$93 Cheap Flights from Montgomery (MGM) to Chicago (MDW)

View $93 flight on Sat, Jun 28, 2025Opens in a new window

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Find available prices by choosing your travel dates.

Cheap Flights from Montgomery to Chicago (MGM-MDW)

Prices were available within the past 7 days and start at $93 for one-way flights and $186 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, Jul 19 - Sat, Jul 26
MGM
Montgomery
MDW
Chicago
$186 Roundtrip, found 3 hours ago
$186
Roundtrip
found 3 hours ago
Select Delta flight, departing Sat, Jul 19 from Montgomery to Chicago, returning Sat, Jul 26, priced at $186 found 3 hours ago
Delta
Mon, Jun 30 - Sat, Jul 5
MGM
Montgomery
MDW
Chicago
$206 Roundtrip, found 10 hours ago
$206
Roundtrip
found 10 hours ago
Select Delta flight, departing Mon, Jun 30 from Montgomery to Chicago, returning Sat, Jul 5, priced at $206 found 10 hours ago
Delta
Mon, May 26 - Thu, May 29
MGM
Montgomery
MDW
Chicago
$207 Roundtrip, found 2 days ago
$207
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, May 26 from Montgomery to Chicago, returning Thu, May 29, priced at $207 found 2 days ago
Delta
Sat, Jul 19 - Sat, Jul 26
MGM
Montgomery
MDW
Chicago
$227 Roundtrip, found 3 hours ago
$227
Roundtrip
found 3 hours ago
Select Delta flight, departing Sat, Jul 19 from Montgomery to Chicago, returning Sat, Jul 26, priced at $227 found 3 hours ago
Delta
Tue, Jul 1 - Tue, Jul 8
MGM
Montgomery
MDW
Chicago
$237 Roundtrip, found 2 days ago
$237
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Jul 1 from Montgomery to Chicago, returning Tue, Jul 8, priced at $237 found 2 days ago
Delta
Sat, May 10 - Sun, May 11
MGM
Montgomery
MDW
Chicago
$246 Roundtrip, found 2 hours ago
$246
Roundtrip
found 2 hours ago
Select Delta flight, departing Sat, May 10 from Montgomery to Chicago, returning Sun, May 11, priced at $246 found 2 hours ago
Delta
Tue, May 13 - Sat, May 17
MGM
Montgomery
MDW
Chicago
$247 Roundtrip, found 2 hours ago
$247
Roundtrip
found 2 hours ago
Select Delta flight, departing Tue, May 13 from Montgomery to Chicago, returning Sat, May 17, priced at $247 found 2 hours ago
Delta
Sat, Jul 19 - Sat, Jul 26
MGM
Montgomery
MDW
Chicago
$256 Roundtrip, found 3 hours ago
$256
Roundtrip
found 3 hours ago
Select Delta flight, departing Sat, Jul 19 from Montgomery to Chicago, returning Sat, Jul 26, priced at $256 found 3 hours ago
Delta
Thu, May 8 - Sun, May 11
MGM
Montgomery
MDW
Chicago
$266 Roundtrip, found 2 hours ago
$266
Roundtrip
found 2 hours ago
Select Delta flight, departing Thu, May 8 from Montgomery to Chicago, returning Sun, May 11, priced at $266 found 2 hours ago
Delta
Mon, Jun 30 - Sat, Jul 5
MGM
Montgomery
MDW
Chicago
$268 Roundtrip, found 10 hours ago
$268
Roundtrip
found 10 hours ago
Select Delta flight, departing Mon, Jun 30 from Montgomery to Chicago, returning Sat, Jul 5, priced at $268 found 10 hours ago
Flights from Montgomery (MGM) to Chicago (MDW)
Origin airport
Montgomery Regional
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
$186
Distance
659 mi

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 July. 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 $93 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.

Frequently asked questions

How much does a flight from Montgomery Regional Airport (MGM) to Midway Intl. Airport (MDW) cost?
Discover the latest flight deals from MGM to MDW by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from MGM to MDW?
The cheapest flights from MGM to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from MGM to MDW?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that’ll take you from MGM to MDW. Sort your results by “Price (lowest to highest)” to snap up a great deal.
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.

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*Available to One Key members.