$104+ 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 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — CHI
Oct 29 — Nov 51
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 Friday or Thursday 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 September 29, 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 September 29, 2026.
This Orbitz deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/289:25 am -
1 stop9h 51m
Wed 11/47:28 pm -
1 stop10h 33m
Deal found 9/28![Frontier logo]()
$189
This Travelocity deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2212:52 pm -
1 stop6h 39m
Mon 10/267:44 pm -
1 stop11h 26m
Deal found 9/28![Frontier logo]()
$190
This Cheapflightsfares deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/239:25 am -
1 stop10h 06m
Tue 10/277:15 am -
1 stop9h 09m
Deal found 9/27![Frontier logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/37:04 am -
1 stop6h 47m
Tue 11/107:28 pm -
1 stop11h 42m
Deal found 9/29![Frontier logo]()
$192
This Cheapflightsfares deal was found by Cheapflights users on 9/24. 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.
Thu 10/2212:52 pm -
1 stop6h 39m
Thu 10/2910:26 am -
1 stop5h 58m
Deal found 9/24![Frontier logo]()
$193
This Cheapflightsfares deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/214:53 pm -
1 stop7h 50m
Tue 10/279:53 am -
1 stop10h 45m
Deal found 9/28![Frontier logo]()
$193
This CheapOair deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/217:10 am -
1 stop5h 22m
Sat 10/246:00 am -
1 stop10h 21m
Deal found 9/28![Frontier logo]()
$194
This Expedia deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2212:52 pm -
1 stop6h 39m
Sun 10/257:44 pm -
1 stop11h 24m
Deal found 9/28![Frontier logo]()
$195
This Expedia deal was found by Cheapflights users on 9/24. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/279:25 am -
1 stop9h 02m
Tue 11/36:16 am -
1 stop10h 08m
Deal found 9/24![Frontier logo]()
$195
This Kiwi.com deal was found by Cheapflights users on 9/24. 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 11/512:54 pm -
1 stop6h 51m
Tue 11/107:28 pm -
1 stop11h 42m
Deal found 9/24![Frontier logo]()
$196
This Cheapflightsfares deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/37:04 am -
1 stop6h 47m
Thu 11/510:26 am -
1 stop10h 12m
Deal found 9/28![Frontier logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 9/24. 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 11/512:54 pm -
1 stop6h 51m
Mon 11/97:50 pm -
1 stop11h 20m
Deal found 9/24![Frontier logo]()
$198
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 September 29, 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 September 29, 2026.
This Southwest deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/119:25 am -
Nonstop2h 55m
Wed 11/184:25 pm -
Nonstop2h 35m
Deal found 9/27![Southwest logo]()
$347
This JetBlue deal was found by Cheapflights users on 9/25. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:50 pm -
1 stop5h 43m
Tue 12/82:59 pm -
1 stop6h 09m
Deal found 9/25![JetBlue logo]()
$353
This Delta deal was found by Cheapflights users on 9/24. 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 12/287:45 pm -
1 stop5h 14m
Wed 1/67:10 am -
1 stop5h 27m
Deal found 9/24![Delta logo]()
$388
This United Airlines deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:30 pm -
Nonstop3h 10m
Mon 11/27:15 am -
Nonstop2h 52m
Deal found 9/28![United Airlines logo]()
$457
This Alaska Airlines deal was found by Cheapflights users on 9/25. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:21 pm -
2 stops25h 16m
Mon 11/92:15 pm -
1 stop14h 01m
Deal found 9/25![Alaska Airlines logo]()
$658
This Southwest deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/39:25 am -
Nonstop2h 55m
Sat 12/56:30 pm -
Nonstop2h 40m
Deal found 9/28![Southwest logo]()
$352
This Southwest deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/278:00 am -
Nonstop2h 50m
Sat 10/318:15 am -
1 stop5h 40m
Deal found 9/27![Southwest logo]()
$353
This Delta deal was found by Cheapflights users on 9/26. 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 10/39:00 am -
1 stop4h 58m
Wed 10/76:30 am -
1 stop6h 01m
Deal found 9/26![Delta logo]()
$415
This Southwest deal was found by Cheapflights users on 9/24. 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 11/35:40 pm -
Nonstop2h 50m
Sat 11/78:25 am -
1 stop4h 55m
Deal found 9/24![Southwest logo]()
$353
This United Airlines deal was found by Cheapflights users on 9/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/108:20 am -
Nonstop3h 05m
Sun 12/136:00 am -
Nonstop2h 48m
Deal found 9/26![United Airlines logo]()
$473
This Southwest deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/228:10 am -
Nonstop2h 50m
Sat 10/245:25 pm -
Nonstop2h 35m
Deal found 9/29![Southwest logo]()
$357
This Southwest deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/274:20 pm -
1 stop4h 20m
Tue 11/35:20 am -
Nonstop2h 30m
