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$243+ 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 3/8. Fares are subject to change and may not be available on all flights or dates of travel.
MGM — CHI
Feb 6 — Feb 131
Fri 2/6
Fri 2/13
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 January 7, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$258
(Delta)

One-way from

$243
(American Airlines)

Popular in

January

Cheapest in

December

Average price

$524
Provider with most accurate pricing for Montgomery Dannelly Field-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Montgomery Dannelly Field-Chicago (CHI) flights.
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From Montgomery Dannelly Field to Chicago (CHI)
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One-way flight from Montgomery Dannelly Field to Chicago (CHI)
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High demand for flights, 8% potential price rise
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Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 7, 2026.

This Delta deal was found by Cheapflights users on 1/6. 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.
Wed 2/1812:40 pmMGM - ORD
1 stop6h 39mDelta
Sat 2/215:25 amORD - MGM
1 stop3h 51mDelta
Deal found 1/6$258
This Delta deal was found by Cheapflights users on 1/7. 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 3/176:25 pmMGM - MDW
1 stop4h 06mDelta
Tue 3/316:25 amMDW - MGM
1 stop5h 30mDelta
Deal found 1/7$258
This American Airlines deal was found by Cheapflights users on 1/6. 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 2/181:35 pmMGM - ORD
1 stop6h 05mAmerican Airlines
Sat 2/214:04 pmORD - MGM
2 stops7h 39mAmerican Airlines
Deal found 1/6$264
This Delta deal was found by Cheapflights users on 1/6. 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 1/206:00 amMGM - ORD
1 stop4h 05mDelta
Sat 1/245:59 pmORD - MGM
1 stop4h 39mDelta
Deal found 1/6$268
This Delta deal was found by Cheapflights users on 1/7. 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.
Wed 1/216:00 amMGM - MDW
1 stop5h 59mDelta
Sat 1/246:25 amMDW - MGM
1 stop5h 37mDelta
Deal found 1/7$268
This American Airlines deal was found by Cheapflights users on 1/6. 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 1/202:03 pmMGM - ORD
2 stops8h 31mAmerican Airlines
Sat 1/245:37 pmORD - MGM
1 stop6h 01mAmerican Airlines
Deal found 1/6$274
This Delta deal was found by Cheapflights users on 1/6. 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.
Thu 3/52:47 pmMGM - ORD
1 stop4h 02mDelta
Mon 3/95:20 amORD - MGM
1 stop6h 35mDelta
Deal found 1/6$283
This American Airlines deal was found by Cheapflights users on 1/6. 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 5/25:55 pmMGM - ORD
1 stop5h 49mAmerican Airlines
Sat 5/93:57 pmORD - MGM
2 stops7h 48mAmerican Airlines
Deal found 1/6$289
This Delta deal was found by Cheapflights users on 1/7. 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 3/219:38 amMGM - MDW
1 stop5h 47mDelta
Sun 4/512:47 pmMDW - MGM
1 stop4h 55mDelta
Deal found 1/7$293
This Delta deal was found by Cheapflights users on 1/7. 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.
Thu 1/155:59 pmMGM - ORD
1 stop6h 00mDelta
Tue 1/205:59 pmORD - MGM
1 stop4h 39mDelta
Deal found 1/7$298
This American Airlines deal was found by Cheapflights users on 1/7. 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 1/156:00 amMGM - ORD
2 stops8h 01mAmerican Airlines
Tue 1/203:21 pmORD - MGM
1 stop7h 09mAmerican Airlines
Deal found 1/7$304
This Delta deal was found by Cheapflights users on 1/6. 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.
Wed 1/145:59 pmMGM - ORD
1 stop6h 00mDelta
Sun 1/182:50 pmORD - MGM
1 stop6h 29mDelta
Deal found 1/6$328

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 January 7, 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

Tue 2/24

6:25 pm-11:56 pm

1 stop5h 31m

Chicago O'Hare Intl

Tue 3/3

5:25 am-11:55 am

1 stop6h 30m

$258

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Tue 3/17

6:25 pm-10:31 pm

1 stop4h 06m

Chicago Midway

Sat 4/4

6:25 am-11:55 am

1 stop5h 30m

$258

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Fri 2/27

6:25 pm-10:31 pm

1 stop4h 06m

Chicago Midway

Sun 3/8

6:25 am-11:55 am

1 stop5h 30m

$258

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Mon 3/23

6:25 pm-10:31 pm

1 stop4h 06m

Chicago Midway

Tue 3/31

6:25 am-11:55 am

1 stop5h 30m

$258

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Mon 3/23

6:25 pm-10:31 pm

1 stop4h 06m

Chicago Midway

Thu 4/2

6:25 am-11:55 am

1 stop5h 30m

$258

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Thu 3/19

12:36 pm-4:55 pm

1 stop4h 19m

Chicago Midway

Thu 4/2

6:25 am-11:55 am

1 stop5h 30m

$258

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Tue 3/17

6:25 pm-10:31 pm

1 stop4h 06m

Chicago Midway

Sun 4/5

12:47 pm-5:42 pm

1 stop4h 55m

$258

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Tue 3/17

6:25 pm-10:31 pm

1 stop4h 06m

Chicago Midway

Tue 3/31

6:25 am-11:55 am

1 stop5h 30m

$258

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Wed 3/18

12:36 pm-4:55 pm

1 stop4h 19m

Chicago Midway

Sat 4/4

10:45 am-2:32 pm

1 stop3h 47m

$258

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Thu 3/19

12:36 pm-4:55 pm

1 stop4h 19m

Chicago Midway

Sun 4/5

6:25 am-11:55 am

1 stop5h 30m

$258

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/5

Showing 1-10 of 34 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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Montgomery, Alabama-Chicago flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 January 7, 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
8,025 reviews

Food

7.2

Overall

7.9

Crew

8.5

Comfort

7.9

Entertainment

7.8

Boarding

8.1

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
8,025 reviews
Delta
7.9
Good
8,025 reviews

Food

7.2

Overall

7.9

Crew

8.5

Comfort

7.9

Entertainment

7.8

Boarding

8.1

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
11,095 reviews
Delta
7.9
Good
8,025 reviews

Food

7.2

Overall

7.9

Crew

8.5

Comfort

7.9

Entertainment

7.8

Boarding

8.1

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 and American Airlines fly from Montgomery, Alabama to Chicago in about 5h 31m. The time it takes to get you to your destination can typically vary by up to 13m. There are 673 mi between Montgomery, Alabama and Chicago. This flight may include one or multiple stops.

  • 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 52% 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

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Alternative routes for Montgomery to Chicago

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 January 7, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$186Average$381FlexibilityNo cancel feeOn-time71%
DeltaCheapest$188Average$424FlexibilityNo cancel feeOn-timeN/A

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