$268+ 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 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
MGM — CHI
Sep 29 — Oct 61
Round-trip
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
Best
Last-minute
One-way
Cheapest flights from Montgomery to ChicagoExplore 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 30, 2026.
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 30, 2026.
This Delta deal was found by Cheapflights users on 8/26. 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 10/72:42 pm -
1 stop5h 56m
Tue 10/135:27 am -
1 stop6h 19m
Deal found 8/26![Delta logo]()
$326
This Delta deal was found by Cheapflights users on 8/26. 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 10/76:23 pm -
1 stop4h 10m
Wed 10/1410:59 am -
1 stop6h 44m
Deal found 8/26![Delta logo]()
$326
This Delta deal was found by Cheapflights users on 8/25. 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 12/309:51 am -
1 stop5h 09m
Sat 1/26:40 am -
1 stop5h 39m
Deal found 8/25![Delta logo]()
$346
This Delta deal was found by Cheapflights users on 8/25. 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 9/101:12 pm -
1 stop5h 29m
Mon 9/146:25 pm -
1 stop4h 40m
Deal found 8/25![Delta logo]()
$358
This Delta deal was found by Cheapflights users on 8/25. 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 9/104:10 pm -
1 stop6h 34m
Mon 9/145:10 pm -
1 stop5h 55m
Deal found 8/25![Delta logo]()
$358
This American Airlines deal was found by Cheapflights users on 8/25. 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 9/512:42 pm -
1 stop7h 04m
Sat 9/1211:00 am -
1 stop6h 40m
Deal found 8/25![American Airlines logo]()
$364
This Delta deal was found by Cheapflights users on 8/27. 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 9/94:10 pm -
1 stop6h 34m
Sat 9/126:05 am -
1 stop6h 25m
Deal found 8/27![Delta logo]()
$364
This Delta deal was found by Cheapflights users on 8/26. 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.
Mon 10/196:23 pm -
1 stop5h 34m
Tue 10/275:27 am -
1 stop6h 19m
Deal found 8/26![Delta logo]()
$367
This American Airlines deal was found by Cheapflights users on 8/27. 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 9/26:14 pm -
1 stop6h 04m
Sat 9/55:05 am -
1 stop7h 10m
Deal found 8/27![American Airlines logo]()
$370
This Delta deal was found by Cheapflights users on 8/27. 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 9/24:19 pm -
1 stop6h 17m
Sat 9/510:56 am -
1 stop4h 25m
Deal found 8/27![Delta logo]()
$370
This Delta deal was found by Cheapflights users on 8/25. 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 10/156:23 pm -
1 stop4h 10m
Mon 10/196:04 am -
1 stop5h 42m
Deal found 8/25![Delta logo]()
$376
This American Airlines deal was found by Cheapflights users on 8/27. 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.
Fri 10/95:27 pm -
1 stop6h 41m
Tue 10/139:02 am -
1 stop7h 10m
Deal found 8/27![American Airlines logo]()
$386
Best flights from Montgomery to ChicagoDiscover carefully curated flight deals from Montgomery to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 30, 2026.
Discover carefully curated flight deals from Montgomery to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 30, 2026.
This Delta deal was found by Cheapflights users on 8/27. 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.
Fri 9/256:28 pm -
1 stop5h 31m
Mon 9/285:30 am -
1 stop6h 18m
Deal found 8/27![Delta logo]()
$326
This United Airlines deal was found by Cheapflights users on 8/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/71:17 pm -
1 stop8h 25m
Wed 10/147:50 pm -
2 stops16h 51m
Deal found 8/25![United Airlines logo]()
$552
This Delta deal was found by Cheapflights users on 8/25. 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 10/72:42 pm -
1 stop5h 56m
Wed 10/146:30 am -
1 stop5h 16m
Deal found 8/25![Delta logo]()
$326
This Delta deal was found by Cheapflights users on 8/27. 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.
Thu 9/246:28 pm -
1 stop5h 31m
Thu 10/18:05 am -
1 stop5h 57m
Deal found 8/27![Delta logo]()
$326
This Delta deal was found by Cheapflights users on 8/28. 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.
Fri 9/256:28 pm -
1 stop5h 31m
Wed 9/306:40 am -
1 stop5h 08m
Deal found 8/28![Delta logo]()
$326
This Delta deal was found by Cheapflights users on 8/26. 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 10/226:23 pm -
1 stop4h 10m
Tue 10/2712:49 pm -
1 stop4h 54m
Deal found 8/26![Delta logo]()
$326
This Delta deal was found by Cheapflights users on 8/28. 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.
