$89+ 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 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — CHI
Jul 22 — Jul 291
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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 13 days in advance, depart on a Friday or Thursday and return on a Friday
Cheap flight deals from Walt Disney World to Chicago
Cheapest
Best
Last-minute
One-way
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 June 22, 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 June 22, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 6/18. 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 8/1110:15 am
MCO
- ORD
1 stop20h 22m
Frontier
Wed 8/125:13 pm
ORD
- MCO
Nonstop3h 12m
Frontier
Deal found 6/18![Frontier logo]()
$177
This Frontier deal was found by Cheapflights users on 6/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/188:59 pm
MCO
- ORD
Nonstop3h 11m
Frontier
Tue 7/215:13 pm
ORD
- MCO
Nonstop3h 12m
Frontier
Deal found 6/17![Frontier logo]()
$178
This Frontier deal was found by Cheapflights users on 6/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/91:57 pm
MCO
- ORD
1 stop8h 37m
Frontier
Wed 9/164:49 pm
ORD
- MCO
Nonstop2h 53m
Frontier
Deal found 6/18![Frontier logo]()
$179
This Frontier deal was found by Cheapflights users on 6/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/39:47 pm
MCO
- ORD
Nonstop3h 08m
Frontier
Thu 10/84:49 pm
ORD
- MCO
Nonstop2h 53m
Frontier
Deal found 6/18![Frontier logo]()
$180
This CheapOair deal was found by Cheapflights users on 6/17. 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 7/157:30 am
SFB
- RFD
Nonstop2h 43m
Allegiant Air
Mon 7/207:50 pm
RFD
- SFB
Nonstop2h 39m
Allegiant Air
Deal found 6/17![Allegiant Air logo]()
$181
This Cheapflightsfares deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 8/54:35 pm
MCO
- ORD
1 stop31h 52m
Frontier
Mon 8/105:13 pm
ORD
- MCO
Nonstop3h 12m
Frontier
Deal found 6/21![Frontier logo]()
$182
This CheapOair deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 9/187:10 am
SFB
- RFD
Nonstop2h 42m
Allegiant Air
Mon 9/2110:22 am
RFD
- SFB
Nonstop2h 34m
Allegiant Air
Deal found 6/20![Allegiant Air logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 8/119:40 am
MCO
- ORD
1 stop7h 20m
Frontier
Thu 8/207:44 pm
ORD
- MCO
Nonstop2h 45m
Frontier
Deal found 6/20![Frontier logo]()
$183
This Frontier deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 9/286:05 am
MCO
- ORD
Nonstop3h 16m
Frontier
Wed 10/76:30 am
ORD
- MCO
1 stop9h 51m
Frontier
Deal found 6/21![Frontier logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/218:59 pm
MCO
- ORD
Nonstop3h 11m
Frontier
Tue 7/285:13 pm
ORD
- MCO
Nonstop3h 12m
Frontier
Deal found 6/17![Frontier logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/37:10 am
MCO
- ORD
1 stop5h 52m
Frontier
Sat 10/34:49 pm
ORD
- MCO
Nonstop2h 53m
Frontier
Deal found 6/21![Frontier logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/105:17 pm
SFB
- RFD
Nonstop2h 43m
Allegiant Air
Mon 7/137:50 pm
RFD
- SFB
Nonstop2h 39m
Allegiant Air
Deal found 6/18![Allegiant Air logo]()
$187
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 June 22, 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 June 22, 2026.
This CheapOair deal was found by Cheapflights users on 6/19. 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 6/277:30 am
SFB
- RFD
Nonstop2h 47m
Allegiant Air
Mon 6/297:48 pm
RFD
- SFB
Nonstop2h 35m
Allegiant Air
Deal found 6/19![Allegiant Air logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 6/19. 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.
