$191 Cheap Flights from Montgomery (MGM) to Chicago (MDW)

View $191 flight on Wed, Dec 17, 2025Opens in a new window

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

Cheap Flights from Montgomery to Chicago (MGM-MDW)

Prices were available within the past 7 days and start at $191 for one-way flights and $328 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, Dec 16 - Thu, Jan 1
MGM
Montgomery
MDW
Chicago
$328 Roundtrip, found 1 day ago
$328
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Dec 16 from Montgomery to Chicago, returning Thu, Jan 1, priced at $328 found 1 day ago
Delta
Fri, Jan 16 - Sat, Jan 31
MGM
Montgomery
MDW
Chicago
$352 Roundtrip, found 4 days ago
$352
Roundtrip
found 4 days ago
Select Delta flight, departing Fri, Jan 16 from Montgomery to Chicago, returning Sat, Jan 31, priced at $352 found 4 days ago
Delta
Sun, Dec 14 - Thu, Jan 1
MGM
Montgomery
MDW
Chicago
$352 Roundtrip, found 1 day ago
$352
Roundtrip
found 1 day ago
Select Delta flight, departing Sun, Dec 14 from Montgomery to Chicago, returning Thu, Jan 1, priced at $352 found 1 day ago
Delta
Wed, Dec 17 - Thu, Jan 1
MGM
Montgomery
MDW
Chicago
$366 Roundtrip, found 1 day ago
$366
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Dec 17 from Montgomery to Chicago, returning Thu, Jan 1, priced at $366 found 1 day ago
Delta
Fri, Jan 16 - Thu, Jan 29
MGM
Montgomery
MDW
Chicago
$376 Roundtrip, found 4 days ago
$376
Roundtrip
found 4 days ago
Select Delta flight, departing Fri, Jan 16 from Montgomery to Chicago, returning Thu, Jan 29, priced at $376 found 4 days ago
Delta
Sun, Dec 14 - Fri, Jan 2
MGM
Montgomery
MDW
Chicago
$376 Roundtrip, found 1 day ago
$376
Roundtrip
found 1 day ago
Select Delta flight, departing Sun, Dec 14 from Montgomery to Chicago, returning Fri, Jan 2, priced at $376 found 1 day ago
Delta
Wed, Oct 15 - Wed, Oct 22
MGM
Montgomery
MDW
Chicago
$380 Roundtrip, found 8 hours ago
$380
Roundtrip
found 8 hours ago
Select Delta flight, departing Wed, Oct 15 from Montgomery to Chicago, returning Wed, Oct 22, priced at $380 found 8 hours ago
Delta
Sun, Dec 14 - Tue, Dec 16
MGM
Montgomery
MDW
Chicago
$382 Roundtrip, found 1 day ago
$382
Roundtrip
found 1 day ago
Select Delta flight, departing Sun, Dec 14 from Montgomery to Chicago, returning Tue, Dec 16, priced at $382 found 1 day ago
Delta
Tue, Oct 7 - Tue, Oct 14
MGM
Montgomery
MDW
Chicago
$384 Roundtrip, found 17 hours ago
$384
Roundtrip
found 17 hours ago
Select Delta flight, departing Tue, Oct 7 from Montgomery to Chicago, returning Tue, Oct 14, priced at $384 found 17 hours ago
Delta
Mon, Mar 2 - Tue, Mar 17
MGM
Montgomery
MDW
Chicago
$388 Roundtrip, found 4 days ago
$388
Roundtrip
found 4 days ago
Select Delta flight, departing Mon, Mar 2 from Montgomery to Chicago, returning Tue, Mar 17, priced at $388 found 4 days ago

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $295
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $295

Frequently asked questions

How much does a flight from Montgomery Regional Airport (MGM) to Midway Intl. Airport (MDW) cost?
Snag a cheap one-way flight from $191 or cheap return flight from $328 from Montgomery Regional Airport (MGM) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Montgomery Regional Airport (MGM) to Midway Intl. Airport (MDW)?
Traveling in December may help you find better deals, as it's the cheapest month for flights between MGM and MDW. You'll usually find the lowest fares during the off-season.
What is the cheapest airline that flies from Montgomery Regional Airport (MGM) to Midway Intl. Airport (MDW)?
To find the cheapest airline flying from MGM to MDW, use Expedia's filter tool. Customize your search based on what's important to you, such as preferred carriers and number of stops. You can then sort your results by "Price (lowest to highest)" to see the cheapest fares upfront.
How many flights per day from Montgomery Regional Airport (MGM) to Midway Intl. Airport (MDW)?
There aren't any daily nonstop flights from Montgomery Regional Airport (MGM) to Midway Intl. Airport (MDW). But you can opt for flights with layovers. Filter your search results on Expedia to include one or more stops, and you'll be cruising above the clouds in no time at all.
What day of the week has the most flights from MGM to MDW?
Friday is typically the busiest day for flights, while Tuesday tends to be the quietest.* Keep in mind that flight schedules can vary based on various factors, including the season and airline.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Montgomery Regional Airport (MGM) to Midway Intl. Airport (MDW)?
Opt for a flight from Montgomery Regional Airport (MGM) to Midway Intl. Airport (MDW) that leaves before 3 PM to reduce the risk of delays and cancellations. Departures after this hour have a 22% higher chance of being canceled, on average.**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 Montgomery Regional Airport (MGM) to Midway Intl. Airport (MDW) last-minute?
Last-minute fares from MGM to MDW are generally more expensive. For the cheapest rates, start looking for flights well in advance. That said, if you're flexible with your travel dates, you may land a cheap ticket just before your departure.
Is it cheaper to book a MGM to MDW flight and hotel package?
Opting for a MGM to MDW flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your travels in one place. Select from our wide range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Montgomery Regional Airport (MGM) to Midway Intl. Airport (MDW)?
If you reserved your MGM to MDW flight in the last 24 hours, you may be able to cancel or modify it at no cost. Depending on the airline and the type of fare you purchased, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal for further details.

Travel information

Travel information

Origin airport
Montgomery Regional
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
$328
Distance
659 mi

Book with confidence

Book with confidence

Montgomery to Chicago Flights

The cheapest times to fly from Montgomery to Chicago

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 Montgomery to Chicago are during the month of December. You can find some of the cheapest flights from Montgomery to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Montgomery to Chicago

Sunday is one of the best days to book for cheap flights from Montgomery to Chicago: 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 Montgomery to Chicago

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 Montgomery to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $191 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 Montgomery to Chicago 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 Montgomery to Chicago 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.

 

Montgomery to Chicago Flights

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*Available to One Key members.