$111+ Cheap flights from Orlando (MCO) 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 1/24. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — CHI
Dec 15 — Dec 221
Round-trip
1 adult, Economy
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Find cheap flights from Orlando 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.Cheapflights Tip: The best prices from Orlando to Chicago are usually found in February or January, booked 70 days in advance, depart on a Thursday or Friday and return on a Tuesday
Cheap flight deals from Orlando to Chicago
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Cheapest flights from Orlando to ChicagoExplore the most affordable flight options available from Orlando to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 15, 2026.
Explore the most affordable flight options available from Orlando to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 15, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/27:15 am -
1 stop5h 18m
Sat 12/512:28 pm -
1 stop7h 25m
Deal found 11/10![Frontier logo]()
$205
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/29:15 am -
1 stop5h 45m
Mon 12/78:30 am -
1 stop11h 23m
Deal found 11/11![Frontier logo]()
$206
This Mytrip deal was found by Cheapflights users on 11/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/39:28 am -
1 stop7h 39m
Sat 12/512:28 pm -
1 stop10h 42m
Deal found 11/11![Frontier logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/39:28 am -
1 stop7h 39m
Mon 12/75:02 pm -
1 stop5h 25m
Deal found 11/10![Frontier logo]()
$207
This Booking.com deal was found by Cheapflights users on 11/11. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/154:07 pm -
1 stop6h 53m
Sat 12/194:45 pm -
1 stop6h 28m
Deal found 11/11![Frontier logo]()
$208
This Frontier deal was found by Cheapflights users on 11/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/312:39 pm -
Nonstop3h 02m
Sun 12/68:37 pm -
Nonstop2h 50m
Deal found 11/12![Frontier logo]()
$208
This Frontier deal was found by Cheapflights users on 11/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/172:11 pm -
Nonstop3h 22m
Fri 12/185:58 am -
1 stop6h 47m
Deal found 11/14![Frontier logo]()
$209
This Frontier deal was found by Cheapflights users on 11/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/27:15 am -
1 stop5h 18m
Thu 12/108:37 pm -
Nonstop2h 50m
Deal found 11/10![Frontier logo]()
$209
This Frontier deal was found by Cheapflights users on 11/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/87:00 am -
1 stop10h 33m
Wed 12/1610:00 am -
1 stop9h 46m
Deal found 11/12![Frontier logo]()
$210
This Frontier deal was found by Cheapflights users on 11/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/89:58 pm -
1 stop12h 47m
Wed 12/912:28 pm -
1 stop9h 59m
Deal found 11/12![Frontier logo]()
$210
This Cheapflightsfares deal was found by Cheapflights users on 11/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2310:38 pm -
Nonstop3h 05m
Fri 11/275:12 pm -
Nonstop3h 00m
Deal found 11/15![Frontier logo]()
$211
This Cheapflightsfares deal was found by Cheapflights users on 11/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/47:15 am -
1 stop9h 52m
Sat 12/510:40 am -
1 stop12h 41m
Deal found 11/11![Frontier logo]()
$211
Best flights from Orlando to ChicagoDiscover carefully curated flight deals from Orlando to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 15, 2026.
Discover carefully curated flight deals from Orlando to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 15, 2026.
This Sun Country Air deal was found by Cheapflights users on 11/10. 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 Sun Country Air is selected, and click “Compare selected ” under the list of providers to see comparable flight deals.
