$111+ Cheap flights from Orlando (ORL) 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 11/13. Fares are subject to change and may not be available on all flights or dates of travel.
ORL — CHI
Nov 18 — Nov 251
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 53 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 October 19, 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 October 19, 2026.
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/49:15 am -
1 stop6h 40m
Fri 12/113:50 pm -
1 stop7h 24m
Deal found 10/14![Frontier logo]()
$202
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/198:07 am -
1 stop11h 38m
Sun 11/227:49 am -
1 stop26h 44m
Deal found 10/14![Frontier logo]()
$203
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/49:25 am -
1 stop9h 22m
Wed 11/116:08 am -
1 stop10h 16m
Deal found 10/14![Frontier logo]()
$203
This deal was found by Cheapflights users on 10/17. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/79:21 pm -
Nonstop3h 10m
Mon 11/99:51 am -
Nonstop2h 56m
Deal found 10/17![Frontier logo]()
$204
This Cheapflightsfares deal was found by Cheapflights users on 10/16. 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 11/66:30 am -
Nonstop3h 16m
Tue 11/107:35 pm -
1 stop11h 35m
Deal found 10/16![Frontier logo]()
$205
This Trip.com deal was found by Cheapflights users on 10/18. 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.
Thu 12/36:45 pm -
Nonstop3h 03m
Tue 12/812:28 pm -
1 stop7h 25m
Deal found 10/18![Frontier logo]()
$205
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/138:30 pm -
2 stops17h 21m
Mon 11/167:50 pm -
1 stop14h 59m
Deal found 10/15![Frontier logo]()
$206
This Cheapflightsfares deal was found by Cheapflights users on 10/18. 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 11/177:00 am -
1 stop11h 47m
Sat 11/212:40 pm -
1 stop5h 46m
Deal found 10/18![Frontier logo]()
$206
This CheapOair deal was found by Cheapflights users on 10/18. 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.
Fri 12/118:30 am -
Nonstop2h 57m
Wed 12/1610:50 am -
Nonstop2h 34m
Deal found 10/18![Allegiant Air logo]()
$207
This Orbitz deal was found by Cheapflights users on 10/16. 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.
Thu 12/310:50 pm -
Nonstop3h 09m
Sun 12/68:15 am -
1 stop11h 38m
Deal found 10/16![Frontier logo]()
$207
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1212:54 pm -
1 stop5h 53m
Sat 11/146:42 pm -
1 stop25h 56m
Deal found 10/15![Frontier logo]()
$207
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/287:00 am -
Nonstop2h 44m
Fri 10/308:44 am -
Nonstop2h 30m
Deal found 10/15![Allegiant Air logo]()
$208
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 October 19, 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 October 19, 2026.
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/48:30 am -
Nonstop2h 57m
Fri 12/1111:17 am -
Nonstop2h 36m
Deal found 10/14![Allegiant Air logo]()
$208
This Southwest deal was found by Cheapflights users on 10/18. 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 11/124:00 pm -
Nonstop3h 00m
Tue 11/178:10 am -
1 stop5h 05m
Deal found 10/18![Southwest logo]()
$266
This United Airlines deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/186:30 pm -
Nonstop3h 10m
Sun 11/227:45 pm -
Nonstop2h 54m
Deal found 10/16![United Airlines logo]()
$376
This JetBlue deal was found by Cheapflights users on 10/17. 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.