Wed 7/85:24 pm
MCO
- RFD
2 stops18h 13m
Multiple Airlines
Sun 7/129:19 am
RFD
- MCO
1 stop28h 06m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$216
This United Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 9/56:00 pm
MCO
- ORD
Nonstop3h 13m
United Airlines
Tue 9/811:01 am
ORD
- MCO
Nonstop2h 57m
United Airlines
Deal found 6/22![United Airlines logo]()
$217
This Southwest deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 8/53:50 pm
MCO
- MDW
Nonstop2h 50m
Southwest
Mon 8/107:50 pm
MDW
- MCO
Nonstop2h 30m
Southwest
Deal found 6/21![Southwest logo]()
$232
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/214:05 pm
MCO
- ORD
1 stop5h 26m
Delta
Wed 7/298:52 am
ORD
- MCO
1 stop5h 07m
Delta
Deal found 6/22![Delta logo]()
$237
This Frontier deal was found by Cheapflights users on 6/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/19:01 pm
MCO
- ORD
Nonstop3h 18m
Frontier
Sat 7/44:59 pm
ORD
- MCO
Nonstop3h 02m
Frontier
Deal found 6/17![Frontier logo]()
$269
This CheapOair deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 7/87:30 am
SFB
- RFD
Nonstop2h 43m
Allegiant Air
Sat 7/1110:05 am
RFD
- SFB
Nonstop2h 39m
Allegiant Air
Deal found 6/20![Allegiant Air logo]()
$205
This United Airlines deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 8/17:40 pm
MCO
- ORD
Nonstop3h 20m
United Airlines
Tue 8/412:45 pm
ORD
- MCO
Nonstop2h 58m
United Airlines
Deal found 6/20![United Airlines logo]()
$217
This CheapOair deal was found by Cheapflights users on 6/18. 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 7/35:17 pm
SFB
- RFD
Nonstop2h 43m
Allegiant Air
Sat 7/410:05 am
RFD
- SFB
Nonstop2h 39m
Allegiant Air
Deal found 6/18![Allegiant Air logo]()
$207
This Delta deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 7/283:40 pm
MCO
- ORD
1 stop5h 53m
Delta
Tue 8/41:59 pm
ORD
- MCO
1 stop6h 06m
Delta
Deal found 6/21![Delta logo]()
$237
This Southwest deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 8/49:00 am
MCO
- MDW
1 stop4h 05m
Southwest
Tue 8/117:40 am
MDW
- MCO
2 stops5h 55m
Southwest
Deal found 6/20![Southwest logo]()
$238
This CheapOair deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 7/157:30 am
SFB
- RFD
Nonstop2h 43m
Allegiant Air
Wed 7/2210:03 am
RFD
- SFB
Nonstop2h 39m
Allegiant Air
Deal found 6/20![Allegiant Air logo]()
$209
This United Airlines deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 7/1510:52 am
MCO
- ORD
Nonstop3h 10m
United Airlines
Wed 7/226:12 pm
ORD
- MCO
1 stop5h 49m
United Airlines
Deal found 6/20![United Airlines logo]()
$246
This Southwest deal was found by Cheapflights users on 6/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/66:55 am
MCO
- MDW
Nonstop2h 50m
Southwest
Mon 8/107:50 pm
MDW
- MCO
Nonstop2h 30m
Southwest
Deal found 6/19![Southwest logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 8/12:49 pm
MCO
- RFD
1 stop18h 40m
Multiple Airlines
Thu 8/69:21 am
RFD
- MCO
1 stop28h 04m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$276
This Cheapflightsfares deal was found by Cheapflights users on 6/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:20 am
MCO
- ORD
1 stop19h 29m
Frontier
Sun 8/307:05 am
ORD
- MCO
1 stop6h 21m
Frontier
Deal found 6/17![Frontier logo]()
$285
This CheapOair deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/227:30 am
SFB
- RFD
Nonstop2h 43m
Allegiant Air
Fri 7/317:50 pm
RFD
- SFB
Nonstop2h 39m
Allegiant Air
Deal found 6/22![Allegiant Air logo]()
$220
This Delta deal was found by Cheapflights users on 6/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/175:40 pm
MCO
- ORD
1 stop7h 19m
Delta
Thu 9/246:25 pm
ORD
- MCO
1 stop5h 43m
Delta
Deal found 6/19![Delta logo]()
$267
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/293:10 pm
MCO
- ORD
1 stop5h 40m
Frontier
Tue 7/285:13 pm
ORD
- MCO
Nonstop3h 12m
Frontier
Deal found 6/17![Frontier logo]()
$295
This Kiwi.com deal was found by Cheapflights users on 6/19. 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.