Sun 12/208:35 pm -
1 stop14h 13m
Fri 1/111:44 am -
1 stop9h 04m
Deal found 11/10![Sun Country Air logo]()
$325
This United Airlines deal was found by Cheapflights users on 11/10. 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 12/197:00 am -
Nonstop3h 18m
Wed 12/307:05 am -
Nonstop2h 51m
Deal found 11/10![United Airlines logo]()
$377
This Southwest deal was found by Cheapflights users on 11/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/278:55 pm -
Nonstop3h 00m
Tue 2/23:35 pm -
Nonstop2h 40m
Deal found 11/10![Southwest logo]()
$377
This Delta deal was found by Cheapflights users on 11/10. 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 12/37:45 pm -
1 stop5h 11m
Sat 12/51:34 pm -
1 stop8h 06m
Deal found 11/10![Delta logo]()
$401
This Alaska Airlines deal was found by Cheapflights users on 11/10. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/34:55 pm -
2 stops13h 42m
Tue 12/83:19 pm -
1 stop15h 01m
Deal found 11/10![Alaska Airlines logo]()
$558
This Southwest deal was found by Cheapflights users on 11/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/82:25 pm -
Nonstop3h 00m
Tue 12/158:10 am -
Nonstop2h 40m
Deal found 11/10![Southwest logo]()
$383
This United Airlines deal was found by Cheapflights users on 11/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/249:22 am -
Nonstop3h 07m
Tue 12/111:05 am -
Nonstop2h 57m
Deal found 11/13![United Airlines logo]()
$397
This Delta deal was found by Cheapflights users on 11/10. 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 12/189:45 am -
1 stop6h 04m
Tue 12/295:25 am -
1 stop13h 15m
Deal found 11/10![Delta logo]()
$421
This Southwest deal was found by Cheapflights users on 11/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/236:05 am -
Nonstop2h 55m
Tue 1/268:35 am -
1 stop4h 40m
Deal found 11/10![Southwest logo]()
$383
This United Airlines deal was found by Cheapflights users on 11/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2612:27 pm -
Nonstop3h 08m
Fri 12/49:00 am -
1 stop5h 13m
Deal found 11/13![United Airlines logo]()
$407
This Southwest deal was found by Cheapflights users on 11/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/56:30 pm -
Nonstop2h 55m
Mon 12/71:15 pm -
Nonstop2h 40m
Deal found 11/11![Southwest logo]()
$387
This Delta deal was found by Cheapflights users on 11/10. 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 11/262:27 pm -
1 stop4h 47m
Mon 11/303:59 pm -
1 stop4h 41m
Deal found 11/10![Delta logo]()
$427
This Southwest deal was found by Cheapflights users on 11/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/242:25 pm -
Nonstop3h 00m
Fri 1/81:30 pm -
Nonstop2h 35m
Deal found 11/12![Southwest logo]()
$387
This Southwest deal was found by Cheapflights users on 11/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/88:55 pm -
Nonstop3h 00m
Sat 1/95:10 am -
Nonstop2h 50m
Deal found 11/13![Southwest logo]()
$392
This Delta deal was found by Cheapflights users on 11/13. 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 11/2612:45 pm -
1 stop4h 55m
Sat 11/286:49 am -
1 stop5h 51m
Deal found 11/13![Delta logo]()
$475
This United Airlines deal was found by Cheapflights users on 11/14. 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 11/192:20 pm -
Nonstop3h 08m
Sun 11/226:00 am -
Nonstop2h 48m
Deal found 11/14![United Airlines logo]()
$497
This Southwest deal was found by Cheapflights users on 11/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/72:35 pm -
1 stop5h 10m
Fri 1/156:15 am -
Nonstop2h 45m
Deal found 11/11![Southwest logo]()
$393
This Southwest deal was found by Cheapflights users on 11/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/15:40 pm -
Nonstop2h 55m
Thu 12/318:25 am -
1 stop4h 25m
Deal found 11/11![Southwest logo]()
$393
This Delta deal was found by Cheapflights users on 11/12. 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 11/229:15 am -
1 stop6h 34m
Thu 12/312:34 pm -
1 stop10h 28m
Deal found 11/12![Delta logo]()
$543
This Southwest deal was found by Cheapflights users on 11/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/99:25 am -
Nonstop2h 55m
Sat 12/125:00 am -
Nonstop2h 35m
Deal found 11/14![Southwest logo]()
$393
This Southwest deal was found by Cheapflights users on 11/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/236:40 pm -
Nonstop2h 55m
Tue 12/13:00 pm -
Nonstop2h 40m
Deal found 11/12![Southwest logo]()
$397
This Southwest deal was found by Cheapflights users on 11/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/212:35 pm -
1 stop4h 25m
Sun 11/227:50 am -
2 stops6h 20m
Deal found 11/12![Southwest logo]()
$403
This Southwest deal was found by Cheapflights users on 11/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/29:25 am -
Nonstop2h 55m
Wed 12/21:20 pm -
1 stop5h 50m
Deal found 11/14![Southwest logo]()
$403
Last-minute flights from Orlando to ChicagoDiscover last-minute flight deals from Orlando to Chicago. Data last updated November 15, 2026 and is based on user searches.
