$69+ Cheap flights from Cleveland (CLE) to Midway (MDW)
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 10/31. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — MDW
Aug 17 — Aug 241
Round-trip
1 adult, Economy
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Find cheap flights from Cleveland to Midway 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 Cleveland to MidwayExplore the most affordable flight options available from Cleveland to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 18, 2026.
Explore the most affordable flight options available from Cleveland to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 18, 2026.
This Delta deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/252:20 pm
CLE
- MDW
1 stop5h 13m
Delta
Wed 8/269:24 am
MDW
- CLE
1 stop3h 16m
Delta
Deal found 7/13![Delta logo]()
$157
This Southwest deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 8/83:15 pm
CLE
- MDW
1 stop6h 15m
Southwest
Thu 8/134:25 pm
MDW
- CLE
Nonstop1h 15m
Southwest
Deal found 7/16![Southwest logo]()
$163
This Delta deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 8/266:43 am
CLE
- MDW
1 stop3h 34m
Delta
Sat 8/299:24 am
MDW
- CLE
1 stop3h 16m
Delta
Deal found 7/16![Delta logo]()
$167
This Delta deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” 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 8/2710:24 am
CLE
- MDW
1 stop3h 15m
Delta
Sat 8/299:24 am
MDW
- CLE
1 stop5h 04m
Delta
Deal found 7/15![Delta logo]()
$178
This Southwest deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” 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 8/107:20 pm
CLE
- MDW
1 stop3h 35m
Southwest
Tue 8/1112:45 pm
MDW
- CLE
2 stops7h 15m
Southwest
Deal found 7/15![Southwest logo]()
$181
This Delta deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:00 am
CLE
- MDW
1 stop4h 18m
Delta
Sat 11/149:30 am
MDW
- CLE
1 stop3h 05m
Delta
Deal found 7/17![Delta logo]()
$186
This Delta deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” 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 8/243:49 pm
CLE
- MDW
1 stop3h 44m
Delta
Thu 8/279:24 am
MDW
- CLE
1 stop3h 16m
Delta
Deal found 7/15![Delta logo]()
$188
This Southwest deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/126:25 am
CLE
- MDW
2 stops11h 25m
Southwest
Sat 8/157:55 am
MDW
- CLE
2 stops7h 50m
Southwest
Deal found 7/16![Southwest logo]()
$192
This Southwest deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” 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 9/47:15 pm
CLE
- MDW
Nonstop1h 15m
Southwest
Mon 9/78:05 am
MDW
- CLE
Nonstop1h 20m
Southwest
Deal found 7/14![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” 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 8/138:18 am
CLE
- MDW
1 stop5h 21m
Delta
Thu 8/206:42 pm
MDW
- CLE
1 stop4h 14m
Delta
Deal found 7/14![Delta logo]()
$198
Best flights from Cleveland to MidwayDiscover carefully curated flight deals from Cleveland to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 18, 2026.
Discover carefully curated flight deals from Cleveland to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 18, 2026.
This Delta deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/252:20 pm
CLE
- MDW
1 stop5h 13m
Delta
Wed 8/269:24 am
MDW
- CLE
1 stop3h 16m
Delta
Deal found 7/13![Delta logo]()
$157
This Southwest deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/125:25 pm
CLE
- MDW
Nonstop1h 15m
Southwest
Thu 8/134:25 pm
MDW
- CLE
Nonstop1h 15m
Southwest
Deal found 7/17![Southwest logo]()
$195
This Southwest deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” 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 8/217:20 pm
CLE
- MDW
1 stop3h 35m
Southwest
Mon 8/244:25 pm
MDW
- CLE
Nonstop1h 15m
Southwest
Deal found 7/14![Southwest logo]()
$207
This Southwest deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1212:50 pm
CLE
- MDW
Nonstop1h 15m
Southwest
Sat 8/157:55 am
MDW
- CLE
2 stops7h 50m
Southwest
Deal found 7/17![Southwest logo]()
$210
This Delta deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” 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 9/208:28 am
CLE
- MDW
1 stop5h 11m
Delta
Mon 9/217:01 pm
MDW
- CLE
1 stop3h 53m
Delta
Deal found 7/15![Delta logo]()
$237
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/281:50 pm
CLE
- MDW
Nonstop1h 15m
Southwest
Mon 8/312:35 pm
MDW
- CLE
2 stops6h 20m
Southwest
Deal found 7/13![Southwest logo]()
$212
This Southwest deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:00 am
CLE
- MDW
1 stop6h 35m
Southwest
Wed 9/164:40 pm
MDW
- CLE
1 stop4h 15m
Southwest
Deal found 7/17![Southwest logo]()
$215
This Southwest deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 9/47:20 pm
CLE
- MDW
1 stop3h 35m
Southwest
Sat 9/56:35 am
MDW
- CLE
1 stop5h 40m
Southwest
Deal found 7/16![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/45:25 pm
CLE
- MDW
Nonstop1h 15m
Southwest
Fri 8/71:00 pm
MDW
- CLE
Nonstop1h 10m
Southwest
Deal found 7/14![Southwest logo]()
$238
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/107:20 pm
CLE
- MDW
1 stop3h 35m
Southwest
Mon 8/1710:10 am
MDW
- CLE
2 stops5h 35m
Southwest
Deal found 7/13![Southwest logo]()
$263
This Southwest deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/78:50 am
CLE
- MDW
Nonstop1h 10m
Southwest
Mon 8/106:30 pm
MDW
- CLE
Nonstop1h 15m
Southwest
Deal found 7/17![Southwest logo]()
$277
Last-minute flights from Cleveland to MidwayDiscover last-minute flight deals from Cleveland to Midway. Data last updated July 18, 2026 and is based on user searches.
