$395+ Cheap flights from Midway (MDW) to Sicily
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 5/20. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CTA
Mar 5 — Mar 121
1 adult, Economy
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Find cheap flights from Midway to Sicily 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
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Cheapest flights from Midway to SicilyExplore the most affordable flight options available from Midway to Sicily. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 3, 2026.
Explore the most affordable flight options available from Midway to Sicily. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 3, 2026.
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/126:00 am
MDW
- PMO
2 stops26h 00m
Delta
Mon 8/243:45 pm
PMO
- MDW
2 stops37h 01m
Delta
Deal found 2/2![Delta logo]()
$737
This Trip.com deal was found by Cheapflights users on 2/2. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/910:45 am
MDW
- SUF
2 stops25h 45m
KLM
Mon 3/1611:15 am
SUF
- MDW
2 stops36h 39m
KLM
Deal found 2/2![KLM logo]()
$825
This Air France deal was found by Cheapflights users on 2/2. 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 Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/61:23 pm
MDW
- PMO
2 stops18h 02m
KLM
Tue 5/196:10 am
PMO
- MDW
2 stops19h 04m
KLM
Deal found 2/2![KLM logo]()
$885
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/181:23 pm
MDW
- PMO
2 stops19h 27m
Delta
Sun 4/264:45 pm
PMO
- MDW
2 stops30h 40m
Delta
Deal found 2/2![Delta logo]()
$909
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/121:05 pm
MDW
- PMO
2 stops18h 55m
Delta
Tue 8/253:45 pm
PMO
- MDW
2 stops33h 46m
Delta
Deal found 2/2![Delta logo]()
$931
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/121:00 pm
MDW
- PMO
2 stops19h 00m
Delta
Fri 8/213:45 pm
PMO
- MDW
2 stops33h 46m
Delta
Deal found 2/2![Delta logo]()
$943
This Air France deal was found by Cheapflights users on 2/2. 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 Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/125:59 pm
MDW
- PMO
2 stops14h 01m
Multiple Airlines
Sat 8/2210:05 am
PMO
- MDW
2 stops18h 41m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$977
This Air France deal was found by Cheapflights users on 2/2. 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 Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/125:59 pm
MDW
- PMO
2 stops14h 01m
Multiple Airlines
Sun 8/236:10 am
PMO
- MDW
2 stops19h 21m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$1,010
This Air France deal was found by Cheapflights users on 2/2. 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 Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/155:59 pm
MDW
- PMO
2 stops14h 01m
Multiple Airlines
Tue 8/256:10 am
PMO
- MDW
2 stops19h 21m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$1,046
This Air France deal was found by Cheapflights users on 2/2. 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 Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/155:59 pm
MDW
- PMO
2 stops14h 01m
Multiple Airlines
Mon 8/246:10 am
PMO
- MDW
2 stops19h 21m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$1,079
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/116:00 am
MDW
- CTA
2 stops18h 55m
Delta
Sat 8/229:55 am
CTA
- MDW
2 stops18h 51m
Delta
Deal found 2/2![Delta logo]()
$1,122
This Expedia deal was found by Cheapflights users on 2/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/156:00 am
MDW
- PMO
2 stops25h 30m
KLM
Mon 3/23:15 pm
PMO
- MDW
2 stops38h 18m
KLM
Deal found 2/2![KLM logo]()
$1,123
Best flights from Midway to SicilyDiscover carefully curated flight deals from Midway to Sicily that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 3, 2026.
Discover carefully curated flight deals from Midway to Sicily that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 3, 2026.
