$104+ Cheap flights from Orlando (ORL) to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/11. Fares are subject to change and may not be available on all flights or dates of travel.
ORL — CHI
Oct 1 — Oct 81
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 September, booked 13 days in advance, depart on a Friday or Thursday and return on a Friday
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 1, 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 1, 2026.
This CheapOair deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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
Mon 12/1411:17 am -
Nonstop2h 36m
Deal found 8/31![Allegiant Air logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:14 am -
1 stop5h 37m
Thu 9/1711:15 am -
Nonstop2h 53m
Deal found 8/27![Frontier logo]()
$176
This Expedia deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/268:51 pm -
Nonstop3h 08m
Wed 9/303:50 pm -
Nonstop2h 56m
Deal found 8/27![Frontier logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/147:00 am -
Nonstop2h 44m
Mon 10/1910:39 am -
Nonstop2h 30m
Deal found 8/31![Allegiant Air logo]()
$178
This Booking.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/125:20 am -
Nonstop3h 11m
Mon 10/198:26 am -
Nonstop2h 39m
Deal found 8/28![Frontier logo]()
$178
This CheapOair deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/108:10 am -
Nonstop3h 10m
Fri 9/113:50 pm -
Nonstop2h 56m
Deal found 8/31![Frontier logo]()
$179
This Cheapflightsfares deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 9/59:00 pm -
Nonstop3h 08m
Wed 9/93:50 pm -
Nonstop2h 56m
Deal found 9/1![Frontier logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/248:10 am -
Nonstop3h 10m
Mon 9/287:28 pm -
1 stop11h 41m
Deal found 8/28![Frontier logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/88:29 am -
1 stop28h 22m
Tue 9/153:50 pm -
Nonstop2h 56m
Deal found 8/27![Frontier logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/18:51 pm -
Nonstop3h 08m
Tue 10/67:25 am -
1 stop7h 34m
Deal found 8/28![Frontier logo]()
$185
This CheapOair deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/26:15 am -
Nonstop2h 44m
Mon 10/510:44 am -
Nonstop2h 30m
Deal found 8/28![Allegiant Air logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/178:10 am -
Nonstop3h 10m
Wed 9/237:25 am -
1 stop11h 23m
Deal found 8/27![Frontier logo]()
$186
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 1, 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 1, 2026.
This CheapOair deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/26:15 am -
Nonstop2h 44m
Mon 10/510:44 am -
Nonstop2h 30m
Deal found 8/28![Allegiant Air logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/127:40 am -
1 stop5h 38m
Sun 11/1510:30 am -
2 stops34h 08m
Deal found 8/29![Multiple Airlines logo]()
$187
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/218:05 pm -
Nonstop2h 55m
Thu 10/228:40 pm -
Nonstop2h 35m
Deal found 8/27![Southwest logo]()
$237
This Delta deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:00 am -
1 stop7h 47m
Mon 11/21:27 pm -
1 stop6h 27m
Deal found 8/27![Delta logo]()
$257
This United Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/89:10 am -
Nonstop3h 10m
Mon 10/127:15 am -
1 stop5h 42m
Deal found 8/27![United Airlines logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:10 am -
Nonstop2h 42m
Sun 9/133:53 pm -
1 stop23h 04m
Deal found 8/27![Allegiant Air logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:40 am -
1 stop7h 46m
Sun 10/410:08 am -
2 stops21h 01m
Deal found 8/28![Multiple Airlines logo]()
$197
This KAYAK deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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.
