$59+ Cheap flights from Cleveland (CLE) to Midway (MDW)
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 10/8. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — MDW
Oct 10 — Oct 171
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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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 Cleveland to Midway
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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 September 10, 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 September 10, 2026.
This Southwest deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/12:40 pm -
Nonstop1h 15m
Mon 10/56:45 pm -
Nonstop1h 15m
Deal found 9/7![Southwest logo]()
$117
This Frontier deal was found by Cheapflights users on 9/8. 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 10/243:46 pm -
1 stop8h 57m
Sat 10/317:25 am -
1 stop5h 09m
Deal found 9/8![Frontier logo]()
$118
This Southwest deal was found by Cheapflights users on 9/9. 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 10/68:35 am -
Nonstop1h 20m
Tue 10/62:45 pm -
2 stops5h 20m
Deal found 9/9![Southwest logo]()
$132
This Travelocity deal was found by Cheapflights users on 9/8. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:00 am -
1 stop11h 45m
Fri 10/161:12 pm -
1 stop6h 14m
Deal found 9/8![Frontier logo]()
$135
This Southwest deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/28:20 pm -
Nonstop1h 15m
Mon 10/52:35 pm -
Nonstop1h 10m
Deal found 9/7![Southwest logo]()
$144
This Southwest deal was found by Cheapflights users on 9/9. 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 10/76:15 am -
2 stops6h 50m
Wed 10/142:45 pm -
2 stops5h 20m
Deal found 9/9![Southwest logo]()
$147
This Priceline deal was found by Cheapflights users on 9/8. 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.
Wed 10/143:46 pm -
1 stop8h 57m
Fri 10/161:12 pm -
1 stop6h 14m
Deal found 9/8![Frontier logo]()
$152
This Southwest deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/24:50 pm -
1 stop3h 25m
Wed 10/71:35 pm -
Nonstop1h 10m
Deal found 9/7![Southwest logo]()
$154
This Delta deal was found by Cheapflights users on 9/9. 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 10/16:30 am -
1 stop3h 37m
Wed 10/79:29 am -
1 stop3h 10m
Deal found 9/9![Delta logo]()
$157
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 September 10, 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 September 10, 2026.
This Southwest deal was found by Cheapflights users on 9/9. 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 11/78:35 am -
Nonstop1h 25m
Mon 11/97:50 am -
Nonstop1h 20m
Deal found 9/9![Southwest logo]()
$117
This Delta deal was found by Cheapflights users on 9/8. 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 10/266:10 am -
1 stop4h 22m
Wed 10/286:44 pm -
1 stop4h 02m
Deal found 9/8![Delta logo]()
$174
This Southwest deal was found by Cheapflights users on 9/9. 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 10/77:25 pm -
Nonstop1h 15m
Wed 10/142:45 pm -
2 stops5h 20m
Deal found 9/9![Southwest logo]()
$132
This Southwest deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/175:25 pm -
Nonstop1h 20m
Tue 10/208:00 am -
Nonstop1h 15m
Deal found 9/6![Southwest logo]()
$239
This Southwest deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/152:40 pm -
Nonstop1h 15m
Mon 10/192:35 pm -
Nonstop1h 10m
Deal found 9/7![Southwest logo]()
$239
This Southwest deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/122:40 pm -
Nonstop1h 15m
Wed 10/148:00 am -
Nonstop1h 15m
Deal found 9/6![Southwest logo]()
$239
This Southwest deal was found by Cheapflights users on 9/9. 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 10/98:20 pm -
Nonstop1h 15m
Sun 10/117:50 am -
Nonstop1h 15m
Deal found 9/9![Southwest logo]()
$239
This Southwest deal was found by Cheapflights users on 9/8. 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 11/510:45 am -
2 stops10h 20m
Mon 11/96:10 pm -
1 stop4h 35m
Deal found 9/8![Southwest logo]()
$243
This Southwest deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/217:25 pm -
Nonstop1h 15m
Wed 10/282:45 pm -
1 stop5h 30m
Deal found 9/6![Southwest logo]()
$249
This Southwest deal was found by Cheapflights users on 9/9. 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 10/18:20 pm -
Nonstop1h 15m
Sun 10/47:05 pm -
Nonstop1h 20m
Deal found 9/9![Southwest logo]()
$253
Last-minute flights from Cleveland to MidwayDiscover last-minute flight deals from Cleveland to Midway. Data last updated September 10, 2026 and is based on user searches.