This Trip.com deal was found by Cheapflights users on 2/2. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/910:45 am
MDW
- SUF
2 stops25h 45m
KLM
Mon 3/1611:15 am
SUF
- MDW
2 stops36h 39m
KLM
Deal found 2/2![KLM logo]()
$825
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/181:23 pm
MDW
- PMO
2 stops19h 27m
Delta
Sun 4/264:45 pm
PMO
- MDW
2 stops30h 40m
Delta
Deal found 2/2![Delta logo]()
$909
This Air France deal was found by Cheapflights users on 2/2. 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 Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3012:53 pm
MDW
- PMO
2 stops16h 12m
Multiple Airlines
Sat 5/96:10 am
PMO
- MDW
2 stops19h 04m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$1,325
This Air France deal was found by Cheapflights users on 2/2. 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 Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/61:23 pm
MDW
- PMO
2 stops18h 02m
KLM
Tue 5/196:10 am
PMO
- MDW
2 stops19h 04m
KLM
Deal found 2/2![KLM logo]()
$885
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/186:00 am
MDW
- CTA
2 stops18h 55m
Delta
Sun 4/269:55 am
CTA
- MDW
2 stops19h 33m
Delta
Deal found 2/2![Delta logo]()
$1,276
This Mytrip deal was found by Cheapflights users on 2/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2710:25 am
MDW
- CTA
3 stops23h 20m
Multiple Airlines
Fri 6/56:15 am
CTA
- MDW
3 stops34h 25m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$1,337
This KLM deal was found by Cheapflights users on 2/2. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/136:40 pm
MDW
- PMO
2 stops40h 45m
KLM
Mon 3/93:15 pm
PMO
- MDW
2 stops37h 16m
KLM
Deal found 2/2![KLM logo]()
$1,297
This Delta deal was found by Cheapflights users on 2/1. 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 4/236:00 am
MDW
- CTA
2 stops18h 55m
Delta
Sun 5/39:55 am
CTA
- MDW
2 stops19h 33m
Delta
Deal found 2/1![Delta logo]()
$1,452
This KLM deal was found by Cheapflights users on 2/1. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/1511:01 am
MDW
- PMO
2 stops20h 29m
KLM
Mon 3/210:05 am
PMO
- MDW
2 stops19h 26m
KLM
Deal found 2/1![KLM logo]()
$1,411
This KLM deal was found by Cheapflights users on 2/3. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:36 pm
MDW
- CTA
2 stops14h 34m
KLM
Sat 5/169:55 am
CTA
- MDW
2 stops18h 14m
KLM
Deal found 2/3![KLM logo]()
$1,465
This Delta deal was found by Cheapflights users on 2/1. 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 4/306:00 am
MDW
- CTA
2 stops18h 55m
Delta
Sun 5/39:55 am
CTA
- MDW
2 stops19h 33m
Delta
Deal found 2/1![Delta logo]()
$1,917
This KLM deal was found by Cheapflights users on 2/2. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/171:22 pm
MDW
- PMO
2 stops18h 03m
KLM
Sun 5/246:10 am
PMO
- MDW
2 stops19h 04m
KLM
Deal found 2/2![KLM logo]()
$1,600
This Air France deal was found by Cheapflights users on 2/2. 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 Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/225:59 pm
MDW
- PMO
2 stops14h 01m
Multiple Airlines
Fri 8/76:10 am
PMO
- MDW
2 stops19h 21m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$2,390
This KLM deal was found by Cheapflights users on 2/3. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/206:34 pm
MDW
- CTA
2 stops14h 51m
KLM
Fri 3/276:00 am
CTA
- MDW
2 stops22h 31m
KLM
Deal found 2/3![KLM logo]()
$1,751
This Air France deal was found by Cheapflights users on 2/2. 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 Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/215:59 pm
MDW
- PMO
2 stops14h 01m
Multiple Airlines
Fri 8/76:10 am
PMO
- MDW
2 stops19h 21m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$2,457
This KLM deal was found by Cheapflights users on 2/2. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:30 am
MDW
- CTA
2 stops18h 25m
KLM
Fri 6/56:00 am
CTA
- MDW
2 stops19h 14m
KLM
Deal found 2/2![KLM logo]()
$1,843
This Air France deal was found by Cheapflights users on 2/2. 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 Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/235:59 pm
MDW
- PMO
2 stops14h 01m
Multiple Airlines
Fri 8/76:10 am
PMO
- MDW
2 stops19h 21m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$2,517
This KLM deal was found by Cheapflights users on 2/2. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/166:36 pm
MDW
- CTA
2 stops14h 34m
KLM
Sat 5/2310:15 am
CTA
- MDW
2 stops17h 54m
KLM
Deal found 2/2![KLM logo]()
$1,931
This Air France deal was found by Cheapflights users on 2/2. 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 Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/225:59 pm
MDW
- PMO
2 stops14h 01m
Multiple Airlines
Sat 8/86:10 am
PMO
- MDW
2 stops19h 21m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$2,812
This KLM deal was found by Cheapflights users on 2/1. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/212:05 pm
MDW
- CTA
2 stops15h 50m
KLM
Fri 3/276:00 am
CTA
- MDW
2 stops22h 31m
KLM
Deal found 2/1![KLM logo]()
$1,931
This KLM deal was found by Cheapflights users on 2/1. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/512:45 pm
MDW
- CTA
2 stops17h 40m
KLM
Wed 3/186:00 am
CTA
- MDW
2 stops22h 31m
KLM
Deal found 2/1![KLM logo]()
$1,949
This Air France deal was found by Cheapflights users on 2/2. 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 Air France is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/215:59 pm
MDW
- PMO
2 stops14h 01m
Multiple Airlines
Sun 8/96:10 am
PMO
- MDW
2 stops19h 21m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$2,879
This KLM deal was found by Cheapflights users on 2/2. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/12:12 pm
MDW
- SUF
2 stops21h 18m
KLM
Sat 5/96:15 am
SUF
- MDW
2 stops18h 59m
KLM
Deal found 2/2![KLM logo]()
$2,454
This KLM deal was found by Cheapflights users on 2/2. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/81:05 pm
MDW
- PMO
2 stops17h 35m
KLM
Mon 7/66:10 am
PMO
- MDW
2 stops19h 21m
KLM
Deal found 2/2![KLM logo]()
$2,885
Last-minute flights from Midway to SicilyDiscover last-minute flight deals from Midway to Sicily. Data last updated February 3, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Sicily. Data last updated February 3, 2026 and is based on user searches.