Sun 9/206:15 am -
Nonstop3h 14m
Thu 9/248:05 am -
1 stop6h 55m
Deal found 8/31![American Airlines logo]()
$401
This Kiwi.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/147:00 am -
Nonstop2h 44m
Sun 10/181:12 pm -
1 stop21h 52m
Deal found 8/31![Allegiant Air logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/286:24 pm -
1 stop18h 58m
Sun 11/11:12 pm -
1 stop22h 31m
Deal found 8/31![Multiple Airlines logo]()
$207
This Booking.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:50 am -
Nonstop2h 42m
Fri 9/259:42 am -
Nonstop2h 34m
Deal found 8/28![Allegiant Air logo]()
$204
This Sun Country Air deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/278:53 pm -
1 stop13h 03m
Sun 11/297:35 pm -
1 stop14h 14m
Deal found 8/29![Sun Country Air logo]()
$535
This Booking.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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.
Mon 9/217:50 am -
Nonstop2h 42m
Mon 9/2810:22 am -
Nonstop2h 34m
Deal found 8/31![Allegiant Air logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/275:03 pm -
2 stops40h 47m
Thu 11/51:08 pm -
1 stop9h 19m
Deal found 8/28![Multiple Airlines logo]()
$246
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/164:00 pm -
1 stop5h 15m
Sun 10/185:25 pm -
Nonstop2h 35m
Deal found 8/27![Southwest logo]()
$323
This CheapOair deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:10 am -
Nonstop2h 42m
Fri 9/189:42 am -
Nonstop2h 34m
Deal found 8/28![Allegiant Air logo]()
$221
This Alaska Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 10/25:13 pm -
2 stops14h 07m
Tue 10/67:20 am -
1 stop10h 36m
Deal found 9/1![Alaska Airlines logo]()
$648
This United Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/59:55 am -
Nonstop3h 04m
Sat 9/56:03 pm -
Nonstop2h 57m
Deal found 8/28![United Airlines logo]()
$327
This Kiwi.com deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 10/227:40 am -
1 stop5h 42m
Sun 10/2510:20 am -
2 stops20h 48m
Deal found 9/1![Multiple Airlines logo]()
$259
This Southwest deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/37:45 am -
Nonstop2h 50m
Tue 10/275:45 am -
Nonstop2h 35m
Deal found 8/29![Southwest logo]()
$327
This Kiwi.com deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 10/166:15 am -
Nonstop2h 44m
Thu 10/229:40 am -
2 stops36h 59m
Deal found 8/30![Allegiant Air logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/218:52 am -
2 stops24h 58m
Thu 10/291:12 pm -
1 stop9h 15m
Deal found 8/29![Multiple Airlines logo]()
$265
This Southwest deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/105:15 pm -
Nonstop2h 50m
Sat 9/127:50 am -
1 stop4h 05m
Deal found 8/29![Southwest logo]()
$333
This United Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/22:24 pm -
Nonstop3h 05m
Mon 10/53:35 pm -
Nonstop2h 56m
Deal found 8/31![United Airlines logo]()
$369
This CheapOair deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 9/117:10 am -
Nonstop2h 42m
Mon 9/1410:22 am -
Nonstop2h 34m
Deal found 8/30![Allegiant Air logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:40 am -
1 stop5h 42m
Thu 10/299:40 am -
2 stops21h 30m
Deal found 8/29![Multiple Airlines logo]()
$276
This United Airlines deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1112:35 pm -
Nonstop3h 04m
Mon 9/146:07 pm -
Nonstop2h 56m
Deal found 8/30![United Airlines logo]()
$373
This Southwest deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/84:30 pm -
1 stop4h 40m
Sat 10/107:00 pm -
Nonstop2h 40m
Deal found 8/31![Southwest logo]()
$348
This Kiwi.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 11/110:20 am -
2 stops21h 10m
Deal found 8/31![Allegiant Air logo]()
$253
This United Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/158:24 pm -
Nonstop3h 05m
Mon 11/161:30 pm -
1 stop5h 45m
Deal found 8/29![United Airlines logo]()
$379
Last-minute flights from Orlando to ChicagoDiscover last-minute flight deals from Orlando to Chicago. Data last updated September 1, 2026 and is based on user searches.
