$83+ 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 6/5. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — CHI
Jun 7 — Jun 141
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 13 days in advance, depart on a Friday or Thursday and return on a Tuesday
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 May 8, 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 May 8, 2026.
This deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/58:58 pm
MCO
- ORD
Nonstop3h 15m
Frontier
Wed 9/234:49 pm
ORD
- MCO
Nonstop2h 53m
Frontier
Deal found 5/3![Frontier logo]()
$115
This deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/12:40 pm
MCO
- ORD
1 stop6h 11m
Frontier
Sun 9/274:49 pm
ORD
- MCO
Nonstop2h 53m
Frontier
Deal found 5/3![Frontier logo]()
$117
This deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/12:40 pm
MCO
- ORD
1 stop6h 11m
Frontier
Mon 9/289:26 am
ORD
- MCO
Nonstop2h 49m
Frontier
Deal found 5/3![Frontier logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/37:30 am
SFB
- RFD
Nonstop2h 47m
Allegiant Air
Fri 6/127:53 pm
RFD
- SFB
Nonstop2h 35m
Allegiant Air
Deal found 5/6![Allegiant Air logo]()
$119
This deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/62:40 pm
MCO
- ORD
1 stop5h 49m
Frontier
Sun 9/279:26 am
ORD
- MCO
Nonstop2h 49m
Frontier
Deal found 5/3![Frontier logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 5/237:30 am
SFB
- RFD
Nonstop2h 51m
Allegiant Air
Wed 5/2710:11 am
RFD
- SFB
Nonstop2h 34m
Allegiant Air
Deal found 5/3![Allegiant Air logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 5/208:58 pm
MCO
- ORD
Nonstop3h 15m
Frontier
Wed 5/275:11 pm
ORD
- MCO
Nonstop3h 02m
Frontier
Deal found 5/4![Frontier logo]()
$121
This Expedia deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/208:58 pm
MCO
- ORD
Nonstop3h 15m
Frontier
Tue 5/265:11 pm
ORD
- MCO
Nonstop3h 02m
Frontier
Deal found 5/5![Frontier logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/67:30 am
SFB
- RFD
Nonstop2h 47m
Allegiant Air
Fri 6/127:53 pm
RFD
- SFB
Nonstop2h 35m
Allegiant Air
Deal found 5/6![Allegiant Air logo]()
$123
This deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/68:58 pm
MCO
- ORD
Nonstop3h 15m
Frontier
Tue 9/294:49 pm
ORD
- MCO
Nonstop2h 53m
Frontier
Deal found 5/3![Frontier logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/305:10 pm
MCO
- ORD
1 stop15h 53m
Frontier
Sat 7/44:59 pm
ORD
- MCO
Nonstop3h 02m
Frontier
Deal found 5/4![Frontier logo]()
$124
This deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/58:58 pm
MCO
- ORD
Nonstop3h 15m
Frontier
Thu 9/244:49 pm
ORD
- MCO
Nonstop2h 53m
Frontier
Deal found 5/3![Frontier logo]()
$125
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 May 8, 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 May 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/37:30 am
SFB
- RFD
Nonstop2h 47m
Allegiant Air
Mon 6/87:53 pm
RFD
- SFB
Nonstop2h 35m
Allegiant Air
Deal found 5/6![Allegiant Air logo]()
$140
This United Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/107:13 am
MCO
- ORD
Nonstop3h 09m
United Airlines
Tue 6/166:02 am
ORD
- MCO
Nonstop2h 43m
United Airlines
Deal found 5/4![United Airlines logo]()
$169
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/239:00 am
MCO
- MDW
1 stop4h 20m
Southwest
Tue 6/235:30 pm
MDW
- MCO
1 stop5h 05m
Southwest
Deal found 5/6![Southwest logo]()
$189
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 7/86:52 pm
MCO
- ORD
1 stop6h 01m
Delta
Wed 7/156:22 pm
ORD
- MCO
1 stop4h 36m
Delta
Deal found 5/6![Delta logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 8/279:00 am
MCO
- RFD
1 stop7h 09m
Multiple Airlines
Sun 8/303:59 pm
RFD
- MCO
1 stop27h 11m
Multiple Airlines
Deal found 5/7![Multiple Airlines logo]()
$274
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/177:30 am
SFB
- RFD
Nonstop2h 47m
Allegiant Air
Fri 6/197:53 pm
RFD
- SFB
Nonstop2h 35m
Allegiant Air
Deal found 5/5![Allegiant Air logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 5/5![Allegiant Air logo]()
$162
This United Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 5/247:13 am
MCO
- ORD
Nonstop3h 09m
United Airlines
Tue 6/165:56 pm
ORD
- MCO
Nonstop2h 59m
United Airlines
Deal found 5/7![United Airlines logo]()
$193
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/18:00 am
MCO
- MDW
1 stop5h 05m
Southwest
Wed 6/312:55 pm
MDW
- MCO
1 stop6h 00m
Southwest
Deal found 5/4![Southwest logo]()
$195
This Gotogate deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/307:30 am
SFB
- RFD
Nonstop2h 51m
Allegiant Air
Mon 6/18:03 pm
RFD
- SFB
Nonstop2h 34m
Allegiant Air
Deal found 5/4![Allegiant Air logo]()
$165
This Delta deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 5/287:20 pm
MCO
- ORD
1 stop5h 39m
Delta
Tue 6/95:30 am
ORD
- MCO
1 stop4h 27m
Delta
Deal found 5/4![Delta logo]()
$208
This Booking.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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.
