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$112+ Cheap flights from Springfield, MA, MA to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/12. Fares are subject to change and may not be available on all flights or dates of travel.
— MDW
Dec 20 — Dec 271
Sat 12/20
Sat 12/27
1 adult, Economy
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Cheap flight deals from Springfield to Midway

Keep the following information in mind while searching for Springfield to Midway flight deals. Data was last updated November 20, 2025.

Round-trip from

$241
(Kiwi.com)

One-way from

$112
(Kiwi.com)

Popular in

March

Cheapest in

August

Average price

$399
From Springfield to Chicago Midway
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One-way flight from Springfield to Chicago Midway
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Highest demand for flights based on searches. 9% potential increase in price ($40 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find flight deals from Springfield to Midway

Cheapest flights from Springfield to Midway
Explore the most affordable flight options available from Springfield to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 20, 2025.

This Delta deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/176:00 amBDL - MDW
1 stop6h 55mDelta
Sun 1/186:14 pmMDW - BDL
1 stop4h 26mDelta
Deal found 11/20$245
This Kiwi.com deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/51:19 pmBDL - MDW
1 stop10h 20mMultiple Airlines
Tue 12/97:44 amMDW - BDL
2 stops30h 05mMultiple Airlines
Deal found 11/20$246
This Kiwi.com deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1211:59 amBDL - MDW
1 stop11h 13mMultiple Airlines
Sun 12/142:59 pmMDW - BDL
2 stops25h 27mMultiple Airlines
Deal found 11/19$247
This Southwest deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/116:00 amBDL - MDW
2 stops8h 00mSouthwest
Sat 12/135:45 pmMDW - BDL
Nonstop2h 00mSouthwest
Deal found 11/19$250
This Delta deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/305:30 amBDL - MDW
1 stop4h 19mDelta
Tue 1/66:45 amMDW - BDL
1 stop5h 48mDelta
Deal found 11/19$266
This Kiwi.com deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/511:59 amBDL - MDW
1 stop8h 43mMultiple Airlines
Sun 12/76:37 pmMDW - BDL
2 stops28h 14mMultiple Airlines
Deal found 11/19$273
This Booking.com deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/511:59 amBDL - MDW
1 stop11h 13mFrontier
Sun 12/76:37 pmMDW - BDL
1 stop17h 35mFrontier
Deal found 11/19$282
This Kiwi.com deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/82:07 pmBDL - MDW
1 stop8h 51mMultiple Airlines
Wed 12/102:49 pmMDW - BDL
2 stops31h 45mMultiple Airlines
Deal found 11/19$292
This Kiwi.com deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3012:05 pmBDL - MDW
1 stop26h 16mMultiple Airlines
Mon 1/53:10 pmMDW - BDL
2 stops26h 56mMultiple Airlines
Deal found 11/19$298
This Southwest deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/245:40 pmBDL - MDW
Nonstop2h 30mSouthwest
Wed 1/141:25 pmMDW - BDL
Nonstop1h 55mSouthwest
Deal found 11/20$303

Cheapflights Fare Finder

 
Customize your flight search to find flights from Springfield to Midway 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, Cheapflights users made 2,558,603 searches. Data last updated November 20, 2025.
Use the filters below to find and compare flights from Springfield to Chicago Midway Airport that are best for you.

Fly from

Springfield

Fly to

Midway

Route

Depart

Return

Price

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sat 1/24

12:30 pm-6:40 pm

2 stops7h 10m

Chicago Midway

Tue 1/27

6:00 am-5:15 pm

2 stops10h 15m

$255

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sat 1/17

12:30 pm-4:55 pm

1 stop5h 25m

Chicago Midway

Mon 1/19

6:15 pm-9:15 pm

Nonstop2h 00m

$269

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Fri 2/13

7:10 pm-8:45 pm

Nonstop2h 35m

Chicago Midway

Tue 2/17

10:45 am-5:20 pm

1 stop5h 35m

$278

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 1/8

9:25 am-4:40 pm

2 stops8h 15m

Chicago Midway

Sat 1/10

8:40 am-2:30 pm

1 stop4h 50m

$284

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Fri 2/20

2:15 pm-7:50 pm

2 stops6h 35m

Chicago Midway

Mon 2/23

3:05 pm-10:45 pm

2 stops6h 40m

$289

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Wed 12/24

5:40 pm-7:10 pm

Nonstop2h 30m

Chicago Midway

Wed 1/14

1:25 pm-4:20 pm

Nonstop1h 55m

$303

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Fri 12/12

7:15 pm-8:45 pm

Nonstop2h 30m

Chicago Midway

Sun 12/14

9:35 am-5:05 pm

1 stop6h 30m

$323

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Wed 12/24

5:30 am-8:49 am

1 stop4h 19m

Chicago Midway

Wed 1/14

6:45 am-1:33 pm

1 stop5h 48m

$328

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Wed 12/17

5:23 am-8:54 am

1 stop4h 31m

Chicago Midway

Thu 12/18

6:00 am-1:17 pm

1 stop6h 17m

$347

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 12/30

2:00 pm-7:35 pm

2 stops6h 35m

Chicago Midway

Tue 1/6

1:20 pm-10:20 pm

1 stop8h 00m

$381

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

Showing 1-10 of 20 results
1
2

Best time to book a flight from Springfield to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Springfield with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Springfield to Chicago Midway Airport
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated November 20, 2025.
Read reviews from past customers who have flown Southwest and United Airlines from Springfield to Chicago Midway Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,249 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,249 reviews
Southwest
8.0
Very good
4,249 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
9,029 reviews
Southwest
8.0
Very good
4,249 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Springfield to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Springfield to Chicago Midway Airport?

    A quick flight from Springfield to Chicago Midway Airport can take about 7h 10m. Southwest provides one of the quickest options available for as low as $255. The distance from Springfield to Chicago Midway Airport is about 773 mi.

  • Can I find deals for flights from Springfield to Midway that include hotel bookings?

    Yes. In addition to deals on Springfield to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Springfield to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Springfield to Midway.

  • Can I find deals for business class flights from Springfield to Midway?

    Yes. Cheapflights offers flight deals from Springfield to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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