Discover last-minute flight deals from Orlando to Chicago. Data last updated September 1, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 9/19:00 pm -
Nonstop3h 08m
Sat 9/57:44 pm -
Nonstop2h 45m
Deal found 8/30![Frontier logo]()
$185
This Expedia deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 9/19:00 pm -
Nonstop3h 08m
Fri 9/113:50 pm -
Nonstop2h 56m
Deal found 8/30![Frontier logo]()
$187
This Cheapflightsfares deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 9/59:00 pm -
Nonstop3h 08m
Wed 9/93:50 pm -
Nonstop2h 56m
Deal found 9/1![Frontier logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/88:29 am -
1 stop28h 22m
Tue 9/153:50 pm -
Nonstop2h 56m
Deal found 8/27![Frontier logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:14 am -
1 stop5h 37m
Thu 9/1711:15 am -
Nonstop2h 53m
Deal found 8/27![Frontier logo]()
$176
This CheapOair deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/108:10 am -
Nonstop3h 10m
Fri 9/113:50 pm -
Nonstop2h 56m
Deal found 8/31![Frontier logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/178:10 am -
Nonstop3h 10m
Wed 9/237:25 am -
1 stop11h 23m
Deal found 8/27![Frontier logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/188:51 pm -
Nonstop3h 08m
Mon 9/216:20 am -
2 stops15h 14m
Deal found 8/28![Multiple Airlines logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/248:10 am -
Nonstop3h 10m
Mon 9/287:28 pm -
1 stop11h 41m
Deal found 8/28![Frontier logo]()
$183
This Expedia deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/268:51 pm -
Nonstop3h 08m
Wed 9/303:50 pm -
Nonstop2h 56m
Deal found 8/27![Frontier logo]()
$177
This CheapOair deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/26:15 am -
Nonstop2h 44m
Mon 10/510:44 am -
Nonstop2h 30m
Deal found 8/28![Allegiant Air logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/147:00 am -
Nonstop2h 44m
Mon 10/1910:39 am -
Nonstop2h 30m
Deal found 8/31![Allegiant Air logo]()
$178
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 1, 2026.
Search for one-way flight options from Orlando to Chicago. Find affordable one-way fares based on user searches. Data last updated September 1, 2026.
This Trip.com deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 9/1112:50 pm -
1 stop11h 54m
Deal found 9/1![Frontier logo]()
$104
This Trip.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/129:30 am -
1 stop9h 53m
Deal found 8/31![Frontier logo]()
$105
This Trip.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/912:50 pm -
1 stop6h 01m
Deal found 8/31![Frontier logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/83:16 pm -
1 stop28h 07m
Deal found 8/31![Frontier logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 9/83:16 pm -
1 stop27h 35m
Deal found 8/30![Frontier logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/1012:50 pm -
1 stop6h 33m
Deal found 8/31![Frontier logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 9/109:30 am -
1 stop9h 16m
Deal found 8/30![Frontier logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/287:03 pm -
1 stop25h 56m
Deal found 8/27![Frontier logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:24 pm -
1 stop18h 54m
Deal found 8/27![Multiple Airlines logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/55:23 pm -
1 stop15h 30m
Deal found 8/27![Frontier logo]()
$110
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2611:49 am -
1 stop7h 38m
Deal found 8/27![Frontier logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/305:19 pm -
2 stops22h 26m
Deal found 8/27![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 (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 September 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $176 (CheapOair) |
One-way from | $105 (Trip.com) |
Popular in | June |
Cheapest in | February |
Average price | $158 |
Good round-trip deal | $196 or less |
Good one-way deal | $76 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 1, 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
Quickest round-trip
OrlandoChicago
SFB Orlando Sanford Intl - RFD Chicago Greater Rockford
SFBRFD