Fri 9/256:28 pm -
1 stop4h 16m
Wed 9/306:05 am -
1 stop5h 43m
Deal found 8/28![Delta logo]()
$326
This Delta deal was found by Cheapflights users on 8/26. 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 10/2312:26 pm -
1 stop3h 48m
Mon 10/266:04 am -
1 stop5h 42m
Deal found 8/26![Delta logo]()
$326
This United Airlines deal was found by Cheapflights users on 8/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/44:55 pm -
2 stops21h 49m
Mon 12/73:55 pm -
1 stop6h 32m
Deal found 8/27![United Airlines logo]()
$552
This Delta deal was found by Cheapflights users on 8/29. 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.
Wed 10/146:00 am -
1 stop5h 54m
Sun 10/186:04 am -
1 stop5h 42m
Deal found 8/29![Delta logo]()
$326
This United Airlines deal was found by Cheapflights users on 8/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/171:17 pm -
2 stops17h 11m
Wed 10/215:30 am -
1 stop7h 11m
Deal found 8/28![United Airlines logo]()
$567
This Delta deal was found by Cheapflights users on 8/28. 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 10/174:05 pm -
1 stop6h 28m
Wed 10/216:04 am -
1 stop5h 42m
Deal found 8/28![Delta logo]()
$326
This United Airlines deal was found by Cheapflights users on 8/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/64:55 pm -
1 stop6h 31m
Sun 11/85:30 am -
1 stop7h 17m
Deal found 8/28![United Airlines logo]()
$568
This Delta deal was found by Cheapflights users on 8/26. 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 10/249:46 am -
1 stop5h 31m
Sun 10/256:04 am -
1 stop5h 42m
Deal found 8/26![Delta logo]()
$326
This United Airlines deal was found by Cheapflights users on 8/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/304:55 pm -
1 stop6h 04m
Wed 2/32:23 pm -
1 stop8h 02m
Deal found 8/29![United Airlines logo]()
$568
This Delta deal was found by Cheapflights users on 8/26. 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 10/16:00 am -
1 stop3h 49m
Sun 10/46:05 am -
1 stop5h 43m
Deal found 8/26![Delta logo]()
$326
This Delta deal was found by Cheapflights users on 8/26. 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 10/236:23 pm -
1 stop4h 10m
Tue 10/276:04 am -
1 stop5h 42m
Deal found 8/26![Delta logo]()
$326
This Delta deal was found by Cheapflights users on 8/28. 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.
Wed 12/309:51 am -
1 stop5h 09m
Sat 1/26:40 am -
1 stop5h 39m
Deal found 8/28![Delta logo]()
$346
This Delta deal was found by Cheapflights users on 8/25. 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 9/101:12 pm -
1 stop5h 29m
Mon 9/146:25 pm -
1 stop4h 40m
Deal found 8/25![Delta logo]()
$358
This Delta deal was found by Cheapflights users on 8/25. 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 9/104:10 pm -
1 stop6h 34m
Mon 9/145:10 pm -
1 stop5h 55m
Deal found 8/25![Delta logo]()
$358
This Delta deal was found by Cheapflights users on 8/27. 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 9/94:10 pm -
1 stop6h 34m
Sat 9/126:05 am -
1 stop6h 25m
Deal found 8/27![Delta logo]()
$364
This Delta deal was found by Cheapflights users on 8/28. 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.
Fri 11/64:05 pm -
1 stop6h 28m
Sun 11/86:04 am -
1 stop5h 42m
Deal found 8/28![Delta logo]()
$407
This Delta deal was found by Cheapflights users on 8/28. 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.
Mon 10/56:28 pm -
1 stop5h 31m
Wed 10/76:30 am -
1 stop5h 16m
Deal found 8/28![Delta logo]()
$566
This Delta deal was found by Cheapflights users on 8/25. 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 10/2712:26 pm -
1 stop3h 48m
Thu 10/296:04 am -
1 stop5h 42m
Deal found 8/25![Delta logo]()
$566
Last-minute flights from Montgomery to ChicagoDiscover last-minute flight deals from Montgomery to Chicago. Data last updated August 30, 2026 and is based on user searches.
Discover last-minute flight deals from Montgomery to Chicago. Data last updated August 30, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 8/28. 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.
