$105+ Cheap flights from Bay Lake, FL 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.
MCO — CHI
Sep 1 — Sep 81
Round-trip
1 adult, Economy
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Find cheap flights from Walt Disney World 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 Walt Disney World to Chicago are usually found in September or February, booked 53 days in advance, depart on a Friday or Thursday and return on a Friday
Cheap flight deals from Walt Disney World to Chicago
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Best
Last-minute
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Cheapest flights from Walt Disney World to ChicagoExplore the most affordable flight options available from Walt Disney World to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 2, 2026.
Explore the most affordable flight options available from Walt Disney World to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/1. 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.
Sat 8/2210:03 am
MCO
- ORD
1 stop11h 05m
Frontier
Mon 8/247:05 am
ORD
- MCO
1 stop11h 55m
Frontier
Deal found 8/1![Frontier logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 7/31. 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.
Sat 9/53:21 pm
MCO
- ORD
1 stop5h 47m
Frontier
Tue 9/81:59 pm
ORD
- MCO
1 stop7h 15m
Frontier
Deal found 7/31![Frontier logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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
SFB
- RFD
Nonstop2h 44m
Allegiant Air
Sun 10/181:12 pm
RFD
- SFB
1 stop21h 52m
Allegiant Air
Deal found 8/2![Allegiant Air logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
Wed 8/191:45 pm
MCO
- ORD
1 stop7h 23m
Frontier
Tue 8/255:59 pm
ORD
- MCO
Nonstop3h 12m
Frontier
Deal found 7/30![Frontier logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 8/197:57 am
MCO
- ORD
1 stop13h 11m
Frontier
Sat 8/225:59 pm
ORD
- MCO
Nonstop3h 12m
Frontier
Deal found 8/2![Frontier logo]()
$195
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 10/77:00 am
SFB
- RFD
Nonstop2h 44m
Allegiant Air
Mon 10/1210:39 am
RFD
- SFB
Nonstop2h 30m
Allegiant Air
Deal found 7/31![Allegiant Air logo]()
$196
This Cheapflightsfares deal was found by Cheapflights users on 7/30. 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.
Thu 10/2912:52 pm
MCO
- ORD
1 stop7h 52m
Frontier
Mon 11/24:44 pm
ORD
- MCO
Nonstop2h 53m
Frontier
Deal found 7/30![Frontier logo]()
$196
This CheapOair deal was found by Cheapflights users on 7/30. 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
SFB
- RFD
Nonstop2h 42m
Allegiant Air
Mon 9/1410:22 am
RFD
- SFB
Nonstop2h 34m
Allegiant Air
Deal found 7/30![Allegiant Air logo]()
$197
This Cheapflightsfares deal was found by Cheapflights users on 7/30. 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.
Fri 9/118:51 pm
MCO
- ORD
Nonstop3h 08m
Frontier
Sun 9/133:50 pm
ORD
- MCO
Nonstop2h 56m
Frontier
Deal found 7/30![Frontier logo]()
$197
This Frontier deal was found by Cheapflights users on 7/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/248:51 pm
MCO
- ORD
Nonstop3h 08m
Frontier
Sun 9/273:50 pm
ORD
- MCO
Nonstop2h 56m
Frontier
Deal found 7/31![Frontier logo]()
$198
This Frontier deal was found by Cheapflights users on 7/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2411:08 am
MCO
- ORD
Nonstop3h 12m
Frontier
Sun 8/307:44 pm
ORD
- MCO
Nonstop2h 45m
Frontier
Deal found 7/30![Frontier logo]()
$199
This Super.com deal was found by Cheapflights users on 7/30. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/159:47 pm
MCO
- ORD
Nonstop3h 08m
Frontier
Sun 10/186:05 am
ORD
- MCO
Nonstop2h 48m
Frontier
Deal found 7/30![Frontier logo]()
$201
Best flights from Walt Disney World to ChicagoDiscover carefully curated flight deals from Walt Disney World to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 2, 2026.