Discover last-minute flight deals from Cleveland to Midway. Data last updated September 10, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/12:40 pm -
Nonstop1h 15m
Mon 10/56:45 pm -
Nonstop1h 15m
Deal found 9/7![Southwest logo]()
$117
This Delta deal was found by Cheapflights users on 9/9. 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 10/16:30 am -
1 stop3h 37m
Mon 10/57:01 pm -
1 stop3h 53m
Deal found 9/9![Delta logo]()
$157
This Southwest deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/28:20 pm -
Nonstop1h 15m
Mon 10/52:35 pm -
Nonstop1h 10m
Deal found 9/7![Southwest logo]()
$144
This Southwest deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/24:50 pm -
1 stop3h 25m
Wed 10/71:35 pm -
Nonstop1h 10m
Deal found 9/7![Southwest logo]()
$154
This Southwest deal was found by Cheapflights users on 9/9. 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 10/68:35 am -
Nonstop1h 20m
Tue 10/62:45 pm -
2 stops5h 20m
Deal found 9/9![Southwest logo]()
$132
This Southwest deal was found by Cheapflights users on 9/9. 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 10/76:15 am -
2 stops6h 50m
Wed 10/142:45 pm -
2 stops5h 20m
Deal found 9/9![Southwest logo]()
$147
This Priceline deal was found by Cheapflights users on 9/8. 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.
Wed 10/143:46 pm -
1 stop8h 57m
Fri 10/161:12 pm -
1 stop6h 14m
Deal found 9/8![Frontier logo]()
$152
This Travelocity deal was found by Cheapflights users on 9/8. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:00 am -
1 stop11h 45m
Fri 10/161:12 pm -
1 stop6h 14m
Deal found 9/8![Frontier logo]()
$135
This Frontier deal was found by Cheapflights users on 9/8. 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 10/243:46 pm -
1 stop8h 57m
Sat 10/317:25 am -
1 stop5h 09m
Deal found 9/8![Frontier logo]()
$118
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 September 10, 2026.
Search for one-way flight options from Cleveland to Midway. Find affordable one-way fares based on user searches. Data last updated September 10, 2026.
This Southwest deal was found by Cheapflights users on 9/8. 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 10/88:20 pm -
Nonstop1h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Southwest logo]()
$59
This Super.com deal was found by Cheapflights users on 9/8. 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.
Thu 10/157:00 am -
1 stop11h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Frontier logo]()
$64
This Frontier deal was found by Cheapflights users on 9/8. 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 10/103:46 pm -
1 stop8h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Frontier logo]()
$65
This Southwest deal was found by Cheapflights users on 9/9. 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 9/303:20 pm -
1 stop6h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Southwest logo]()
$69
This Delta deal was found by Cheapflights users on 9/9. 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 10/611:03 am -
1 stop6h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Delta logo]()
$79
This Frontier deal was found by Cheapflights users on 9/8. 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.
