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Midway

$99+ 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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
— MDW
Nov 9 — Nov 161
Sun 11/9
Sun 11/16
1 adult, Economy
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Cheapflights Tip: The best prices from Springfield to Chicago Midway are usually found in August or September, booked 37 days in advance, depart on a Wednesday or Tuesday 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 October 10, 2025.

Round-trip from

$215
(Kiwi.com)

One-way from

$99
(Delta)

Popular in

March

Cheapest in

August

Average price

$342
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. 11% potential increase in price ($48 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 October 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 October 10, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/7. 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.
Sat 11/1511:13 amBDL - MDW
1 stop11h 22mMultiple Airlines
Mon 11/176:06 pmMDW - BDL
2 stops17h 07mMultiple Airlines
Deal found 10/7$215
This Kiwi.com deal was found by Cheapflights users on 10/8. 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 11/36:00 amBDL - MDW
1 stop19h 30mMultiple Airlines
Wed 11/52:06 pmMDW - BDL
1 stop18h 36mMultiple Airlines
Deal found 10/8$217
This Kiwi.com deal was found by Cheapflights users on 10/7. 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.
Wed 10/298:05 amBDL - MDW
1 stop26h 07mMultiple Airlines
Sun 11/210:12 amMDW - BDL
1 stop25h 29mMultiple Airlines
Deal found 10/7$219
This Mytrip deal was found by Cheapflights users on 10/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/147:36 pmBDL - MDW
1 stop26h 46mFrontier
Sun 11/1610:12 amMDW - BDL
1 stop27h 00mFrontier
Deal found 10/7$220
This Southwest deal was found by Cheapflights users on 10/7. 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.
Tue 10/289:10 amBDL - MDW
1 stop7h 45mSouthwest
Thu 10/309:30 amMDW - BDL
Nonstop2h 05mSouthwest
Deal found 10/7$222
This Southwest deal was found by Cheapflights users on 10/8. 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 10/301:20 pmBDL - MDW
Nonstop2h 25mSouthwest
Sat 11/112:50 pmMDW - BDL
Nonstop2h 00mSouthwest
Deal found 10/8$225
This Gotogate deal was found by Cheapflights users on 10/8. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/238:31 pmBDL - MDW
1 stop15h 46mFrontier
Sun 10/2611:57 amMDW - BDL
1 stop21h 49mFrontier
Deal found 10/8$227
This Mytrip deal was found by Cheapflights users on 10/8. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2411:39 amBDL - MDW
1 stop23h 42mFrontier
Sun 10/2611:57 amMDW - BDL
1 stop21h 49mFrontier
Deal found 10/8$228
This Southwest deal was found by Cheapflights users on 10/7. 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.
Tue 11/185:15 amBDL - MDW
Nonstop2h 30mSouthwest
Wed 11/1911:15 amMDW - BDL
2 stops7h 50mSouthwest
Deal found 10/7$230
This Kiwi.com deal was found by Cheapflights users on 10/8. 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.
Sat 11/811:13 amBDL - MDW
1 stop8h 26mMultiple Airlines
Tue 11/111:56 pmMDW - BDL
2 stops33h 01mMultiple Airlines
Deal found 10/8$231
This Southwest deal was found by Cheapflights users on 10/9. 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.
Tue 11/45:15 amBDL - MDW
Nonstop2h 30mSouthwest
Sat 11/85:45 pmMDW - BDL
Nonstop2h 00mSouthwest
Deal found 10/9$235
This Kiwi.com deal was found by Cheapflights users on 10/6. 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 11/412:53 pmBDL - MDW
2 stops12h 02mMultiple Airlines
Fri 11/76:15 amMDW - BDL
1 stop27h 02mMultiple Airlines
Deal found 10/6$236

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 October 10, 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

Tue 11/4

5:15 am-6:45 am

Nonstop2h 30m

Chicago Midway

Wed 11/5

6:15 pm-9:25 pm

Nonstop2h 10m

$225

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 11/4

5:15 am-6:45 am

Nonstop2h 30m

Chicago Midway

Sat 11/8

5:45 pm-8:45 pm

Nonstop2h 00m

$235

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 10/30

9:00 am-2:10 pm

1 stop6h 10m

Chicago Midway

Tue 11/4

1:25 pm-10:10 pm

2 stops7h 45m

$237

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 11/13

5:15 am-6:45 am

Nonstop2h 30m

Chicago Midway

Fri 11/14

7:25 pm-10:25 pm

Nonstop2h 00m

$240

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Wed 12/17

1:01 pm-6:00 pm

1 stop5h 59m

Chicago Midway

Sun 1/18

5:59 pm-11:39 pm

1 stop4h 40m

$245

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 11/4

5:15 am-6:45 am

Nonstop2h 30m

Chicago Midway

Fri 11/7

11:55 am-2:55 pm

Nonstop2h 00m

$250

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 11/6

5:30 am-8:40 am

1 stop4h 10m

Chicago Midway

Sat 11/8

3:00 pm-11:30 pm

1 stop7h 30m

$255

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sun 11/16

7:15 pm-8:45 pm

Nonstop2h 30m

Chicago Midway

Sat 11/22

12:25 pm-7:25 pm

1 stop6h 00m

$270

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Fri 10/31

4:40 pm-6:10 pm

Nonstop2h 30m

Chicago Midway

Sun 11/2

11:55 am-2:55 pm

Nonstop2h 00m

$272

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 11/6

5:30 am-8:40 am

1 stop4h 10m

Chicago Midway

Sun 11/9

6:48 pm-11:22 pm

1 stop3h 34m

$278

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/7

Showing 1-10 of 22 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 October 3, 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 37 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 October 10, 2025.
Read reviews from past customers who have flown Southwest, Delta, 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
4,236 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

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
4,236 reviews
Southwest
8.0
Very good
4,236 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

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
Delta
8.0
Very good
7,971 reviews
Southwest
8.0
Very good
4,236 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

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
8,966 reviews
Southwest
8.0
Very good
4,236 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

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
Frontier
5.8
Fair
3,143 reviews
Southwest
8.0
Very good
4,236 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

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. Southwest provides one of the quickest options available for as low as $225. 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.

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
Porter
Benton Harbor
Chesterton

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