Sat 7/47:18 pm
SFB
- RFD
1 stop14h 11m
Allegiant Air
Mon 7/137:50 pm
RFD
- SFB
Nonstop2h 39m
Allegiant Air
Deal found 6/19![Allegiant Air logo]()
$223
This Southwest deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 7/217:10 am
MCO
- MDW
Nonstop2h 50m
Southwest
Thu 7/236:35 pm
MDW
- MCO
Nonstop2h 35m
Southwest
Deal found 6/21![Southwest logo]()
$278
This CheapOair deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/205:17 pm
SFB
- RFD
Nonstop2h 43m
Allegiant Air
Mon 7/277:50 pm
RFD
- SFB
Nonstop2h 39m
Allegiant Air
Deal found 6/22![Allegiant Air logo]()
$231
This Delta deal was found by Cheapflights users on 6/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/223:40 pm
MCO
- ORD
1 stop5h 53m
Delta
Fri 7/315:30 am
ORD
- MCO
1 stop4h 27m
Delta
Deal found 6/18![Delta logo]()
$308
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/214:40 pm
MCO
- MDW
1 stop4h 10m
Southwest
Sun 7/268:20 pm
MDW
- MCO
Nonstop2h 35m
Southwest
Deal found 6/22![Southwest logo]()
$284
This United Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 8/87:07 am
MCO
- ORD
Nonstop3h 09m
United Airlines
Mon 8/102:00 pm
ORD
- MCO
Nonstop2h 57m
United Airlines
Deal found 6/22![United Airlines logo]()
$313
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/259:01 pm
MCO
- ORD
Nonstop3h 18m
Frontier
Mon 6/294:59 pm
ORD
- MCO
Nonstop3h 02m
Frontier
Deal found 6/17![Frontier logo]()
$318
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/319:48 pm
MCO
- RFD
2 stops19h 31m
Multiple Airlines
Thu 8/69:21 am
RFD
- MCO
1 stop28h 04m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$364
This Kiwi.com deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 7/17:30 am
SFB
- RFD
Nonstop2h 43m
Allegiant Air
Mon 7/137:50 pm
RFD
- SFB
Nonstop2h 39m
Allegiant Air
Deal found 6/20![Allegiant Air logo]()
$233
This Southwest deal was found by Cheapflights users on 6/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/34:55 pm
MCO
- MDW
1 stop5h 15m
Southwest
Sat 7/410:15 am
MDW
- MCO
1 stop5h 10m
Southwest
Deal found 6/19![Southwest logo]()
$308
This Kiwi.com deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 8/25:15 pm
MCO
- RFD
2 stops15h 34m
Multiple Airlines
Thu 8/69:21 am
RFD
- MCO
1 stop28h 04m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$385
Last-minute flights from Walt Disney World to ChicagoDiscover last-minute flight deals from Walt Disney World to Chicago. Data last updated June 22, 2026 and is based on user searches.
Discover last-minute flight deals from Walt Disney World to Chicago. Data last updated June 22, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 6/19. 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.
