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$328+ Cheap flights from Montgomery, AL (MGM) to Chicago (CHI)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
MGM — CHI
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheap flight deals from Montgomery to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Montgomery (MGM) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 14, 2025.

Round-trip from

$328
(Delta)

Popular in

November

Cheapest in

August

Average price

$243
From Montgomery Dannelly Field to Chicago (CHI)
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Highest demand for flights based on searches. 17% potential increase in price ($80 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Montgomery to Chicago

Cheapest flights from Montgomery to Chicago
Explore the most affordable flight options available from Montgomery to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 2025.

This Delta deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/812:46 pmMGM - ORD
1 stop4h 14mDelta
Tue 11/117:10 amORD - MGM
1 stop6h 34mDelta
Deal found 8/14$328
This Delta deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/89:28 amMGM - MDW
1 stop5h 58mDelta
Tue 11/116:00 amMDW - MGM
1 stop5h 49mDelta
Deal found 8/14$328
This American Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/85:35 amMGM - ORD
2 stops7h 31mAmerican Airlines
Tue 11/1111:40 amORD - MGM
1 stop5h 35mAmerican Airlines
Deal found 8/12$334
This Delta deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/302:00 pmMGM - ORD
1 stop5h 19mDelta
Wed 9/36:00 amORD - MGM
2 stops11h 45mDelta
Deal found 8/13$336
This Delta deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/302:00 pmMGM - ORD
1 stop5h 19mDelta
Thu 9/49:47 amORD - MGM
1 stop3h 33mDelta
Deal found 8/13$342
This American Airlines deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/315:22 pmMGM - ORD
1 stop6h 00mAmerican Airlines
Wed 9/310:05 amORD - MGM
2 stops7h 11mAmerican Airlines
Deal found 8/14$348
This Delta deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/266:25 pmMGM - ORD
1 stop4h 12mDelta
Sat 8/303:30 pmORD - MGM
1 stop7h 15mDelta
Deal found 8/13$356
This Delta deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/306:25 pmMGM - MDW
2 stops14h 10mDelta
Thu 9/46:00 amMDW - MGM
1 stop4h 24mDelta
Deal found 8/13$361
This American Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/46:36 amMGM - ORD
1 stop4h 54mAmerican Airlines
Sat 9/63:33 pmORD - MGM
2 stops7h 18mAmerican Airlines
Deal found 8/13$362
This Delta deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/266:25 pmMGM - ORD
1 stop4h 12mDelta
Wed 9/36:00 amORD - MGM
2 stops11h 45mDelta
Deal found 8/13$369
This American Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/31:55 pmMGM - ORD
1 stop6h 32mAmerican Airlines
Fri 9/511:30 amORD - MGM
1 stop5h 46mAmerican Airlines
Deal found 8/13$384
This Delta deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1112:46 pmMGM - ORD
1 stop6h 03mDelta
Sun 10/125:20 amORD - MGM
1 stop6h 46mDelta
Deal found 8/13$388

Cheapflights Fare Finder

 
Customize your flight search to find flights from Montgomery to Chicago 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, Cheapflights users made 2,558,603 searches. Data last updated August 14, 2025.
Use the filters below to find and compare flights from Montgomery to Chicago that are best for you.

Fly from

Montgomery

Fly to

Chicago

Route

Depart

Return

Price

MontgomeryChicago

MGM - ORD

MGMORD

Montgomery Dannelly Field

Sat 11/8

5:37 pm-11:37 pm

1 stop6h 00m

Chicago O'Hare Intl

Tue 11/11

4:05 pm-10:25 pm

1 stop6h 20m

$328

MontgomeryChicago

MGM - ORD

MGMORD

Montgomery Dannelly Field

Sat 11/8

12:46 pm-6:49 pm

1 stop6h 03m

Chicago O'Hare Intl

Tue 11/11

6:00 am-11:49 am

1 stop5h 49m

$328

MontgomeryChicago

MGM - ORD

MGMORD

Montgomery Dannelly Field

Sat 8/30

2:00 pm-7:19 pm

1 stop5h 19m

Chicago O'Hare Intl

Sun 8/31

5:45 am-10:29 am

1 stop4h 44m

$328

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 - ORD

MGMORD

Montgomery Dannelly Field

Sat 8/30

2:00 pm-7:19 pm

1 stop5h 19m

Chicago O'Hare Intl

Wed 9/3

6:00 am-5:45 pm

2 stops11h 45m

$336

MontgomeryChicago

MGM - ORD

MGMORD

Montgomery Dannelly Field

Sat 8/30

2:00 pm-7:19 pm

1 stop5h 19m

Chicago O'Hare Intl

Thu 9/4

9:47 am-1:20 pm

1 stop3h 33m

$342

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Sat 8/30

6:25 pm-8:35 am

2 stops14h 10m

Chicago Midway

Wed 9/3

6:00 am-10:24 am

1 stop4h 24m

$361

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

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/14

Showing 1-10 of 29 results
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Best time to book a flight from Montgomery to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Montgomery with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Montgomery to Chicago

What is the cheapest month to book a flight from Montgomery, Alabama to Chicago?

Currently, August is the cheapest month in which you can book a flight from Montgomery, Alabama to Chicago (average of $245). Flying from Montgomery, Alabama to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

How much does it cost to fly round-trip from Montgomery, Alabama to Chicago?

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated August 14, 2025.
Get a feel of what it's like to fly with Delta and American Airlines from Montgomery to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,980 reviews

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,980 reviews

Overall

8.0

Entertainment

7.9

Crew

8.5

Comfort

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

Find useful and relevant information for your journey from Montgomery to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Montgomery to Chicago?

    Montgomery Dannelly Field (MGM) is the airport you will fly out of if you book a flight from Montgomery to Chicago. You should not have trouble finding flights to Chicago from Dannelly Field; the airport handles an average of 0 outbound flights to Chicago per day. You should also have plenty of airline options to choose from since 2 airlines have flights from the Montgomery airport to Chicago. It is only a 7.1 mi journey to Dannelly Field (MGM) from Montgomery’s city center.

  • What are the cheapest airlines flying from Montgomery, Alabama to Chicago round-trip?

    Cheapflights users have booked flights from Montgomery, Alabama to Chicago round-trip from $148. Another airline that can offer you cheap pricing is Delta. American Airlines is 62% cheaper than the average price of flights available within the next 90 days to this destination.

  • Can I find deals for flights from Montgomery to Chicago that include hotel bookings?

    Yes. In addition to deals on Montgomery to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Montgomery to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Montgomery to Chicago.

  • Can I find deals for business class flights from Montgomery to Chicago?

    Yes. Cheapflights offers flight deals from Montgomery to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Montgomery, Alabama to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Montgomery, Alabama to Chicago (average of $245). Flying from Montgomery, Alabama to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Montgomery to Chicago

Discover the top 2 airlines that operate flights from Montgomery to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$148Average$403FlexibilityNo cancel feeOn-time71%
DeltaCheapest$186Average$413FlexibilityNo cancel feeOn-timeN/A

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