Discover last-minute flight deals from Orlando to Chicago. Data last updated November 15, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 11/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2110:38 pm -
Nonstop3h 05m
Mon 12/78:30 am -
1 stop11h 23m
Deal found 11/10![Frontier logo]()
$210
This Frontier deal was found by Cheapflights users on 11/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:46 pm -
Nonstop3h 01m
Mon 11/308:42 pm -
Nonstop2h 43m
Deal found 11/11![Frontier logo]()
$213
This Cheapflightsfares deal was found by Cheapflights users on 11/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2310:38 pm -
Nonstop3h 05m
Fri 11/275:12 pm -
Nonstop3h 00m
Deal found 11/15![Frontier logo]()
$211
This Frontier deal was found by Cheapflights users on 11/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2310:38 pm -
Nonstop3h 05m
Tue 12/11:19 pm -
Nonstop2h 57m
Deal found 11/15![Frontier logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/27:15 am -
1 stop5h 18m
Sat 12/512:28 pm -
1 stop7h 25m
Deal found 11/10![Frontier logo]()
$205
This Frontier deal was found by Cheapflights users on 11/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/27:15 am -
1 stop5h 18m
Thu 12/108:37 pm -
Nonstop2h 50m
Deal found 11/10![Frontier logo]()
$209
This Mytrip deal was found by Cheapflights users on 11/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/39:28 am -
1 stop7h 39m
Sat 12/512:28 pm -
1 stop10h 42m
Deal found 11/11![Frontier logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/39:28 am -
1 stop7h 39m
Mon 12/75:02 pm -
1 stop5h 25m
Deal found 11/10![Frontier logo]()
$207
This Frontier deal was found by Cheapflights users on 11/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/312:39 pm -
Nonstop3h 02m
Sun 12/68:37 pm -
Nonstop2h 50m
Deal found 11/12![Frontier logo]()
$208
This Cheapflightsfares deal was found by Cheapflights users on 11/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/47:15 am -
1 stop9h 52m
Sat 12/510:40 am -
1 stop12h 41m
Deal found 11/11![Frontier logo]()
$211
This Frontier deal was found by Cheapflights users on 11/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/89:58 pm -
1 stop12h 47m
Wed 12/912:28 pm -
1 stop9h 59m
Deal found 11/12![Frontier logo]()
$210
This Cheapflightsfares deal was found by Cheapflights users on 11/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/135:41 pm -
Nonstop3h 01m
Tue 12/1512:28 pm -
1 stop10h 42m
Deal found 11/11![Frontier logo]()
$212
One-way flights from Orlando to ChicagoSearch for one-way flight options from Orlando to Chicago. Find affordable one-way fares based on user searches. Data last updated November 15, 2026.
Search for one-way flight options from Orlando to Chicago. Find affordable one-way fares based on user searches. Data last updated November 15, 2026.
This Super.com deal was found by Cheapflights users on 11/11. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/246:59 pm -
1 stop6h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/11![Frontier logo]()
$111
This Super.com deal was found by Cheapflights users on 11/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2010:38 pm -
Nonstop3h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/15![Frontier logo]()
$112
This Kiwi.com deal was found by Cheapflights users on 11/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/174:31 pm -
1 stop7h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/13![Frontier logo]()
$112
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/238:08 pm -
2 stops21h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/12![Frontier logo]()
$113
This CheapOair deal was found by Cheapflights users on 11/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/27:15 am -
1 stop5h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/12![Frontier logo]()
$113
This Trip.com deal was found by Cheapflights users on 11/13. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/810:57 pm -
Nonstop3h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/13![Frontier logo]()
$114
This Priceline deal was found by Cheapflights users on 11/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/205:46 pm -
Nonstop3h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/15![Frontier logo]()
$114
This Trip.com deal was found by Cheapflights users on 11/13. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/221:41 pm -
Nonstop3h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/13![Frontier logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 11/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/53:49 pm -
1 stop25h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/14![Frontier logo]()
$115
This Kissandfly.com deal was found by Cheapflights users on 11/11. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2110:38 pm -
Nonstop3h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/11![Frontier logo]()
$117
This Cheapflightsfares deal was found by Cheapflights users on 11/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:46 pm -
Nonstop3h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/12![Frontier logo]()
$117
This Super.com deal was found by Cheapflights users on 11/12. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/255:46 pm -
Nonstop3h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/12![Frontier logo]()
$118
Find flight deals from Orlando to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Orlando (MCO) 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 November 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $205 (Kiwi.com) |
One-way from | $111 (Super.com) |
Popular in | October |
Cheapest in | February |
Average price | $294 |
Good round-trip deal | $282 or less |
Good one-way deal | $110 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Orlando 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 November 15, 2026.
