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Midway

$296+ Cheap flights from Montgomery (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 8/3. Fares are subject to change and may not be available on all flights or dates of travel.
MGM — MDW
Aug 1 — Aug 81
Sat 8/1
Sat 8/8
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 July 2, 2026.

This Delta deal was found by Cheapflights users on 6/30. 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 10/1312:26 pm
MGM
-
MDW
1 stop3h 54m
Delta
Mon 10/196:00 am
MDW
-
MGM
1 stop5h 46m
Delta
Deal found 6/30$334
This Delta deal was found by Cheapflights users on 7/1. 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 8/206:28 pm
MGM
-
MDW
1 stop4h 08m
Delta
Mon 8/245:10 pm
MDW
-
MGM
1 stop5h 58m
Delta
Deal found 7/1$371
This Delta deal was found by Cheapflights users on 6/30. 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 7/246:28 pm
MGM
-
MDW
1 stop3h 47m
Delta
Mon 7/276:00 am
MDW
-
MGM
1 stop6h 02m
Delta
Deal found 6/30$408
This Delta deal was found by Cheapflights users on 7/1. 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 7/36:27 pm
MGM
-
MDW
1 stop3h 50m
Delta
Tue 7/75:10 pm
MDW
-
MGM
1 stop6h 05m
Delta
Deal found 7/1$410
This Delta deal was found by Cheapflights users on 6/29. 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 7/309:53 am
MGM
-
MDW
1 stop6h 22m
Delta
Sun 8/26:00 am
MDW
-
MGM
1 stop6h 02m
Delta
Deal found 6/29$566
This Delta deal was found by Cheapflights users on 7/1. 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 8/14:30 pm
MGM
-
MDW
1 stop5h 45m
Delta
Mon 8/36:05 am
MDW
-
MGM
1 stop5h 45m
Delta
Deal found 7/1$569
This Delta deal was found by Cheapflights users on 6/30. 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 8/286:28 pm
MGM
-
MDW
1 stop4h 08m
Delta
Sun 8/3010:54 am
MDW
-
MGM
1 stop6h 54m
Delta
Deal found 6/30$591
This Delta deal was found by Cheapflights users on 6/28. 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 7/196:00 am
MGM
-
MDW
1 stop5h 56m
Delta
Wed 7/226:00 am
MDW
-
MGM
1 stop6h 02m
Delta
Deal found 6/28$592
This Delta deal was found by Cheapflights users on 7/1. 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 12/275:55 pm
MGM
-
MDW
1 stop4h 15m
Delta
Wed 12/3010:35 am
MDW
-
MGM
1 stop6h 39m
Delta
Deal found 7/1$642
This Delta deal was found by Cheapflights users on 6/30. 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 10/196:00 am
MGM
-
MDW
1 stop6h 05m
Delta
Mon 10/195:15 pm
MDW
-
MGM
1 stop5h 55m
Delta
Deal found 6/30$664
This Delta deal was found by Cheapflights users on 6/30. 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 7/26:00 am
MGM
-
MDW
1 stop4h 09m
Delta
Sun 7/56:00 am
MDW
-
MGM
1 stop6h 00m
Delta
Deal found 6/30$672
This Delta deal was found by Cheapflights users on 6/29. 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 11/256:00 am
MGM
-
MDW
1 stop5h 56m
Delta
Sun 11/296:00 am
MDW
-
MGM
1 stop5h 50m
Delta
Deal found 6/29$781

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 July 2, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$334
(Delta)

One-way from

$296
(Delta)

Popular in

January

Cheapest in

December

Average price

$334
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
One-way flight from Montgomery Dannelly Field to Chicago Midway
Search Deals
High demand for flights, 10% potential price rise
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 July 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 July 2, 2026.
Use the filters below to find and compare flights from Montgomery to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Fri 10/16

6:23 pm-10:25 pm

1 stop4h 02m

Chicago Midway

Tue 10/20

1:00 pm-5:43 pm

1 stop4h 43m

$334

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Tue 7/28

6:00 am-10:05 am

1 stop4h 05m

Chicago Midway

Tue 8/4

6:05 am-11:50 am

1 stop5h 45m

$334

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Mon 8/10

12:30 pm-4:15 pm

1 stop3h 45m

Chicago Midway

Mon 8/17

5:10 pm-11:08 pm

1 stop5h 58m

$334

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Sat 9/26

4:10 pm-10:45 pm

1 stop6h 35m

Chicago Midway

Mon 9/28

6:05 am-11:48 am

1 stop5h 43m

$334

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Thu 10/15

6:23 pm-10:25 pm

1 stop4h 02m

Chicago Midway

Wed 10/21

1:00 pm-5:43 pm

1 stop4h 43m

$334

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Fri 9/11

9:43 am-3:25 pm

1 stop5h 42m

Chicago Midway

Sun 9/13

6:05 am-12:30 pm

1 stop6h 25m

$334

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Mon 7/20

6:28 pm-10:15 pm

1 stop3h 47m

Chicago Midway

Mon 7/27

6:00 am-12:02 pm

1 stop6h 02m

$334

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Thu 8/20

6:28 pm-10:36 pm

1 stop4h 08m

Chicago Midway

Mon 8/24

5:10 pm-11:08 pm

1 stop5h 58m

$371

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Sat 8/1

4:30 pm-10:15 pm

1 stop5h 45m

Chicago Midway

Mon 8/3

6:05 am-11:50 am

1 stop5h 45m

$569

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Wed 10/28

6:00 am-9:52 am

1 stop3h 52m

Chicago Midway

Wed 10/28

5:15 pm-11:10 pm

1 stop5h 55m

$592

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/29

Showing 1-10 of 15 resultsSorted by cheapest first
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 July.
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-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-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Montgomery-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Montgomery-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-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.

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 July 2, 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
7.8
Good
8,452 reviews

Entertainment

7.8

Food

7.2

Comfort

7.8

Overall

7.8

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
Delta
7.8
Good
8,452 reviews
Delta
7.8
Good
8,452 reviews

Entertainment

7.8

Food

7.2

Comfort

7.8

Overall

7.8

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional

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 to Chicago Midway Airport?

    Departing from Montgomery to Chicago Midway Airport will take you 4h 02m. Montgomery and Chicago Midway Airport are separated by a distance of 659 mi.

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

    Delta, at $298, was found to be the cheapest airline from Montgomery 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.

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
Benton Harbor
Hammond
Lansing
Merrillville
Valparaiso
Porter

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 July 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$298Average$499FlexibilityNo cancel feeOn-timeN/A

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