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Cheap flights from Montgomery, Alabama to Chicago from $283

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 10/25. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Montgomery, Alabama to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:28 pm - 10:44 pm-
4h 16m
Delta Logo
5:10 pm - 11:05 pm-
5h 55m
$326Delta
Fri, Sep 18 - Fri, Sep 25
Delta Logo
6:00 am - 10:36 am-
4h 36m
Delta Logo
6:04 am - 12:22 pm-
6h 18m
$326Delta
Sat, Oct 3 - Sat, Oct 10
Delta Logo
6:28 pm - 10:44 pm-
4h 16m
Delta Logo
6:05 am - 11:48 am-
5h 43m
$326Delta
Fri, Sep 18 - Tue, Sep 22
Delta Logo
9:43 am - 3:24 pm-
5h 41m
Delta Logo
4:19 pm - 8:33 pm-
4h 14m
$326Delta
Sat, Oct 3 - Sat, Oct 10
Delta Logo
6:28 pm - 10:36 pm-
4h 08m
Delta Logo
5:10 pm - 11:08 pm-
5h 58m
$326Delta
Fri, Aug 28 - Fri, Sep 4
Delta Logo
6:00 am - 10:03 am-
4h 03m
Delta Logo
5:15 pm - 11:20 pm-
6h 05m
$376Delta
Thu, Oct 15 - Sun, Oct 18

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Delta flights from Montgomery, Alabama to Chicago Midway Airport

Our best Delta deals on Montgomery, Alabama to Chicago Midway Airport flight tickets
Delta
Sep 18
MGM6:28 pmMontgomery Dannelly Field
4h 16m
1 stop
MDW10:44 pmChicago Midway
Sep 25
MDW5:10 pmChicago Midway
5h 55m
1 stop
MGM11:05 pmMontgomery Dannelly Field
$326
Delta
Oct 15
MGM6:00 amMontgomery Dannelly Field
4h 03m
1 stop
MDW10:03 amChicago Midway
Oct 18
MDW5:15 pmChicago Midway
6h 05m
1 stop
MGM11:20 pmMontgomery Dannelly Field
$376
Delta
Aug 13
MGM9:53 amMontgomery Dannelly Field
6h 22m
1 stop
MDW4:15 pmChicago Midway
Aug 19
MDW6:05 amChicago Midway
5h 45m
1 stop
MGM11:50 amMontgomery Dannelly Field
$390

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 5, 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

Cheapest round-trip

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Fri 9/18

6:28 pm-10:44 pm

1 stop4h 16m

Chicago Midway

Fri 9/25

5:10 pm-11:05 pm

1 stop5h 55m

$326

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Sat 10/3

6:00 am-10:36 am

1 stop4h 36m

Chicago Midway

Sat 10/10

6:04 am-12:22 pm

1 stop6h 18m

$326

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Fri 9/18

6:28 pm-10:44 pm

1 stop4h 16m

Chicago Midway

Tue 9/22

6:05 am-11:48 am

1 stop5h 43m

$326
Quickest round-trip

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Sat 10/3

9:43 am-3:24 pm

1 stop5h 41m

Chicago Midway

Sat 10/10

4:19 pm-8:33 pm

1 stop4h 14m

$326

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Fri 8/28

6:28 pm-10:36 pm

1 stop4h 08m

Chicago Midway

Fri 9/4

5:10 pm-11:08 pm

1 stop5h 58m

$326

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Thu 10/15

6:00 am-10:03 am

1 stop4h 03m

Chicago Midway

Sun 10/18

5:15 pm-11:20 pm

1 stop6h 05m

$376
Cheapest one-way

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Sun 10/25

9:46 am-4:19 pm

1 stop6h 33m

$283

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Sun 9/20

6:28 pm-10:44 pm

1 stop4h 16m

$283

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Wed 8/12

6:00 am-11:51 am

1 stop5h 51m

$387
Quickest one-way

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Sun 9/20

6:00 am-9:49 am

1 stop3h 49m

$484

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 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 month to fly to Chicago Midway Airport?

The month of December is, on average, the cheapest month to fly to Chicago Midway Airport from Montgomery, Alabama, with most prices found around $0. If you are unable to visit Chicago Midway Airport during the month of December, then departing from Montgomery, Alabama during the month March is also very affordable. Most momondo users find prices during this month for around $0.

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 59m

Direct flights

None
The fastest flight from Montgomery, Alabama to Chicago Midway Airport takes 3h 59m
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.
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Frequently asked questions about flying from Montgomery, Alabama to Chicago Midway Airport

  • 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 59m.

  • 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 $298Free CancellationRating
7.8
8,490 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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Munster
Chesterton
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Crown Point
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Saint John

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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