Use the filters below to find and compare flights from Orlando Airport to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
OrlandoChicago
MCO Orlando - ORD Chicago O'Hare Intl
MCOORD
Orlando
Wed 2/24
1:00 pm-3:14 pm
Nonstop3h 14m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$189
Quickest round-trip
OrlandoChicago
MCO Orlando - MDW Chicago Midway
MCOMDW
Orlando
Sat 1/30
10:25 am-12:20 pm
Nonstop2h 55m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$189
OrlandoChicago
MCO Orlando - MDW Chicago Midway
MCOMDW
Orlando
Tue 12/15
9:25 am-11:20 am
Nonstop2h 55m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$189
OrlandoChicago
MCO Orlando - MDW Chicago Midway
MCOMDW
Orlando
Tue 2/2
6:55 pm-9:05 pm
Nonstop3h 10m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$194
OrlandoChicago
MCO Orlando - MDW Chicago Midway
MCOMDW
Orlando
Wed 2/3
11:40 am-1:40 pm
Nonstop3h 00m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$194
OrlandoChicago
MCO Orlando - MDW Chicago Midway
MCOMDW
Orlando
Thu 11/26
7:10 am-9:05 am
Nonstop2h 55m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$194
OrlandoChicago
MCO Orlando - MDW Chicago Midway
MCOMDW
Orlando
Wed 12/16
9:25 am-11:20 am
Nonstop2h 55m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$194
OrlandoChicago
MCO Orlando - MDW Chicago Midway
MCOMDW
Orlando
Sat 12/26
7:35 pm-9:30 pm
Nonstop2h 55m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$194
OrlandoChicago
MCO Orlando - MDW Chicago Midway
MCOMDW
Orlando
Wed 11/18
9:25 am-11:20 am
Nonstop2h 55m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$194
OrlandoChicago
MCO Orlando - MDW Chicago Midway
MCOMDW
Orlando
Thu 12/24
7:20 pm-9:20 pm
Nonstop3h 00m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$194
Showing 1-10 of 44 resultsSorted by cheapest first
Compare providers for flights from Orlando 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 Orlando to Chicago in November.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Orlando Airport-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Orlando Airport-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Orlando Airport-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Orlando Airport-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 Orlando Airport-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 Orlando to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Orlando with our price prediction graph.
MCO-CHI
MCO-ORD
MCO-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 Orlando Airport to Chicago
MCO-CHI
MCO-ORD
MCO-MDW
What is the cheapest month to book a flight from Orlando Airport to Chicago?
Currently, February is the cheapest month in which you can book a flight from Orlando Airport to Chicago (average of $179). Flying from Orlando Airport to Chicago in June is currently the most expensive (average of $371). 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.
What is the cheapest time of day to fly from MCO to CHI?
Find hourly flight availability from Orlando to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 15, 2026.
It’s typically best to fly out from Orlando Airport to Chicago in the evening. Doing so could potentially save you 44% on the flight price compared to flying at noon, which is usually more expensive.
Weekly flight availability from Orlando Airport to Chicago
Explore weekly flight availability from Orlando to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated November 15, 2026.
The most flights from MCO to CHI are scheduled on a Saturday (77 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (28 on average).
How much does it cost to fly round-trip from Orlando Airport to Chicago?
Airfare is below average for this route at the moment.
Orlando Airport to Chicago flights typically cost between $231 and $369 in December.The cheapest round-trip price found within the last 5 days was $205 on Frontier (Dec 2-Dec 5).
How often are flights from Orlando to Chicago delayed?
About 18% of weekly flights between Orlando and Chicago have experienced delays in the past year, with the average delay time being 144 minutes.
What is the most punctual flight time for Orlando to Chicago flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Wednesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Orlando to Chicago flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 9% of flights being delayed.
How far ahead should I book a flight from Orlando Airport to Chicago?
The best time to book flights from Orlando Airport to Chicago is 77 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest day to fly from Orlando Airport to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Orlando to Chicago. Price data was last updated on November 14, 2026.
Travelers seeking maximum savings on their Orlando Airport to Chicago flight should consider departing on Saturday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
The best insider tips for Orlando Airport to Chicago flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Orlando Airport to Chicago trip
Our travel experts
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 November 15, 2026.
See what other customers who have flown with Southwest,United Airlines, andJetBlue from Orlando Airport to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.4
Overall
8.0
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Entertainment
7.4
Overall
8.0
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Entertainment
7.4
Overall
8.0
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Entertainment
7.4
Overall
8.0
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Entertainment
7.4
Overall
8.0
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Entertainment
7.4
Overall
8.0
Boarding
8.1
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Related info for your journey
Find useful and relevant information for your journey from Orlando 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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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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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 November 15, 2026.
Complete your trip
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Orlando and Chicago flights
Browse other Orlando and Chicago flight options. Last updated on November 15, 2026.
Other flights from Orlando
Browse through other flights departing from Orlando. Flights are based on user searches made on Cheapflights and were last updated on November 15, 2026.
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Check out other popular destinations found by fellow travelers in 2026
Top 4 airlines flying from Orlando to Chicago
Discover the top 4 airlines that operate flights from Orlando 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 November 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$86 | Average$219 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$157 | Average$367 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$187 | Average$346 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$195 | Average$387 | FlexibilityNo cancel fee | On-time69% |