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Cheap flights from Chicago Midway Airport to Springfield from $145

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Springfield departing on 9/2. 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

Find the cheapest flights from Chicago Midway Airport to Springfield

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
7:30 am - 1:00 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
4h 30m1 stop Baltimore/Washington
Southwest Logo
6:20 pm - 7:40 pmBDL  Hartford Bradley Intl-MDW Chicago Midway
2h 20mnonstop
$291Southwest
Thu, Sep 10 - Mon, Sep 14
Southwest Logo
6:45 pm - 9:50 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
2h 05mnonstop
Southwest Logo
7:05 pm - 8:25 pmBDL  Hartford Bradley Intl-MDW Chicago Midway
2h 20mnonstop
$292Southwest
Fri, Oct 2 - Mon, Oct 5
Southwest Logo
7:50 am - 11:00 amMDW  Chicago Midway-BDL Hartford Bradley Intl
2h 10mnonstop
Southwest Logo
7:05 pm - 8:25 pmBDL  Hartford Bradley Intl-MDW Chicago Midway
2h 20mnonstop
$292Southwest
Fri, Oct 2 - Mon, Oct 5
Delta Logo
6:44 pm - 11:32 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
3h 48m1 stop Detroit Metropolitan Wayne County
Delta Logo
7:00 am - 11:50 amBDL  Hartford Bradley Intl-MDW Chicago Midway
5h 50m1 stop Atlanta Hartsfield-Jackson
$296Delta
Fri, Oct 16 - Tue, Oct 20
Delta Logo
6:42 pm - 11:51 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
4h 09m1 stop Detroit Metropolitan Wayne County
Delta Logo
5:30 am - 9:07 amBDL  Hartford Bradley Intl-MDW Chicago Midway
4h 37m1 stop Detroit Metropolitan Wayne County
$296Delta
Fri, Sep 4 - Tue, Sep 8
Southwest Logo
5:30 am - 1:00 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
6h 30m2 stops Atlanta Hartsfield-Jackson Baltimore/Washington
Southwest Logo
6:20 pm - 7:40 pmBDL  Hartford Bradley Intl-MDW Chicago Midway
2h 20mnonstop
$296Southwest
Thu, Sep 10 - Mon, Sep 14
Delta Logo
6:44 pm - 11:32 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
3h 48m1 stop Detroit Metropolitan Wayne County
Delta Logo
7:00 am - 11:50 amBDL  Hartford Bradley Intl-MDW Chicago Midway
5h 50m1 stop Atlanta Hartsfield-Jackson
$296Delta
Fri, Oct 16 - Wed, Oct 21
Southwest Logo
7:10 pm - 10:20 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
2h 10mnonstop
Southwest Logo
6:20 pm - 7:40 pmBDL  Hartford Bradley Intl-MDW Chicago Midway
2h 20mnonstop
$299Southwest
Fri, Sep 25 - Mon, Sep 28
Southwest Logo
6:25 pm - 11:50 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
4h 25m1 stop Baltimore/Washington
Southwest Logo
7:05 pm - 8:25 pmBDL  Hartford Bradley Intl-MDW Chicago Midway
2h 20mnonstop
$302Southwest
Fri, Oct 2 - Mon, Oct 5
Southwest Logo
2:45 pm - 11:50 pmMDW  Chicago Midway-BDL Hartford Bradley Intl
8h 05m2 stops Lambert-St Louis Baltimore/Washington
Southwest Logo
7:05 pm - 8:25 pmBDL  Hartford Bradley Intl-MDW Chicago Midway
2h 20mnonstop
$307Southwest
Fri, Oct 2 - Mon, Oct 5

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Southwest flights from Chicago Midway Airport to Hartford

Our best Southwest deals on Chicago Midway Airport to Hartford flight tickets
Southwest
Sep 10
MDW7:30 amChicago Midway
4h 30m
1 stop
BDL1:00 pmHartford Bradley Intl
Sep 14
BDL6:20 pmHartford Bradley Intl
2h 20m
MDW7:40 pmChicago Midway
$291
Southwest
Oct 2
MDW7:50 amChicago Midway
2h 10m
BDL11:00 amHartford Bradley Intl
Oct 5
BDL7:05 pmHartford Bradley Intl
2h 20m
MDW8:25 pmChicago Midway
$292
Southwest
Sep 25
MDW7:10 pmChicago Midway
2h 10m
BDL10:20 pmHartford Bradley Intl
Sep 28
BDL6:20 pmHartford Bradley Intl
2h 20m
MDW7:40 pmChicago Midway
$299

