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$248+ Cheap flights from Montgomery, AL (MGM) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/18. Fares are subject to change and may not be available on all flights or dates of travel.
MGM — CHI
Mar 24 — Mar 311
Tue 3/24
Tue 3/31
1 adult, Economy
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Cheap 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 February 22, 2026.

This Delta deal was found by Cheapflights users on 2/19. 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 7/145:55 pm
MGM
-
ORD
1 stop4h 30m
Delta
Wed 7/226:00 am
ORD
-
MGM
1 stop5h 47m
Delta
Deal found 2/19$268
This Delta deal was found by Cheapflights users on 2/19. 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 3/176:00 am
MGM
-
MDW
1 stop3h 56m
Delta
Tue 3/246:07 pm
MDW
-
MGM
1 stop4h 34m
Delta
Deal found 2/19$268
This Delta deal was found by Cheapflights users on 2/18. 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.
Fri 3/66:25 pm
MGM
-
ORD
1 stop5h 31m
Delta
Wed 3/115:30 am
ORD
-
MGM
1 stop6h 25m
Delta
Deal found 2/18$273
This Delta deal was found by Cheapflights users on 2/20. 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 3/712:40 pm
MGM
-
ORD
1 stop4h 14m
Delta
Tue 3/107:10 am
ORD
-
MGM
1 stop4h 45m
Delta
Deal found 2/20$278
This American Airlines deal was found by Cheapflights users on 2/20. 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 3/712:38 pm
MGM
-
ORD
1 stop7h 02m
American Airlines
Tue 3/104:04 pm
ORD
-
MGM
2 stops6h 44m
American Airlines
Deal found 2/20$284
This Delta deal was found by Cheapflights users on 2/19. 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.
Fri 5/12:42 pm
MGM
-
ORD
1 stop5h 34m
Delta
Fri 5/87:05 am
ORD
-
MGM
1 stop7h 08m
Delta
Deal found 2/19$308
This Delta deal was found by Cheapflights users on 2/19. 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.
Fri 3/66:25 pm
MGM
-
ORD
1 stop5h 31m
Delta
Tue 3/109:50 am
ORD
-
MGM
1 stop4h 26m
Delta
Deal found 2/19$323
This American Airlines deal was found by Cheapflights users on 2/19. 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 2/265:30 am
MGM
-
ORD
1 stop7h 05m
American Airlines
Sun 3/16:22 pm
ORD
-
MGM
1 stop5h 21m
American Airlines
Deal found 2/19$338
This Delta deal was found by Cheapflights users on 2/19. 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.
Fri 2/2712:40 pm
MGM
-
MDW
1 stop5h 05m
Delta
Mon 3/212:45 pm
MDW
-
MGM
1 stop4h 58m
Delta
Deal found 2/19$338
This American Airlines deal was found by Cheapflights users on 2/18. 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 5/2012:56 pm
MGM
-
ORD
1 stop5h 02m
American Airlines
Sun 5/248:50 am
ORD
-
MGM
1 stop6h 02m
American Airlines
Deal found 2/18$346
This American Airlines deal was found by Cheapflights users on 2/19. 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.
Tue 3/177:00 am
MGM
-
ORD
2 stops8h 08m
American Airlines
Tue 3/243:16 pm
ORD
-
MGM
1 stop7h 32m
American Airlines
Deal found 2/19$352
This American Airlines deal was found by Cheapflights users on 2/22. 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.
Tue 7/145:23 am
MGM
-
ORD
2 stops7h 34m
American Airlines
Tue 7/2110:42 am
ORD
-
MGM
1 stop8h 02m
American Airlines
Deal found 2/22$357

Find 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 February 22, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$268
(Delta)

One-way from

$248
(American Airlines)

Popular in

July

Cheapest in

December

Average price

$281
Provider with most accurate pricing for Montgomery Dannelly Field-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Montgomery Dannelly Field-Chicago (CHI) flights.
Search Deals
From Montgomery Dannelly Field to Chicago (CHI)
Search Deals
One-way flight from Montgomery Dannelly Field to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($84 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

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 February 22, 2026.
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 8/1