Discover last-minute flight deals from Cleveland to Midway. Data last updated July 18, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 8/83:15 pm
CLE
- MDW
1 stop6h 15m
Southwest
Thu 8/134:25 pm
MDW
- CLE
Nonstop1h 15m
Southwest
Deal found 7/16![Southwest logo]()
$163
This Southwest deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” 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 8/107:20 pm
CLE
- MDW
1 stop3h 35m
Southwest
Tue 8/1112:45 pm
MDW
- CLE
2 stops7h 15m
Southwest
Deal found 7/15![Southwest logo]()
$181
This Southwest deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/121:15 pm
CLE
- MDW
2 stops9h 35m
Southwest
Sat 8/157:55 am
MDW
- CLE
2 stops7h 50m
Southwest
Deal found 7/14![Southwest logo]()
$186
This Delta deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” 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 8/138:18 am
CLE
- MDW
1 stop5h 21m
Delta
Thu 8/206:42 pm
MDW
- CLE
1 stop4h 14m
Delta
Deal found 7/14![Delta logo]()
$198
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/237:20 pm
CLE
- MDW
Nonstop1h 15m
Southwest
Mon 8/316:30 pm
MDW
- CLE
Nonstop1h 15m
Southwest
Deal found 7/13![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” 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 8/243:49 pm
CLE
- MDW
1 stop3h 44m
Delta
Thu 8/279:24 am
MDW
- CLE
1 stop3h 16m
Delta
Deal found 7/15![Delta logo]()
$188
This Delta deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/252:20 pm
CLE
- MDW
1 stop5h 13m
Delta
Wed 8/269:24 am
MDW
- CLE
1 stop3h 16m
Delta
Deal found 7/13![Delta logo]()
$157
This Delta deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 8/266:43 am
CLE
- MDW
1 stop3h 34m
Delta
Sat 8/299:24 am
MDW
- CLE
1 stop3h 16m
Delta
Deal found 7/16![Delta logo]()
$167
This Delta deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” 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 8/2710:24 am
CLE
- MDW
1 stop3h 15m
Delta
Sat 8/299:24 am
MDW
- CLE
1 stop5h 04m
Delta
Deal found 7/15![Delta logo]()
$178
One-way flights from Cleveland to MidwaySearch for one-way flight options from Cleveland to Midway. Find affordable one-way fares based on user searches. Data last updated July 18, 2026.
Search for one-way flight options from Cleveland to Midway. Find affordable one-way fares based on user searches. Data last updated July 18, 2026.
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/123:20 pm
CLE
- MDW
1 stop6h 25m
Southwest
Deal found 7/13![Southwest logo]()
$69
This Delta deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” 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 8/126:43 am
CLE
- MDW
1 stop3h 34m
Delta
Deal found 7/15![Delta logo]()
$79
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 9/141:15 pm
CLE
- MDW
2 stops9h 40m
Southwest
Deal found 7/13![Southwest logo]()
$80
This Delta deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 8/154:09 pm
CLE
- MDW
1 stop3h 24m
Delta
Deal found 7/16![Delta logo]()
$84
This Southwest deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/154:35 pm
CLE
- MDW
Nonstop1h 20m
Southwest
Deal found 7/17![Southwest logo]()
$98
This Delta deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” 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 8/103:49 pm
CLE
- MDW
1 stop3h 44m
Delta
Deal found 7/14![Delta logo]()
$100
This Delta deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 10/1210:34 am
CLE
- MDW
1 stop3h 14m
Delta
Deal found 7/16![Delta logo]()
$105
This CheapOair deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/53:46 pm
CLE
- MDW
1 stop7h 17m
Frontier
Deal found 7/15![Frontier logo]()
$112
This Southwest deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/105:40 am
CLE
- MDW
2 stops7h 40m
Southwest
Deal found 7/18![Southwest logo]()
$113
This Super.com deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” 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.
Fri 8/285:15 pm
CLE
- MDW
1 stop6h 32m
Frontier
Deal found 7/14![Frontier logo]()
$118
Find flight deals from Cleveland to Midway
Discover tips and strategies to find the most affordable flight options for your journey from Cleveland (CLE) to Midway (MDW). 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 July 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $157 (Delta) |
One-way from | $69 (Southwest) |
Popular in | January |
Cheapest in | September |
Average price | $277 |
Good round-trip deal | $270 or less |
Good one-way deal | $213 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Cleveland to Midway 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 July 18, 2026.