Wed 7/17:30 am
SFB
- RFD
Nonstop2h 43m
Allegiant Air
Fri 7/37:50 pm
RFD
- SFB
Nonstop2h 39m
Allegiant Air
Deal found 6/19![Allegiant Air logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/105:17 pm
SFB
- RFD
Nonstop2h 43m
Allegiant Air
Mon 7/137:50 pm
RFD
- SFB
Nonstop2h 39m
Allegiant Air
Deal found 6/18![Allegiant Air logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/135:17 pm
SFB
- RFD
Nonstop2h 43m
Allegiant Air
Mon 7/207:50 pm
RFD
- SFB
Nonstop2h 39m
Allegiant Air
Deal found 6/18![Allegiant Air logo]()
$188
This Frontier deal was found by Cheapflights users on 6/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/188:59 pm
MCO
- ORD
Nonstop3h 11m
Frontier
Tue 7/215:13 pm
ORD
- MCO
Nonstop3h 12m
Frontier
Deal found 6/17![Frontier logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/208:59 pm
MCO
- ORD
Nonstop3h 11m
Frontier
Tue 7/215:13 pm
ORD
- MCO
Nonstop3h 12m
Frontier
Deal found 6/22![Frontier logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/218:59 pm
MCO
- ORD
Nonstop3h 11m
Frontier
Tue 7/285:13 pm
ORD
- MCO
Nonstop3h 12m
Frontier
Deal found 6/17![Frontier logo]()
$185
This Frontier deal was found by Cheapflights users on 6/19. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/218:59 pm
MCO
- ORD
Nonstop3h 11m
Frontier
Thu 7/235:13 pm
ORD
- MCO
Nonstop3h 12m
Frontier
Deal found 6/19![Frontier logo]()
$188
This Frontier deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 7/218:59 pm
MCO
- ORD
Nonstop3h 11m
Frontier
Mon 7/275:13 pm
ORD
- MCO
Nonstop3h 12m
Frontier
Deal found 6/21![Frontier logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/218:59 pm
MCO
- ORD
Nonstop3h 11m
Frontier
Fri 7/2410:16 am
ORD
- MCO
Nonstop3h 07m
Frontier
Deal found 6/18![Frontier logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/245:17 pm
SFB
- RFD
Nonstop2h 43m
Allegiant Air
Mon 7/277:50 pm
RFD
- SFB
Nonstop2h 39m
Allegiant Air
Deal found 6/22![Allegiant Air logo]()
$192
This Booking.com deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/288:59 pm
MCO
- ORD
Nonstop3h 11m
Frontier
Fri 7/3110:16 am
ORD
- MCO
Nonstop3h 07m
Frontier
Deal found 6/21![Frontier logo]()
$190
This Super.com deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/298:59 pm
MCO
- ORD
Nonstop3h 11m
Frontier
Sun 8/25:13 pm
ORD
- MCO
Nonstop3h 12m
Frontier
Deal found 6/21![Frontier logo]()
$186
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 June 22, 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 June 22, 2026.
This iWofly deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure iWofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/166:05 am
MCO
- ORD
Nonstop3h 16m
Frontier
Deal found 6/21![Frontier logo]()
$89
This Frontier deal was found by Cheapflights users on 6/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/178:59 pm
MCO
- ORD
Nonstop3h 11m
Frontier
Deal found 6/18![Frontier logo]()
$90
This CheapOair deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 7/245:17 pm
SFB
- RFD
Nonstop2h 43m
Allegiant Air
Deal found 6/21![Allegiant Air logo]()
$91
This Kiwi.com deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/257:00 am
MCO
- ORD
1 stop18h 49m
Frontier
Deal found 6/22![Frontier logo]()
$92
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/105:17 pm
SFB
- RFD
Nonstop2h 43m
Allegiant Air
Deal found 6/18![Allegiant Air logo]()
$93
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/145:29 pm
MCO
- MDW
1 stop5h 29m
Frontier
Deal found 6/18![Frontier logo]()
$93
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/147:10 am
MCO
- ORD
1 stop5h 52m
Frontier
Deal found 6/18![Frontier logo]()
$94
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/157:00 am
MCO
- ORD
1 stop18h 49m
Frontier
Deal found 6/18![Frontier logo]()
$96
This CheapOair deal was found by Cheapflights users on 6/18. 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.
Mon 9/78:55 am
SFB
- RFD
Nonstop2h 42m
Allegiant Air
Deal found 6/18![Allegiant Air logo]()
$97
This Trip.com deal was found by Cheapflights users on 6/18. 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.
