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Cheap flights from Montgomery, Alabama to Chicago from $328

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Montgomery, Alabama to Chicago departing on 11/8. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Montgomery, Alabama to Chicago (MGM-MDW)

Cheap round-trip flights

Delta Logo
4:00 pm - 10:14 pmMGM-MDW
6h 14m1 stop
Delta Logo
6:00 am - 11:49 amMDW-MGM
5h 49m1 stop
$328Delta
Find Deal
Sat, Nov 8 - Tue, Nov 11
Delta Logo
6:25 pm - 8:35 amMGM-MDW
14h 10m2 stops
Delta Logo
6:00 am - 10:24 amMDW-MGM
4h 24m1 stop
$361Delta
Find Deal
Sat, Aug 30 - Thu, Sep 4
Delta Logo
2:00 pm - 9:12 pmMGM-MDW
7h 12m1 stop
Delta Logo
6:00 am - 10:29 amMDW-MGM
4h 29m1 stop
$422Delta
Find Deal
Sat, Aug 30 - Sun, Aug 31
Delta Logo
12:29 pm - 5:51 pmMGM-MDW
5h 22m1 stop
Delta Logo
6:00 am - 11:49 amMDW-MGM
5h 49m1 stop
$507Delta
Find Deal
Fri, Sep 26 - Sun, Sep 28
Delta Logo
6:00 am - 9:40 amMGM-MDW
3h 40m1 stop
Delta Logo
6:00 am - 11:49 amMDW-MGM
5h 49m1 stop
$597Delta
Find Deal
Sun, Sep 28 - Wed, Oct 1
Delta Logo
6:00 am - 11:48 amMGM-MDW
5h 48m1 stop
Delta Logo
4:25 pm - 10:45 pmMDW-MGM
6h 20m1 stop
$707Delta
Find Deal
Sun, Aug 24 - Tue, Aug 26
Delta Logo
6:05 am - 9:45 amMGM-MDW
3h 40m1 stop
Delta Logo
4:23 pm - 10:33 pmMDW-MGM
6h 10m1 stop
$718Delta
Find Deal
Fri, Oct 31 - Fri, Oct 31
Delta Logo
9:28 am - 3:26 pmMGM-MDW
5h 58m1 stop
Delta Logo
9:30 am - 5:14 pmMDW-MGM
7h 44m2 stops
$721Delta
Find Deal
Sat, Nov 8 - Tue, Nov 11
Delta Logo
9:31 am - 6:35 pmMGM-MDW
9h 04m2 stops
Delta Logo
6:00 am - 11:49 amMDW-MGM
5h 49m1 stop
$766Delta
Find Deal
Fri, Sep 26 - Sun, Sep 28
Delta Logo
6:00 am - 9:36 amMGM-MDW
3h 36m1 stop
Delta Logo
6:00 am - 11:49 amMDW-MGM
5h 49m1 stop
$788Delta
Find Deal
Thu, Sep 4 - Thu, Sep 11

Delta flights from Montgomery, Alabama to Chicago Midway Airport

Our best Delta deals on Montgomery, Alabama to Chicago Midway Airport flight tickets
Delta
Nov 8
MGM4:00 pmMontgomery Dannelly Field
6h 14m
1 stop
MDW10:14 pmChicago Midway
Nov 11
MDW6:00 amChicago Midway
5h 49m
1 stop
MGM11:49 amMontgomery Dannelly Field
$328
Find similar
Delta
Aug 30
MGM6:25 pmMontgomery Dannelly Field
14h 10m
2 stops
MDW8:35 amChicago Midway
Sep 4
MDW6:00 amChicago Midway
4h 24m
1 stop
MGM10:24 amMontgomery Dannelly Field
$361
Find similar
Delta
Aug 30
MGM2:00 pmMontgomery Dannelly Field
7h 12m
1 stop
MDW9:12 pmChicago Midway
Aug 31
MDW6:00 amChicago Midway
4h 29m
1 stop
MGM10:29 amMontgomery Dannelly Field
$422
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Montgomery, Alabama to Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated August 14, 2025.
Use the filters below to find and compare flights from Montgomery, Alabama to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Sat 11/8