Wed 6/247:30 am
SFB
- RFD
Nonstop2h 47m
Allegiant Air
Mon 6/297:48 pm
RFD
- SFB
Nonstop2h 35m
Allegiant Air
Deal found 5/3![Allegiant Air logo]()
$169
This United Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 9/312:33 pm
MCO
- ORD
1 stop5h 19m
United Airlines
Mon 9/76:03 pm
ORD
- MCO
Nonstop2h 55m
United Airlines
Deal found 5/7![United Airlines logo]()
$209
This Southwest deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 6/48:15 am
MCO
- MDW
Nonstop2h 45m
Southwest
Sat 6/68:00 am
MDW
- MCO
1 stop5h 10m
Southwest
Deal found 5/3![Southwest logo]()
$209
This United Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 9/94:21 pm
MCO
- ORD
Nonstop3h 12m
United Airlines
Wed 9/168:40 am
ORD
- MCO
1 stop5h 18m
United Airlines
Deal found 5/3![United Airlines logo]()
$219
This Booking.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/265:13 pm
SFB
- RFD
Nonstop2h 45m
Allegiant Air
Mon 6/297:48 pm
RFD
- SFB
Nonstop2h 35m
Allegiant Air
Deal found 5/3![Allegiant Air logo]()
$182
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 5/307:15 am
MCO
- ORD
2 stops9h 15m
Southwest
Mon 6/110:30 am
ORD
- MCO
1 stop7h 30m
Southwest
Deal found 5/4![Southwest logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/243:18 pm
MCO
- RFD
1 stop18h 11m
Multiple Airlines
Sun 6/289:19 am
RFD
- MCO
1 stop10h 05m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$283
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 5/279:10 pm
MCO
- ORD
2 stops16h 40m
Southwest
Fri 5/292:40 pm
ORD
- MCO
2 stops8h 25m
Southwest
Deal found 5/6![Southwest logo]()
$229
This Booking.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/225:22 pm
SFB
- RFD
Nonstop2h 51m
Allegiant Air
Mon 5/258:03 pm
RFD
- SFB
Nonstop2h 34m
Allegiant Air
Deal found 5/3![Allegiant Air logo]()
$199
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 8/209:00 am
MCO
- RFD
1 stop7h 09m
Multiple Airlines
Sun 8/233:59 pm
RFD
- MCO
1 stop27h 11m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$296
This Southwest deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 5/279:10 pm
MCO
- ORD
2 stops16h 40m
Southwest
Sat 5/301:55 pm
ORD
- MCO
1 stop7h 25m
Southwest
Deal found 5/7![Southwest logo]()
$239
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/195:18 pm
SFB
- RFD
Nonstop2h 45m
Allegiant Air
Mon 6/297:48 pm
RFD
- SFB
Nonstop2h 35m
Allegiant Air
Deal found 5/5![Allegiant Air logo]()
$201
This United Airlines deal was found by Cheapflights users on 5/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/303:17 pm
MCO
- ORD
1 stop6h 04m
United Airlines
Sat 6/62:00 pm
ORD
- MCO
Nonstop2h 57m
United Airlines
Deal found 5/2![United Airlines logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 7/293:08 pm
MCO
- RFD
1 stop18h 21m
Multiple Airlines
Sun 8/29:19 am
RFD
- MCO
1 stop10h 04m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$313
This Kiwi.com deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 7/87:30 am
SFB
- RFD
Nonstop2h 43m
Allegiant Air
Sun 7/1211:27 am
RFD
- SFB
2 stops29h 50m
Allegiant Air
Deal found 5/7![Allegiant Air logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 9/249:00 am
MCO
- RFD
1 stop7h 03m
Multiple Airlines
Sun 9/273:53 pm
RFD
- MCO
1 stop5h 45m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$324
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/107:13 am
MCO
- ORD
Nonstop3h 09m
United Airlines
Sun 6/147:20 am
ORD
- MCO
Nonstop2h 55m
United Airlines
Deal found 5/5![United Airlines logo]()
$303
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 5/237:12 pm
SFB
- RFD
1 stop14h 19m
Allegiant Air
Wed 5/2710:11 am
RFD
- SFB
Nonstop2h 34m
Allegiant Air
Deal found 5/5![Allegiant Air logo]()
$216
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 7/1512:34 pm
MCO
- ORD
Nonstop3h 08m
United Airlines
Sun 7/199:12 am
ORD
- MCO
Nonstop3h 01m
United Airlines
Deal found 5/5![United Airlines logo]()
$303
Last-minute flights from Walt Disney World to ChicagoDiscover last-minute flight deals from Walt Disney World to Chicago. Data last updated May 8, 2026 and is based on user searches.