Fri 8/286:14 pm -
1 stop6h 04m
Sat 8/294:53 pm -
1 stop5h 37m
Deal found 8/28![American Airlines logo]()
$399
This American Airlines deal was found by Cheapflights users on 8/27. 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 9/26:14 pm -
1 stop6h 04m
Sat 9/55:05 am -
1 stop7h 10m
Deal found 8/27![American Airlines logo]()
$370
This Delta deal was found by Cheapflights users on 8/27. 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 9/24:19 pm -
1 stop6h 17m
Sat 9/510:56 am -
1 stop4h 25m
Deal found 8/27![Delta logo]()
$370
This Delta deal was found by Cheapflights users on 8/27. 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 9/29:53 am -
1 stop6h 58m
Mon 9/75:30 am -
1 stop3h 42m
Deal found 8/27![Delta logo]()
$396
This Delta deal was found by Cheapflights users on 8/27. 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 9/24:19 pm -
1 stop6h 17m
Sun 9/66:05 am -
1 stop6h 11m
Deal found 8/27![Delta logo]()
$396
This American Airlines deal was found by Cheapflights users on 8/25. 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 9/512:42 pm -
1 stop7h 04m
Sat 9/1211:00 am -
1 stop6h 40m
Deal found 8/25![American Airlines logo]()
$364
This Delta deal was found by Cheapflights users on 8/27. 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 9/94:10 pm -
1 stop6h 34m
Sat 9/126:05 am -
1 stop6h 25m
Deal found 8/27![Delta logo]()
$364
This Delta deal was found by Cheapflights users on 8/25. 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 9/101:12 pm -
1 stop5h 29m
Mon 9/146:25 pm -
1 stop4h 40m
Deal found 8/25![Delta logo]()
$358
This Delta deal was found by Cheapflights users on 8/25. 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 9/104:10 pm -
1 stop6h 34m
Mon 9/145:10 pm -
1 stop5h 55m
Deal found 8/25![Delta logo]()
$358
This Delta deal was found by Cheapflights users on 8/27. 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.
Thu 9/176:28 pm -
1 stop5h 31m
Sun 9/205:30 am -
1 stop6h 18m
Deal found 8/27![Delta logo]()
$367
This Delta deal was found by Cheapflights users on 8/28. 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.
Fri 9/256:28 pm -
1 stop5h 31m
Wed 9/306:40 am -
1 stop5h 08m
Deal found 8/28![Delta logo]()
$326
This Delta deal was found by Cheapflights users on 8/28. 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.
Fri 9/256:28 pm -
1 stop4h 16m
Wed 9/306:05 am -
1 stop5h 43m
Deal found 8/28![Delta logo]()
$326
One-way flights from Montgomery to ChicagoSearch for one-way flight options from Montgomery to Chicago. Find affordable one-way fares based on user searches. Data last updated August 30, 2026.
Search for one-way flight options from Montgomery to Chicago. Find affordable one-way fares based on user searches. Data last updated August 30, 2026.
This United Airlines deal was found by Cheapflights users on 8/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/24:53 pm -
1 stop6h 33m
Deal found 8/27![United Airlines logo]()
$268
This American Airlines deal was found by Cheapflights users on 8/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/305:30 am -
1 stop6h 52m
Deal found 8/29![American Airlines logo]()
$283
This Delta deal was found by Cheapflights users on 8/27. 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 11/189:46 am -
1 stop6h 32m
Deal found 8/27![Delta logo]()
$283
This United Airlines deal was found by Cheapflights users on 8/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/31:17 pm -
2 stops18h 22m
Deal found 8/25![United Airlines logo]()
$344
This United Airlines deal was found by Cheapflights users on 8/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/104:55 pm -
2 stops16h 05m
Deal found 8/25![United Airlines logo]()
$376
This American Airlines deal was found by Cheapflights users on 8/28. 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.
Wed 9/91:40 pm -
1 stop5h 58m
Deal found 8/28![American Airlines logo]()
$387
This Delta deal was found by Cheapflights users on 8/28. 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.