Fri 11/63:46 pm -
1 stop9h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Frontier logo]()
$82
This Southwest deal was found by Cheapflights users on 9/9. 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 10/28:20 pm -
Nonstop1h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Southwest logo]()
$86
This Frontier deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/93:46 pm -
1 stop7h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Frontier logo]()
$100
This Super.com deal was found by Cheapflights users on 9/5. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/213:46 pm -
1 stop8h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Frontier logo]()
$105
This Frontier deal was found by Cheapflights users on 9/5. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/37:00 am -
1 stop11h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Frontier logo]()
$106
This CheapOair deal was found by Cheapflights users on 9/8. 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 10/163:46 pm -
1 stop8h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Frontier logo]()
$107
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 September 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $117 (Southwest) |
One-way from | $59 (Southwest) |
Popular in | January |
Cheapest in | April |
Average price | $292 |
Good round-trip deal | $291 or less |
Good one-way deal | $192 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 7,457,451 searches. Data last updated September 10, 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 Cleveland Hopkins Intl - MDW Chicago Midway
CLEMDW
Cleveland Hopkins Intl
Sat 10/10
9:10 am-9:30 am
Nonstop1h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$59
Quickest round-trip
ClevelandChicago
CLE Cleveland Hopkins Intl - MDW Chicago Midway
CLEMDW
Cleveland Hopkins Intl
Thu 10/8
8:20 pm-8:35 pm
Nonstop1h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$59
ClevelandChicago
CLE Cleveland Hopkins Intl - MDW Chicago Midway
CLEMDW
Cleveland Hopkins Intl
Wed 9/30
12:50 pm-1:05 pm
Nonstop1h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$59
ClevelandChicago
CLE Cleveland Hopkins Intl - MDW Chicago Midway
CLEMDW
Cleveland Hopkins Intl
Tue 10/6
2:20 pm-2:35 pm
Nonstop1h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$59
ClevelandChicago
CLE Cleveland Hopkins Intl - MDW Chicago Midway
CLEMDW
Cleveland Hopkins Intl
Sat 10/10
3:46 pm-11:43 pm
1 stop8h 57m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$65
ClevelandChicago
CLE Cleveland Hopkins Intl - MDW Chicago Midway
CLEMDW
Cleveland Hopkins Intl
Sat 10/10
4:07 pm-6:00 pm
1 stop2h 53m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$79
ClevelandChicago
CLE Cleveland Hopkins Intl - MDW Chicago Midway
CLEMDW
Cleveland Hopkins Intl
Sat 12/5
11:45 am-4:50 pm
1 stop6h 05m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$79
ClevelandChicago
CLE Cleveland Hopkins Intl - MDW Chicago Midway
CLEMDW
Cleveland Hopkins Intl
Tue 10/6
11:03 am-4:47 pm
1 stop6h 44m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$79
ClevelandChicago
CLE Cleveland Hopkins Intl - MDW Chicago Midway
CLEMDW
Cleveland Hopkins Intl
Thu 10/8
6:10 am-9:32 am
1 stop4h 22m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$79
ClevelandChicago
CLE Cleveland Hopkins Intl - MDW Chicago Midway
CLEMDW
Cleveland Hopkins Intl
Fri 10/9
8:20 pm-8:35 pm
Nonstop1h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$86
Showing 1-10 of 22 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 September.
| 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, April is the cheapest month in which you can book a flight from Cleveland to Chicago Midway Airport (average of $234). 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 September 10, 2026.
It’s optimal to fly from Cleveland to Chicago Midway Airport in the afternoon. By choosing this option you can save up to 22% 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 September 5, 2026.
Travelers seeking maximum savings on their Cleveland to Chicago Midway Airport flight should consider departing on Saturday at noon when fares are most often at their lowest. Tuesday evenings 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
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 Cleveland to Chicago Midway Airport trip
Our travel experts
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 September 10, 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.
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
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
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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Alternative routes for Cleveland to Midway
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Complete your trip
Complete your trip to Midway by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Cleveland to Midway by cabin class
Find flights from Cleveland to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Midway
Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 10, 2026.
Cleveland and Midway flights
Browse other Cleveland and Midway flight options. Last updated on September 10, 2026.
Other flights from Cleveland
Browse through other flights departing from Cleveland. Flights are based on user searches made on Cheapflights and were last updated on September 10, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 7,457,451 searches. Data last updated September 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$137 | Average$262 | FlexibilityNo cancel fee | On-time63% |