This Ovago deal was found by Cheapflights users on 2/1. 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 Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/26:14 pm
MDW
- CTA
2 stops37h 26m
Air Europa
Mon 2/910:05 am
CTA
- MDW
2 stops19h 17m
Air Europa
Deal found 2/1![Air Europa logo]()
$1,619
This KLM deal was found by Cheapflights users on 2/1. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/512:46 pm
MDW
- CTA
2 stops18h 54m
KLM
Sat 2/1410:15 am
CTA
- MDW
2 stops19h 16m
KLM
Deal found 2/1![KLM logo]()
$1,314
This KLM deal was found by Cheapflights users on 1/31. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/512:46 pm
MDW
- CTA
2 stops18h 54m
KLM
Wed 2/186:00 am
CTA
- MDW
2 stops23h 31m
KLM
Deal found 1/31![KLM logo]()
$1,432
This KLM deal was found by Cheapflights users on 2/2. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/136:40 pm
MDW
- PMO
2 stops40h 45m
KLM
Mon 3/93:15 pm
PMO
- MDW
2 stops37h 16m
KLM
Deal found 2/2![KLM logo]()
$1,297
This Expedia deal was found by Cheapflights users on 2/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/156:00 am
MDW
- PMO
2 stops25h 30m
KLM
Mon 3/23:15 pm
PMO
- MDW
2 stops38h 18m
KLM
Deal found 2/2![KLM logo]()
$1,123
This KLM deal was found by Cheapflights users on 2/1. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/512:45 pm
MDW
- CTA
2 stops17h 40m
KLM
Wed 3/186:00 am
CTA
- MDW
2 stops22h 31m
KLM
Deal found 2/1![KLM logo]()
$1,949
This Trip.com deal was found by Cheapflights users on 2/2. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/910:45 am
MDW
- SUF
2 stops25h 45m
KLM
Mon 3/1611:15 am
SUF
- MDW
2 stops36h 39m
KLM
Deal found 2/2![KLM logo]()
$825
This KLM deal was found by Cheapflights users on 2/1. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1812:47 pm
MDW
- PMO
2 stops16h 53m
KLM
Wed 3/256:10 am
PMO
- MDW
2 stops22h 21m
KLM
Deal found 2/1![KLM logo]()
$1,804
This KLM deal was found by Cheapflights users on 2/3. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/206:34 pm
MDW
- CTA
2 stops14h 51m
KLM
Fri 3/276:00 am
CTA
- MDW
2 stops22h 31m
KLM
Deal found 2/3![KLM logo]()
$1,751
This KLM deal was found by Cheapflights users on 2/1. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/212:05 pm
MDW
- CTA
2 stops15h 50m
KLM
Fri 3/276:00 am
CTA
- MDW
2 stops22h 31m
KLM
Deal found 2/1![KLM logo]()
$1,931
This KLM deal was found by Cheapflights users on 2/1. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/286:34 pm
MDW
- CTA
2 stops14h 36m
KLM
Wed 4/86:00 am
CTA
- MDW
2 stops19h 40m
KLM
Deal found 2/1![KLM logo]()
$1,411
One-way flights from Midway to SicilySearch for one-way flight options from Midway to Sicily. Find affordable one-way fares based on user searches. Data last updated February 3, 2026.
