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Cheap flights from Montgomery, Alabama to Chicago from $243

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Montgomery, Alabama to Chicago departing on 3/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Montgomery, Alabama to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:25 pm - 10:33 pm
MGM
-
MDW
4h 08m
1 stop
Delta Logo
12:45 pm - 5:43 pm
MDW
-
MGM
4h 58m
1 stop
$263Delta
Tue, Feb 24 - Tue, Mar 3
Delta Logo
6:00 am - 9:54 am
MGM
-
MDW
3h 54m
1 stop
Delta Logo
6:00 am - 11:55 am
MDW
-
MGM
5h 55m
1 stop
$268Delta
Fri, Mar 6 - Wed, Mar 11
Delta Logo
12:40 pm - 5:45 pm
MGM
-
MDW
5h 05m
1 stop
Delta Logo
6:00 am - 11:55 am
MDW
-
MGM
5h 55m
1 stop
$278Delta
Wed, Feb 25 - Sun, Mar 1
Delta Logo
6:00 am - 10:21 am
MGM
-
MDW
4h 21m
1 stop
Delta Logo
6:40 pm - 10:41 pm
MDW
-
MGM
4h 01m
1 stop
$298Delta
Sat, Feb 21 - Wed, Feb 25
Delta Logo
6:00 am - 9:54 am
MGM
-
MDW
3h 54m
1 stop
Delta Logo
6:00 am - 11:55 am
MDW
-
MGM
5h 55m
1 stop
$318Delta
Tue, Feb 24 - Sun, Mar 1
Delta Logo
6:25 pm - 10:31 pm
MGM
-
MDW
4h 06m
1 stop
Delta Logo
6:00 am - 11:55 am
MDW
-
MGM
5h 55m
1 stop
$328Delta
Mon, Feb 23 - Sat, Feb 28
Delta Logo
12:37 pm - 4:25 pm
MGM
-
MDW
3h 48m
1 stop
Delta Logo
6:00 am - 11:56 am
MDW
-
MGM
5h 56m
1 stop
$398Delta
Fri, May 1 - Mon, May 4
Delta Logo
6:26 pm - 10:28 pm
MGM
-
MDW
4h 02m
1 stop
Delta Logo
6:00 am - 11:56 am
MDW
-
MGM
5h 56m
1 stop
$408Delta
Fri, May 1 - Mon, May 4
Delta Logo
4:00 pm - 9:09 pm
MGM
-
MDW
5h 09m
1 stop
Delta Logo
5:14 pm - 10:58 pm
MDW
-
MGM
5h 44m
1 stop
$468Delta
Sat, May 16 - Mon, May 18
Delta Logo
12:36 pm - 5:22 pm
MGM
-
MDW
4h 46m
1 stop
Delta Logo
6:00 am - 11:56 am
MDW
-
MGM
5h 56m
1 stop
$486Delta
Sun, Apr 12 - Thu, Apr 16

Delta flights from Montgomery, Alabama to Chicago Midway Airport

Our best Delta deals on Montgomery, Alabama to Chicago Midway Airport flight tickets
Delta
Feb 24
MGM6:25 pmMontgomery Dannelly Field
4h 08m
1 stop
MDW10:33 pmChicago Midway
Mar 3
MDW12:45 pmChicago Midway
4h 58m
1 stop
MGM5:43 pmMontgomery Dannelly Field
$263
Delta
Mar 6
MGM6:00 amMontgomery Dannelly Field
3h 54m
1 stop
MDW9:54 amChicago Midway
Mar 11
MDW6:00 amChicago Midway
5h 55m
1 stop
MGM11:55 amMontgomery Dannelly Field
$268
Delta
Feb 25
MGM12:40 pmMontgomery Dannelly Field
5h 05m
1 stop
MDW5:45 pmChicago Midway
Mar 1
MDW6:00 amChicago Midway
5h 55m
1 stop
MGM11:55 amMontgomery Dannelly Field
$278

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 February 11, 2026.
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

Tue 2/24

6:25 pm-10:33 pm

1 stop4h 08m

Chicago Midway

Tue 3/3

12:45 pm-5:43 pm

1 stop4h 58m

$263

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Fri 3/6

6:00 am-9:54 am

1 stop3h 54m

Chicago Midway

Wed 3/11

6:00 am-11:55 am

1 stop5h 55m

$268

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Wed 2/25

12:40 pm-5:45 pm

1 stop5h 05m

Chicago Midway

Sun 3/1

6:00 am-11:55 am

1 stop5h 55m

$278

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Sat 2/21

6:00 am-10:21 am

1 stop4h 21m

Chicago Midway

Wed 2/25

6:40 pm-10:41 pm

1 stop4h 01m

$298

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Tue 2/24

6:00 am-9:54 am

1 stop3h 54m

Chicago Midway

Sun 3/1

6:00 am-11:55 am

1 stop5h 55m

$318

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Mon 2/23

6:25 pm-10:31 pm

1 stop4h 06m

Chicago Midway

Sat 2/28

6:00 am-11:55 am

1 stop5h 55m

$328

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Fri 5/1

12:37 pm-4:25 pm

1 stop3h 48m

Chicago Midway

Mon 5/4

6:00 am-11:56 am

1 stop5h 56m

$398

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Fri 5/1

6:26 pm-10:28 pm

1 stop4h 02m

Chicago Midway

Mon 5/4

6:00 am-11:56 am

1 stop5h 56m

$408

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Sat 5/16

4:00 pm-9:09 pm

1 stop5h 09m

Chicago Midway

Mon 5/18

5:14 pm-10:58 pm

1 stop5h 44m

$468

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Sun 4/12

12:36 pm-5:22 pm

1 stop4h 46m

Chicago Midway

Thu 4/16

6:00 am-11:56 am

1 stop5h 56m

$486

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 cheapest airline that flies from Montgomery Dannelly Field to Chicago Midway?

Delta is the most popular carrier operating from Montgomery Dannelly Field to Chicago Midway

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

Fastest flight time

3h 55m

Direct flights

None
The fastest flight from Montgomery, Alabama to Chicago Midway Airport takes 3h 55m
There are no direct flights from Montgomery, Alabama to Chicago Midway Airport. There are no popular flight routes from Montgomery, Alabama to 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 55m.

  • 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
7.9
8,179 reviews
Search Delta flights

Traveling to a place near Chicago?

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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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