HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$294+ Cheap flights from Montgomery (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 7/26. Fares are subject to change and may not be available on all flights or dates of travel.
MGM — CHI
Aug 6 — Aug 131
Thu 8/6
Thu 8/13
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Montgomery to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 July 7, 2026.

This Delta deal was found by Cheapflights users on 7/5. 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 10/212:28 pm
MGM
-
ORD
1 stop6h 17m
Delta
Sun 10/48:05 am
ORD
-
MGM
1 stop3h 43m
Delta
Deal found 7/5$334
This Delta deal was found by Cheapflights users on 7/2. 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 10/26:28 pm
MGM
-
MDW
1 stop4h 17m
Delta
Sun 10/46:05 am
MDW
-
MGM
1 stop5h 43m
Delta
Deal found 7/2$334
This American Airlines deal was found by Cheapflights users on 7/6. 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 7/145:23 am
MGM
-
ORD
1 stop6h 56m
American Airlines
Tue 7/216:04 am
ORD
-
MGM
1 stop5h 57m
American Airlines
Deal found 7/6$360
This Delta deal was found by Cheapflights users on 7/4. 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 7/119:53 am
MGM
-
ORD
1 stop4h 32m
Delta
Sun 7/195:30 am
ORD
-
MGM
1 stop6h 32m
Delta
Deal found 7/4$369
This Delta deal was found by Cheapflights users on 7/4. 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 7/119:53 am
MGM
-
ORD
1 stop4h 32m
Delta
Wed 7/155:30 am
ORD
-
MGM
1 stop3h 42m
Delta
Deal found 7/4$370
This Delta deal was found by Cheapflights users on 7/4. 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 12/2312:30 pm
MGM
-
MDW
1 stop3h 55m
Delta
Sat 12/266:00 am
MDW
-
MGM
1 stop5h 50m
Delta
Deal found 7/4$371
This American Airlines deal was found by Cheapflights users on 7/6. 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.
Sun 7/195:23 am
MGM
-
ORD
1 stop5h 37m
American Airlines
Fri 7/315:45 pm
ORD
-
MGM
1 stop5h 48m
American Airlines
Deal found 7/6$385
This Delta deal was found by Cheapflights users on 7/6. 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.
Sun 7/196:00 am
MGM
-
MDW
1 stop4h 05m
Delta
Fri 7/315:10 pm
MDW
-
MGM
1 stop6h 05m
Delta
Deal found 7/6$385
This American Airlines deal was found by Cheapflights users on 7/5. 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.
Fri 9/46:14 pm
MGM
-
ORD
1 stop6h 04m
American Airlines
Sun 9/61:15 pm
ORD
-
MGM
1 stop7h 51m
American Airlines
Deal found 7/5$392
This Delta deal was found by Cheapflights users on 7/4. 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.
Sun 7/126:28 pm
MGM
-
ORD
1 stop5h 25m
Delta
Mon 7/208:03 am
ORD
-
MGM
1 stop3h 59m
Delta
Deal found 7/4$402
This Delta deal was found by Cheapflights users on 7/4. 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 7/119:53 am
MGM
-
ORD
1 stop7h 19m
Delta
Fri 7/175:30 am
ORD
-
MGM
1 stop3h 42m
Delta
Deal found 7/4$403
This Delta deal was found by Cheapflights users on 7/4. 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 7/106:28 pm
MGM
-
ORD
1 stop5h 25m
Delta
Mon 7/208:03 am
ORD
-
MGM
1 stop3h 59m
Delta
Deal found 7/4$409

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 July 7, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$334
(American Airlines)

One-way from

$294
(United Airlines)

Popular in

January

Cheapest in

September

Average price

$334
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
High demand for flights, 4% potential price rise
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 7, 2026.
Use the filters below to find and compare flights from Montgomery to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MontgomeryChicago

