$59+ Cheap flights from Midway (MDW) to Cleveland (CLE)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/26. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CLE
Dec 5 — Dec 121
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Cleveland 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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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Midway to Cleveland
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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 November 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 November 5, 2026.
This Southwest deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/151:15 pm -
2 stops7h 30m
Tue 12/226:40 am -
1 stop6h 35m
Deal found 10/31![Southwest logo]()
$142
This Priceline deal was found by Cheapflights users on 11/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/226:43 am -
1 stop8h 52m
Tue 12/297:04 pm -
1 stop5h 57m
Deal found 11/3![Frontier logo]()
$143
This Orbitz deal was found by Cheapflights users on 10/31. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/218:42 pm -
1 stop10h 59m
Mon 11/239:31 pm -
1 stop23h 16m
Deal found 10/31![Frontier logo]()
$153
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/257:35 pm -
Nonstop1h 15m
Fri 11/277:55 pm -
Nonstop1h 35m
Deal found 11/2![Southwest logo]()
$154
This Delta deal was found by Cheapflights users on 11/2. 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.
Mon 11/239:30 am -
1 stop4h 43m
Wed 12/22:05 pm -
1 stop4h 56m
Deal found 11/2![Delta logo]()
$157
This Southwest deal was found by Cheapflights users on 11/4. 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 12/77:35 am -
1 stop4h 30m
Mon 12/77:10 pm -
Nonstop1h 25m
Deal found 11/4![Southwest logo]()
$164
This Expedia deal was found by Cheapflights users on 11/4. 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.
Sat 12/1212:28 pm -
1 stop11h 28m
Sun 12/136:01 am -
1 stop11h 05m
Deal found 11/4![Frontier logo]()
$169
This Southwest deal was found by Cheapflights users on 11/1. 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.
Wed 11/257:35 pm -
Nonstop1h 15m
Mon 1/410:45 am -
2 stops10h 20m
Deal found 11/1![Southwest logo]()
$175
This Frontier deal was found by Cheapflights users on 11/4. 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.
Sat 12/191:11 pm -
1 stop10h 40m
Fri 12/256:00 pm -
1 stop7h 01m
Deal found 11/4![Frontier logo]()
$179
This CheapOair deal was found by Cheapflights users on 11/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/43:36 pm -
1 stop6h 50m
Sun 12/65:18 pm -
1 stop24h 58m
Deal found 11/1![Frontier logo]()
$180
This Trip.com deal was found by Cheapflights users on 11/2. 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.
Tue 12/1512:28 pm -
1 stop11h 28m
Sun 1/101:38 pm -
1 stop6h 57m
Deal found 11/2![Frontier logo]()
$181
This Trip.com deal was found by Cheapflights users on 11/1. 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.
Tue 11/248:42 pm -
1 stop10h 59m
Thu 11/265:30 am -
1 stop7h 51m
Deal found 11/1![Frontier logo]()
$185
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 November 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 November 5, 2026.
This Southwest deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/151:15 pm -
2 stops7h 30m
Tue 12/226:40 am -
1 stop6h 35m
Deal found 10/31![Southwest logo]()
$142
This Delta deal was found by Cheapflights users on 11/1. 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.
Mon 11/239:30 am -
1 stop2h 58m
Wed 12/22:05 pm -
1 stop4h 56m
Deal found 11/1![Delta logo]()
$157
This Frontier deal was found by Cheapflights users on 11/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/251:16 pm -
1 stop5h 53m
Mon 1/411:39 am -
1 stop8h 51m
Deal found 11/2![Frontier logo]()
$243
This Southwest deal was found by Cheapflights users on 11/2. 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.
Mon 1/412:45 pm -
2 stops9h 10m
Wed 1/66:00 am -
2 stops9h 20m
Deal found 11/2![Southwest logo]()
$153
This Southwest deal was found by Cheapflights users on 11/4. 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.
Thu 12/31:50 pm -
Nonstop1h 20m
Mon 12/77:10 pm -
Nonstop1h 25m
Deal found 11/4![Southwest logo]()
$188
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/21:15 pm -
2 stops7h 30m
Sat 12/54:25 pm -
1 stop4h 10m
Deal found 11/2![Southwest logo]()
$213
This Delta deal was found by Cheapflights users on 11/3. 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.
