$288+ Cheap flights from Montgomery (MGM) to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/9. Fares are subject to change and may not be available on all flights or dates of travel.
MGM — CHI
Nov 14 — Nov 211
Round-trip
1 adult, Economy
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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 October 15, 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 October 15, 2026.
This American Airlines deal was found by Cheapflights users on 10/12. 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 11/195:43 pm -
1 stop4h 51m
Fri 11/276:41 am -
1 stop5h 46m
Deal found 10/12![American Airlines logo]()
$384
This Delta deal was found by Cheapflights users on 10/14. 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 11/166:24 pm -
1 stop4h 30m
Thu 11/264:13 pm -
1 stop4h 32m
Deal found 10/14![Delta logo]()
$384
This Delta deal was found by Cheapflights users on 10/11. 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 11/31:13 pm -
1 stop4h 34m
Tue 11/108:04 am -
1 stop6h 05m
Deal found 10/11![Delta logo]()
$387
This American Airlines deal was found by Cheapflights users on 10/12. 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 10/274:38 pm -
1 stop6h 22m
Sat 10/316:00 am -
1 stop5h 53m
Deal found 10/12![American Airlines logo]()
$390
This Delta deal was found by Cheapflights users on 10/12. 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 10/276:00 am -
1 stop4h 03m
Sat 10/316:04 am -
1 stop6h 18m
Deal found 10/12![Delta logo]()
$390
This Delta deal was found by Cheapflights users on 10/11. 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 11/79:46 am -
1 stop7h 12m
Sun 11/85:27 am -
1 stop6h 19m
Deal found 10/11![Delta logo]()
$392
This American Airlines deal was found by Cheapflights users on 10/11. 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 11/65:59 pm -
1 stop6h 00m
Sun 11/85:19 am -
1 stop7h 06m
Deal found 10/11![American Airlines logo]()
$394
This Delta deal was found by Cheapflights users on 10/14. 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 11/1912:32 pm -
1 stop3h 46m
Thu 11/266:00 am -
1 stop6h 32m
Deal found 10/14![Delta logo]()
$394
This American Airlines deal was found by Cheapflights users on 10/15. 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 11/147:00 am -
1 stop7h 12m
Sun 11/156:00 am -
1 stop5h 51m
Deal found 10/15![American Airlines logo]()
$404
This Delta deal was found by Cheapflights users on 10/14. 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 10/296:00 am -
1 stop5h 54m
Mon 11/26:04 am -
1 stop6h 18m
Deal found 10/14![Delta logo]()
$404
This Delta deal was found by Cheapflights users on 10/13. 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 10/171:13 pm -
1 stop5h 58m
Wed 10/215:27 am -
1 stop6h 19m
Deal found 10/13![Delta logo]()
$410
This Delta deal was found by Cheapflights users on 10/13. 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
Tue 10/206:04 am -
1 stop5h 42m
Deal found 10/13![Delta logo]()
$410
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 October 15, 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 October 15, 2026.
This Delta deal was found by Cheapflights users on 10/14. 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 11/1912:32 pm -
1 stop3h 46m
Thu 11/266:00 am -
1 stop6h 32m
Deal found 10/14![Delta logo]()
$394
This United Airlines deal was found by Cheapflights users on 10/15. 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.
Thu 3/184:55 pm -
1 stop7h 45m
Mon 3/227:45 am -
1 stop8h 32m
Deal found 10/15![United Airlines logo]()
$574
This Delta deal was found by Cheapflights users on 10/14. 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 3/1912:30 pm -
1 stop3h 55m
Mon 3/225:25 pm -
1 stop5h 17m
Deal found 10/14![Delta logo]()
$404
This Delta deal was found by Cheapflights users on 10/11. 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 12/186:24 pm -
1 stop4h 30m
Mon 12/219:58 am -
1 stop6h 19m
Deal found 10/11![Delta logo]()
$493
This United Airlines deal was found by Cheapflights users on 10/12. 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 11/71:22 pm -
2 stops17h 37m
Mon 11/910:00 pm -
2 stops14h 47m
Deal found 10/12![United Airlines logo]()
$610
This Delta deal was found by Cheapflights users on 10/14. 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 11/214:15 pm -
1 stop6h 39m
Wed 11/251:31 pm -
2 stops19h 34m
Deal found 10/14![Delta logo]()
$505
This United Airlines deal was found by Cheapflights users on 10/11. 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 1/306:25 am -
1 stop6h 33m
Wed 2/310:42 am -
2 stops29h 29m
Deal found 10/11![United Airlines logo]()
$635
This United Airlines deal was found by Cheapflights users on 10/14. 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.