Discover carefully curated flight deals from Walt Disney World to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 10/77:00 am
SFB
- RFD
Nonstop2h 44m
Allegiant Air
Mon 10/1210:39 am
RFD
- SFB
Nonstop2h 30m
Allegiant Air
Deal found 7/31![Allegiant Air logo]()
$196
This Southwest deal was found by Cheapflights users on 7/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:40 am
MCO
- MDW
Nonstop2h 45m
Southwest
Wed 9/212:20 pm
MDW
- MCO
Nonstop2h 40m
Southwest
Deal found 7/30![Southwest logo]()
$237
This JetBlue deal was found by Cheapflights users on 7/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:24 pm
MCO
- ORD
1 stop6h 20m
JetBlue
Thu 10/222:35 pm
ORD
- MCO
1 stop6h 34m
JetBlue
Deal found 7/30![JetBlue logo]()
$244
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/298:50 am
MCO
- ORD
1 stop6h 38m
Delta
Mon 11/21:55 pm
ORD
- MCO
1 stop5h 59m
Delta
Deal found 7/28![Delta logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 9/247:40 am
MCO
- RFD
1 stop8h 23m
Multiple Airlines
Sun 9/279:29 pm
RFD
- MCO
2 stops25h 30m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$258
This United Airlines deal was found by Cheapflights users on 7/31. 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 10/99:10 am
MCO
- ORD
Nonstop3h 10m
United Airlines
Mon 10/127:57 pm
ORD
- MCO
Nonstop2h 56m
United Airlines
Deal found 7/31![United Airlines logo]()
$303
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 9/117:10 am
SFB
- RFD
Nonstop2h 42m
Allegiant Air
Mon 9/1410:22 am
RFD
- SFB
Nonstop2h 34m
Allegiant Air
Deal found 7/30![Allegiant Air logo]()
$197
This KAYAK deal was found by Cheapflights users on 7/29. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/308:01 am
MCO
- ORD
Nonstop3h 09m
American Airlines
Fri 9/46:45 pm
ORD
- MCO
Nonstop2h 52m
American Airlines
Deal found 7/29![American Airlines logo]()
$401
This Southwest deal was found by Cheapflights users on 7/28. 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 9/108:15 am
MCO
- MDW
Nonstop2h 45m
Southwest
Mon 9/147:50 pm
MDW
- MCO
Nonstop2h 35m
Southwest
Deal found 7/28![Southwest logo]()
$237
This CheapOair deal was found by Cheapflights users on 7/30. 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.
Mon 8/103:45 pm
SFB
- RFD
Nonstop2h 51m
Allegiant Air
Fri 8/146:26 pm
RFD
- SFB
Nonstop2h 39m
Allegiant Air
Deal found 7/30![Allegiant Air logo]()
$221
This Delta deal was found by Cheapflights users on 7/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:30 pm
MCO
- MDW
1 stop7h 03m
Delta
Sat 8/291:25 pm
MDW
- MCO
1 stop6h 40m
Delta
Deal found 7/29![Delta logo]()
$257
This CheapOair deal was found by Cheapflights users on 7/28. 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 9/46:20 am
SFB
- RFD
Nonstop2h 42m
Allegiant Air
Mon 9/711:27 am
RFD
- SFB
Nonstop2h 34m
Allegiant Air
Deal found 7/28![Allegiant Air logo]()
$222
This Southwest deal was found by Cheapflights users on 8/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/118:55 pm
MCO
- MDW
Nonstop2h 50m
Southwest
Mon 9/147:50 pm
MDW
- MCO
Nonstop2h 35m
Southwest
Deal found 8/1![Southwest logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 10/17:40 am
MCO
- RFD
1 stop7h 46m
Multiple Airlines
Sun 10/41:56 pm
RFD
- MCO
1 stop6h 10m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$276
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 8/146:40 pm
SFB
- RFD
2 stops41h 07m
Allegiant Air
Mon 8/176:26 pm
RFD
- SFB
Nonstop2h 39m
Allegiant Air
Deal found 7/30![Allegiant Air logo]()
$227
This Delta deal was found by Cheapflights users on 7/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/65:30 am
MCO
- ORD
1 stop4h 55m
Delta
Thu 10/151:55 pm
ORD
- MCO
1 stop4h 44m
Delta
Deal found 7/31![Delta logo]()
$277
This Southwest deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 10/158:10 am
MCO
- MDW
Nonstop2h 50m
Southwest
Sat 10/178:20 am
MDW
- MCO
1 stop4h 50m
Southwest
Deal found 8/2![Southwest logo]()
$263
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 8/209:05 am
MCO
- RFD
1 stop7h 04m
Multiple Airlines
Sun 8/239:35 pm
RFD
- MCO
2 stops23h 39m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$298
This United Airlines deal was found by Cheapflights users on 7/31. 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.