Wed 3/39:33 am -
1 stop2h 50m
Sun 3/74:00 pm -
1 stop3h 37m
Deal found 11/3![Delta logo]()
$262
This Southwest deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/227:35 pm -
Nonstop1h 15m
Tue 12/298:05 pm -
Nonstop1h 25m
Deal found 10/31![Southwest logo]()
$232
This Southwest deal was found by Cheapflights users on 11/3. 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.
Tue 12/18:25 am -
Nonstop1h 15m
Tue 12/17:10 pm -
Nonstop1h 25m
Deal found 11/3![Southwest logo]()
$259
This Southwest deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/307:35 am -
Nonstop1h 10m
Mon 12/76:05 pm -
1 stop4h 30m
Deal found 10/31![Southwest logo]()
$272
Last-minute flights from Midway to ClevelandDiscover last-minute flight deals from Midway to Cleveland. Data last updated November 5, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Cleveland. Data last updated November 5, 2026 and is based on user searches.
This Orbitz deal was found by Cheapflights users on 10/31. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/218:42 pm -
1 stop10h 59m
Mon 11/239:31 pm -
1 stop23h 16m
Deal found 10/31![Frontier logo]()
$153
This Delta deal was found by Cheapflights users on 11/2. 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.
Mon 11/239:30 am -
1 stop4h 43m
Wed 12/22:05 pm -
1 stop4h 56m
Deal found 11/2![Delta logo]()
$157
This Trip.com deal was found by Cheapflights users on 11/1. 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.
Tue 11/248:42 pm -
1 stop10h 59m
Thu 11/265:30 am -
1 stop7h 51m
Deal found 11/1![Frontier logo]()
$185
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/257:35 pm -
Nonstop1h 15m
Fri 11/277:55 pm -
Nonstop1h 35m
Deal found 11/2![Southwest logo]()
$154
This Southwest deal was found by Cheapflights users on 11/1. 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.
Wed 11/257:35 pm -
Nonstop1h 15m
Mon 1/410:45 am -
2 stops10h 20m
Deal found 11/1![Southwest logo]()
$175
This CheapOair deal was found by Cheapflights users on 11/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/43:36 pm -
1 stop6h 50m
Sun 12/65:18 pm -
1 stop24h 58m
Deal found 11/1![Frontier logo]()
$180
This Southwest deal was found by Cheapflights users on 11/4. 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 12/77:35 am -
1 stop4h 30m
Mon 12/77:10 pm -
Nonstop1h 25m
Deal found 11/4![Southwest logo]()
$164
This Expedia deal was found by Cheapflights users on 11/4. 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.
Sat 12/1212:28 pm -
1 stop11h 28m
Sun 12/136:01 am -
1 stop11h 05m
Deal found 11/4![Frontier logo]()
$169
This Southwest deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/151:15 pm -
2 stops7h 30m
Tue 12/226:40 am -
1 stop6h 35m
Deal found 10/31![Southwest logo]()
$142
This Trip.com deal was found by Cheapflights users on 11/2. 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.
Tue 12/1512:28 pm -
1 stop11h 28m
Sun 1/101:38 pm -
1 stop6h 57m
Deal found 11/2![Frontier logo]()
$181
This Frontier deal was found by Cheapflights users on 11/4. 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.
Sat 12/191:11 pm -
1 stop10h 40m
Fri 12/256:00 pm -
1 stop7h 01m
Deal found 11/4![Frontier logo]()
$179
This Priceline deal was found by Cheapflights users on 11/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/226:43 am -
1 stop8h 52m
Tue 12/297:04 pm -
1 stop5h 57m
Deal found 11/3![Frontier logo]()
$143
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 November 5, 2026.
Search for one-way flight options from Midway to Cleveland. Find affordable one-way fares based on user searches. Data last updated November 5, 2026.
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/261:40 pm -
Nonstop1h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Southwest logo]()
$59
This CheapOair deal was found by Cheapflights users on 11/4. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/261:16 pm -
1 stop5h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Frontier logo]()
$60
This Super.com deal was found by Cheapflights users on 11/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/249:09 am -
1 stop10h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$64
This Priceline deal was found by Cheapflights users on 11/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/226:43 am -
1 stop8h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Frontier logo]()
$65
This Frontier deal was found by Cheapflights users on 11/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/239:09 am -
1 stop10h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$66
This Trip.com deal was found by Cheapflights users on 11/1. 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.