Thu 10/291:22 pm -
2 stops17h 37m
Mon 11/26:55 am -
1 stop5h 52m
Deal found 10/14![United Airlines logo]()
$665
This Delta deal was found by Cheapflights users on 10/12. 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 3/116:00 am -
1 stop5h 56m
Sun 3/141:05 pm -
1 stop4h 09m
Deal found 10/12![Delta logo]()
$666
This United Airlines deal was found by Cheapflights users on 10/12. 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.
Thu 11/191:22 pm -
2 stops17h 37m
Fri 11/273:47 pm -
2 stops21h 00m
Deal found 10/12![United Airlines logo]()
$670
This Delta deal was found by Cheapflights users on 10/12. 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 11/196:24 pm -
1 stop4h 30m
Fri 11/276:00 am -
1 stop6h 32m
Deal found 10/12![Delta logo]()
$711
This Delta deal was found by Cheapflights users on 10/14. 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 11/2012:32 pm -
1 stop3h 46m
Tue 11/246:00 am -
1 stop5h 46m
Deal found 10/14![Delta logo]()
$913
This Delta deal was found by Cheapflights users on 10/12. 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 3/269:30 am -
2 stops9h 07m
Sun 3/2810:35 am -
1 stop6h 39m
Deal found 10/12![Delta logo]()
$974
Last-minute flights from Montgomery to ChicagoDiscover last-minute flight deals from Montgomery to Chicago. Data last updated October 15, 2026 and is based on user searches.
Discover last-minute flight deals from Montgomery to Chicago. Data last updated October 15, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 10/13. 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 stop4h 33m
Tue 10/206:30 am -
1 stop5h 16m
Deal found 10/13![Delta logo]()
$410
This Delta deal was found by Cheapflights users on 10/13. 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
Tue 10/206:04 am -
1 stop5h 42m
Deal found 10/13![Delta logo]()
$410
This American Airlines deal was found by Cheapflights users on 10/12. 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 10/274:38 pm -
1 stop6h 22m
Sat 10/316:00 am -
1 stop5h 53m
Deal found 10/12![American Airlines logo]()
$390
This Delta deal was found by Cheapflights users on 10/12. 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 10/276:00 am -
1 stop4h 03m
Sat 10/316:04 am -
1 stop6h 18m
Deal found 10/12![Delta logo]()
$390
This Delta deal was found by Cheapflights users on 10/14. 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 10/296:00 am -
1 stop5h 54m
Mon 11/26:04 am -
1 stop6h 18m
Deal found 10/14![Delta logo]()
$404
This Delta deal was found by Cheapflights users on 10/11. 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 11/31:13 pm -
1 stop4h 34m
Tue 11/108:04 am -
1 stop6h 05m
Deal found 10/11![Delta logo]()
$387
This American Airlines deal was found by Cheapflights users on 10/11. 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 11/65:59 pm -
1 stop6h 00m
Sun 11/85:19 am -
1 stop7h 06m
Deal found 10/11![American Airlines logo]()
$394
This Delta deal was found by Cheapflights users on 10/11. 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 11/79:46 am -
1 stop7h 12m
Sun 11/85:27 am -
1 stop6h 19m
Deal found 10/11![Delta logo]()
$392
This American Airlines deal was found by Cheapflights users on 10/15. 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 11/1412:21 pm -
1 stop8h 51m
Mon 11/169:00 am -
1 stop7h 16m
Deal found 10/15![American Airlines logo]()
$404
This Delta deal was found by Cheapflights users on 10/14. 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 11/166:24 pm -
1 stop4h 30m
Thu 11/264:13 pm -
1 stop4h 32m
Deal found 10/14![Delta logo]()
$384
This American Airlines deal was found by Cheapflights users on 10/12. 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 11/195:43 pm -
1 stop4h 51m
Fri 11/276:41 am -
1 stop5h 46m
Deal found 10/12![American Airlines logo]()
$384
This Delta deal was found by Cheapflights users on 10/14. 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 11/1912:32 pm -
1 stop3h 46m
Thu 11/266:00 am -
1 stop6h 32m
Deal found 10/14![Delta logo]()
$394
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 October 15, 2026.
Search for one-way flight options from Montgomery to Chicago. Find affordable one-way fares based on user searches. Data last updated October 15, 2026.
This United Airlines deal was found by Cheapflights users on 10/12. 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.
