$88+ Cheap flights from Midway (MDW) to Cleveland (CLE)
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 7/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CLE
Jun 4 — Jun 111
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Cleveland with Cheapflights
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Cheapest flights from Midway to ClevelandExplore the most affordable flight options available from Midway to Cleveland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 5, 2026.
Explore the most affordable flight options available from Midway to Cleveland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 5, 2026.
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/38:05 am
MDW
- CLE
Nonstop1h 20m
Southwest
Sat 9/54:35 pm
CLE
- MDW
Nonstop1h 20m
Southwest
Deal found 5/5![Southwest logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/256:00 am
MDW
- CLE
1 stop13h 54m
Frontier
Mon 6/13:46 pm
CLE
- MDW
1 stop7h 16m
Frontier
Deal found 4/30![Frontier logo]()
$195
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/233:40 pm
MDW
- CLE
Nonstop1h 10m
Southwest
Tue 5/262:45 pm
CLE
- MDW
Nonstop1h 20m
Southwest
Deal found 5/2![Southwest logo]()
$199
This Southwest deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2112:50 pm
MDW
- CLE
Nonstop1h 15m
Southwest
Mon 5/258:10 pm
CLE
- MDW
1 stop3h 35m
Southwest
Deal found 4/30![Southwest logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 5/1. 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.
Sun 5/316:00 am
MDW
- CLE
1 stop12h 34m
Frontier
Mon 6/13:46 pm
CLE
- MDW
1 stop20h 26m
Frontier
Deal found 5/1![Frontier logo]()
$202
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/312:04 pm
MDW
- CLE
1 stop5h 23m
Frontier
Sat 6/63:46 pm
CLE
- MDW
1 stop7h 16m
Frontier
Deal found 5/4![Frontier logo]()
$204
This Frontier deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2311:59 am
MDW
- CLE
1 stop5h 28m
Frontier
Sat 5/303:46 pm
CLE
- MDW
1 stop7h 16m
Frontier
Deal found 4/30![Frontier logo]()
$205
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/184:52 pm
MDW
- CLE
1 stop19h 17m
Frontier
Wed 6/33:36 pm
CLE
- MDW
1 stop7h 26m
Frontier
Deal found 5/4![Frontier logo]()
$206
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 7/86:15 pm
MDW
- CLE
Nonstop1h 10m
Southwest
Sat 7/1112:30 pm
CLE
- MDW
Nonstop1h 15m
Southwest
Deal found 5/4![Southwest logo]()
$207
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/712:11 pm
MDW
- CLE
1 stop7h 41m
Frontier
Thu 8/63:46 pm
CLE
- MDW
1 stop7h 22m
Frontier
Deal found 5/3![Frontier logo]()
$210
This Delta deal was found by Cheapflights users on 5/1. 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.
Sat 5/231:22 pm
MDW
- CLE
1 stop4h 25m
Delta
Mon 5/256:35 am
CLE
- MDW
1 stop3h 08m
Delta
Deal found 5/1![Delta logo]()
$211
Best flights from Midway to ClevelandDiscover carefully curated flight deals from Midway to Cleveland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 5, 2026.
Discover carefully curated flight deals from Midway to Cleveland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 5, 2026.