Wed 7/81:45 pm
MCO
- ORD
1 stop7h 08m
Frontier
Deal found 6/18![Frontier logo]()
$98
This Kiwi.com deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/47:51 am
MCO
- ORD
1 stop12h 59m
Frontier
Deal found 6/22![Frontier logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/47:51 am
MCO
- MDW
1 stop15h 20m
Frontier
Deal found 6/22![Frontier logo]()
$99
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 June 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $177 (Cheapflightsfares) |
One-way from | $89 (Super.com) |
Popular in | June |
Cheapest in | September |
Average price | $318 |
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 June 22, 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
OrlandoChicago
SFB - RFD
SFBRFD
Orlando Sanford Intl
Sat 6/27
7:30 am-9:17 am
Nonstop2h 47m
Chicago Greater Rockford
Mon 6/29
7:48 pm-11:23 pm
Nonstop2h 35m
$197
OrlandoChicago
SFB - RFD
SFBRFD
Orlando Sanford Intl
Wed 7/8
7:30 am-9:13 am
Nonstop2h 43m
Chicago Greater Rockford
Sat 7/11
10:05 am-1:44 pm
Nonstop2h 39m
$205
OrlandoChicago
SFB - RFD
SFBRFD
Orlando Sanford Intl
Fri 7/3
5:17 pm-7:00 pm
Nonstop2h 43m
Chicago Greater Rockford
Sat 7/4
10:05 am-1:44 pm
Nonstop2h 39m
$207
OrlandoChicago
SFB - RFD
SFBRFD
Orlando Sanford Intl
Wed 7/15
7:30 am-9:13 am
Nonstop2h 43m
Chicago Greater Rockford
Wed 7/22
10:03 am-1:42 pm
Nonstop2h 39m
$209
OrlandoChicago
MCO - RFD
MCORFD
Orlando
Wed 7/8
5:24 pm-10:37 am
2 stops18h 13m
Chicago Greater Rockford
Sun 7/12
9:19 am-2:25 pm
1 stop28h 06m
$216
OrlandoChicago
MCO - ORD
MCOORD
Orlando
Sat 9/5
6:00 pm-8:13 pm
Nonstop3h 13m
Chicago O'Hare Intl
Tue 9/8
11:01 am-2:58 pm
Nonstop2h 57m
$217
OrlandoChicago
MCO - ORD
MCOORD
Orlando
Sat 8/1
7:40 pm-10:00 pm
Nonstop3h 20m
Chicago O'Hare Intl
Tue 8/4
12:45 pm-4:43 pm
Nonstop2h 58m
$217
OrlandoChicago
SFB - RFD
SFBRFD
Orlando Sanford Intl
Wed 7/22
7:30 am-9:13 am
Nonstop2h 43m
Chicago Greater Rockford
Fri 7/31
7:50 pm-11:29 pm
Nonstop2h 39m
$220
OrlandoChicago
SFB - RFD
SFBRFD
Orlando Sanford Intl
Sat 7/4
7:18 pm-8:29 am
1 stop14h 11m
Chicago Greater Rockford
Mon 7/13
7:50 pm-11:29 pm
Nonstop2h 39m
$223
OrlandoChicago
SFB - RFD
SFBRFD
Orlando Sanford Intl
Mon 7/20
5:17 pm-7:00 pm
Nonstop2h 43m
Chicago Greater Rockford
Mon 7/27
7:50 pm-11:29 pm
Nonstop2h 39m
$231
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.
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 Bay Lake to Chicago
W9D-CHI
SFB-RFD
MCO-ORD
MCO-MDW
MCO-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 June 22, 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 29% 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 June 22, 2026.
The most flights from W9D to CHI are scheduled on a Friday (81 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (49 on average).
How much does it cost to fly round-trip from Walt Disney World to Chicago?
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 June 20, 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. Tuesday at noon 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 June 22, 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.
Entertainment
7.5
Overall
7.9
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
7.9
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
7.9
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
7.9
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
7.9
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
7.9
Crew
8.6
Boarding
8.1
Food
7.0
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
Hammond
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.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
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 June 22, 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 June 22, 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 June 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$46 | Average$167 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$82 | Average$182 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$146 | Average$324 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$156 | Average$345 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$157 | Average$288 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$157 | Average$333 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$228 | Average$802 | FlexibilityNo cancel fee | On-timeN/A |