4:00 pm-10:14 pm

1 stop6h 14m

Chicago Midway

Tue 11/11

6:00 am-11:49 am

1 stop5h 49m

$328

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Sat 8/30

6:25 pm-8:35 am

2 stops14h 10m

Chicago Midway

Thu 9/4

6:00 am-10:24 am

1 stop4h 24m

$361

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Sat 8/30

2:00 pm-9:12 pm

1 stop7h 12m

Chicago Midway

Sun 8/31

6:00 am-10:29 am

1 stop4h 29m

$422

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Fri 9/26

12:29 pm-5:51 pm

1 stop5h 22m

Chicago Midway

Sun 9/28

6:00 am-11:49 am

1 stop5h 49m

$507

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Sun 9/28

6:00 am-9:40 am

1 stop3h 40m

Chicago Midway

Wed 10/1

6:00 am-11:49 am

1 stop5h 49m

$597

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Sun 8/24

6:00 am-11:48 am

1 stop5h 48m

Chicago Midway

Tue 8/26

4:25 pm-10:45 pm

1 stop6h 20m

$707

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Fri 10/31

6:05 am-9:45 am

1 stop3h 40m

Chicago Midway

Fri 10/31

4:23 pm-10:33 pm

1 stop6h 10m

$718

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Sat 11/8

9:28 am-3:26 pm

1 stop5h 58m

Chicago Midway

Tue 11/11

9:30 am-5:14 pm

2 stops7h 44m

$721

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Fri 9/26

9:31 am-6:35 pm

2 stops9h 04m

Chicago Midway

Sun 9/28

6:00 am-11:49 am

1 stop5h 49m

$766

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Thu 9/4

6:00 am-9:36 am

1 stop3h 36m

Chicago Midway

Thu 9/11

6:00 am-11:49 am

1 stop5h 49m

$788

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

See travel insights to Chicago from

How to get the cheapest flight ticket from Montgomery, Alabama to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Montgomery, Alabama and Chicago Midway Airport?

What is the cheapest month to fly to Chicago Midway Airport?

The month of April is, on average, the cheapest month to fly to Chicago Midway Airport from Montgomery, Alabama, with most prices found around $257. If you are unable to visit Chicago Midway Airport during the month of April, then departing from Montgomery, Alabama during the month May is also very affordable. Most momondo users find prices during this month for around $357.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from Montgomery, Alabama. The lowest ticket price found for a Tuesday departure recently was $343. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Thursday is the most expensive day to depart from Montgomery, Alabama because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $827.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Montgomery, Alabama in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $458 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $587. Of course, these prices can vary depending on the time of year and what airport you fly to.

When to book flights from Montgomery, Alabama to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Montgomery, Alabama to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Montgomery, Alabama to Chicago Midway Airport (MGM to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Montgomery, Alabama to Chicago Midway Airport

Best Price Found

$328

Fastest flight time

3h 36m

Direct flights

None
The best flight deal from Montgomery, Alabama to Chicago Midway Airport found on momondo in the last 72 hours is $328
The fastest flight from Montgomery, Alabama to Chicago Midway Airport takes 3h 36m
There are no direct flights from Montgomery, Alabama to Chicago Midway Airport. Popular non-direct route for this connection is Montgomery Dannelly Field Airport - Chicago Midway Airport.
Search flight deals

  • How far is Montgomery Dannelly Field to Chicago Midway by plane?

    There are 655.2 mi between Montgomery Dannelly Field and Chicago Midway. By plane, this route typically takes 3h 36m.

  • When did momondo last update prices for flights from Montgomery Dannelly Field Airport to Chicago Midway Airport?

    Prices for flights from Montgomery Dannelly Field Airport to Chicago Midway Airport are updated daily.

  • How many operators does momondo search for flights from Montgomery Dannelly Field Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Montgomery Dannelly Field Airport to Chicago Midway Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Montgomery Dannelly Field Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Montgomery, Alabama to Chicago Midway Airport?

Best airlines flying from Montgomery, Alabama to Chicago Midway Airport

Compare and see reviews for airlines that fly from Montgomery, Alabama to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $206Free CancellationRating
8.0
7,980 reviews
Search Delta flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Why use momondo?

Why should I use momondo to find a flight deal from Montgomery to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Montgomery.

Can I find flights from Montgomery to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Montgomery with this policy.

How can momondo help me find flights from Montgomery to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Montgomery.

I’m not ready to book a flight from Montgomery to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Montgomery to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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