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/233:40 pm
MDW
- CLE
Nonstop1h 10m
Southwest
Tue 5/265:50 am
CLE
- MDW
1 stop5h 50m
Southwest
Deal found 5/1![Southwest logo]()
$201
This Delta deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/299:22 am
MDW
- CLE
1 stop3h 01m
Delta
Fri 5/295:35 pm
CLE
- MDW
1 stop4h 34m
Delta
Deal found 4/30![Delta logo]()
$297
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/128:00 am
MDW
- CLE
Nonstop1h 15m
Southwest
Mon 7/134:45 pm
CLE
- MDW
Nonstop1h 20m
Southwest
Deal found 5/2![Southwest logo]()
$277
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/187:50 am
MDW
- CLE
Nonstop1h 15m
Southwest
Mon 7/208:10 pm
CLE
- MDW
Nonstop1h 15m
Southwest
Deal found 5/2![Southwest logo]()
$277
This Delta deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/246:23 am
MDW
- CLE
1 stop5h 40m
Delta
Sun 5/245:35 pm
CLE
- MDW
1 stop4h 34m
Delta
Deal found 4/30![Delta logo]()
$338
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/1511:00 am
MDW
- CLE
1 stop3h 20m
Southwest
Mon 6/2212:05 pm
CLE
- MDW
Nonstop1h 15m
Southwest
Deal found 5/1![Southwest logo]()
$287
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/512:15 pm
MDW
- CLE
Nonstop1h 10m
Southwest
Sun 6/79:10 pm
CLE
- MDW
1 stop4h 10m
Southwest
Deal found 5/2![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/136:00 pm
MDW
- CLE
1 stop4h 25m
Southwest
Sun 7/198:20 am
CLE
- MDW
Nonstop1h 15m
Southwest
Deal found 5/1![Southwest logo]()
$287
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/2612:45 pm
MDW
- CLE
2 stops6h 55m
Southwest
Sun 6/288:10 pm
CLE
- MDW
Nonstop1h 15m
Southwest
Deal found 5/2![Southwest logo]()
$292
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/251:00 pm
MDW
- CLE
2 stops6h 40m
Southwest
Sun 6/286:00 am
CLE
- MDW
2 stops8h 05m
Southwest
Deal found 5/1![Southwest logo]()
$317
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 5/282:10 pm
MDW
- CLE
2 stops8h 10m
Southwest
Mon 6/112:40 pm
CLE
- MDW
2 stops8h 25m
Southwest
Deal found 5/3![Southwest logo]()
$340
This Southwest deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/292:10 pm
MDW
- CLE
2 stops8h 10m
Southwest
Fri 6/56:50 am
CLE
- MDW
2 stops7h 45m
Southwest
Deal found 5/1![Southwest logo]()
$342
Last-minute flights from Midway to ClevelandDiscover last-minute flight deals from Midway to Cleveland. Data last updated May 5, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Cleveland. Data last updated May 5, 2026 and is based on user searches.
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/184:52 pm
MDW
- CLE
1 stop19h 17m
Frontier
Wed 6/33:36 pm
CLE
- MDW
1 stop7h 26m
Frontier
Deal found 5/4![Frontier logo]()
$206
This Southwest deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2112:50 pm
MDW
- CLE
Nonstop1h 15m
Southwest
Mon 5/258:10 pm
CLE
- MDW
1 stop3h 35m
Southwest
Deal found 4/30![Southwest logo]()
$201
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/233:40 pm
MDW
- CLE
Nonstop1h 10m
Southwest
Tue 5/262:45 pm
CLE
- MDW
Nonstop1h 20m
Southwest
Deal found 5/2![Southwest logo]()
$199
This Frontier deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2311:59 am
MDW
- CLE
1 stop5h 28m
Frontier
Sat 5/303:46 pm
CLE
- MDW
1 stop7h 16m
Frontier
Deal found 4/30![Frontier logo]()
$205
This Delta deal was found by Cheapflights users on 5/1. 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.
Sat 5/231:22 pm
MDW
- CLE
1 stop4h 25m
Delta
Mon 5/256:35 am
CLE
- MDW
1 stop3h 08m
Delta
Deal found 5/1![Delta logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/256:00 am
MDW
- CLE
1 stop13h 54m
Frontier
Mon 6/13:46 pm
CLE
- MDW
1 stop7h 16m
Frontier
Deal found 4/30![Frontier logo]()
$195
This Kiwi.com deal was found by Cheapflights users on 5/1. 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.
Sun 5/316:00 am
MDW
- CLE
1 stop12h 34m
Frontier
Mon 6/13:46 pm
CLE
- MDW
1 stop20h 26m
Frontier
Deal found 5/1![Frontier logo]()
$202
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/312:04 pm
MDW
- CLE
1 stop5h 23m
Frontier
Sat 6/63:46 pm
CLE
- MDW
1 stop7h 16m
Frontier
Deal found 5/4![Frontier logo]()
$204
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.
