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$79+ 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 9/25. Fares are subject to change and may not be available on all flights or dates of travel.
— MDW
Aug 26 — Sep 21
Tue 8/26
Tue 9/2
1 adult, Economy
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Cheapflights Tip: The best prices from Springfield to Chicago Midway are usually found in September or August, booked 72 days in advance, depart on a Tuesday or Wednesday and return on a Tuesday

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 August 21, 2025.

Round-trip from

$169
(FlightHub)

One-way from

$79
(Southwest)

Popular in

March

Cheapest in

September

Average price

$331
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 ($38 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 August 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 August 21, 2025.

This FlightHub deal was found by Cheapflights users on 8/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/244:20 pmBDL - MDW
1 stop8h 05mFrontier
Sun 10/2611:57 amMDW - BDL
1 stop21h 49mFrontier
Deal found 8/20$169
This Priceline deal was found by Cheapflights users on 8/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/210:30 amBDL - MDW
1 stop6h 28mFrontier
Sun 10/510:13 amMDW - BDL
1 stop8h 39mFrontier
Deal found 8/20$180
This Southwest deal was found by Cheapflights users on 8/21. 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 11/65:15 amBDL - MDW
Nonstop2h 30mSouthwest
Tue 11/119:20 amMDW - BDL
1 stop5h 55mSouthwest
Deal found 8/21$192
This FlightHub deal was found by Cheapflights users on 8/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1711:24 amBDL - MDW
1 stop23h 57mFrontier
Sun 10/199:26 pmMDW - BDL
1 stop16h 55mFrontier
Deal found 8/20$196
This Delta deal was found by Cheapflights users on 8/21. 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.
Thu 9/255:35 amBDL - MDW
1 stop4h 05mDelta
Tue 9/309:35 amMDW - BDL
1 stop5h 38mDelta
Deal found 8/21$197
This FlightHub deal was found by Cheapflights users on 8/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1610:04 amBDL - MDW
1 stop11h 17mFrontier
Sun 10/1912:09 pmMDW - BDL
1 stop21h 37mFrontier
Deal found 8/20$204
This Southwest deal was found by Cheapflights users on 8/20. 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.
Sat 10/255:10 pmBDL - MDW
Nonstop2h 25mSouthwest
Tue 10/2810:00 amMDW - BDL
Nonstop2h 00mSouthwest
Deal found 8/20$205
This Frontier deal was found by Cheapflights users on 8/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1610:04 amBDL - MDW
1 stop11h 17mFrontier
Fri 10/1710:33 amMDW - BDL
1 stop7h 21mFrontier
Deal found 8/20$209
This FlightHub deal was found by Cheapflights users on 8/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/2411:05 amBDL - MDW
1 stop29h 24mFrontier
Sat 8/3010:51 amMDW - BDL
1 stop22h 19mFrontier
Deal found 8/20$215
This Southwest deal was found by Cheapflights users on 8/20. 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.
Thu 9/255:30 amBDL - MDW
Nonstop2h 20mSouthwest
Sun 9/285:35 amMDW - BDL
1 stop5h 25mSouthwest
Deal found 8/20$217
This Frontier deal was found by Cheapflights users on 8/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/410:30 amBDL - MDW
1 stop6h 28mFrontier
Sun 9/710:13 amMDW - BDL
1 stop8h 39mFrontier
Deal found 8/21$218

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 August 21, 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

Fri 10/24

4:20 pm-11:25 pm

1 stop8h 05m

Chicago Midway

Sun 10/26

11:57 am-10:46 am

1 stop21h 49m

$169

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-7:52 pm

1 stop8h 39m

$180

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 11/6

5:15 am-6:45 am

Nonstop2h 30m

Chicago Midway

Tue 11/11

9:20 am-4:15 pm

1 stop5h 55m

$192

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Fri 10/17

11:24 am-10:21 am

1 stop23h 57m

Chicago Midway

Sun 10/19

9:26 pm-3:21 pm

1 stop16h 55m

$196

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sun 10/12

5:30 am-8:40 am

1 stop4h 10m

Chicago Midway

Tue 10/21

6:23 pm-11:14 pm

1 stop3h 51m

$197

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 10/16

5:30 am-8:40 am

1 stop4h 10m

Chicago Midway

Tue 10/21

6:00 am-1:17 pm

1 stop6h 17m

$197

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 9/25

5:35 am-8:40 am

1 stop4h 05m

Chicago Midway

Tue 9/30

9:35 am-4:13 pm

1 stop5h 38m

$197

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 10/16

10:04 am-8:21 pm

1 stop11h 17m

Chicago Midway

Sun 10/19

12:09 pm-10:46 am

1 stop21h 37m

$204

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Wed 11/12

5:15 am-6:45 am

Nonstop2h 30m

Chicago Midway

Thu 11/13

7:25 pm-10:25 pm

Nonstop2h 00m

$205

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sat 10/25

5:10 pm-6:35 pm

Nonstop2h 25m

Chicago Midway

Tue 10/28

6:10 pm-9:15 pm

Nonstop2h 05m

$205

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/20

Showing 1-10 of 21 results
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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

How far ahead should I book a flight from Springfield to Chicago Midway Airport?

Use this chart to determine the optimal time to book a round-trip flight from Springfield to Midway. Price data was last updated on August 8, 2025.

To ensure you get the cheapest price possible for a flight from Springfield to Chicago Midway Airport, you should look to book at least 72 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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 August 21, 2025.
Read reviews from past customers who have flown Southwest 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
4,245 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

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
4,245 reviews
Southwest
8.0
Very good
4,245 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

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 2h 30m. Frontier provides one of the quickest options available for as low as $192. The distance from Springfield to Chicago Midway Airport is about 773 mi. This flight may include one or multiple stops.

  • 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.

  • What is the cheapest month to book a flight from Springfield to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Springfield to Chicago Midway Airport (average of $160). Flying from Springfield to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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