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$136+ Cheap flights from Akron (CAK) 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 12/25. Fares are subject to change and may not be available on all flights or dates of travel.
CAK — MDW
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Find flight deals from Akron to Midway

Cheapest flights from Akron to Midway
Explore the most affordable flight options available from Akron to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/30. 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 12/412:10 pmCAK - MDW
1 stop10h 48mMultiple Airlines
Fri 12/53:52 pmMDW - CAK
1 stop7h 06mMultiple Airlines
Deal found 10/30$247
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 11/246:00 amCAK - MDW
1 stop11h 52mMultiple Airlines
Thu 11/276:20 amMDW - CAK
2 stops14h 03mMultiple Airlines
Deal found 10/30$274
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 11/246:00 amCAK - MDW
1 stop11h 52mMultiple Airlines
Wed 11/265:57 pmMDW - CAK
2 stops26h 26mMultiple Airlines
Deal found 10/30$286
This Kiwi.com deal was found by Cheapflights users on 10/30. 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.
Sun 12/77:05 amCAK - MDW
2 stops16h 07mMultiple Airlines
Mon 12/83:10 pmMDW - CAK
1 stop7h 48mMultiple Airlines
Deal found 10/30$287
This Kiwi.com deal was found by Cheapflights users on 10/30. 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.
Sun 11/167:00 amCAK - MDW
1 stop26h 32mMultiple Airlines
Tue 11/181:56 pmMDW - CAK
2 stops23h 39mMultiple Airlines
Deal found 10/30$292
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 11/157:45 amCAK - MDW
2 stops11h 54mMultiple Airlines
Mon 11/179:27 amMDW - CAK
1 stop13h 31mMultiple Airlines
Deal found 10/28$293
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 11/166:00 amCAK - MDW
1 stop19h 30mMultiple Airlines
Mon 11/179:27 amMDW - CAK
1 stop13h 31mMultiple Airlines
Deal found 10/28$304
This Kiwi.com deal was found by Cheapflights users on 10/30. 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.
Fri 12/56:00 amCAK - MDW
2 stops14h 42mMultiple Airlines
Mon 12/83:10 pmMDW - CAK
1 stop7h 48mMultiple Airlines
Deal found 10/30$321
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 12/412:10 pmCAK - MDW
1 stop10h 48mMultiple Airlines
Mon 12/83:10 pmMDW - CAK
1 stop7h 48mMultiple Airlines
Deal found 10/29$324
This Kiwi.com deal was found by Cheapflights users on 10/30. 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.
Tue 11/188:00 amCAK - MDW
2 stops29h 41mMultiple Airlines
Thu 11/2010:12 amMDW - CAK
1 stop7h 29mMultiple Airlines
Deal found 10/30$329
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 12/56:00 amCAK - MDW
2 stops14h 42mMultiple Airlines
Sun 12/76:37 pmMDW - CAK
1 stop28h 21mMultiple Airlines
Deal found 10/28$350

Cheap flight deals from Akron to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Akron (CAK) 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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$247
(Kiwi.com)

One-way from

$136
(Kiwi.com)

Popular in

December

Cheapest in

August

Average price

$294
Provider with most accurate pricing for Akron/Canton-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Akron/Canton-Chicago Midway flights.
Search Deals
From Akron/Canton to Chicago Midway
Search Deals
One-way flight from Akron/Canton to Chicago Midway
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($14 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($2 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Akron 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 October 30, 2025.
Use the filters below to find and compare flights from Akron to Chicago Midway Airport that are best for you.