Sat 8/226:00 pm
MCO
- ORD
Nonstop3h 13m
United Airlines
Sun 8/2312:45 pm
ORD
- MCO
Nonstop2h 49m
United Airlines
Deal found 7/31![United Airlines logo]()
$328
This Delta deal was found by Cheapflights users on 8/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/274:05 pm
MCO
- ORD
1 stop5h 25m
Delta
Sat 8/296:40 am
ORD
- MCO
1 stop6h 54m
Delta
Deal found 8/1![Delta logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 8/152:50 pm
SFB
- RFD
2 stops20h 57m
Allegiant Air
Mon 8/246:56 pm
RFD
- SFB
Nonstop2h 36m
Allegiant Air
Deal found 7/28![Allegiant Air logo]()
$240
This Delta deal was found by Cheapflights users on 7/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:40 pm
MCO
- MDW
1 stop4h 53m
Delta
Thu 10/151:27 pm
MDW
- MCO
1 stop5h 12m
Delta
Deal found 7/31![Delta logo]()
$277
This Southwest deal was found by Cheapflights users on 7/31. 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 9/37:10 am
MCO
- MDW
1 stop5h 15m
Southwest
Tue 9/87:40 am
MDW
- MCO
2 stops5h 55m
Southwest
Deal found 7/31![Southwest logo]()
$278
This Kiwi.com deal was found by Cheapflights users on 7/29. 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 8/279:05 am
MCO
- RFD
1 stop7h 04m
Multiple Airlines
Sun 8/309:35 pm
RFD
- MCO
2 stops17h 01m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$306
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 8/279:05 am
MCO
- RFD
1 stop7h 04m
Multiple Airlines
Thu 9/39:29 pm
RFD
- MCO
1 stop21h 25m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$309
This Southwest deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 9/161:00 pm
MCO
- MDW
Nonstop2h 45m
Southwest
Wed 9/236:20 pm
MDW
- MCO
Nonstop2h 45m
Southwest
Deal found 8/2![Southwest logo]()
$282
This CheapOair deal was found by Cheapflights users on 7/31. 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 8/73:45 pm
SFB
- RFD
Nonstop2h 51m
Allegiant Air
Mon 8/106:26 pm
RFD
- SFB
Nonstop2h 39m
Allegiant Air
Deal found 7/31![Allegiant Air logo]()
$258
This KAYAK deal was found by Cheapflights users on 7/28. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1110:00 am
MCO
- ORD
1 stop5h 22m
American Airlines
Thu 8/135:49 pm
ORD
- MCO
1 stop4h 25m
American Airlines
Deal found 7/28![American Airlines logo]()
$427
This United Airlines deal was found by Cheapflights users on 7/29. 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.
Fri 8/147:40 pm
MCO
- ORD
Nonstop3h 14m
United Airlines
Mon 8/179:02 am
ORD
- MCO
Nonstop2h 57m
United Airlines
Deal found 7/29![United Airlines logo]()
$399
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 8/143:45 pm
SFB
- RFD
Nonstop2h 51m
Allegiant Air
Mon 8/246:56 pm
RFD
- SFB
Nonstop2h 36m
Allegiant Air
Deal found 7/31![Allegiant Air logo]()
$264
Last-minute flights from Walt Disney World to ChicagoDiscover last-minute flight deals from Walt Disney World to Chicago. Data last updated August 2, 2026 and is based on user searches.
Discover last-minute flight deals from Walt Disney World to Chicago. Data last updated August 2, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 7/31. 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.
Mon 8/173:45 pm
SFB
- RFD
Nonstop2h 51m
Allegiant Air
Fri 8/216:56 pm
RFD
- SFB
Nonstop2h 36m
Allegiant Air
Deal found 7/31![Allegiant Air logo]()
$203
This Kiwi.com deal was found by Cheapflights users on 7/29. 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.
Mon 8/1710:29 am
MCO
- MDW
1 stop5h 30m
Multiple Airlines
Tue 8/1811:50 am
MDW
- MCO
1 stop5h 43m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
Wed 8/191:45 pm
MCO
- ORD
1 stop7h 23m
Frontier
Tue 8/255:59 pm
ORD
- MCO
Nonstop3h 12m
Frontier
Deal found 7/30![Frontier logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 8/197:57 am
MCO
- ORD
1 stop13h 11m
Frontier
Sat 8/225:59 pm
ORD
- MCO
Nonstop3h 12m
Frontier
Deal found 8/2![Frontier logo]()
$195
This Kiwi.com deal was found by Cheapflights users on 7/29. 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 8/191:45 pm
MCO
- ORD
1 stop7h 23m
Frontier
Mon 8/247:05 am
ORD
- MCO
1 stop6h 21m
Frontier
Deal found 7/29![Frontier logo]()
$200
This Frontier deal was found by Cheapflights users on 7/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/203:21 pm
MCO
- ORD
1 stop5h 38m
Frontier
Mon 8/246:05 am
ORD
- MCO
Nonstop2h 58m
Frontier
Deal found 7/30![Frontier logo]()
$198
This CheapOair deal was found by Cheapflights users on 7/30. 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 8/214:18 pm
SFB
- RFD
Nonstop2h 48m
Allegiant Air
Mon 8/246:56 pm
RFD
- SFB
Nonstop2h 36m
Allegiant Air
Deal found 7/30![Allegiant Air logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 8/1. 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.