Orlando Sanford Intl
Fri 10/2
6:15 am-7:59 am
Nonstop2h 44m
Chicago Greater Rockford
Mon 10/5
10:44 am-2:14 pm
Nonstop2h 30m
$186
OrlandoChicago
MCO Orlando - RFD Chicago Greater Rockford
MCORFD
Orlando
Thu 11/12
7:40 am-12:18 pm
1 stop5h 38m
Chicago Greater Rockford
Sun 11/15
10:30 am-9:38 pm
2 stops34h 08m
$187
OrlandoChicago
SFB Orlando Sanford Intl - RFD Chicago Greater Rockford
SFBRFD
Orlando Sanford Intl
Fri 9/11
7:10 am-8:52 am
Nonstop2h 42m
Chicago Greater Rockford
Sun 9/13
3:53 pm-3:57 pm
1 stop23h 04m
$191
OrlandoChicago
SFB Orlando Sanford Intl - RFD Chicago Greater Rockford
SFBRFD
Orlando Sanford Intl
Wed 10/14
7:00 am-8:44 am
Nonstop2h 44m
Chicago Greater Rockford
Sun 10/18
1:12 pm-12:04 pm
1 stop21h 52m
$194
OrlandoChicago
MCO Orlando - RFD Chicago Greater Rockford
MCORFD
Orlando
Thu 10/1
7:40 am-2:26 pm
1 stop7h 46m
Chicago Greater Rockford
Sun 10/4
10:08 am-8:09 am
2 stops21h 01m
$197
OrlandoChicago
SFB Orlando Sanford Intl - RFD Chicago Greater Rockford
SFBRFD
Orlando Sanford Intl
Mon 9/21
7:50 am-9:32 am
Nonstop2h 42m
Chicago Greater Rockford
Fri 9/25
9:42 am-1:16 pm
Nonstop2h 34m
$204
OrlandoChicago
MCO Orlando - RFD Chicago Greater Rockford
MCORFD
Orlando
Wed 10/28
6:24 pm-12:22 pm
1 stop18h 58m
Chicago Greater Rockford
Sun 11/1
1:12 pm-12:43 pm
1 stop22h 31m
$207
OrlandoChicago
SFB Orlando Sanford Intl - RFD Chicago Greater Rockford
SFBRFD
Orlando Sanford Intl
Mon 9/21
7:50 am-9:32 am
Nonstop2h 42m
Chicago Greater Rockford
Mon 9/28
10:22 am-1:56 pm
Nonstop2h 34m
$211
OrlandoChicago
SFB Orlando Sanford Intl - RFD Chicago Greater Rockford
SFBRFD
Orlando Sanford Intl
Fri 9/11
7:10 am-8:52 am
Nonstop2h 42m
Chicago Greater Rockford
Fri 9/18
9:42 am-1:16 pm
Nonstop2h 34m
$221
OrlandoChicago
SFB Orlando Sanford Intl - RFD Chicago Greater Rockford
SFBRFD
Orlando Sanford Intl
Fri 10/16
6:15 am-7:59 am
Nonstop2h 44m
Chicago Greater Rockford
Thu 10/22
9:40 am-11:39 pm
2 stops36h 59m
$232
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 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*1 star | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| 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
SFB-RFD
MCO-ORD
MCO-MDW
MCO-RFD
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
SFB-RFD
MCO-ORD
MCO-MDW
MCO-RFD
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 $170). Flying from Orlando to Chicago in June is currently the most expensive (average of $358). 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 September 1, 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 September 1, 2026.
The most flights from ORL to CHI are scheduled on a Sunday (72 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (55 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 $92 and $246 in December.The cheapest round-trip price found within the last 5 days was $176 on Allegiant Air (Dec 11-Dec 14).
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 147 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 69 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 August 29, 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 September 1, 2026.
Read through reviews of airlines operating flights from Orlando to Chicago, such as Southwest,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
Entertainment
7.5
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
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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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 September 1, 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 September 1, 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 September 1, 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 September 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$68 | Average$202 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$82 | Average$193 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$157 | Average$299 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$157 | Average$334 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$169 | Average$319 | FlexibilityNo cancel fee | On-time71% |