Mon 1/118:30 pm -
1 stop27h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Frontier logo]()
$70
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/21:15 pm -
2 stops7h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Southwest logo]()
$74
This Delta deal was found by Cheapflights users on 11/2. 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.
Mon 12/216:15 pm -
1 stop4h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Delta logo]()
$79
This CheapOair deal was found by Cheapflights users on 11/3. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/115:02 pm -
1 stop6h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Frontier logo]()
$86
This Super.com deal was found by Cheapflights users on 11/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/238:35 pm -
1 stop25h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$88
This Super.com deal was found by Cheapflights users on 11/1. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/65:02 pm -
1 stop6h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Frontier logo]()
$89
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 November 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $142 (Southwest) |
One-way from | $59 (Southwest) |
Popular in | April |
Cheapest in | May |
Average price | $312 |
Good round-trip deal | $117 or less |
Good one-way deal | $250 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 7,457,451 searches. Data last updated November 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
Quickest round-trip
ChicagoCleveland
MDW Chicago Midway - CLE Cleveland Hopkins Intl
MDWCLE
Chicago Midway
Wed 12/30
7:35 am-9:45 am
Nonstop1h 10m
Cleveland Hopkins Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$59
ChicagoCleveland
MDW Chicago Midway - CLE Cleveland Hopkins Intl
MDWCLE
Chicago Midway
Thu 12/24
8:25 am-10:40 am
Nonstop1h 15m
Cleveland Hopkins Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$59
ChicagoCleveland
MDW Chicago Midway - CLE Cleveland Hopkins Intl
MDWCLE
Chicago Midway
Thu 11/26
1:40 pm-3:55 pm
Nonstop1h 15m
Cleveland Hopkins Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$59
ChicagoCleveland
MDW Chicago Midway - CLE Cleveland Hopkins Intl
MDWCLE
Chicago Midway
Mon 12/7
1:50 pm-4:10 pm
Nonstop1h 20m
Cleveland Hopkins Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$59
ChicagoCleveland
MDW Chicago Midway - CLE Cleveland Hopkins Intl
MDWCLE
Chicago Midway
Fri 12/11
6:41 pm-11:59 pm
1 stop4h 18m
Cleveland Hopkins Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$79
ChicagoCleveland
MDW Chicago Midway - CLE Cleveland Hopkins Intl
MDWCLE
Chicago Midway
Thu 12/24
6:15 pm-10:52 pm
1 stop3h 37m
Cleveland Hopkins Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$79
ChicagoCleveland
MDW Chicago Midway - CLE Cleveland Hopkins Intl
MDWCLE
Chicago Midway
Thu 1/21
9:38 am-1:28 pm
1 stop2h 50m
Cleveland Hopkins Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$79
ChicagoCleveland
MDW Chicago Midway - CLE Cleveland Hopkins Intl
MDWCLE
Chicago Midway
Sun 12/6
7:45 am-10:05 am
Nonstop1h 20m
Cleveland Hopkins Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$130
ChicagoCleveland
MDW Chicago Midway - CLE Cleveland Hopkins Intl
MDWCLE
Chicago Midway
Wed 11/25
1:10 pm-3:25 pm
Nonstop1h 15m
Cleveland Hopkins Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$130
ChicagoCleveland
MDW Chicago Midway - CLE Cleveland Hopkins Intl
MDWCLE
Chicago Midway
Fri 12/11
12:50 pm-3:00 pm
Nonstop1h 10m
Cleveland Hopkins Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$130
Showing 1-10 of 21 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 November.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 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.
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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 November 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 50% 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 October 31, 2026.
Travelers seeking maximum savings on their Chicago Midway Airport to Cleveland flight should consider departing on Thursday afternoons 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.
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 November 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.
Overall
8.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Overall
8.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
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
Beachwood
Independence
Mansfield
Strongsville
Lakewood
Avon
Medina
Streetsboro
North Olmsted
Cuyahoga Falls
Westlake
Elyria
Kent
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Alternative routes for Midway to Cleveland
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Other flights to Cleveland
Explore flights to Cleveland departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on November 5, 2026.
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Midway and Cleveland flights
Browse other Midway and Cleveland flight options. Last updated on November 5, 2026.
Other flights from Midway
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Popular flight searches
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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 7,457,451 searches. Data last updated November 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$117 | Average$509 | FlexibilityNo cancel fee | On-time63% |