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Midway

$328+ Cheap flights from Montgomery, AL (MGM) to Midway (MDW)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/8. Fares are subject to change and may not be available on all flights or dates of travel.
MGM — MDW
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheap flight deals from Montgomery to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Montgomery (MGM) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 14, 2025.

Round-trip from

$328
(Delta)

Popular in

August

Cheapest in

April

Average price

$868
From Montgomery Dannelly Field to Chicago Midway
Search Deals
Highest demand for flights based on searches. 20% potential increase in price ($136 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($33 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 Montgomery to Midway

Cheapest flights from Montgomery to Midway
Explore the most affordable flight options available from Montgomery to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 2025.

This Delta deal was found by Cheapflights users on 8/14. 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.
Sat 11/89:28 amMGM - MDW
1 stop5h 58mDelta
Tue 11/116:00 amMDW - MGM
1 stop5h 49mDelta
Deal found 8/14$328
This Delta deal was found by Cheapflights users on 8/13. 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.
Sat 8/306:25 pmMGM - MDW
2 stops14h 10mDelta
Thu 9/46:00 amMDW - MGM
1 stop4h 24mDelta
Deal found 8/13$361
This Delta deal was found by Cheapflights users on 8/13. 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.
Sat 8/302:00 pmMGM - MDW
1 stop7h 12mDelta
Sun 8/316:00 amMDW - MGM
1 stop4h 29mDelta
Deal found 8/13$422
This Delta deal was found by Cheapflights users on 8/12. 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.
Fri 9/2612:29 pmMGM - MDW
1 stop5h 22mDelta
Sun 9/286:00 amMDW - MGM
1 stop5h 49mDelta
Deal found 8/12$507
This KAYAK deal was found by Cheapflights users on 8/12. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/132:00 pmMGM - MDW
1 stop3h 47mDelta
Sat 8/166:04 amMDW - MGM
1 stop4h 20mDelta
Deal found 8/12$528
This Delta deal was found by Cheapflights users on 8/14. 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.
Sun 10/266:05 amMGM - MDW
1 stop3h 35mDelta
Thu 10/306:00 amMDW - MGM
1 stop6h 06mDelta
Deal found 8/14$546
This Delta deal was found by Cheapflights users on 8/14. 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 9/176:00 amMGM - MDW
1 stop5h 48mDelta
Fri 9/196:00 amMDW - MGM
1 stop5h 49mDelta
Deal found 8/14$597
This Delta deal was found by Cheapflights users on 8/12. 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.
Sun 8/246:00 amMGM - MDW
1 stop5h 48mDelta
Tue 8/264:25 pmMDW - MGM
1 stop6h 20mDelta
Deal found 8/12$707
This Delta deal was found by Cheapflights users on 8/11. 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.
Fri 10/316:05 amMGM - MDW
1 stop3h 40mDelta
Fri 10/314:23 pmMDW - MGM
1 stop6h 10mDelta
Deal found 8/11$718
This Delta deal was found by Cheapflights users on 8/14. 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.
Sat 8/166:00 amMGM - MDW
1 stop3h 36mDelta
Mon 8/186:42 pmMDW - MGM
1 stop4h 03mDelta
Deal found 8/14$727
This Delta deal was found by Cheapflights users on 8/13. 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 8/196:00 amMGM - MDW
1 stop3h 36mDelta
Wed 8/206:04 amMDW - MGM
1 stop5h 44mDelta
Deal found 8/13$765

Cheapflights Fare Finder

 
Customize your flight search to find flights from Montgomery 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 14, 2025.
Use the filters below to find and compare flights from Montgomery to Chicago Midway Airport that are best for you.

Fly from

Montgomery

Fly to

Midway

Route

Depart

Return

Price

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Sat 11/8

4:00 pm-10:14 pm

1 stop6h 14m

Chicago Midway

Tue 11/11

6:00 am-11:49 am

1 stop5h 49m

$328

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Sat 8/30

6:25 pm-8:35 am

2 stops14h 10m

Chicago Midway

Wed 9/3

6:00 am-10:24 am

1 stop4h 24m

$361

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Sat 8/30

6:25 pm-8:35 am

2 stops14h 10m

Chicago Midway

Thu 9/4

6:00 am-10:24 am

1 stop4h 24m

$361

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Sat 8/30

2:00 pm-9:12 pm

1 stop7h 12m

Chicago Midway

Sun 8/31

6:00 am-10:29 am

1 stop4h 29m

$422

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Fri 9/26

12:29 pm-5:51 pm

1 stop5h 22m

Chicago Midway

Sun 9/28

6:00 am-11:49 am

1 stop5h 49m

$507

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Sun 10/26

6:05 am-9:40 am

1 stop3h 35m

Chicago Midway

Thu 10/30

6:00 am-12:06 pm

1 stop6h 06m

$546

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Sun 9/28

6:00 am-9:40 am

1 stop3h 40m

Chicago Midway

Wed 10/1

6:00 am-11:49 am

1 stop5h 49m

$597

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Wed 9/17

6:00 am-11:48 am

1 stop5h 48m

Chicago Midway

Fri 9/19

6:00 am-11:49 am

1 stop5h 49m

$597

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Sun 8/24

6:00 am-11:48 am

1 stop5h 48m

Chicago Midway

Tue 8/26

4:25 pm-10:45 pm

1 stop6h 20m

$707

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Fri 10/31

6:05 am-9:45 am

1 stop3h 40m

Chicago Midway

Fri 10/31

4:23 pm-10:33 pm

1 stop6h 10m

$718

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/14

Showing 1-10 of 16 results
1
2

Best time to book a flight from Montgomery to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Montgomery 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 Montgomery to Chicago Midway Airport

What is the cheapest month to book a flight from Montgomery, Alabama to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Montgomery, Alabama to Chicago Midway Airport (average of $160). Flying from Montgomery, Alabama 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.

How much does it cost to fly round-trip from Montgomery, Alabama to Chicago Midway Airport?

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 14, 2025.
Get a feel of what it's like to fly with Delta from Montgomery to Chicago Midway Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,980 reviews

Overall

8.0

Entertainment

7.9

Boarding

8.2

Crew

8.5

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Overall

8.0

Entertainment

7.9

Boarding

8.2

Crew

8.5

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

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

  • What airport do you fly from for flights from Montgomery to Chicago Midway?

    For a flight from Montgomery to Chicago Midway, you will be flying from Dannelly Field. Montgomery Dannelly Field (MGM) is just 7.1 mi from the center of the city. Dannelly Field is the only Montgomery airport and it handles 0 outbound flights to Chicago Midway per day. 1 airline has flights to Chicago Midway from Montgomery Dannelly Field on a regular basis.

  • What is the cheapest airline to fly from Montgomery, Alabama to Chicago Midway Airport round-trip?

    Delta, at $206, was found to be the cheapest airline from Montgomery, Alabama to Chicago Midway Airport.. Users have found that Delta is 59% cheaper than the other options available to this destination.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Montgomery 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 Montgomery, Alabama to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Montgomery, Alabama to Chicago Midway Airport (average of $160). Flying from Montgomery, Alabama 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

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Montgomery to Midway

Discover the top airline that operate flights from Montgomery to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$206Average$461FlexibilityNo cancel feeOn-timeN/A

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