Fly from

Akron

Fly to

Midway

Route

Depart

Return

Price

AkronChicago

CAK - MDW

CAKMDW

Akron/Canton

Mon 11/24

6:00 am-4:52 pm

1 stop11h 52m

Chicago Midway

Thu 11/27

6:20 am-9:23 pm

2 stops14h 03m

$274

AkronChicago

CAK - MDW

CAKMDW

Akron/Canton

Mon 11/24

6:00 am-4:52 pm

1 stop11h 52m

Chicago Midway

Wed 11/26

5:57 pm-9:23 pm

2 stops26h 26m

$286

AkronChicago

CAK - MDW

CAKMDW

Akron/Canton

Sat 11/15

7:45 am-6:39 pm

2 stops11h 54m

Chicago Midway

Mon 11/17

9:27 am-11:58 pm

1 stop13h 31m

$293

AkronChicago

CAK - MDW

CAKMDW

Akron/Canton

Sun 11/16

6:00 am-12:30 am

1 stop19h 30m

Chicago Midway

Mon 11/17

9:27 am-11:58 pm

1 stop13h 31m

$304

AkronChicago

CAK - MDW

CAKMDW

Akron/Canton

Sun 12/7

7:05 am-10:12 pm

2 stops16h 07m

Chicago Midway

Mon 12/8

3:10 pm-11:58 pm

1 stop7h 48m

$331

AkronChicago

CAK - MDW

CAKMDW

Akron/Canton

Fri 12/12

6:00 am-10:39 pm

1 stop17h 39m

Chicago Midway

Mon 12/15

3:10 pm-11:58 pm

1 stop7h 48m

$331

AkronChicago

CAK - MDW

CAKMDW

Akron/Canton

Fri 12/5

6:00 am-7:42 pm

2 stops14h 42m

Chicago Midway

Sun 12/7

6:37 pm-11:58 pm

1 stop28h 21m

$350

AkronChicago

CAK - MDW

CAKMDW

Akron/Canton

Mon 11/10

6:00 am-3:14 pm

2 stops10h 14m

Chicago Midway

Thu 11/13

10:12 am-10:49 pm

1 stop11h 37m

$357

AkronChicago

CAK - MDW

CAKMDW

Akron/Canton

Sat 11/22

8:00 am-5:07 pm

1 stop10h 07m

Chicago Midway

Thu 11/27

6:20 am-9:23 pm

2 stops14h 03m

$361

AkronChicago

CAK - MDW

CAKMDW

Akron/Canton

Sat 12/13

8:00 am-9:22 pm

2 stops14h 22m

Chicago Midway

Mon 12/15

3:10 pm-11:58 pm

1 stop7h 48m

$363

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 17 results
1
2

Compare providers for flights from Akron 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 Akron to Midway in October.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Akron-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Akron-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Akron-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Akron-Chicago Midway Airport flights, Cheapflights users trust eDreams the most. eDreams 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 Akron-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 Akron to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Akron with our price prediction graph.
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 Akron to Chicago Midway Airport

What is the cheapest month to book a flight from Akron to Chicago Midway Airport?

Currently, September is the cheapest month in which you can book a flight from Akron to Chicago Midway Airport (average of $94). Flying from Akron to Chicago Midway Airport in February is currently the most expensive (average of $153). 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.

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 October 30, 2025.
Peruse reviews from past customers who have flown with United Airlines from Akron to Chicago Midway Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,998 reviews

Overall

7.4

Boarding

7.7

Comfort

7.3

Crew

8.1

Food

6.6

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
8,998 reviews
United Airlines
7.4
Good
8,998 reviews

Overall

7.4

Boarding

7.7

Comfort

7.3

Crew

8.1

Food

6.6

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

Related info for your journey

Find useful and relevant information for your journey from Akron to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Akron to Chicago Midway?

    Most people fly from Akron/Canton (CAK) if they book a flight from Akron to Chicago Midway. On average, Akron/Canton has 0 outbound flights to Chicago Midway per day from 1 airline. Akron/Canton is conveniently located just 12.1 mi from Akron’s city center.

  • What is the cheapest airline to fly from Akron to Chicago Midway Airport round-trip?

    Cheapflights users have booked flights from Akron to Chicago Midway Airport round-trip from $217.

  • Can I find deals for flights from Akron to Midway that include hotel bookings?

    Yes. In addition to deals on Akron to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Akron to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Akron to Midway.

  • Can I find deals for business class flights from Akron to Midway?

    Yes. Cheapflights offers flight deals from Akron to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Akron to Chicago Midway Airport?

    Currently, September is the cheapest month in which you can book a flight from Akron to Chicago Midway Airport (average of $94). Flying from Akron to Chicago Midway Airport in February is currently the most expensive (average of $153). 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.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Akron to Midway

Discover the top airline that operate flights from Akron 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$217Average$319FlexibilityNo cancel feeOn-time69%

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