Thu 12/39:50 am -
1 stop14h 43m
Mon 12/72:59 pm -
1 stop19h 17m
Deal found 10/17![JetBlue logo]()
$404
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/296:30 am -
Nonstop2h 55m
Sat 1/26:42 pm -
Nonstop2h 34m
Deal found 10/15![Allegiant Air logo]()
$213
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/92:21 pm -
1 stop6h 35m
Thu 11/126:49 pm -
1 stop4h 32m
Deal found 10/14![American Airlines logo]()
$462
This Delta deal was found by Cheapflights users on 10/17. 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 11/225:30 am -
1 stop4h 55m
Sun 11/292:44 pm -
1 stop5h 28m
Deal found 10/17![Delta logo]()
$509
This CheapOair deal was found by Cheapflights users on 10/17. 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 11/256:15 am -
Nonstop2h 51m
Fri 11/276:04 pm -
Nonstop2h 32m
Deal found 10/17![Allegiant Air logo]()
$235
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:10 am -
Nonstop2h 44m
Sun 11/11:12 pm -
1 stop21h 32m
Deal found 10/15![Allegiant Air logo]()
$238
This Southwest deal was found by Cheapflights users on 10/18. 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 11/256:45 pm -
Nonstop3h 00m
Wed 12/24:25 pm -
Nonstop2h 35m
Deal found 10/18![Southwest logo]()
$300
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/36:18 pm -
2 stops19h 52m
Wed 12/97:27 am -
1 stop10h 28m
Deal found 10/15![Alaska Airlines logo]()
$619
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/258:15 am -
Nonstop2h 55m
Wed 12/306:42 pm -
Nonstop2h 34m
Deal found 10/14![Allegiant Air logo]()
$254
This CheapOair deal was found by Cheapflights users on 10/19. 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 12/261:50 pm -
1 stop22h 45m
Tue 12/296:00 pm -
1 stop18h 00m
Deal found 10/19![Contour logo]()
$689
This Southwest deal was found by Cheapflights users on 10/18. 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 11/185:40 pm -
Nonstop2h 50m
Sat 11/218:50 pm -
Nonstop2h 40m
Deal found 10/18![Southwest logo]()
$323
This Kissandfly.com deal was found by Cheapflights users on 10/19. 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.
Wed 11/412:56 pm -
Nonstop2h 48m
Fri 11/69:28 am -
Nonstop2h 36m
Deal found 10/19![Allegiant Air logo]()
$269
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.
Sun 12/2711:02 am -
Nonstop3h 13m
Sun 12/277:54 pm -
Nonstop2h 59m
Deal found 10/14![United Airlines logo]()
$402
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/177:20 pm -
Nonstop3h 00m
Tue 12/18:10 am -
Nonstop2h 40m
Deal found 10/14![Southwest logo]()
$357
This JetBlue deal was found by Cheapflights users on 10/18. 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.
Thu 10/2911:05 am -
1 stop9h 24m
Tue 11/31:00 pm -
1 stop8h 59m
Deal found 10/18![JetBlue logo]()
$436
This CheapOair deal was found by Cheapflights users on 10/18. 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.
Fri 12/187:05 am -
Nonstop2h 55m
Mon 12/219:50 am -
Nonstop2h 34m
Deal found 10/18![Allegiant Air logo]()
$280
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/55:00 pm -
Nonstop2h 55m
Thu 11/127:00 am -
Nonstop2h 45m
Deal found 10/14![Southwest logo]()
$357
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/296:51 pm -
1 stop5h 42m
Wed 12/302:32 pm -
1 stop6h 52m
Deal found 10/14![JetBlue logo]()
$438
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.
Sat 1/27:00 am -
Nonstop3h 18m
Tue 1/58:40 am -
Nonstop2h 55m
Deal found 10/14![United Airlines logo]()
$467
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/136:50 am -
Nonstop2h 48m
Sun 11/151:08 pm -
1 stop25h 48m
Deal found 10/14![Allegiant Air logo]()
$294
This Southwest deal was found by Cheapflights users on 10/18. 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 12/24:10 pm -
Nonstop2h 55m
Wed 12/93:00 pm -
Nonstop2h 40m
Deal found 10/18![Southwest logo]()
$367
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/247:25 pm -
1 stop5h 55m
Sat 3/272:20 pm -
1 stop5h 05m
Deal found 10/15![Southwest logo]()
$382
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.
Sat 10/249:10 am -
Nonstop3h 10m
Sat 10/242:30 pm -
Nonstop2h 58m
Deal found 10/15![United Airlines logo]()
$510
This CheapOair deal was found by Cheapflights users on 10/17. 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 12/233:57 pm -
Nonstop2h 55m
Fri 12/2511:00 am -
Nonstop2h 34m
Deal found 10/17![Allegiant Air logo]()
$325
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/223:00 pm -
1 stop4h 20m
Sat 11/286:10 pm -
Nonstop2h 40m
Deal found 10/15![Southwest logo]()
$386
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/266:51 pm -
1 stop5h 42m
Mon 12/282:32 pm -
1 stop6h 52m
Deal found 10/14![JetBlue logo]()
$568
This Booking.com deal was found by Cheapflights users on 10/16. 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.
Fri 11/136:50 am -
Nonstop2h 48m
Fri 11/206:08 pm -
Nonstop2h 32m
Deal found 10/16![Allegiant Air logo]()
$326
Last-minute flights from Orlando to ChicagoDiscover last-minute flight deals from Orlando to Chicago. Data last updated October 19, 2026 and is based on user searches.