Discover last-minute flight deals from Walt Disney World to Chicago. Data last updated May 8, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 5/207:30 am
SFB
- RFD
Nonstop2h 51m
Allegiant Air
Wed 5/2710:11 am
RFD
- SFB
Nonstop2h 34m
Allegiant Air
Deal found 5/3![Allegiant Air logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 5/237:30 am
SFB
- RFD
Nonstop2h 51m
Allegiant Air
Wed 5/2710:11 am
RFD
- SFB
Nonstop2h 34m
Allegiant Air
Deal found 5/3![Allegiant Air logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 5/237:30 am
SFB
- RFD
Nonstop2h 51m
Allegiant Air
Sat 5/3010:11 am
RFD
- SFB
Nonstop2h 34m
Allegiant Air
Deal found 5/3![Allegiant Air logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/23:10 pm
MCO
- MDW
1 stop7h 52m
Frontier
Tue 6/912:27 pm
MDW
- MCO
1 stop17h 18m
Frontier
Deal found 5/6![Frontier logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/37:30 am
SFB
- RFD
Nonstop2h 47m
Allegiant Air
Fri 6/127:53 pm
RFD
- SFB
Nonstop2h 35m
Allegiant Air
Deal found 5/6![Allegiant Air logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 6/33:10 pm
MCO
- MDW
1 stop7h 52m
Frontier
Tue 6/912:27 pm
MDW
- MCO
1 stop17h 18m
Frontier
Deal found 5/7![Frontier logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/37:30 am
SFB
- RFD
Nonstop2h 47m
Allegiant Air
Mon 6/87:53 pm
RFD
- SFB
Nonstop2h 35m
Allegiant Air
Deal found 5/6![Allegiant Air logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/33:10 pm
MCO
- MDW
1 stop7h 52m
Frontier
Wed 6/1012:04 pm
MDW
- MCO
1 stop5h 27m
Frontier
Deal found 5/4![Frontier logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/35:10 pm
MCO
- MDW
1 stop5h 52m
Frontier
Mon 6/812:04 pm
MDW
- MCO
1 stop17h 41m
Frontier
Deal found 5/5![Frontier logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/47:56 am
MCO
- MDW
1 stop15h 06m
Frontier
Tue 6/912:27 pm
MDW
- MCO
1 stop17h 18m
Frontier
Deal found 5/6![Frontier logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/67:30 am
SFB
- RFD
Nonstop2h 47m
Allegiant Air
Fri 6/127:53 pm
RFD
- SFB
Nonstop2h 35m
Allegiant Air
Deal found 5/6![Allegiant Air logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/175:25 am
MCO
- MDW
1 stop6h 44m
Frontier
Tue 6/2312:27 pm
MDW
- MCO
1 stop17h 18m
Frontier
Deal found 5/5![Frontier logo]()
$131
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 May 8, 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 May 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/55:18 pm
SFB
- RFD
Nonstop2h 45m
Allegiant Air
Deal found 5/6![Allegiant Air logo]()
$83
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/15:22 pm
SFB
- RFD
Nonstop2h 51m
Allegiant Air
Deal found 5/6![Allegiant Air logo]()
$84
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/35:10 pm
MCO
- ORD
1 stop15h 45m
Frontier
Deal found 5/5![Frontier logo]()
$84
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/47:56 am
MCO
- MDW
1 stop15h 06m
Frontier
Deal found 5/5![Frontier logo]()
$84
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/37:35 am
MCO
- ORD
Nonstop3h 10m
Southwest
Deal found 5/4![Southwest logo]()
$85
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 5/277:15 am
MCO
- MDW
Nonstop2h 55m
Southwest
Deal found 5/6![Southwest logo]()
$85
This American Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/98:02 am
MCO
- ORD
Nonstop3h 08m
American Airlines
Deal found 5/6![American Airlines logo]()
$87
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 7/17:00 am
MCO
- ORD
1 stop18h 48m
Frontier
Deal found 5/5![Frontier logo]()
$88
This Super.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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.