Sat 8/2210:03 am
MCO
- ORD
1 stop11h 05m
Frontier
Mon 8/247:05 am
ORD
- MCO
1 stop11h 55m
Frontier
Deal found 8/1![Frontier logo]()
$192
This Frontier deal was found by Cheapflights users on 7/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2411:08 am
MCO
- ORD
Nonstop3h 12m
Frontier
Sun 8/307:44 pm
ORD
- MCO
Nonstop2h 45m
Frontier
Deal found 7/30![Frontier logo]()
$199
This Cheapflightsfares deal was found by Cheapflights users on 7/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/259:00 pm
MCO
- ORD
Nonstop3h 08m
Frontier
Sun 8/307:44 pm
ORD
- MCO
Nonstop2h 45m
Frontier
Deal found 7/29![Frontier logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 8/259:00 pm
MCO
- ORD
Nonstop3h 08m
Frontier
Sun 10/259:33 pm
ORD
- MCO
1 stop8h 34m
Frontier
Deal found 7/30![Frontier logo]()
$204
This Frontier deal was found by Cheapflights users on 7/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/293:45 pm
MCO
- ORD
1 stop15h 14m
Frontier
Sat 9/57:44 pm
ORD
- MCO
Nonstop2h 45m
Frontier
Deal found 7/30![Frontier logo]()
$203
One-way flights from Walt Disney World to ChicagoSearch for one-way flight options from Walt Disney World to Chicago. Find affordable one-way fares based on user searches. Data last updated August 2, 2026.
Search for one-way flight options from Walt Disney World to Chicago. Find affordable one-way fares based on user searches. Data last updated August 2, 2026.
This Trip.com deal was found by Cheapflights users on 7/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/119:30 am
MCO
- ORD
1 stop9h 53m
Frontier
Deal found 7/28![Frontier logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 8/175:24 pm
MCO
- ORD
1 stop27h 44m
Frontier
Deal found 7/28![Frontier logo]()
$106
This eDestinos deal was found by Cheapflights users on 7/30. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/265:24 am
MCO
- ORD
1 stop27h 29m
Frontier
Deal found 7/30![Frontier logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
Wed 9/239:30 am
MCO
- MDW
1 stop9h 21m
Frontier
Deal found 7/30![Frontier logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 10/277:10 am
MCO
- ORD
2 stops23h 25m
Frontier
Deal found 7/31![Frontier logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 7/29. 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.
Mon 10/195:29 pm
MCO
- MDW
1 stop29h 29m
Frontier
Deal found 7/29![Frontier logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 7/29. 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.
Sun 8/239:05 am
MCO
- RFD
1 stop7h 04m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$108
This Trip.com deal was found by Cheapflights users on 7/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/255:24 am
MCO
- MDW
1 stop6h 31m
Frontier
Deal found 7/29![Frontier logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 7/29. 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.
Sat 8/296:20 am
MCO
- ORD
1 stop10h 39m
Frontier
Deal found 7/29![Frontier logo]()
$110
This Trip.com deal was found by Cheapflights users on 7/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/25:24 am
MCO
- MDW
1 stop6h 31m
Frontier
Deal found 7/30![Frontier logo]()
$110
This Cheapflightsfares deal was found by Cheapflights users on 8/1. 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.
Wed 8/128:59 pm
MCO
- ORD
Nonstop3h 11m
Frontier
Deal found 8/1![Frontier logo]()
$111
This Trip.com deal was found by Cheapflights users on 7/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/265:24 am
MCO
- MDW
1 stop6h 31m
Frontier
Deal found 7/29![Frontier logo]()
$111
Find flight deals from Walt Disney World to Chicago
Keep the following information in mind while searching for Walt Disney World to Chicago flight deals. Data was last updated August 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $192 (Kiwi.com) |
One-way from | $105 (Trip.com) |
Popular in | June |
Cheapest in | September |
Average price | $193 |
Cheapflights Fare Finder
Customize your flight search to find flights from Walt Disney World 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 2,558,603 searches. Data last updated August 2, 2026.