Delta flights from Chicago Midway Airport to Hartford

Our best Delta deals on Chicago Midway Airport to Hartford flight tickets
Delta
Oct 16
MDW6:44 pmChicago Midway
3h 48m
1 stop
BDL11:32 pmHartford Bradley Intl
Oct 21
BDL7:00 amHartford Bradley Intl
5h 50m
1 stop
MDW11:50 amChicago Midway
$296
Delta
Sep 4
MDW6:42 pmChicago Midway
4h 09m
1 stop
BDL11:51 pmHartford Bradley Intl
Sep 6
BDL1:09 pmHartford Bradley Intl
4h 50m
1 stop
MDW4:59 pmChicago Midway
$318
Delta
Oct 29
MDW5:31 pmChicago Midway
5h 18m
1 stop
BDL11:49 pmHartford Bradley Intl
Nov 2
BDL5:23 amHartford Bradley Intl
4h 54m
1 stop
MDW9:17 amChicago Midway
$337

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Hartford 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 Chicago Midway Airport to Hartford that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoHartford

MDW Chicago Midway - BDL Hartford Bradley Intl

MDWBDL

Chicago Midway

Thu 9/10

7:30 am-1:00 pm

1 stop4h 30m

Hartford Bradley Intl

Mon 9/14

6:20 pm-7:40 pm

Nonstop2h 20m

$291
Quickest round-trip

ChicagoHartford

MDW Chicago Midway - BDL Hartford Bradley Intl

MDWBDL

Chicago Midway

Fri 10/2

6:45 pm-9:50 pm

Nonstop2h 05m

Hartford Bradley Intl

Mon 10/5

7:05 pm-8:25 pm

Nonstop2h 20m

$292

ChicagoHartford

MDW Chicago Midway - BDL Hartford Bradley Intl

MDWBDL

Chicago Midway

Fri 10/2

7:50 am-11:00 am

Nonstop2h 10m

Hartford Bradley Intl

Mon 10/5

7:05 pm-8:25 pm

Nonstop2h 20m

$292

ChicagoHartford

MDW Chicago Midway - BDL Hartford Bradley Intl

MDWBDL

Chicago Midway

Fri 10/16

6:44 pm-11:32 pm

1 stop3h 48m

Hartford Bradley Intl

Tue 10/20

7:00 am-11:50 am

1 stop5h 50m

$296

ChicagoHartford

MDW Chicago Midway - BDL Hartford Bradley Intl

MDWBDL

Chicago Midway

Fri 9/4

6:42 pm-11:51 pm

1 stop4h 09m

Hartford Bradley Intl

Tue 9/8

5:30 am-9:07 am

1 stop4h 37m

$296

ChicagoHartford

MDW Chicago Midway - BDL Hartford Bradley Intl

MDWBDL

Chicago Midway

Thu 9/10

5:30 am-1:00 pm

2 stops6h 30m

Hartford Bradley Intl

Mon 9/14

6:20 pm-7:40 pm

Nonstop2h 20m

$296

ChicagoHartford

MDW Chicago Midway - BDL Hartford Bradley Intl

MDWBDL

Chicago Midway

Fri 10/16

6:44 pm-11:32 pm

1 stop3h 48m

Hartford Bradley Intl

Wed 10/21

7:00 am-11:50 am

1 stop5h 50m

$296

ChicagoHartford

MDW Chicago Midway - BDL Hartford Bradley Intl

MDWBDL

Chicago Midway

Fri 9/25

7:10 pm-10:20 pm

Nonstop2h 10m

Hartford Bradley Intl

Mon 9/28

6:20 pm-7:40 pm

Nonstop2h 20m

$299

ChicagoHartford

MDW Chicago Midway - BDL Hartford Bradley Intl

MDWBDL

Chicago Midway

Fri 10/2

6:25 pm-11:50 pm

1 stop4h 25m

Hartford Bradley Intl

Mon 10/5

7:05 pm-8:25 pm

Nonstop2h 20m

$302

ChicagoHartford

MDW Chicago Midway - BDL Hartford Bradley Intl

MDWBDL

Chicago Midway

Fri 10/2

2:45 pm-11:50 pm

2 stops8h 05m

Hartford Bradley Intl

Mon 10/5

7:05 pm-8:25 pm

Nonstop2h 20m

$307

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 Springfield from

How to get the cheapest flight ticket from Chicago Midway Airport to Hartford

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 Hartford?

