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Midway

$243+ 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 2/4. Fares are subject to change and may not be available on all flights or dates of travel.
MGM — MDW
Feb 5 — Feb 121
Thu 2/5
Thu 2/12
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 January 6, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$258
(Delta)

One-way from

$243
(Delta)

Popular in

November

Cheapest in

April

Average price

$427
Provider with most accurate pricing for Montgomery Dannelly Field-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Montgomery Dannelly Field-Chicago Midway flights.
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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. 40% potential increase in price ($354 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease ($40 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 6, 2026.

This Delta deal was found by Cheapflights users on 1/4. 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 2/116:00 amMGM - MDW
1 stop3h 53mDelta
Tue 2/176:00 amMDW - MGM
1 stop5h 55mDelta
Deal found 1/4$258
This Delta deal was found by Cheapflights users on 1/5. 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 1/2112:43 pmMGM - MDW
1 stop4h 46mDelta
Sun 1/256:00 amMDW - MGM
1 stop6h 02mDelta
Deal found 1/5$268
This Delta deal was found by Cheapflights users on 1/4. 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 2/136:25 pmMGM - MDW
1 stop4h 06mDelta
Sat 2/1411:06 amMDW - MGM
1 stop3h 42mDelta
Deal found 1/4$283
This Delta deal was found by Cheapflights users on 1/4. 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 2/144:00 pmMGM - MDW
1 stop6h 31mDelta
Sun 2/156:00 amMDW - MGM
1 stop5h 55mDelta
Deal found 1/4$313
This Delta deal was found by Cheapflights users on 1/4. 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 1/165:59 pmMGM - MDW
1 stop4h 08mDelta
Tue 1/2010:48 amMDW - MGM
1 stop6h 38mDelta
Deal found 1/4$338
This Delta deal was found by Cheapflights users on 1/4. 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 2/136:25 pmMGM - MDW
2 stops14h 29mDelta
Sun 2/156:00 amMDW - MGM
1 stop5h 55mDelta
Deal found 1/4$361
This Delta deal was found by Cheapflights users on 1/4. 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 2/96:11 pmMGM - MDW
2 stops14h 41mDelta
Sat 2/1411:06 amMDW - MGM
1 stop3h 42mDelta
Deal found 1/4$364
This Delta deal was found by Cheapflights users on 1/4. 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 2/126:25 pmMGM - MDW
1 stop4h 06mDelta
Sat 2/1411:45 amMDW - MGM
2 stops10h 56mDelta
Deal found 1/4$365
This Delta deal was found by Cheapflights users on 1/4. 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 2/912:47 pmMGM - MDW
1 stop4h 42mDelta
Fri 2/136:40 pmMDW - MGM
1 stop14h 36mDelta
Deal found 1/4$381
This Delta deal was found by Cheapflights users on 1/4. 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 2/86:00 amMGM - MDW
1 stop3h 53mDelta
Fri 2/136:40 pmMDW - MGM
1 stop14h 36mDelta
Deal found 1/4$436

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 January 6, 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 2/27

6:25 pm-10:31 pm

1 stop4h 06m

Chicago Midway

Sun 3/8

6:25 am-11:55 am

1 stop5h 30m

$258

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Wed 2/11

6:11 pm-10:22 pm

1 stop4h 11m

Chicago Midway

Sun 2/15

6:00 am-11:55 am

1 stop5h 55m

$258

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Thu 2/12

12:40 pm-5:45 pm

1 stop5h 05m

Chicago Midway

Mon 2/16

6:40 pm-10:41 pm

1 stop4h 01m

$258

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Wed 2/11

6:00 am-11:59 am

1 stop5h 59m

Chicago Midway

Sat 2/14

11:06 am-2:48 pm

1 stop3h 42m

$258

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Thu 2/12

6:25 pm-10:31 pm

1 stop4h 06m

Chicago Midway

Sun 2/15

6:00 am-11:55 am

1 stop5h 55m

$258

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Thu 2/12

12:40 pm-5:45 pm

1 stop5h 05m

Chicago Midway

Wed 2/18

6:40 pm-10:41 pm

1 stop4h 01m

$258

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Wed 1/21

12:43 pm-5:29 pm

1 stop4h 46m

Chicago Midway

Sun 1/25

6:00 am-12:02 pm

1 stop6h 02m

$268

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Fri 2/13

6:25 pm-10:31 pm

1 stop4h 06m

Chicago Midway

Sat 2/14

11:06 am-2:48 pm

1 stop3h 42m

$283

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Fri 2/13

6:25 pm-10:31 pm

1 stop4h 06m

Chicago Midway

Mon 2/16

6:40 pm-10:41 pm

1 stop4h 01m

$283

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Fri 1/16

5:59 pm-10:07 pm

1 stop4h 08m

Chicago Midway

Tue 1/20

10:48 am-5:26 pm

1 stop6h 38m

$338

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/4

Showing 1-10 of 22 results
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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 January.
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 January 6, 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
8,018 reviews

Overall

7.9

Boarding

8.1

Food

7.2

Entertainment

7.8

Comfort

7.9

Crew

8.5

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
8,018 reviews
Delta
7.9
Good
8,018 reviews

Overall

7.9

Boarding

8.1

Food

7.2

Entertainment

7.8

Comfort

7.9

Crew

8.5

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.. Users have found that Delta is 60% 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 January 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$206Average$488FlexibilityNo cancel feeOn-timeN/A

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