Fri 6/512:04 pm
MDW
- CLE
1 stop5h 23m
Frontier
Sat 6/63:46 pm
CLE
- MDW
1 stop7h 16m
Frontier
Deal found 5/4![Frontier logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1112:27 pm
MDW
- CLE
1 stop7h 28m
Frontier
Sun 6/145:51 pm
CLE
- MDW
1 stop18h 18m
Frontier
Deal found 4/30![Frontier logo]()
$207
One-way flights from Midway to ClevelandSearch for one-way flight options from Midway to Cleveland. Find affordable one-way fares based on user searches. Data last updated May 5, 2026.
Search for one-way flight options from Midway to Cleveland. Find affordable one-way fares based on user searches. Data last updated May 5, 2026.
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 7/16:00 am
MDW
- CLE
1 stop13h 55m
Frontier
Deal found 5/4![Frontier logo]()
$88
This Frontier deal was found by Cheapflights users on 5/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2812:27 pm
MDW
- CLE
1 stop6h 07m
Frontier
Deal found 5/1![Frontier logo]()
$90
This Trip.com deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1611:59 am
MDW
- CLE
1 stop7h 58m
Frontier
Deal found 5/1![Frontier logo]()
$93
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/186:00 am
MDW
- CLE
1 stop11h 27m
Frontier
Deal found 5/3![Frontier logo]()
$95
This Southwest deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/85:25 pm
MDW
- CLE
Nonstop1h 10m
Southwest
Deal found 4/30![Southwest logo]()
$96
This Kiwi.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1112:27 pm
MDW
- CLE
1 stop7h 28m
Frontier
Deal found 4/30![Frontier logo]()
$104
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.
Mon 6/86:58 pm
MDW
- CLE
1 stop4h 01m
Delta
Deal found 5/4![Delta logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/1612:11 pm
MDW
- CLE
1 stop22h 38m
Frontier
Deal found 4/30![Frontier logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/136:00 am
MDW
- CLE
1 stop13h 55m
Frontier
Deal found 4/30![Frontier logo]()
$109
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.
Mon 7/276:00 am
MDW
- CLE
1 stop13h 52m
Frontier
Deal found 5/5![Frontier logo]()
$110
This Delta deal was found by Cheapflights users on 5/1. 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 5/281:22 pm
MDW
- CLE
2 stops8h 48m
Delta
Deal found 5/1![Delta logo]()
$111
Find flight deals from Midway to Cleveland
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Cleveland (CLE). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $195 (Kiwi.com) |
One-way from | $88 (Kiwi.com) |
Popular in | July |
Cheapest in | June |
Average price | $234 |
Good round-trip deal | $234 or less |
Good one-way deal | $148 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Cleveland 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 5, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Cleveland that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoCleveland
MDW - CLE
MDWCLE
Chicago Midway
Sat 5/23
3:40 pm-5:50 pm
Nonstop1h 10m
Cleveland Hopkins Intl
Tue 5/26
5:50 am-10:40 am
1 stop5h 50m
$201
ChicagoCleveland
MDW - CLE
MDWCLE
Chicago Midway
Sun 7/12
8:00 am-10:15 am
Nonstop1h 15m
Cleveland Hopkins Intl
Mon 7/13
4:45 pm-5:05 pm
Nonstop1h 20m
$277
Quickest round-trip
ChicagoCleveland
MDW - CLE
MDWCLE
Chicago Midway
Sat 7/18
7:50 am-10:05 am
Nonstop1h 15m
Cleveland Hopkins Intl
Mon 7/20
8:10 pm-8:25 pm
Nonstop1h 15m
$277
ChicagoCleveland
MDW - CLE
MDWCLE
Chicago Midway
Mon 6/15
11:00 am-3:20 pm
1 stop3h 20m
Cleveland Hopkins Intl
Mon 6/22
12:05 pm-12:20 pm
Nonstop1h 15m
$287
ChicagoCleveland
MDW - CLE
MDWCLE
Chicago Midway
Fri 6/5
12:15 pm-2:25 pm
Nonstop1h 10m
Cleveland Hopkins Intl
Sun 6/7
9:10 pm-12:20 am
1 stop4h 10m
$287
ChicagoCleveland
MDW - CLE
MDWCLE
Chicago Midway
Mon 7/13
6:00 pm-11:25 pm
1 stop4h 25m