Mon 11/91:22 pm -
1 stop6h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![United Airlines logo]()
$288
This Delta deal was found by Cheapflights users on 10/12. 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 11/126:00 am -
1 stop4h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Delta logo]()
$317
This Delta deal was found by Cheapflights users on 10/12. 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 11/96:24 pm -
1 stop4h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Delta logo]()
$332
This American Airlines deal was found by Cheapflights users on 10/15. 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 11/65:30 am -
1 stop6h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![American Airlines logo]()
$342
This United Airlines deal was found by Cheapflights users on 10/12. 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 1/24:50 pm -
1 stop7h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![United Airlines logo]()
$357
This United Airlines deal was found by Cheapflights users on 10/12. 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.
Thu 11/121:22 pm -
2 stops19h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![United Airlines logo]()
$372
This United Airlines deal was found by Cheapflights users on 10/15. 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.
Sun 11/11:22 pm -
1 stop6h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![United Airlines logo]()
$373
This KAYAK deal was found by Cheapflights users on 10/13. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/235:27 pm -
1 stop5h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![American Airlines logo]()
$385
This Delta deal was found by Cheapflights users on 10/13. 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 10/296:23 pm -
1 stop4h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Delta logo]()
$387
This American Airlines deal was found by Cheapflights users on 10/13. 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 11/275:30 am -
2 stops7h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![American Airlines logo]()
$455
This United Airlines deal was found by Cheapflights users on 10/15. 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 11/61:22 pm -
2 stops20h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![United Airlines logo]()
$466
This Delta deal was found by Cheapflights users on 10/12. 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 1/39:52 am -
1 stop6h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Delta logo]()
$467
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 October 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $384 (American Airlines) |
One-way from | $288 (United Airlines) |
Popular in | September |
Cheapest in | February |
Average price | $384 |
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 October 15, 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
Mon 11/9
1:22 pm-7:55 pm
1 stop6h 33m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$288
MontgomeryChicago
MGM Montgomery Dannelly Field - ORD Chicago O'Hare Intl
MGMORD
Montgomery Dannelly Field
Thu 11/12
4:55 pm-12:45 am
1 stop7h 50m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$288
MontgomeryChicago
MGM Montgomery Dannelly Field - ORD Chicago O'Hare Intl
MGMORD
Montgomery Dannelly Field
Fri 11/27
4:55 pm-11:26 pm
1 stop6h 31m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$288
MontgomeryChicago
MGM Montgomery Dannelly Field - MDW Chicago Midway
MGMMDW
Montgomery Dannelly Field
Mon 11/9
6:24 pm-10:54 pm
1 stop4h 30m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$332
MontgomeryChicago
MGM Montgomery Dannelly Field - ORD Chicago O'Hare Intl
MGMORD
Montgomery Dannelly Field
Sun 1/3
5:30 am-11:00 am
1 stop5h 30m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$357
MontgomeryChicago
MGM Montgomery Dannelly Field - ORD Chicago O'Hare Intl
MGMORD
Montgomery Dannelly Field
Sat 1/2
4:50 pm-12:44 am
1 stop7h 54m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$357
MontgomeryChicago
MGM Montgomery Dannelly Field - ORD Chicago O'Hare Intl
MGMORD
Montgomery Dannelly Field
Fri 10/23
5:27 pm-11:00 pm
1 stop5h 33m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$385
MontgomeryChicago
MGM Montgomery Dannelly Field - MDW Chicago Midway
MGMMDW
Montgomery Dannelly Field
Sat 1/2
4:58 pm-10:22 pm
1 stop5h 24m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$387
MontgomeryChicago
MGM Montgomery Dannelly Field - MDW Chicago Midway
MGMMDW
Montgomery Dannelly Field
Sun 11/1
6:00 am-10:47 am
1 stop4h 47m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$387
Quickest round-trip
MontgomeryChicago
MGM Montgomery Dannelly Field - MDW Chicago Midway
MGMMDW
Montgomery Dannelly Field
Thu 10/29
6:23 pm-10:33 pm
1 stop4h 10m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$387
Showing 1-10 of 30 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 October.
| 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 September is currently the most expensive (average of $679). 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 October 15, 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.
Overall
7.8
Entertainment
7.8
Comfort
7.8
Food
7.2
Crew
8.5
Boarding
8.1
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Overall
7.8
Entertainment
7.8
Comfort
7.8
Food
7.2
Crew
8.5
Boarding
8.1
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - 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
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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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 October 15, 2026.
Complete your trip
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Montgomery and Chicago flights
Browse other Montgomery and Chicago flight options. Last updated on October 15, 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 October 15, 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 October 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$238 | Average$422 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$263 | Average$446 | FlexibilityNo cancel fee | On-timeN/A |