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$191+ 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 11/3. Fares are subject to change and may not be available on all flights or dates of travel.
MGM — CHI
Oct 29 — Nov 51
Wed 10/29
Wed 11/5
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 September 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$328
(Delta)

One-way from

$191
(American Airlines)

Popular in

October

Cheapest in

April

Average price

$326
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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Highest demand for flights based on searches. 6% potential increase in price ($27 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 29, 2025.

This Delta deal was found by Cheapflights users on 9/29. 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 11/115:23 amORD - MGM
1 stop5h 49mDelta
Deal found 9/29$328
This Delta deal was found by Cheapflights users on 9/29. 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 11/84:00 pmMGM - MDW
1 stop6h 14mDelta
Tue 11/115:34 pmMDW - MGM
1 stop4h 59mDelta
Deal found 9/29$328
This American Airlines deal was found by Cheapflights users on 9/27. 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 11/812:57 pmMGM - ORD
1 stop4h 58mAmerican Airlines
Tue 11/116:06 amORD - MGM
2 stops7h 27mAmerican Airlines
Deal found 9/27$334
This Delta deal was found by Cheapflights users on 9/27. 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 10/296:05 amMGM - ORD
1 stop6h 11mDelta
Sun 11/25:45 amORD - MGM
1 stop5h 21mDelta
Deal found 9/27$352
This American Airlines deal was found by Cheapflights users on 9/27. 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 10/294:34 pmMGM - ORD
2 stops7h 16mAmerican Airlines
Sun 11/25:18 amORD - MGM
1 stop7h 16mAmerican Airlines
Deal found 9/27$358
This Delta deal was found by Cheapflights users on 9/28. 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 12/274:39 pmMGM - MDW
1 stop5h 43mDelta
Mon 12/295:10 pmMDW - MGM
1 stop4h 11mDelta
Deal found 9/28$366
This Delta deal was found by Cheapflights users on 9/28. 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 11/136:03 amMGM - ORD
1 stop4h 16mDelta
Sun 11/166:45 amORD - MGM
1 stop6h 30mDelta
Deal found 9/28$376
This Delta deal was found by Cheapflights users on 9/28. 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 11/136:03 amMGM - MDW
1 stop5h 49mDelta
Sun 11/166:00 amMDW - MGM
1 stop5h 33mDelta
Deal found 9/28$376
This American Airlines deal was found by Cheapflights users on 9/28. 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.
Mon 11/36:00 amMGM - ORD
2 stops7h 11mAmerican Airlines
Mon 11/175:10 pmORD - MGM
1 stop6h 05mAmerican Airlines
Deal found 9/28$382
This Delta deal was found by Cheapflights users on 9/28. 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 9/306:26 pmMGM - ORD
1 stop3h 48mDelta
Tue 10/76:45 amORD - MGM
1 stop5h 21mDelta
Deal found 9/28$384
This Delta deal was found by Cheapflights users on 9/28. 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 9/302:00 pmMGM - MDW
1 stop3h 35mDelta
Tue 10/76:00 amMDW - MGM
1 stop6h 06mDelta
Deal found 9/28$384
This American Airlines deal was found by Cheapflights users on 9/28. 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 11/95:36 amMGM - ORD
1 stop5h 06mAmerican Airlines
Mon 11/106:06 amORD - MGM
2 stops7h 27mAmerican Airlines
Deal found 9/28$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 September 29, 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

1:05 pm-7:40 pm

1 stop6h 35m

Chicago O'Hare Intl

Tue 11/11

3:44 pm-10:25 pm

1 stop6h 41m

$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

6:45 am-1:15 pm

1 stop6h 30m

$328

MontgomeryChicago

MGM - ORD

MGMORD

Montgomery Dannelly Field

Sat 2/21

12:30 pm-4:39 pm

1 stop4h 09m

Chicago O'Hare Intl

Wed 2/25

5:50 am-11:49 am

1 stop5h 59m

$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-11:12 am

1 stop5h 12m

$328

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Sat 2/21

9:30 am-3:25 pm

1 stop5h 55m

Chicago Midway

Tue 2/24

6:00 am-11:49 am

1 stop5h 49m

$328

MontgomeryChicago

MGM - ORD

MGMORD

Montgomery Dannelly Field

Wed 10/29

6:05 am-12:16 pm

1 stop6h 11m

Chicago O'Hare Intl

Sun 11/2

5:45 am-11:06 am

1 stop5h 21m

$352

MontgomeryChicago

MGM - ORD

MGMORD

Montgomery Dannelly Field

Wed 10/29

4:34 pm-11:50 pm

2 stops7h 16m

Chicago O'Hare Intl

Sun 11/2

5:18 am-12:34 pm

1 stop7h 16m

$358

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Sat 12/27

4:39 pm-10:22 pm

1 stop5h 43m

Chicago Midway

Mon 12/29

5:10 pm-9:21 pm

1 stop4h 11m

$366

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Thu 11/13

6:03 am-11:52 am

1 stop5h 49m

Chicago Midway

Sun 11/16

6:00 am-11:33 am

1 stop5h 33m

$376

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Sun 11/9

6:03 am-11:52 am

1 stop5h 49m

Chicago Midway

Mon 11/10

6:00 am-11:12 am

1 stop5h 12m

$404

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/27

Showing 1-10 of 17 results
1
2

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 September.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
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 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, 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 September 29, 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
7,964 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

Crew

8.5

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
7,964 reviews
Delta
8.0
Very good
7,964 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

Crew

8.5

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
7,964 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

Crew

8.5

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.

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

    Airlines like American Airlines and Delta fly from Montgomery, Alabama to Chicago in about 6h 03m. The time it takes to get you to your destination can typically vary by up to 32m. 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 $148. Another airline that can offer you cheap pricing is Delta. American Airlines is 64% 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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Alternative routes for Montgomery to Chicago

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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 September 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$148Average$383FlexibilityNo cancel feeOn-time71%
DeltaCheapest$186Average$412FlexibilityNo cancel feeOn-timeN/A

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