Discover last-minute flight deals from Orlando to Chicago. Data last updated October 19, 2026 and is based on user searches.
This 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/253:38 pm -
Nonstop3h 15m
Sun 11/19:51 am -
Nonstop2h 52m
Deal found 10/15![Frontier logo]()
$214
This CheapOair deal was found by Cheapflights users on 10/18. 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.
Tue 10/275:03 pm -
1 stop26h 13m
Thu 10/299:51 am -
Nonstop2h 52m
Deal found 10/18![Frontier logo]()
$204
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/287:00 am -
Nonstop2h 44m
Fri 10/308:44 am -
Nonstop2h 30m
Deal found 10/15![Allegiant Air logo]()
$208
This FlightHub deal was found by Cheapflights users on 10/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/282:48 pm -
Nonstop3h 15m
Wed 11/49:51 am -
Nonstop2h 52m
Deal found 10/16![Frontier logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 10/306:10 am -
Nonstop2h 44m
Sun 11/11:12 pm -
1 stop21h 32m
Deal found 10/19![Allegiant Air logo]()
$213
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/49:25 am -
1 stop9h 22m
Wed 11/116:08 am -
1 stop10h 16m
Deal found 10/14![Frontier logo]()
$203
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/49:25 am -
1 stop9h 22m
Mon 11/96:08 am -
1 stop10h 16m
Deal found 10/14![Frontier logo]()
$208
This Expedia deal was found by Cheapflights users on 10/17. 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.
Sat 11/74:48 pm -
1 stop7h 59m
Mon 11/96:08 am -
1 stop10h 16m
Deal found 10/17![Frontier logo]()
$213
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1212:54 pm -
1 stop5h 53m
Sat 11/146:42 pm -
1 stop25h 56m
Deal found 10/15![Frontier logo]()
$207
This Cheapflightsfares deal was found by Cheapflights users on 10/18. 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 11/177:00 am -
1 stop11h 47m
Sat 11/212:40 pm -
1 stop5h 46m
Deal found 10/18![Frontier logo]()
$206
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/236:40 am -
1 stop6h 41m
Fri 11/271:29 pm -
1 stop6h 57m
Deal found 10/15![Frontier logo]()
$211
This CheapOair deal was found by Cheapflights users on 10/19. 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.
Thu 11/268:56 am -
1 stop24h 16m
Fri 11/278:42 pm -
Nonstop2h 43m
Deal found 10/19![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 October 19, 2026.
Search for one-way flight options from Orlando to Chicago. Find affordable one-way fares based on user searches. Data last updated October 19, 2026.
This Trip.com deal was found by Cheapflights users on 10/16. 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.
Fri 11/136:50 am -
Nonstop2h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Allegiant Air logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 11/164:48 pm -
1 stop26h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Frontier logo]()
$111
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/54:48 pm -
1 stop7h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Frontier logo]()
$111
This Trip.com deal was found by Cheapflights users on 10/16. 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.
Sat 12/127:10 am -
1 stop5h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Frontier logo]()
$112
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/217:45 am -
1 stop29h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Frontier logo]()
$113
This Booking.com deal was found by Cheapflights users on 10/19. 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.
Thu 11/124:48 pm -
1 stop7h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Frontier logo]()
$113
This Super.com deal was found by Cheapflights users on 10/16. 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.
Sat 11/145:55 am -
1 stop19h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Frontier logo]()
$114
This Cheapflightsfares deal was found by Cheapflights users on 10/16. 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 12/19:55 pm -
1 stop12h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Frontier logo]()
$114
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/177:03 pm -
2 stops24h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Frontier logo]()
$115
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/308:08 pm -
1 stop4h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Frontier logo]()
$115
This Cheapflightsfares deal was found by Cheapflights users on 10/16. 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 1/247:01 am -
1 stop5h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Frontier logo]()
$116
This Frontier deal was found by Cheapflights users on 10/16. 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 11/107:00 am -
1 stop11h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Frontier logo]()
$116
Find flight deals from Orlando to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Orlando (ORL) 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 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $202 (CheapOair) |
One-way from | $111 (Trip.com) |
Popular in | June |
Cheapest in | February |
Average price | $265 |
Good round-trip deal | $158 or less |
Good one-way deal | $62 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 October 19, 2026.