MGM - ORD

MGMORD

Montgomery Dannelly Field

Wed 8/12

9:53 am-4:51 pm

1 stop6h 58m

Chicago O'Hare Intl

Sun 8/16

5:30 am-9:12 am

1 stop3h 42m

$334

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Fri 10/2

6:28 pm-10:45 pm

1 stop4h 17m

Chicago Midway

Sun 10/4

6:05 am-11:48 am

1 stop5h 43m

$334

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Sat 9/26

4:10 pm-10:45 pm

1 stop6h 35m

Chicago Midway

Mon 9/28

6:05 am-11:48 am

1 stop5h 43m

$334
Quickest round-trip

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Wed 12/23

12:30 pm-4:25 pm

1 stop3h 55m

Chicago Midway

Sat 12/26

6:00 am-11:50 am

1 stop5h 50m

$371

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Sun 7/19

6:00 am-10:05 am

1 stop4h 05m

Chicago Midway

Fri 7/31

5:10 pm-11:15 pm

1 stop6h 05m

$385

MontgomeryChicago

MGM - ORD

MGMORD

Montgomery Dannelly Field

Fri 9/4

1:17 pm-6:30 am

2 stops17h 13m

Chicago O'Hare Intl

Sun 9/6

10:40 am-4:17 pm

1 stop5h 37m

$552

MontgomeryChicago

MGM - MDW

MGMMDW

Montgomery Dannelly Field

Sat 8/1

4:30 pm-10:15 pm

1 stop5h 45m

Chicago Midway

Sun 8/2

6:00 am-12:02 pm

1 stop6h 02m

$569

MontgomeryChicago

MGM - ORD

MGMORD

Montgomery Dannelly Field

Fri 7/24

4:51 pm-12:45 am

1 stop7h 54m

Chicago O'Hare Intl

Sun 7/26

6:29 am-12:40 pm

1 stop6h 11m

$579

MontgomeryChicago

MGM - ORD

MGMORD

Montgomery Dannelly Field

Mon 7/27

4:51 pm-11:15 pm

1 stop6h 24m

Chicago O'Hare Intl

Fri 7/31

8:51 am-4:16 pm

1 stop7h 25m

$588

MontgomeryChicago

MGM - ORD

MGMORD

Montgomery Dannelly Field

Wed 8/12

1:17 pm-9:00 am

2 stops19h 43m

Chicago O'Hare Intl

Sun 8/16

8:50 am-4:17 pm

1 stop7h 27m

$591

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/5

Showing 1-10 of 28 resultsSorted by cheapest first
1
2
3

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 July.
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-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Montgomery-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Montgomery-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Montgomery-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-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 to Chicago?

Currently, October is the cheapest month in which you can book a flight from Montgomery to Chicago (average of $78). Flying from Montgomery to Chicago in May is currently the most expensive (average of $334). 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 July 7, 2026.
Get a feel of what it's like to fly with Delta 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
7.8
Good
8,450 reviews

Boarding

8.1

Entertainment

7.8

Crew

8.5

Comfort

7.8

Food

7.2

Overall

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
Delta
7.8
Good
8,450 reviews
Delta
7.8
Good
8,450 reviews

Boarding

8.1

Entertainment

7.8

Crew

8.5

Comfort

7.8

Food

7.2

Overall

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional

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 to Chicago?

    Delta and United Airlines can get you from Montgomery to Chicago in just under 6h 47m. Your travel time can differ by up to 10h 26m. Montgomery and Chicago are separated by a distance of 673 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    Currently priced at $238, Delta will fly you from Montgomery to Chicago and back. In addition to Delta, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on American Airlines for as low as $238. Delta is 33% 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 to Chicago?

    Currently, October is the cheapest month in which you can book a flight from Montgomery to Chicago (average of $78). Flying from Montgomery to Chicago in May is currently the most expensive (average of $334). 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
Benton Harbor
Hammond
Lansing
Merrillville
Valparaiso
Porter

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 July 7, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$238Average$422FlexibilityNo cancel feeOn-time71%
DeltaCheapest$238Average$433FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.