12:30 pm-7:48 pm

1 stop7h 18m

Chicago O'Hare Intl

Thu 8/6

6:00 am-11:47 am

1 stop5h 47m

$268

MontgomeryChicago

MGM - ORD

MGMORD

Montgomery Dannelly Field

Fri 4/17

6:26 pm-11:59 pm

1 stop5h 33m

Chicago O'Hare Intl

Sun 4/19

7:10 am-11:56 am

1 stop4h 46m

$268

MontgomeryChicago

MGM - ORD

MGMORD

Montgomery Dannelly Field

Tue 6/2

12:39 pm-6:41 pm

1 stop6h 02m

Chicago O'Hare Intl

Tue 6/9

7:10 am-1:43 pm

1 stop6h 33m

$268

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Fri 4/24

12:37 pm-4:26 pm

1 stop3h 49m

Chicago Midway

Sun 4/26

6:00 am-11:56 am

1 stop5h 56m

$268

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Tue 3/17

6:00 am-9:56 am

1 stop3h 56m

Chicago Midway

Tue 3/24

6:07 pm-10:41 pm

1 stop4h 34m

$268

MontgomeryChicago

MGM - ORD

MGMORD

Montgomery Dannelly Field

Fri 3/6

6:25 pm-11:56 pm

1 stop5h 31m

Chicago O'Hare Intl

Wed 3/11

5:30 am-11:55 am

1 stop6h 25m

$273

MontgomeryChicago

MGM - ORD

MGMORD

Montgomery Dannelly Field

Sat 3/7

12:40 pm-4:54 pm

1 stop4h 14m

Chicago O'Hare Intl

Tue 3/10

7:10 am-11:55 am

1 stop4h 45m

$278

MontgomeryChicago

MGM - ORD

MGMORD

Montgomery Dannelly Field

Wed 7/15

5:55 pm-11:55 pm

1 stop6h 00m

Chicago O'Hare Intl

Mon 7/20

6:00 am-11:47 am

1 stop5h 47m

$308

MontgomeryChicago

MGM - ORD

MGMORD

Montgomery Dannelly Field

Fri 5/1

6:26 pm-11:59 pm

1 stop5h 33m

Chicago O'Hare Intl

Sun 5/3

5:15 am-9:04 am

1 stop3h 49m

$308

MontgomeryChicago

MGM - ORD

MGMORD

Montgomery Dannelly Field

Wed 5/20

12:56 pm-5:58 pm

1 stop5h 02m

Chicago O'Hare Intl

Sun 5/24

8:50 am-2:52 pm

1 stop6h 02m

$346

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 26 results
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Compare providers for flights from Montgomery to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Montgomery to Chicago in February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Montgomery, Alabama-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Montgomery, Alabama-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Montgomery, Alabama-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Montgomery, Alabama-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Montgomery, Alabama-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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, March is the cheapest month in which you can book a flight from Montgomery, Alabama to Chicago (average of $113). Flying from Montgomery, Alabama to Chicago in June is currently the most expensive (average of $269). 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.

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 February 22, 2026.
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
7.9
Good
8,241 reviews

Overall

7.9

Boarding

8.1

Entertainment

7.8

Food

7.2

Comfort

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,241 reviews
Delta
7.9
Good
8,241 reviews

Overall

7.9

Boarding

8.1

Entertainment

7.8

Food

7.2

Comfort

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,338 reviews
Delta
7.9
Good
8,241 reviews

Overall

7.9

Boarding

8.1

Entertainment

7.8

Food

7.2

Comfort

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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.

  • How long is the flight from Montgomery, Alabama to Chicago?

    Airlines like Delta fly from Montgomery, Alabama to Chicago in about 7h 18m. The time it takes to get you to your destination can typically vary by up to . There are 673 mi between Montgomery, Alabama and Chicago.

  • 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 $186. Another airline that can offer you cheap pricing is Delta. American Airlines is 51% 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, March is the cheapest month in which you can book a flight from Montgomery, Alabama to Chicago (average of $113). Flying from Montgomery, Alabama to Chicago in June is currently the most expensive (average of $269). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

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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 February 22, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$186Average$412FlexibilityNo cancel feeOn-time71%
DeltaCheapest$206Average$427FlexibilityNo cancel feeOn-timeN/A

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