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Midway

$268+ 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 3/6. Fares are subject to change and may not be available on all flights or dates of travel.
MGM — MDW
Mar 16 — Mar 231
Mon 3/16
Mon 3/23
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 February 14, 2026.

This Delta deal was found by Cheapflights users on 2/12. 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 3/66:25 pm
MGM
-
MDW
1 stop4h 06m
Delta
Wed 3/116:00 am
MDW
-
MGM
1 stop5h 55m
Delta
Deal found 2/12$268
This Delta deal was found by Cheapflights users on 2/10. 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 2/2512:40 pm
MGM
-
MDW
1 stop5h 05m
Delta
Sun 3/16:00 am
MDW
-
MGM
1 stop5h 55m
Delta
Deal found 2/10$278
This Delta deal was found by Cheapflights users on 2/11. 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.
Thu 3/266:25 pm
MGM
-
MDW
1 stop4h 06m
Delta
Sun 3/296:00 am
MDW
-
MGM
1 stop5h 55m
Delta
Deal found 2/11$308
This Delta deal was found by Cheapflights users on 2/13. 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 5/112:37 pm
MGM
-
MDW
1 stop3h 48m
Delta
Mon 5/46:00 am
MDW
-
MGM
1 stop5h 56m
Delta
Deal found 2/13$358
This Delta deal was found by Cheapflights users on 2/11. 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.
Thu 9/1012:30 pm
MGM
-
MDW
1 stop3h 57m
Delta
Tue 9/151:05 pm
MDW
-
MGM
1 stop4h 10m
Delta
Deal found 2/11$363
This Delta deal was found by Cheapflights users on 2/10. 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 2/1112:47 pm
MGM
-
MDW
1 stop4h 42m
Delta
Sun 2/156:00 am
MDW
-
MGM
1 stop5h 55m
Delta
Deal found 2/10$368
This Delta deal was found by Cheapflights users on 2/12. 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.
Thu 8/136:00 am
MGM
-
MDW
1 stop3h 50m
Delta
Mon 8/171:05 pm
MDW
-
MGM
1 stop4h 10m
Delta
Deal found 2/12$398
This Delta deal was found by Cheapflights users on 2/12. 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 3/156:25 pm
MGM
-
MDW
1 stop4h 06m
Delta
Sat 3/216:00 am
MDW
-
MGM
1 stop5h 55m
Delta
Deal found 2/12$448
This Delta deal was found by Cheapflights users on 2/10. 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 5/164:00 pm
MGM
-
MDW
1 stop5h 09m
Delta
Mon 5/185:14 pm
MDW
-
MGM
1 stop5h 44m
Delta
Deal found 2/10$468

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 February 14, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$268
(Delta)

Popular in

July

Cheapest in

December

Average price

$281
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. 18% potential increase in price ($84 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 February 14, 2026.
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

Fri 3/6

6:25 pm-10:31 pm

1 stop4h 06m

Chicago Midway

Wed 3/11

6:00 am-11:55 am

1 stop5h 55m

$268

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Wed 2/25

12:40 pm-5:45 pm

1 stop5h 05m

Chicago Midway

Sun 3/1

6:00 am-11:55 am

1 stop5h 55m

$278

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Sat 2/28

9:59 am-3:21 pm

1 stop5h 22m

Chicago Midway

Mon 3/2

6:00 am-11:55 am

1 stop5h 55m

$278

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Fri 5/1

12:37 pm-4:25 pm

1 stop3h 48m

Chicago Midway

Mon 5/4

6:00 am-11:56 am

1 stop5h 56m

$358

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Sun 3/15

6:25 pm-10:31 pm

1 stop4h 06m

Chicago Midway

Sat 3/21

6:00 am-11:55 am

1 stop5h 55m

$448

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Fri 6/12

5:55 pm-9:45 pm

1 stop3h 50m

Chicago Midway

Sat 6/20

6:00 am-11:47 am

1 stop5h 47m

$458

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Sat 5/16

4:00 pm-9:09 pm

1 stop5h 09m

Chicago Midway

Mon 5/18

5:14 pm-10:58 pm

1 stop5h 44m

$468

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Mon 4/6

6:00 am-9:56 am

1 stop3h 56m

Chicago Midway

Fri 4/10

12:47 pm-5:42 pm

1 stop4h 55m

$496

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Fri 2/27

6:00 am-11:59 am

1 stop5h 59m

$331

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Sat 2/21

6:00 am-10:21 am

1 stop4h 21m

$356

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/12

Showing 1-10 of 11 results
1
2

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 February.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Montgomery, Alabama-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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, November is the cheapest month in which you can book a flight from Montgomery, Alabama to Chicago Midway Airport (average of $222). Flying from Montgomery, Alabama to Chicago Midway Airport in January is currently the most expensive (average of $437). 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 February 14, 2026.
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
8,203 reviews

Crew

8.5

Entertainment

7.8

Food

7.2

Boarding

8.1

Comfort

7.9

Overall

7.9

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
8,203 reviews
Delta
7.9
Good
8,203 reviews

Crew

8.5

Entertainment

7.8

Food

7.2

Boarding

8.1

Comfort

7.9

Overall

7.9

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 4h 06m. 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..

  • 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, November is the cheapest month in which you can book a flight from Montgomery, Alabama to Chicago Midway Airport (average of $222). Flying from Montgomery, Alabama to Chicago Midway Airport in January is currently the most expensive (average of $437). 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 February 14, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$206Average$488FlexibilityNo cancel feeOn-timeN/A

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