Wed 9/94:10 pm -
1 stop6h 34m
Deal found 8/28![Delta logo]()
$387
This United Airlines deal was found by Cheapflights users on 8/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/184:55 pm -
2 stops13h 04m
Deal found 8/27![United Airlines logo]()
$469
This United Airlines deal was found by Cheapflights users on 8/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/94:53 pm -
2 stops14h 45m
Deal found 8/28![United Airlines logo]()
$583
This United Airlines deal was found by Cheapflights users on 8/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/304:50 pm -
2 stops14h 08m
Deal found 8/29![United Airlines logo]()
$612
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 August 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $326 (Delta) |
One-way from | $268 (United Airlines) |
Popular in | September |
Cheapest in | February |
Average price | $298 |
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 7,457,451 searches. Data last updated August 30, 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
Cheapest round-trip
MontgomeryChicago
MGM Montgomery Dannelly Field - ORD Chicago O'Hare Intl
MGMORD
Montgomery Dannelly Field
Fri 9/25
6:28 pm-11:59 pm
1 stop5h 31m
Chicago O'Hare Intl
Mon 9/28
5:30 am-11:48 am
1 stop6h 18m
$326
MontgomeryChicago
MGM Montgomery Dannelly Field - ORD Chicago O'Hare Intl
MGMORD
Montgomery Dannelly Field
Wed 10/7
2:42 pm-8:38 pm
1 stop5h 56m
Chicago O'Hare Intl
Wed 10/14
6:30 am-11:46 am
1 stop5h 16m
$326
MontgomeryChicago
MGM Montgomery Dannelly Field - ORD Chicago O'Hare Intl
MGMORD
Montgomery Dannelly Field
Thu 9/24
6:28 pm-11:59 pm
1 stop5h 31m
Chicago O'Hare Intl
Thu 10/1
8:05 am-2:02 pm
1 stop5h 57m
$326
MontgomeryChicago
MGM Montgomery Dannelly Field - ORD Chicago O'Hare Intl
MGMORD
Montgomery Dannelly Field
Fri 9/25
6:28 pm-11:59 pm
1 stop5h 31m
Chicago O'Hare Intl
Wed 9/30
6:40 am-11:48 am
1 stop5h 08m
$326
Quickest round-trip
MontgomeryChicago
MGM Montgomery Dannelly Field - MDW Chicago Midway
MGMMDW
Montgomery Dannelly Field
Thu 10/22
6:23 pm-10:33 pm
1 stop4h 10m
Chicago Midway
Tue 10/27
12:49 pm-5:43 pm
1 stop4h 54m
$326
MontgomeryChicago
MGM Montgomery Dannelly Field - MDW Chicago Midway
MGMMDW
Montgomery Dannelly Field
Fri 9/25
6:28 pm-10:44 pm
1 stop4h 16m
Chicago Midway
Wed 9/30
6:05 am-11:48 am
1 stop5h 43m
$326
MontgomeryChicago
MGM Montgomery Dannelly Field - MDW Chicago Midway
MGMMDW
Montgomery Dannelly Field
Fri 10/23
12:26 pm-4:14 pm
1 stop3h 48m
Chicago Midway
Mon 10/26
6:04 am-11:46 am
1 stop5h 42m
$326
MontgomeryChicago
MGM Montgomery Dannelly Field - MDW Chicago Midway
MGMMDW
Montgomery Dannelly Field
Wed 10/14
6:00 am-11:54 am
1 stop5h 54m
Chicago Midway
Sun 10/18
6:04 am-11:46 am
1 stop5h 42m
$326
MontgomeryChicago
MGM Montgomery Dannelly Field - MDW Chicago Midway
MGMMDW
Montgomery Dannelly Field
Sat 10/17
4:05 pm-10:33 pm
1 stop6h 28m
Chicago Midway
Wed 10/21
6:04 am-11:46 am
1 stop5h 42m
$326
MontgomeryChicago
MGM Montgomery Dannelly Field - MDW Chicago Midway
MGMMDW
Montgomery Dannelly Field
Sat 10/24
9:46 am-3:17 pm
1 stop5h 31m
Chicago Midway
Sun 10/25
6:04 am-11:46 am
1 stop5h 42m
$326
Showing 1-10 of 35 resultsSorted by cheapest first
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 August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- 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.
MGM-CHI
MGM-ORD
MGM-MDW
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
MGM-CHI
MGM-ORD
MGM-MDW
What is the cheapest month to book a flight from Montgomery to Chicago?
Currently, January is the cheapest month in which you can book a flight from Montgomery to Chicago (average of $328). Flying from Montgomery to Chicago in April is currently the most expensive (average of $554). 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 August 30, 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.
Comfort
7.8
Crew
8.5
Entertainment
7.8
Food
7.2
Overall
7.8
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Comfort
7.8
Crew
8.5
Entertainment
7.8
Food
7.2
Overall
7.8
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
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.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
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.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Montgomery
Popular flights
Alternative routes for Montgomery to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 30, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Montgomery to Chicago by cabin class
Find flights from Montgomery to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Montgomery and Chicago flights
Browse other Montgomery and Chicago flight options. Last updated on August 30, 2026.
Other flights from Montgomery
Browse through other flights departing from Montgomery. Flights are based on user searches made on Cheapflights and were last updated on August 30, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 7,457,451 searches. Data last updated August 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$238 | Average$422 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$258 | Average$447 | FlexibilityNo cancel fee | On-timeN/A |