Use the filters below to find and compare flights from Cleveland to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ClevelandChicago
CLE - MDW
CLEMDW
Cleveland Hopkins Intl
Tue 8/25
2:20 pm-6:33 pm
1 stop5h 13m
Chicago Midway
Wed 8/26
9:24 am-1:40 pm
1 stop3h 16m
$157
ClevelandChicago
CLE - MDW
CLEMDW
Cleveland Hopkins Intl
Wed 8/12
5:25 pm-5:40 pm
Nonstop1h 15m
Chicago Midway
Thu 8/13
4:25 pm-6:40 pm
Nonstop1h 15m
$195
ClevelandChicago
CLE - MDW
CLEMDW
Cleveland Hopkins Intl
Fri 8/21
7:20 pm-9:55 pm
1 stop3h 35m
Chicago Midway
Mon 8/24
4:25 pm-6:40 pm
Nonstop1h 15m
$207
ClevelandChicago
CLE - MDW
CLEMDW
Cleveland Hopkins Intl
Wed 8/12
12:50 pm-1:05 pm
Nonstop1h 15m
Chicago Midway
Sat 8/15
7:55 am-4:45 pm
2 stops7h 50m
$210
ClevelandChicago
CLE - MDW
CLEMDW
Cleveland Hopkins Intl
Fri 8/28
1:50 pm-2:05 pm
Nonstop1h 15m
Chicago Midway
Mon 8/31
2:35 pm-9:55 pm
2 stops6h 20m
$212
ClevelandChicago
CLE - MDW
CLEMDW
Cleveland Hopkins Intl
Wed 9/16
6:00 am-11:35 am
1 stop6h 35m
Chicago Midway
Wed 9/16
4:40 pm-9:55 pm
1 stop4h 15m
$215
ClevelandChicago
CLE - MDW
CLEMDW
Cleveland Hopkins Intl
Fri 9/4
7:20 pm-9:55 pm
1 stop3h 35m
Chicago Midway
Sat 9/5
6:35 am-1:15 pm
1 stop5h 40m
$217
ClevelandChicago
CLE - MDW
CLEMDW
Cleveland Hopkins Intl
Sun 9/20
8:28 am-12:39 pm
1 stop5h 11m
Chicago Midway
Mon 9/21
7:01 pm-11:54 pm
1 stop3h 53m
$237
Quickest round-trip
ClevelandChicago
CLE - MDW
CLEMDW
Cleveland Hopkins Intl
Tue 8/4
5:25 pm-5:40 pm
Nonstop1h 15m
Chicago Midway
Fri 8/7
1:00 pm-3:10 pm
Nonstop1h 10m
$238
ClevelandChicago
CLE - MDW
CLEMDW
Cleveland Hopkins Intl
Mon 8/10
7:20 pm-9:55 pm
1 stop3h 35m
Chicago Midway
Mon 8/17
10:10 am-4:45 pm
2 stops5h 35m
$263
Showing 1-10 of 21 resultsSorted by cheapest first
Compare providers for flights from Cleveland to Midway
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 Cleveland to Midway in July.
| 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 Cleveland-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Cleveland-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Cleveland-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Cleveland-Chicago Midway Airport 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 Cleveland-Chicago Midway Airport 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 Cleveland to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Cleveland with our price prediction graph.
CLE-MDW
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 Cleveland to Chicago Midway Airport
What is the cheapest month to book a flight from Cleveland to Chicago Midway Airport?
Currently, September is the cheapest month in which you can book a flight from Cleveland to Chicago Midway Airport (average of $205). Flying from Cleveland to Chicago Midway Airport in January is currently the most expensive (average of $591). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CLE to MDW?
Find hourly flight availability from Cleveland to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 18, 2026.
It’s optimal to fly from Cleveland to Chicago Midway Airport in the afternoon. By choosing this option you can save up to 23% on the cost of your flight, compared to a flight in the morning.
What is the cheapest day to fly from Cleveland to Chicago Midway Airport?
Use this chart to determine the cheapest time to fly round-trip from Cleveland to Midway. Price data was last updated on July 18, 2026.
Travelers seeking maximum savings on their Cleveland to Chicago Midway Airport flight should consider departing on Wednesday at noon when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
The best insider tips for Cleveland to Chicago Midway Airport flights
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Cheapflights partnered with top experts to bring you the best recommendations for your Cleveland to Chicago Midway Airport trip
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Reviews of airlines servicing Midway
Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated July 18, 2026.
Get a feel of what it's like to fly with Southwest from Cleveland to Chicago Midway Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Cleveland to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Top airline flying from Cleveland to Midway
Discover the top airline that operate flights from Cleveland to Midway. 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 July 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$137 | Average$259 | FlexibilityNo cancel fee | On-time63% |