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Midway

$258+ 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 1/19. Fares are subject to change and may not be available on all flights or dates of travel.
MGM — MDW
Jan 20 — Jan 271
Tue 1/20
Tue 1/27
1 adult, Economy
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Cheap 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 December 21, 2025.

This Delta deal was found by Cheapflights users on 12/20. 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.
Thu 12/254:39 pmMGM - MDW
1 stop5h 43mDelta
Sat 1/36:00 amMDW - MGM
1 stop6h 29mDelta
Deal found 12/20$298
This Delta deal was found by Cheapflights users on 12/20. 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.
Mon 12/226:00 amMGM - MDW
1 stop5h 58mDelta
Sat 1/36:00 amMDW - MGM
1 stop6h 29mDelta
Deal found 12/20$313
This Delta deal was found by Cheapflights users on 12/20. 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.
Thu 12/254:39 pmMGM - MDW
1 stop5h 43mDelta
Fri 1/25:05 pmMDW - MGM
1 stop4h 16mDelta
Deal found 12/20$328
This Delta deal was found by Cheapflights users on 12/20. 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.
Mon 12/224:39 pmMGM - MDW
1 stop5h 43mDelta
Fri 1/25:05 pmMDW - MGM
1 stop4h 16mDelta
Deal found 12/20$343
This Delta deal was found by Cheapflights users on 12/20. 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.
Thu 12/254:39 pmMGM - MDW
1 stop5h 43mDelta
Sun 1/49:50 amMDW - MGM
1 stop6h 09mDelta
Deal found 12/20$348
This Delta deal was found by Cheapflights users on 12/20. 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.
Mon 12/224:39 pmMGM - MDW
1 stop5h 43mDelta
Sun 1/49:50 amMDW - MGM
1 stop6h 09mDelta
Deal found 12/20$363
This Delta deal was found by Cheapflights users on 12/20. 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.
Sun 12/286:00 amMGM - MDW
1 stop5h 58mDelta
Sat 1/36:00 amMDW - MGM
1 stop6h 29mDelta
Deal found 12/20$378
This Delta deal was found by Cheapflights users on 12/20. 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 12/2411:00 amMGM - MDW
1 stop3h 44mDelta
Sat 1/36:00 amMDW - MGM
1 stop6h 29mDelta
Deal found 12/20$398
This Delta deal was found by Cheapflights users on 12/20. 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.
Thu 12/254:39 pmMGM - MDW
1 stop5h 43mDelta
Thu 1/19:29 amMDW - MGM
2 stops23h 36mDelta
Deal found 12/20$406
This Delta deal was found by Cheapflights users on 12/20. 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.
Thu 12/254:39 pmMGM - MDW
1 stop5h 43mDelta
Mon 12/296:00 amMDW - MGM
1 stop6h 29mDelta
Deal found 12/20$408
This Delta deal was found by Cheapflights users on 12/20. 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.
Mon 12/224:39 pmMGM - MDW
1 stop5h 43mDelta
Thu 1/19:29 amMDW - MGM
2 stops11h 06mDelta
Deal found 12/20$421
This Delta deal was found by Cheapflights users on 12/20. 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.
Mon 12/226:00 amMGM - MDW
1 stop5h 58mDelta
Mon 12/296:00 amMDW - MGM
1 stop6h 29mDelta
Deal found 12/20$423

Find 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 December 21, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$258
(Delta)

Popular in

November

Cheapest in

April

Average price

$296
Provider with most accurate pricing for Montgomery Dannelly Field-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Montgomery Dannelly Field-Chicago Midway flights.
Search Deals
From Montgomery Dannelly Field to Chicago Midway
Search Deals
Highest demand for flights based on searches. 41% potential increase in price ($361 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($41 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 21, 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

Mon 1/19

12:43 pm-5:29 pm

1 stop4h 46m

Chicago Midway

Mon 1/26

6:00 am-12:02 pm

1 stop6h 02m

$258

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Thu 1/22

6:11 pm-10:22 pm

1 stop4h 11m

Chicago Midway

Sun 1/25

6:14 pm-10:38 pm

1 stop4h 24m

$258

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Mon 4/13

5:55 pm-9:45 pm

1 stop3h 50m

Chicago Midway

Wed 4/22

6:00 am-11:47 am

1 stop5h 47m

$362

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Wed 12/31

4:39 pm-10:22 pm

1 stop5h 43m

Chicago Midway

Sun 1/4

9:50 am-3:59 pm

1 stop6h 09m

$428

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Thu 1/8

5:59 pm-10:07 pm

1 stop4h 08m

Chicago Midway

Tue 1/13

6:45 am-12:59 pm

1 stop6h 14m

$438

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Thu 1/1

11:00 am-2:44 pm

1 stop3h 44m

Chicago Midway

Sun 1/4

9:50 am-3:59 pm

1 stop6h 09m

$498

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Wed 12/31

4:39 pm-10:22 pm

1 stop5h 43m

Chicago Midway

Mon 1/5

11:21 am-9:19 pm

1 stop9h 58m

$734

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Sat 1/3

9:45 am-5:26 pm

2 stops7h 41m

Chicago Midway

Wed 1/7

6:45 am-12:59 pm

1 stop6h 14m

$911

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/20

Compare providers for flights from Montgomery to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Montgomery to Midway in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Montgomery, Alabama-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Montgomery, Alabama-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Montgomery, Alabama-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Montgomery, Alabama-Chicago Midway Airport flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Montgomery, Alabama-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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, March is the cheapest month in which you can book a flight from Montgomery, Alabama to Chicago Midway Airport (average of $113). Flying from Montgomery, Alabama to Chicago Midway Airport in February is currently the most expensive (average of $366). 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 December 21, 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
7.9
Good
8,021 reviews

Overall

7.9

Entertainment

7.9

Boarding

8.1

Crew

8.5

Comfort

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,021 reviews
Delta
7.9
Good
8,021 reviews

Overall

7.9

Entertainment

7.9

Boarding

8.1

Crew

8.5

Comfort

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 3h 53m. 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 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, March is the cheapest month in which you can book a flight from Montgomery, Alabama to Chicago Midway Airport (average of $113). Flying from Montgomery, Alabama to Chicago Midway Airport in February is currently the most expensive (average of $366). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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 December 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$206Average$480FlexibilityNo cancel feeOn-timeN/A

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