Cleveland Hopkins Intl
Sun 7/19
8:20 am-8:35 am
Nonstop1h 15m
$287
ChicagoCleveland
MDW - CLE
MDWCLE
Chicago Midway
Fri 6/26
12:45 pm-8:40 pm
2 stops6h 55m
Cleveland Hopkins Intl
Sun 6/28
8:10 pm-8:25 pm
Nonstop1h 15m
$292
ChicagoCleveland
MDW - CLE
MDWCLE
Chicago Midway
Fri 5/29
9:22 am-1:23 pm
1 stop3h 01m
Cleveland Hopkins Intl
Fri 5/29
5:35 pm-9:09 pm
1 stop4h 34m
$297
ChicagoCleveland
MDW - CLE
MDWCLE
Chicago Midway
Thu 6/25
1:00 pm-8:40 pm
2 stops6h 40m
Cleveland Hopkins Intl
Sun 6/28
6:00 am-1:05 pm
2 stops8h 05m
$317
ChicagoCleveland
MDW - CLE
MDWCLE
Chicago Midway
Sun 5/24
6:23 am-1:03 pm
1 stop5h 40m
Cleveland Hopkins Intl
Sun 5/24
5:35 pm-9:09 pm
1 stop4h 34m
$338
Showing 1-10 of 24 resultsSorted by cheapest first
Compare providers for flights from Midway to Cleveland
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Cleveland in May.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago Midway Airport-Cleveland flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Cleveland flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Cleveland flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-Cleveland flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Cleveland flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Midway to Cleveland
Have a flexible travel schedule? Discover the best time to fly to Cleveland from Midway with our price prediction graph.
MDW-CLE
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 Cleveland
What is the cheapest time of day to fly from MDW to CLE?
Find hourly flight availability from Midway to Cleveland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 5, 2026.
When flying from Chicago Midway Airport to Cleveland, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 30% versus a flight in the evening.
What is the cheapest day to fly from Chicago Midway Airport to Cleveland?
Use this chart to determine the cheapest time to fly round-trip from Midway to Cleveland. Price data was last updated on May 2, 2026.
Travelers seeking maximum savings on their Chicago Midway Airport to Cleveland flight should consider departing on Wednesday at noon when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
How much does it cost to fly round-trip from Chicago Midway Airport to Cleveland?
The best insider tips for Chicago Midway Airport to Cleveland flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago Midway Airport to Cleveland trip
Our travel experts
Reviews of airlines servicing Cleveland
Get insights into the airlines that provide service to Cleveland. 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 Cleveland. Reviews last updated May 5, 2026.
See what other customers who have flown with Southwest from Chicago Midway Airport to Cleveland have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
7.9
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
7.9
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Midway to Cleveland. 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 Cleveland?
Book flights to Cleveland if you plan to visit one of these locationsSandusky
Mentor
Avon
Mansfield
Beachwood
Wooster
Strongsville
Lakewood
Independence
Streetsboro
Medina
North Olmsted
Cuyahoga Falls
Macedonia
Kent
Elyria
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Midway and Cleveland flights
Browse other Midway and Cleveland flight options. Last updated on May 5, 2026.
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Top airline flying from Midway to Cleveland
Discover the top airline that operate flights from Midway to Cleveland. 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 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$97 | Average$457 | FlexibilityNo cancel fee | On-time63% |