The month of February is, on average, the cheapest month to fly to Hartford from Chicago Midway Airport, with most prices found around $0. The month of October is another great option to travel to Hartford, with average flight prices from Chicago Midway Airport averaging around $300.

What is the cheapest day to depart on your flight to Hartford?

The cheapest day to depart from Chicago Midway Airport to Hartford is on a Thursday when prices can be found for as low as $358. Be sure to avoid booking your departure on a Monday as prices are generally higher than usual. According to our data, the average ticket price to Hartford on Monday is $553.

What is the cheapest time of day to depart on your flight to Hartford?

According to our data, the cheapest time of day to fly to Hartford is in the morning. momondo users have found flights departing from Chicago Midway Airport to Hartford in the morning for as low as $408. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets in the afternoon because they tend to be around $523. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Chicago Midway to Hartford Bradley Intl flight route?

Fly from Chicago Midway to Hartford Bradley Intl for the best Chicago Midway - Hartford Bradley Intl flight prices

What cabin class options are available on Chicago Midway Airport to Hartford flights?

There is only 1 cabin class available to choose from on Chicago Midway Airport to Hartford 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 Chicago Midway Airport to Hartford flights?

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

When to book flights from Chicago Midway Airport to Hartford

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Hartford according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Hartford (MDW to BDL) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Hartford

Best Price Found

$238

Fastest flight time

2h 00m

Direct flights

Every day

Airports in Hartford

1 airport
The best one-way flight to Hartford from Chicago Midway Airport in the past 72 hours is $238. The best round-trip flight deal from Chicago Midway Airport to Hartford found on momondo in the last 72 hours is $315.
The fastest flight from Chicago Midway Airport to Hartford takes 2h 00m
Direct flights go from Chicago Midway Airport to Hartford every day.
There is 1 airport in Hartford. From Chicago Midway Airport there are direct flights to Hartford Bradley Intl (BDL).
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Hartford

  • How far is Chicago Midway to Hartford Bradley Intl by plane?

    The distance between Chicago Midway and Hartford Bradley Intl is about 774.9 mi. By plane, this route typically takes 2h 00m.

  • When did momondo last update prices for flights from Chicago Midway Airport to Hartford Bradley Intl Airport?

    Prices for flights from Chicago Midway Airport to Hartford Bradley Intl Airport were last updated today.

  • How many operators does momondo search for flights from Chicago Midway Airport to Hartford Bradley Intl Airport?

  • How old do you have to be to fly from Chicago Midway Airport to Hartford Bradley Intl Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Hartford Bradley Intl Airport.

  • What documentation or ID do you need to fly to Hartford Bradley Intl Airport?

    The required travel and health documents for your Hartford Bradley Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Hartford Bradley Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Chicago Midway Airport to Hartford?

  • What is the most popular airline from Chicago Midway Airport to Hartford?

Best airlines flying from Chicago Midway Airport to Hartford

Compare and see reviews for airlines that fly from Chicago Midway Airport to Hartford with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $248Free CancellationRating
8.0
4,218 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to Hartford

    The lowest priced Southwest flight from Chicago Midway Airport to Hartford from the last 72 hours was $248. Generally, Southwest has 14 flights on this route every week with an average price of $403. Southwest is rated 8.0/10 by our users.

Traveling to a place near Springfield?

Book flights to Springfield if you plan to visit one of these locations
Uncasville
Springfield
Norwich
West Springfield
Windsor Locks
New Britain
Meriden
East Hartford
Brattleboro
Southington
Chicopee
Enfield
Newington
Windsor
Holyoke
West Hartford
Middletown
Northampton
Stockbridge
Lenox

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Hartford?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Hartford. momondo saves you time and could save you money on your trip.

Can I find flights from Chicago to Hartford with flexible booking policies on momondo?

Flights from Chicago to Hartford with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Chicago to Hartford?

momondo helps you find the best flight between Chicago and Hartford 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 Chicago to Hartford right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Chicago to Hartford 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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