Mon 6/85:10 pm
MCO
- MDW
1 stop5h 52m
Frontier
Deal found 5/4![Frontier logo]()
$89
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 7/84:40 pm
MCO
- MDW
1 stop4h 10m
Southwest
Deal found 5/6![Southwest logo]()
$90
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 5/188:05 am
SFB
- RFD
Nonstop2h 54m
Allegiant Air
Deal found 5/6![Allegiant Air logo]()
$93
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 5/198:58 pm
MCO
- ORD
Nonstop3h 15m
Frontier
Deal found 5/5![Frontier logo]()
$93
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 May 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $115 |
One-way from | $83 (Kiwi.com) |
Popular in | March |
Cheapest in | September |
Average price | $162 |
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 May 8, 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
Wed 6/3
7:30 am-9:17 am
Nonstop2h 47m
Chicago Greater Rockford
Mon 6/8
7:53 pm-11:28 pm
Nonstop2h 35m
$140
OrlandoChicago
SFB - RFD
SFBRFD
Orlando Sanford Intl
Wed 6/17
7:30 am-9:17 am
Nonstop2h 47m
Chicago Greater Rockford
Fri 6/19
7:53 pm-11:28 pm
Nonstop2h 35m
$162
OrlandoChicago
SFB - RFD
SFBRFD
Orlando Sanford Intl
Fri 7/10
5:17 pm-7:00 pm
Nonstop2h 43m
Chicago Greater Rockford
Mon 7/13
7:50 pm-11:29 pm
Nonstop2h 39m
$162
OrlandoChicago
SFB - RFD
SFBRFD
Orlando Sanford Intl
Sat 5/30
7:30 am-9:21 am
Nonstop2h 51m
Chicago Greater Rockford
Mon 6/1
8:03 pm-11:37 pm
Nonstop2h 34m
$165
OrlandoChicago
MCO - ORD
MCOORD
Orlando
Wed 6/10
7:13 am-9:22 am
Nonstop3h 09m
Chicago O'Hare Intl
Tue 6/16
6:02 am-9:45 am
Nonstop2h 43m
$169
OrlandoChicago
SFB - RFD
SFBRFD
Orlando Sanford Intl
Wed 6/24
7:30 am-9:17 am
Nonstop2h 47m
Chicago Greater Rockford
Mon 6/29
7:48 pm-11:23 pm
Nonstop2h 35m
$169
Quickest round-trip
OrlandoChicago
SFB - RFD
SFBRFD
Orlando Sanford Intl
Fri 6/26
5:13 pm-6:58 pm
Nonstop2h 45m
Chicago Greater Rockford
Mon 6/29
7:48 pm-11:23 pm
Nonstop2h 35m
$182
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
Tue 6/23
9:00 am-12:20 pm
1 stop4h 20m
Chicago Midway
Tue 6/23
5:30 pm-11:35 pm
1 stop5h 05m
$189
OrlandoChicago
MCO - ORD
MCOORD
Orlando
Sun 5/24
7:13 am-9:22 am
Nonstop3h 09m
Chicago O'Hare Intl
Tue 6/16
5:56 pm-9:55 pm
Nonstop2h 59m
$193
OrlandoChicago
MCO - MDW
MCOMDW
Orlando
Mon 6/1
8:00 am-12:05 pm
1 stop5h 05m
Chicago Midway
Wed 6/3
12:55 pm-7:55 pm
1 stop6h 00m
$195
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 May 8, 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 in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 20% on airfare.
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 May 2, 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.
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 May 8, 2026.
The most flights from W9D to CHI are scheduled on a Thursday (78 on average). You will have fewer flight options on Tuesday, 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?
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 May 8, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andAmerican Airlines 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
Food
7.0
Crew
8.6
Boarding
8.1
Overall
7.9
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Overall
7.9
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Overall
7.9
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Overall
7.9
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Overall
7.9
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Overall
7.9
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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
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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
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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 May 8, 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 May 8, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 8 airlines flying from Walt Disney World to Chicago
Discover the top 8 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 May 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$46 | Average$163 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$68 | Average$157 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$76 | Average$177 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$98 | Average$437 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$146 | Average$324 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$157 | Average$317 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$157 | Average$280 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$157 | Average$346 | FlexibilityNo cancel fee | On-time71% |