Use the filters below to find and compare flights from Orlando to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
OrlandoChicago
MCO Orlando - MDW Chicago Midway
MCOMDW
Orlando
Sat 12/19
7:35 pm-9:30 pm
Nonstop2h 55m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$117
OrlandoChicago
MCO Orlando - MDW Chicago Midway
MCOMDW
Orlando
Sat 11/21
9:10 pm-11:05 pm
Nonstop2h 55m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$117
OrlandoChicago
SFB Orlando Sanford Intl - RFD Chicago Greater Rockford
SFBRFD
Orlando Sanford Intl
Fri 12/11
8:30 am-10:27 am
Nonstop2h 57m
Chicago Greater Rockford
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$132
OrlandoChicago
SFB Orlando Sanford Intl - ORD Chicago O'Hare Intl
SFBORD
Orlando Sanford Intl
Fri 11/13
6:35 am-3:37 pm
2 stops34h 02m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$135
OrlandoChicago
SFB Orlando Sanford Intl - RFD Chicago Greater Rockford
SFBRFD
Orlando Sanford Intl
Wed 12/23
3:57 pm-5:52 pm
Nonstop2h 55m
Chicago Greater Rockford
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$137
Quickest round-trip
OrlandoChicago
SFB Orlando Sanford Intl - RFD Chicago Greater Rockford
SFBRFD
Orlando Sanford Intl
Fri 10/23
6:10 am-7:54 am
Nonstop2h 44m
Chicago Greater Rockford
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$142
OrlandoChicago
SFB Orlando Sanford Intl - RFD Chicago Greater Rockford
SFBRFD
Orlando Sanford Intl
Fri 11/13
6:50 am-8:38 am
Nonstop2h 48m
Chicago Greater Rockford
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$146
OrlandoChicago
SFB Orlando Sanford Intl - RFD Chicago Greater Rockford
SFBRFD
Orlando Sanford Intl
Mon 10/26
8:10 am-9:54 am
Nonstop2h 44m
Chicago Greater Rockford
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$148
OrlandoChicago
MCO Orlando - ORD Chicago O'Hare Intl
MCOORD
Orlando
Sun 12/27
8:18 pm-6:40 pm
1 stop23h 22m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$178
OrlandoChicago
MCO Orlando - ORD Chicago O'Hare Intl
MCOORD
Orlando
Tue 3/9
4:30 pm-9:47 pm
1 stop6h 17m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$179
Showing 1-10 of 60 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 October.
| 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 Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy- | 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-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Orlando-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Orlando-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Orlando-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-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.
ORL-CHI
MCO-MDW
MCO-ORD
SFB-RFD
SFB-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 to Chicago
ORL-CHI
MCO-MDW
MCO-ORD
SFB-RFD
SFB-ORD
What is the cheapest month to book a flight from Orlando to Chicago?
Currently, February is the cheapest month in which you can book a flight from Orlando to Chicago (average of $168). Flying from Orlando to Chicago in June is currently the most expensive (average of $357). 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 ORL 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 October 19, 2026.
One of the essential ways to save on airfare from Orlando to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 49% on airfare.
Weekly flight availability from Orlando 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 October 19, 2026.
The most flights from ORL to CHI are scheduled on a Sunday (83 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (50 on average).
How much does it cost to fly round-trip from Orlando to Chicago?
Airfare is typical for this route at the moment.
Orlando to Chicago flights typically cost between $128 and $415 in December.The cheapest round-trip price found within the last 5 days was $202 on Frontier (Dec 4-Dec 11).
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 to Chicago?
To ensure you get the cheapest price possible for a flight from Orlando to Chicago, you should look to book at least 77 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest day to fly from Orlando to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Orlando to Chicago. Price data was last updated on October 17, 2026.
Travelers seeking maximum savings on their Orlando 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.
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 19, 2026.
Read through reviews of airlines operating flights from Orlando to Chicago, such as Southwest,United Airlines, andJetBlue. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Entertainment
7.5
Overall
7.9
Boarding
8.1
Food
7.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Overall
7.9
Boarding
8.1
Food
7.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Overall
7.9
Boarding
8.1
Food
7.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Overall
7.9
Boarding
8.1
Food
7.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Overall
7.9
Boarding
8.1
Food
7.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Overall
7.9
Boarding
8.1
Food
7.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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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 19, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Orlando to Chicago by cabin class
Find flights from Orlando to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Orlando and Chicago flights
Browse other Orlando and Chicago flight options. Last updated on October 19, 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 October 19, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 5 airlines flying from Orlando to Chicago
Discover the top 5 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 October 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$68 | Average$213 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$96 | Average$192 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$155 | Average$339 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$161 | Average$368 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$176 | Average$340 | FlexibilityNo cancel fee | On-time71% |