Deal found 9/28![Southwest logo]()
$358
This United Airlines deal was found by Cheapflights users on 9/24. 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 10/69:10 am -
Nonstop3h 10m
Thu 10/87:57 pm -
Nonstop2h 57m
Deal found 9/24![United Airlines logo]()
$522
This Southwest deal was found by Cheapflights users on 9/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2610:35 pm -
Nonstop2h 50m
Mon 11/21:20 pm -
1 stop5h 35m
Deal found 9/26![Southwest logo]()
$363
This Southwest deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/228:10 am -
Nonstop2h 50m
Mon 10/264:15 pm -
1 stop4h 00m
Deal found 9/28![Southwest logo]()
$363
This Alaska Airlines deal was found by Cheapflights users on 9/25. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/126:00 am -
2 stops18h 59m
Mon 12/147:27 am -
1 stop20h 39m
Deal found 9/25![Alaska Airlines logo]()
$668
This Southwest deal was found by Cheapflights users on 9/24. 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 10/278:00 am -
Nonstop2h 50m
Fri 10/303:45 pm -
Nonstop2h 35m
Deal found 9/24![Southwest logo]()
$366
This Alaska Airlines deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/195:21 pm -
2 stops13h 19m
Mon 11/232:16 pm -
1 stop13h 53m
Deal found 9/29![Alaska Airlines logo]()
$698
This Southwest deal was found by Cheapflights users on 9/24. 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 10/3112:30 pm -
Nonstop2h 50m
Sun 11/18:40 pm -
Nonstop2h 35m
Deal found 9/24![Southwest logo]()
$368
This Alaska Airlines deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/166:00 am -
2 stops18h 59m
Wed 12/307:00 am -
1 stop21h 23m
Deal found 9/27![Alaska Airlines logo]()
$711
This Southwest deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/267:10 am -
Nonstop2h 55m
Mon 11/302:30 pm -
Nonstop2h 35m
Deal found 9/28![Southwest logo]()
$373
This Alaska Airlines deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/106:00 am -
2 stops24h 37m
Wed 12/167:27 am -
1 stop10h 28m
Deal found 9/27![Alaska Airlines logo]()
$716
This Southwest deal was found by Cheapflights users on 9/24. 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 10/1411:05 am -
Nonstop2h 50m
Tue 10/2011:10 am -
Nonstop2h 35m
Deal found 9/24![Southwest logo]()
$376
This Alaska Airlines deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/224:49 pm -
2 stops26h 31m
Sun 10/257:49 pm -
1 stop32h 38m
Deal found 9/28![Alaska Airlines logo]()
$759
Last-minute flights from Orlando to ChicagoDiscover last-minute flight deals from Orlando to Chicago. Data last updated September 29, 2026 and is based on user searches.
Discover last-minute flight deals from Orlando to Chicago. Data last updated September 29, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/78:51 pm -
Nonstop3h 08m
Mon 11/27:50 pm -
1 stop11h 20m
Deal found 9/27![Frontier logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 9/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/209:48 pm -
2 stops26h 55m
Tue 10/279:53 am -
1 stop6h 31m
Deal found 9/26![Frontier logo]()
$205
This Cheapflightsfares deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/214:53 pm -
1 stop7h 50m
Tue 10/279:53 am -
1 stop10h 45m
Deal found 9/28![Frontier logo]()
$193
This CheapOair deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/214:53 pm -
1 stop7h 50m
Sat 10/246:21 am -
1 stop10h 00m
Deal found 9/27![Frontier logo]()
$211
This Cheapflightsfares deal was found by Cheapflights users on 9/25. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/224:53 pm -
1 stop7h 50m
Sat 10/246:21 am -
1 stop10h 00m
Deal found 9/25![Frontier logo]()
$198
This Travelocity deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/224:53 pm -
1 stop7h 50m
Tue 10/279:53 am -
1 stop10h 45m
Deal found 9/27![Frontier logo]()
$200
This Cheapflightsfares deal was found by Cheapflights users on 9/24. 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.
Thu 10/2212:52 pm -
1 stop5h 53m
Thu 10/296:16 am -
1 stop10h 08m
Deal found 9/24![Frontier logo]()
$203
This Kiwi.com deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:25 am -
2 stops18h 18m
Mon 10/266:15 am -
1 stop24h 55m
Deal found 9/28![Frontier logo]()
$207
This CheapOair deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/242:52 pm -
1 stop9h 51m
Tue 10/279:53 am -
1 stop6h 31m
Deal found 9/28![Frontier logo]()
$208
This Expedia deal was found by Cheapflights users on 9/24. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/279:25 am -
1 stop9h 02m
Tue 11/36:16 am -
1 stop10h 08m
Deal found 9/24![Frontier logo]()
$195
This Kiwi.com deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:25 am -
2 stops18h 22m
Sat 10/317:25 am -
1 stop13h 13m
Deal found 9/28![Frontier logo]()
$206
This Expedia deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/287:04 am -
1 stop11h 43m
Wed 11/46:42 pm -
1 stop11h 19m
Deal found 9/28![Frontier logo]()
$209
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 September 29, 2026.
