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Midway

$191+ Cheap flights from Montgomery, AL (MGM) 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 10/13. Fares are subject to change and may not be available on all flights or dates of travel.
MGM — MDW
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
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 September 15, 2025.

Round-trip from

$328
(Delta)

One-way from

$191
(Delta)

Popular in

September

Cheapest in

April

Average price

$818
From Montgomery Dannelly Field to Chicago Midway
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One-way flight from Montgomery Dannelly Field to Chicago Midway
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Highest demand for flights based on searches. 28% potential increase in price ($192 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($34 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 15, 2025.

This Delta deal was found by Cheapflights users on 9/15. 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 11/84:00 pmMGM - MDW
1 stop6h 14mDelta
Tue 11/116:00 amMDW - MGM
1 stop5h 12mDelta
Deal found 9/15$328
This Delta deal was found by Cheapflights users on 9/13. 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 10/49:31 amMGM - MDW
1 stop5h 55mDelta
Wed 10/86:00 amMDW - MGM
1 stop6h 06mDelta
Deal found 9/13$376
This Delta deal was found by Cheapflights users on 9/13. 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 9/306:00 amMGM - MDW
1 stop3h 40mDelta
Wed 10/86:00 amMDW - MGM
1 stop6h 06mDelta
Deal found 9/13$380
This Delta deal was found by Cheapflights users on 9/15. 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 9/306:00 amMGM - MDW
1 stop5h 48mDelta
Sat 10/411:00 amMDW - MGM
1 stop4h 24mDelta
Deal found 9/15$384
This Delta deal was found by Cheapflights users on 9/13. 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.
Mon 10/66:24 pmMGM - MDW
1 stop3h 50mDelta
Tue 10/76:00 amMDW - MGM
1 stop6h 06mDelta
Deal found 9/13$404
This Delta deal was found by Cheapflights users on 9/14. 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.
Tue 9/306:00 amMGM - MDW
1 stop5h 48mDelta
Wed 10/16:00 amMDW - MGM
1 stop5h 49mDelta
Deal found 9/14$450
This Delta deal was found by Cheapflights users on 9/15. 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 10/286:05 amMGM - MDW
1 stop3h 35mDelta
Mon 11/36:00 amMDW - MGM
1 stop6h 06mDelta
Deal found 9/15$453
This Delta deal was found by Cheapflights users on 9/13. 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.
Thu 10/212:29 pmMGM - MDW
1 stop5h 06mDelta
Tue 10/76:00 amMDW - MGM
1 stop6h 06mDelta
Deal found 9/13$487
This Delta deal was found by Cheapflights users on 9/13. 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 10/44:30 pmMGM - MDW
1 stop4h 40mDelta
Thu 10/96:00 amMDW - MGM
1 stop6h 06mDelta
Deal found 9/13$517
This Delta deal was found by Cheapflights users on 9/14. 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.
Tue 12/166:23 pmMGM - MDW
1 stop5h 09mDelta
Sat 12/206:00 amMDW - MGM
1 stop6h 29mDelta
Deal found 9/14$533
This Delta deal was found by Cheapflights users on 9/13. 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.
Fri 10/36:00 amMGM - MDW
1 stop3h 40mDelta
Wed 10/86:00 amMDW - MGM
1 stop6h 06mDelta
Deal found 9/13$537
This Delta deal was found by Cheapflights users on 9/13. 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.
Fri 10/36:00 amMGM - MDW
1 stop3h 40mDelta
Mon 10/66:00 amMDW - MGM
1 stop6h 06mDelta
Deal found 9/13$538

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 September 15, 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

9:28 am-3:26 pm

1 stop5h 58m

Chicago Midway

Tue 11/11

6:00 am-11:12 am

1 stop5h 12m

$328

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Sat 10/18

9:32 am-3:26 pm

1 stop5h 54m

Chicago Midway

Sat 10/25

4:23 pm-10:33 pm

1 stop6h 10m

$328

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Sat 10/4

4:30 pm-9:10 pm

1 stop4h 40m

Chicago Midway

Sat 10/11

4:23 pm-10:33 pm

1 stop6h 10m

$376

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Mon 10/6

9:32 am-4:09 pm

1 stop6h 37m

Chicago Midway

Sat 10/11

10:35 am-3:16 pm

1 stop4h 41m

$376

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Sat 10/4

9:31 am-3:26 pm

1 stop5h 55m

Chicago Midway

Wed 10/8

6:00 am-12:06 pm

1 stop6h 06m

$376

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Tue 9/30

6:00 am-9:40 am

1 stop3h 40m

Chicago Midway

Sat 10/11

10:35 am-3:16 pm

1 stop4h 41m

$380

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Wed 10/1

2:00 pm-5:35 pm

1 stop3h 35m

Chicago Midway

Sat 10/11

4:23 pm-10:33 pm

1 stop6h 10m

$380

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Wed 10/1

2:00 pm-5:35 pm

1 stop3h 35m

Chicago Midway

Tue 10/7

6:00 am-12:06 pm

1 stop6h 06m

$380

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Tue 9/30

6:00 am-9:40 am

1 stop3h 40m

Chicago Midway

Wed 10/8

6:00 am-12:06 pm

1 stop6h 06m

$380

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Tue 9/30

2:00 pm-5:35 pm

1 stop3h 35m

Chicago Midway

Tue 10/7

6:00 am-12:06 pm

1 stop6h 06m

$380

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 15 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.

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 September 15, 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
7,954 reviews

Comfort

7.9

Food

7.3

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

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
7,954 reviews
Delta
8.0
Very good
7,954 reviews

Comfort

7.9

Food

7.3

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

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.

  • How long is the flight from Montgomery, Alabama to Chicago Midway Airport?

    There are many flights that can get you from Montgomery, Alabama to Chicago Midway Airport in 5h 58m. Fly via Delta to get the fastest option. The distance from Montgomery, Alabama to Chicago Midway Airport is about 659 mi.

  • 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 56% 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$206Average$461FlexibilityNo cancel feeOn-timeN/A

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