$164 Cheap Flights from Chicago (MDW) to Montgomery (MGM)

View $164 flight on Sun, Aug 31, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Montgomery Regional Airport (MGM)

  • Plan, book, fly with confidence

  • trending down icon

    Be in the know

    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon

    Book smarter

    Save up to 30% on select hotels after you book a flight*
  • one key icon

    Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

Cheap Flights from Chicago to Montgomery (MDW-MGM)

Prices were available within the past 7 days and start at $164 for one-way flights and $295 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Thu, Nov 13 - Thu, Nov 27
MDW
Chicago
MGM
Montgomery
$295 Roundtrip, found 9 hours ago
$295
Roundtrip
found 9 hours ago
Select Delta flight, departing Thu, Nov 13 from Chicago to Montgomery, returning Thu, Nov 27, priced at $295 found 9 hours ago
Delta
Sat, Aug 30 - Wed, Sep 17
MDW
Chicago
MGM
Montgomery
$298 Roundtrip, found 5 days ago
$298
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Aug 30 from Chicago to Montgomery, returning Wed, Sep 17, priced at $298 found 5 days ago
Delta
Thu, Nov 13 - Tue, Nov 25
MDW
Chicago
MGM
Montgomery
$312 Roundtrip, found 9 hours ago
$312
Roundtrip
found 9 hours ago
Select Delta flight, departing Thu, Nov 13 from Chicago to Montgomery, returning Tue, Nov 25, priced at $312 found 9 hours ago
Delta
Tue, Sep 30 - Tue, Oct 14
MDW
Chicago
MGM
Montgomery
$319 Roundtrip, found 5 days ago
$319
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Sep 30 from Chicago to Montgomery, returning Tue, Oct 14, priced at $319 found 5 days ago
Delta
Mon, Sep 29 - Tue, Oct 14
MDW
Chicago
MGM
Montgomery
$322 Roundtrip, found 5 days ago
$322
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, Sep 29 from Chicago to Montgomery, returning Tue, Oct 14, priced at $322 found 5 days ago
Delta
Wed, Oct 1 - Tue, Oct 14
MDW
Chicago
MGM
Montgomery
$324 Roundtrip, found 5 days ago
$324
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, Oct 1 from Chicago to Montgomery, returning Tue, Oct 14, priced at $324 found 5 days ago
Delta
Tue, Sep 9 - Mon, Sep 15
MDW
Chicago
MGM
Montgomery
$325 Roundtrip, found 22 hours ago
$325
Roundtrip
found 22 hours ago
Select Delta flight, departing Tue, Sep 9 from Chicago to Montgomery, returning Mon, Sep 15, priced at $325 found 22 hours ago
Delta
Thu, Nov 13 - Mon, Nov 24
MDW
Chicago
MGM
Montgomery
$326 Roundtrip, found 9 hours ago
$326
Roundtrip
found 9 hours ago
Select Delta flight, departing Thu, Nov 13 from Chicago to Montgomery, returning Mon, Nov 24, priced at $326 found 9 hours ago
Delta
Wed, Dec 24 - Thu, Dec 25
MDW
Chicago
MGM
Montgomery
$327 Roundtrip, found 6 days ago
$327
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Dec 24 from Chicago to Montgomery, returning Thu, Dec 25, priced at $327 found 6 days ago
Delta
Sat, Aug 30 - Thu, Sep 18
MDW
Chicago
MGM
Montgomery
$328 Roundtrip, found 5 days ago
$328
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Aug 30 from Chicago to Montgomery, returning Thu, Sep 18, priced at $328 found 5 days ago

Alternative airports near Montgomery

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Montgomery Regional MGM. Cheapest and Closest option available. Average driving time to city center is 12 minutes. Flights from $358
MGM
Montgomery Regional
CheapestClosest
Average driving time to city center12 min
Flights from $358
Flights from Chicago (MDW) to Montgomery (MGM)
Origin airport
Midway Intl.
Destination airport
Montgomery Regional
Airlines serving
Delta
Roundtrip price
$294
Distance
659 mi

Chicago to Montgomery Flights

The cheapest times to fly from Chicago to Montgomery

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Montgomery are during the month of November. You can find some of the cheapest flights from Chicago to Montgomery with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Montgomery

Sunday is one of the best days to book for cheap flights from Chicago to Montgomery: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Montgomery

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Montgomery in 2025. You can also book with separate airlines for your outbound and return journeys, from $164 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Montgomery flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Montgomery airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Montgomery Regional Airport (MGM) cost?
Get a cheap one-way flight from $164 or cheap return flight from $295 from Midway Intl. Airport (MDW) to Montgomery Regional Airport (MGM) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Montgomery Regional Airport (MGM)?
Planning your getaway for November can help you save, as it's the cheapest month for flights between MDW and MGM. You'll typically find the lowest fares during off-peak months.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Montgomery Regional Airport (MGM)?
To find the cheapest airline flying from MDW to MGM, use Expedia's filter tool. Customize your search based on what's important to you, such as preferred carriers and flight duration. You can then sort your results by "Price (lowest to highest)" to see the most affordable options first.
How many flights per day from Midway Intl. Airport (MDW) to Montgomery Regional Airport (MGM)?
There are no daily nonstop flights departing from Midway Intl. Airport (MDW) to Montgomery Regional Airport (MGM). But you can book flights with layovers. Filter your search results on Expedia to include one or more stops, and you'll be on your way in no time at all.
What day of the week has the most flights from MDW to MGM?
Friday is generally the busiest day for flights, while Tuesday is often the quietest.* Keep in mind that flight schedules can vary based on various factors, such as the airline and season.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Montgomery Regional Airport (MGM)?
To avoid potential delays on the Midway Intl. Airport (MDW) to Montgomery Regional Airport (MGM) route, fly before 3 PM. Later departures have a 22% higher chance of cancellation.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Montgomery Regional Airport (MGM) last-minute?
Last-minute fares from MDW to MGM are usually more expensive. For the lowest prices, start searching for flights well in advance. That said, if you're flexible with your travel plans, you may land a cheap ticket right before you leave.
Is it cheaper to book a MDW to MGM flight and hotel package?
Booking a MDW to MGM flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your travels all in one place. Choose from our extensive range of hotels and then add car rentals, activities and flights to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Montgomery Regional Airport (MGM)?
In most cases, you can reschedule or cancel your MDW to MGM flight. However, additional fees may apply, especially if you made your booking over 24 hours ago. Double-check your itinerary for the airline's fees and guidelines on flight changes, or if you want more details, go to our Customer Service portal.

Explore a world of travel with Expedia

*Available to One Key members.