Search for one-way flight options from Orlando to Chicago. Find affordable one-way fares based on user searches. Data last updated September 29, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/239:48 pm -
2 stops26h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Frontier logo]()
$104
This Kiwi.com deal was found by Cheapflights users on 9/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2212:52 pm -
1 stop6h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Frontier logo]()
$105
This Trip.com deal was found by Cheapflights users on 9/24. 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.
Wed 10/214:53 pm -
1 stop7h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Frontier logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/25:25 am -
1 stop14h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Frontier logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 9/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/264:53 pm -
1 stop20h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Frontier logo]()
$108
This Cheapflightsfares deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/239:25 am -
1 stop10h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Frontier logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/285:03 pm -
1 stop7h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Frontier logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1412:55 pm -
1 stop19h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Frontier logo]()
$110
This Kiwi.com deal was found by Cheapflights users on 9/24. 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.
Sat 11/216:40 am -
1 stop7h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Frontier logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 9/24. 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.
Sun 11/16:07 am -
1 stop28h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Frontier logo]()
$112
This Kiwi.com deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/242:52 pm -
1 stop9h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Frontier logo]()
$113
This Cheapflightsfares deal was found by Cheapflights users on 9/24. 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 11/147:04 am -
1 stop6h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Frontier logo]()
$114
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 September 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $188 (Cheapflightsfares) |
One-way from | $104 (Kiwi.com) |
Popular in | July |
Cheapest in | February |
Average price | $263 |
Good round-trip deal | $285 or less |
Good one-way deal | $170 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 September 29, 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
Fri 12/25
10:54 am-6:45 pm
1 stop8h 51m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$163
OrlandoChicago
MCO Orlando - ORD Chicago O'Hare Intl
MCOORD
Orlando
Tue 12/1
8:20 am-10:25 am
Nonstop3h 05m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$174
OrlandoChicago
MCO Orlando - MDW Chicago Midway
MCOMDW
Orlando
Wed 1/6
4:55 pm-6:50 pm
Nonstop2h 55m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$174
Quickest round-trip
OrlandoChicago
MCO Orlando - MDW Chicago Midway
MCOMDW
Orlando
Sat 10/31
4:25 pm-6:15 pm
Nonstop2h 50m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$174
OrlandoChicago
MCO Orlando - MDW Chicago Midway
MCOMDW
Orlando
Wed 1/20
7:00 am-8:55 am
Nonstop2h 55m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$174
OrlandoChicago
MCO Orlando - MDW Chicago Midway
MCOMDW
Orlando
Tue 11/17
2:35 pm-4:35 pm
Nonstop3h 00m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$174
OrlandoChicago
MCO Orlando - MDW Chicago Midway
MCOMDW
Orlando
Thu 10/29
6:30 pm-8:20 pm
Nonstop2h 50m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$179
OrlandoChicago
MCO Orlando - MDW Chicago Midway
MCOMDW
Orlando
Mon 11/9
9:05 pm-11:00 pm
Nonstop2h 55m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$179
OrlandoChicago
MCO Orlando - ORD Chicago O'Hare Intl
MCOORD
Orlando
Sat 11/21
4:45 pm-8:49 pm
1 stop5h 04m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$184
OrlandoChicago
MCO Orlando - MDW Chicago Midway
MCOMDW
Orlando
Wed 3/24
11:45 am-4:25 pm
1 stop5h 40m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$184
Showing 1-10 of 45 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 September.
| 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 Accuracy2 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | 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-MDW
MCO-ORD
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-MDW
MCO-ORD
What is the cheapest month to book a flight from Orlando Airport to Chicago?
Currently, January is the cheapest month in which you can book a flight from Orlando Airport to Chicago (average of $168). 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 September 29, 2026.
It’s typically best to fly out from Orlando Airport to Chicago in the evening. Doing so could potentially save you 49% 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 September 29, 2026.
The most flights from MCO to CHI are scheduled on a Monday (74 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (36 on average).
How much does it cost to fly round-trip from Orlando Airport to Chicago?
Airfare is typical for this route at the moment.
Orlando Airport to Chicago flights typically cost between $160 and $327 in October.The cheapest round-trip price found within the last 5 days was $188 on Frontier (Oct 14-Oct 21).
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 69 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 September 26, 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 September 29, 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.
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
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
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Other flights to Chicago
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Orlando and Chicago flights
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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 September 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$68 | Average$205 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$157 | Average$332 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$159 | Average$351 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$173 | Average$337 | FlexibilityNo cancel fee | On-time71% |