MGM - MDW

$258 Find Cheap Flights from Montgomery to Chicago Midway Airport

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Montgomery to Midway departing on 2/9. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Montgomery to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Montgomery to Chicago, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$258
Delta
Mon 2/9Mon 2/16
MGM - MDW • 1 stop
Cheapest one-way
$394
Delta
Sat 12/27
MGM - MDW • 1 stop
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We hope you love your trip to Midway!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Montgomery to Midway (MGM-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Montgomery to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Montgomery to Midway

Mon, Feb 9 - Mon, Feb 16
Delta Logo
6:11 pm - 10:22 pm
MGM
-
MDW
4h 11m1 stop
Delta Logo
6:40 pm - 10:41 pm
MDW
-
MGM
4h 01m1 stop
$258Delta
Fri, Mar 20 - Tue, Mar 24
Delta Logo
6:25 pm - 10:31 pm
MGM
-
MDW
4h 06m1 stop
Delta Logo
6:25 am - 11:55 am
MDW
-
MGM
5h 30m1 stop
$363Delta
Mon, Mar 16 - Wed, Mar 18
Delta Logo
6:25 pm - 10:31 pm
MGM
-
MDW
4h 06m1 stop
Delta Logo
5:40 pm - 10:41 pm
MDW
-
MGM
5h 01m1 stop
$486Delta
Mon, Feb 9 - Mon, Feb 16
Delta Logo
6:00 am - 12:46 pm
MGM
-
MDW
6h 46m2 stops
Delta Logo
6:40 pm - 10:41 pm
MDW
-
MGM
4h 01m1 stop
$856Delta
Tue, Jan 6 - Sat, Jan 10
Delta Logo
5:59 pm - 10:07 pm
MGM
-
MDW
4h 08m1 stop
Delta Logo
1:28 pm - 9:19 pm
MDW
-
MGM
7h 51m2 stops
$861Delta
Fri, Mar 20 - Tue, Mar 24
Delta Logo
6:25 pm - 10:31 pm
MGM
-
MDW
4h 06m1 stop
Delta Logo
9:35 am - 5:42 pm
MDW
-
MGM
8h 07m2 stops
$961Delta
Mon, Mar 16 - Wed, Mar 18
Delta Logo
6:25 pm - 10:31 pm
MGM
-
MDW
4h 06m1 stop
Delta Logo
9:35 am - 5:42 pm
MDW
-
MGM
8h 07m2 stops
$970Delta
Tue, Jan 6 - Sat, Jan 10
Delta Logo
6:00 am - 12:48 pm
MGM
-
MDW
6h 48m2 stops
Delta Logo
1:28 pm - 9:19 pm
MDW
-
MGM
7h 51m2 stops
$1,383Delta
Mon, Mar 16 - Wed, Mar 18
Delta Logo
9:38 am - 5:54 pm
MGM
-
MDW
8h 16m2 stops
Delta Logo
9:35 am - 5:42 pm
MDW
-
MGM
8h 07m2 stops
$1,443Delta
Mon, Feb 9 - Mon, Feb 16
Delta Logo
6:00 am - 12:46 pm
MGM
-
MDW
6h 46m2 stops
Delta Logo
1:26 pm - 10:41 pm
MDW
-
MGM
9h 15m2 stops
$1,463Delta
Booking Insights

KAYAK's insights & trends for Montgomery to Midway flights

Get data-powered insights and trends into flights from Montgomery to Midway to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Montgomery to Chicago Midway Airport?

The average price of all round-trip flights from Montgomery to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Chicago Midway Airport on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Thursday is the most expensive day to fly from Montgomery to Chicago Midway Airport. For your return ticket, we recommend flying on a Friday and avoiding Thursdays for the best deals.

Find deals

Good to know

Low seasonApril
Cheapest flight$258
Best time to beat the crowds with an average 50% drop in price.
Most popular time to fly and prices are also 30% lower on average.
Flight from Montgomery to Chicago Midway Airport

When to book flights from Montgomery to Midway

Are your dates flexible? Find out the best times to travel from Montgomery to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Montgomery to Chicago Midway Airport flights

  • What is the cheapest flight from Montgomery to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from Montgomery to Chicago Midway Airport was $258 for a round-trip ticket.

  • Do I need a passport to fly between Montgomery and Chicago Midway Airport?

    No, a passport isn't needed to fly from Montgomery to Chicago Midway Airport. However, local authorities might ask for an official ID.

  • Which aircraft models fly most regularly from Montgomery to Chicago Midway Airport?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Montgomery to Chicago Midway Airport?

    SkyTeam is the only airline alliance operating flights between Montgomery and Chicago Midway Airport.

  • How does KAYAK find such low prices on flights from Montgomery to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Montgomery to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Montgomery to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Montgomery is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Montgomery to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Montgomery with another airline. Booking your flights between Montgomery and MDW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Montgomery to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Montgomery up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Montgomery to Midway

 
See real verified KAYAK customer reviews for airlines flying from Montgomery to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Montgomery to Midway? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
DeltaOverall score based on 8014 reviews
7.9Comfort
7.9Entertainment
8.1Boarding
7.3Food
8.5Crew
Airline reviews

The plant way delayed departing by 3 hours. It was an old airplane with broken seats and armrests. The bathroom made a hollering sound. A really crappy flight experience and travel day all around.

2.0 MediocrePeter, Dec 2025
JFK - MEM
Read more Delta reviews

The plant way delayed departing by 3 hours. It was an old airplane with broken seats and armrests. The bathroom made a hollering sound. A really crappy flight experience and travel day all around.

Flight delays both to Detroits and return flight . The flight to Detroit was associated with mechanical difficulty

I am extremely disappointed that delta internal pilot manuals now refer to the Gulf of Mexico as the “gulf of America”. You can bow down to the Orange turd on your own. I will never fly delta again

Wasn't a Delta issue I don't think, but seems there was a Delta flight at each of the 2 Dallas airports at the same exact time, both to Atlanta. I was evidently booked on the one at Love Airport, but the Carey transport shuttle took me to DFW instead and I ended up missing the flight by just a few minutes. Was able to book a Southwest flight from Love Airport, but was a big loss of time and an inconvenience.

Great. I had to modify a flight. That was easy and free. Thank You

I noticed that the planes seem to be outdated. There was no entertainment per se. Also, the waiting area did not have any working electrical outlets

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The food is terrible. The staff is wonderful. Comfort is good.

Left on time, a bit delayed due to headwinds most of the trip.

Everything you need to know for your flight from Montgomery to Midway

Information on your arrival and departure airports

Montgomery (MGM)
Midway (MDW)