmHartford Bradley Intl
$255
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 September 8, 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

Fri 10/17

4:20 pm-11:46 pm

1 stop8h 26m

Chicago Midway

Mon 10/20

10:33 am-6:54 pm

1 stop7h 21m

$176

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 9/25

10:30 am-3:58 pm

1 stop6h 28m

Chicago Midway

Sun 9/28

10:13 am-7:42 pm

1 stop8h 29m

$178

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 9/18

10:30 am-3:58 pm

1 stop6h 28m

Chicago Midway

Fri 9/19

9:48 am-7:57 pm

1 stop9h 09m

$185

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Fri 10/17

4:20 pm-11:46 pm

1 stop8h 26m

Chicago Midway

Mon 10/20

10:33 am-6:54 pm

1 stop7h 21m

$188

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 12/9

5:25 am-8:54 am

1 stop4h 29m

Chicago Midway

Sun 12/14

6:40 pm-11:35 pm

1 stop3h 55m

$197

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 12/9

8:55 am-1:45 pm

1 stop5h 50m

Chicago Midway

Sun 12/14

7:25 pm-10:25 pm

Nonstop2h 00m

$212

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 10/2

10:30 am-3:58 pm

1 stop6h 28m

Chicago Midway

Sun 10/5

10:13 am-5:56 pm

2 stops30h 43m

$221

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Fri 9/26

8:52 pm-9:51 am

1 stop13h 59m

Chicago Midway

Mon 9/29

8:15 am-9:20 pm

2 stops12h 05m

$222

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sat 10/18

5:10 pm-6:35 pm

Nonstop2h 25m

Chicago Midway

Tue 10/21

10:00 am-1:00 pm

Nonstop2h 00m

$225

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 11/13

5:30 am-8:52 am

1 stop4h 22m

Chicago Midway

Sat 11/15

9:32 am-4:27 pm

1 stop5h 55m

$250

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 September is, on average, the cheapest month to fly to Chicago Midway Airport from Hartford, with most prices found around $313. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Hartford during the month August is also very affordable. Most momondo users find prices during this month for around $331.

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

How far in advance should I book a flight to Chicago Midway Airport?

You are more likely to see cheaper flights to Chicago Midway Airport from Hartford when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $375 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Hartford for as low as $265 on momondo.

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?

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?

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

$202

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 $202. The best round-trip flight deal from Hartford to Chicago Midway Airport found on momondo in the last 72 hours is $305.
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
FrontierPriceFrom $108Free CancellationRating
5.8
3,187 reviews
Search Frontier flights
SouthwestPriceFrom $177Free CancellationRating
8.0
4,244 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 4,244 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
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
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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