Search for one-way flight options from Midway to Sicily. Find affordable one-way fares based on user searches. Data last updated February 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Wed 5/207:30 am
MDW
- CTA
3 stops31h 00m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$395
This KLM deal was found by Cheapflights users on 2/1. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1110:46 am
MDW
- PMO
2 stops17h 44m
KLM
Deal found 2/1![KLM logo]()
$605
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 5/2210:25 am
MDW
- CTA
3 stops22h 10m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$653
This Delta deal was found by Cheapflights users on 2/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:30 am
MDW
- CTA
2 stops21h 45m
Delta
Deal found 2/3![Delta logo]()
$758
This Gurufare deal was found by Cheapflights users on 2/2. 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 Gurufare is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/129:30 am
MDW
- PMO
2 stops21h 55m
Scandinavian Airlines
Deal found 2/2![Scandinavian Airlines logo]()
$938
This KLM deal was found by Cheapflights users on 1/31. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/226:36 pm
MDW
- CTA
2 stops14h 34m
KLM
Deal found 1/31![KLM logo]()
$1,073
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 4/3011:00 am
MDW
- PMO
3 stops26h 20m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$1,167
This KLM deal was found by Cheapflights users on 2/2. 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 KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/125:59 pm
MDW
- CTA
2 stops15h 11m
KLM
Deal found 2/2![KLM logo]()
$1,376
This Ovago deal was found by Cheapflights users on 2/1. 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 Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/309:27 am
MDW
- PMO
2 stops27h 18m
Air Europa
Deal found 2/1![Air Europa logo]()
$1,641
Find flight deals from Midway to Sicily
Keep the following information in mind while searching for Midway to Sicily flight deals. Data was last updated February 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $825 (Trip.com) |
One-way from | $395 (Kiwi.com) |
Popular in | June |
Cheapest in | February |
Average price | $711 |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Sicily 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 February 3, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Sicily that are best for you.
Fly from
Midway
Fly to
Sicily
Route
Depart
Return
Price
ChicagoLamezia Terme
MDW - SUF
MDWSUF
Chicago Midway
Mon 3/9
10:45 am-6:30 pm
2 stops25h 45m
Lamezia Terme Intl
Mon 3/16
11:15 am-5:54 pm
2 stops36h 39m
$825
ChicagoPalermo
MDW - PMO
MDWPMO
Chicago Midway
Wed 5/6
1:23 pm-2:25 pm
2 stops18h 02m
Palermo Punta Raisi
Tue 5/19
6:10 am-6:14 pm
2 stops19h 04m
$885
ChicagoPalermo
MDW - PMO
MDWPMO
Chicago Midway
Sat 4/18
1:23 pm-3:50 pm
2 stops19h 27m
Palermo Punta Raisi
Sun 4/26
4:45 pm-4:25 pm
2 stops30h 40m
$909
ChicagoCatania
MDW - CTA
MDWCTA
Chicago Midway
Sat 4/18
6:00 am-7:55 am
2 stops18h 55m
Catania Fontanarossa
Sun 4/26
9:55 am-10:28 pm
2 stops19h 33m
$1,276
ChicagoPalermo
MDW - PMO
MDWPMO
Chicago Midway
Fri 2/13
6:40 pm-6:25 pm
2 stops40h 45m
Palermo Punta Raisi
Mon 3/9
3:15 pm-10:31 pm
2 stops37h 16m
$1,297
ChicagoPalermo
MDW - PMO
MDWPMO
Chicago Midway
Thu 4/30
12:53 pm-12:05 pm
2 stops16h 12m
Palermo Punta Raisi
Sat 5/9
6:10 am-6:14 pm
2 stops19h 04m
$1,325
ChicagoCatania
MDW - CTA
MDWCTA
Chicago Midway
Wed 5/27
10:25 am-4:45 pm
3 stops23h 20m
Catania Fontanarossa
Fri 6/5
6:15 am-9:40 am
3 stops34h 25m
$1,337
ChicagoPalermo
MDW - PMO
MDWPMO
Chicago Midway
Sun 2/15
11:01 am-2:30 pm
2 stops20h 29m
Palermo Punta Raisi
Mon 3/2
10:05 am-10:31 pm
2 stops19h 26m
$1,411
ChicagoCatania
MDW - CTA
MDWCTA
Chicago Midway
Thu 4/23
6:00 am-7:55 am
2 stops18h 55m
Catania Fontanarossa
Sun 5/3
9:55 am-10:28 pm
2 stops19h 33m
$1,452
ChicagoCatania
MDW - CTA
MDWCTA
Chicago Midway
Sat 5/9
6:36 pm-4:10 pm
2 stops14h 34m
Catania Fontanarossa
Sat 5/16
9:55 am-9:09 pm
2 stops18h 14m
$1,465
Showing 1-10 of 32 results
Best time to book a flight from Midway to Sicily
Have a flexible travel schedule? Discover the best time to fly to Sicily from Midway with our price prediction graph.
MDW-CTA
MDW-PMO
MDW-SUF
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 Chicago Midway Airport to Sicily
MDW-ITSI
MDW-CTA
MDW-PMO
MDW-SUF
No data available for this route at this time. Please check back soon.