Use the filters below to find and compare flights from Bay Lake to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
OrlandoChicago
SFB - RFD
SFBRFD
Orlando Sanford Intl
Wed 10/7
7:00 am-8:44 am
Nonstop2h 44m
Chicago Greater Rockford
Mon 10/12
10:39 am-2:09 pm
Nonstop2h 30m
$196
OrlandoChicago
SFB - RFD
SFBRFD
Orlando Sanford Intl
Fri 9/11
7:10 am-8:52 am
Nonstop2h 42m
Chicago Greater Rockford
Mon 9/14
10:22 am-1:56 pm
Nonstop2h 34m
$197
OrlandoChicago
SFB - RFD
SFBRFD
Orlando Sanford Intl
Mon 8/10
3:45 pm-5:36 pm
Nonstop2h 51m
Chicago Greater Rockford
Fri 8/14
6:26 pm-10:05 pm
Nonstop2h 39m
$221
OrlandoChicago
SFB - RFD
SFBRFD
Orlando Sanford Intl
Fri 9/4
6:20 am-8:02 am
Nonstop2h 42m
Chicago Greater Rockford
Mon 9/7
11:27 am-3:01 pm
Nonstop2h 34m
$222
OrlandoChicago
SFB - RFD
SFBRFD
Orlando Sanford Intl
Fri 8/14
6:40 pm-10:47 am
2 stops41h 07m
Chicago Greater Rockford
Mon 8/17
6:26 pm-10:05 pm
Nonstop2h 39m
$227
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
Wed 9/2
7:40 am-9:25 am
Nonstop2h 45m
Chicago Midway
Wed 9/2
12:20 pm-4:00 pm
Nonstop2h 40m
$237
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
Thu 9/10
8:15 am-10:00 am
Nonstop2h 45m
Chicago Midway
Mon 9/14
7:50 pm-11:25 pm
Nonstop2h 35m
$237
OrlandoChicago
SFB - RFD
SFBRFD
Orlando Sanford Intl
Sat 8/15
2:50 pm-10:47 am
2 stops20h 57m
Chicago Greater Rockford
Mon 8/24
6:56 pm-10:32 pm
Nonstop2h 36m
$240
OrlandoChicago
MCO - ORD
MCOORD
Orlando
Fri 8/21
6:24 pm-11:44 pm
1 stop6h 20m
Chicago O'Hare Intl
Thu 10/22
2:35 pm-10:09 pm
1 stop6h 34m
$244
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
Fri 9/11
8:55 pm-10:45 pm
Nonstop2h 50m
Chicago Midway
Mon 9/14
7:50 pm-11:25 pm
Nonstop2h 35m
$247
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Walt Disney World to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Walt Disney World with our price prediction graph.
MCO-ORD
MCO-MDW
MCO-RFD
SFB-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 Bay Lake to Chicago
W9D-CHI
MCO-ORD
MCO-MDW
MCO-RFD
SFB-RFD
What is the cheapest time of day to fly from W9D to CHI?
Find hourly flight availability from Walt Disney World 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 August 2, 2026.
One of the essential ways to save on airfare from Walt Disney World 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 35% on airfare.
Weekly flight availability from Walt Disney World to Chicago
Explore weekly flight availability from Walt Disney World 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 August 2, 2026.
The most flights from W9D to CHI are scheduled on a Saturday (83 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (32 on average).
How much does it cost to fly round-trip from Walt Disney World to Chicago?
Airfare is typical for this route at the moment.
Walt Disney World to Chicago flights typically cost between $129 and $278 in August.The cheapest round-trip price found within the last 5 days was $192 on Frontier (Aug 22-Aug 24).
What is the cheapest day to fly from Walt Disney World to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Walt Disney World to Chicago. Price data was last updated on July 25, 2026.
Travelers seeking maximum savings on their Walt Disney World to Chicago flight should consider departing on Saturday at noon 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 August 2, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andAllegiant Air from Bay Lake to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Walt Disney World 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
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Porter
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Alternative routes for Walt Disney World to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
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 August 2, 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 Walt Disney World to Chicago by cabin class
Find flights from Walt Disney World to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Walt Disney World and Chicago flights
Browse other Walt Disney World and Chicago flight options. Last updated on August 2, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 7 airlines flying from Walt Disney World to Chicago
Discover the top 7 airlines that operate flights from Walt Disney World 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 2,558,603 searches. Data last updated August 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$46 | Average$191 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$82 | Average$188 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$98 | Average$425 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$146 | Average$329 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$156 | Average$332 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$157 | Average$298 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$157 | Average$342 | FlexibilityNo cancel fee | On-time69% |