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Midway

$149+ 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 2/4. Fares are subject to change and may not be available on all flights or dates of travel.
CAK — MDW
Feb 23 — Mar 21
Mon 2/23
Mon 3/2
1 adult, Economy
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Cheap 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 January 24, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/21. 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 2/38:00 am
CAK
-
MDW
2 stops29h 05m
Multiple Airlines
Fri 2/61:00 pm
MDW
-
CAK
1 stop8h 24m
Multiple Airlines
Deal found 1/21$339
This Kiwi.com deal was found by Cheapflights users on 1/23. 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 3/129:05 pm
CAK
-
MDW
1 stop27h 46m
Multiple Airlines
Wed 3/1811:19 am
MDW
-
CAK
1 stop8h 37m
Multiple Airlines
Deal found 1/23$344
This Kiwi.com deal was found by Cheapflights users on 1/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/118:00 am
CAK
-
MDW
1 stop11h 13m
Multiple Airlines
Sun 3/158:43 pm
MDW
-
CAK
1 stop17h 42m
Multiple Airlines
Deal found 1/22$355
This Kiwi.com deal was found by Cheapflights users on 1/22. 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 3/87:05 am
CAK
-
MDW
2 stops16h 14m
Multiple Airlines
Sun 3/158:43 pm
MDW
-
CAK
1 stop17h 42m
Multiple Airlines
Deal found 1/22$357
This Kiwi.com deal was found by Cheapflights users on 1/22. 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 5/198:00 am
CAK
-
MDW
2 stops12h 31m
Multiple Airlines
Sun 5/249:14 am
MDW
-
CAK
1 stop9h 02m
Multiple Airlines
Deal found 1/22$362
This Kiwi.com deal was found by Cheapflights users on 1/22. 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 3/159:05 pm
CAK
-
MDW
1 stop17h 03m
Multiple Airlines
Wed 3/1811:19 am
MDW
-
CAK
2 stops21h 27m
Multiple Airlines
Deal found 1/22$367
This Kiwi.com deal was found by Cheapflights users on 1/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/188:05 am
CAK
-
MDW
2 stops12h 02m
Multiple Airlines
Fri 2/207:30 am
MDW
-
CAK
1 stop13h 54m
Multiple Airlines
Deal found 1/23$371
This Kiwi.com deal was found by Cheapflights users on 1/22. 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 3/129:05 pm
CAK
-
MDW
1 stop17h 03m
Multiple Airlines
Sun 3/158:43 pm
MDW
-
CAK
1 stop17h 42m
Multiple Airlines
Deal found 1/22$374
This Kiwi.com deal was found by Cheapflights users on 1/23. 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 3/97:00 am
CAK
-
MDW
1 stop7h 08m
Multiple Airlines
Mon 3/169:51 pm
MDW
-
CAK
1 stop22h 22m
Multiple Airlines
Deal found 1/23$380
This Kiwi.com deal was found by Cheapflights users on 1/22. 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 3/136:00 am
CAK
-
MDW
2 stops17h 19m
Multiple Airlines
Sun 3/158:43 pm
MDW
-
CAK
1 stop17h 42m
Multiple Airlines
Deal found 1/22$382
This Kiwi.com deal was found by Cheapflights users on 1/22. 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 3/146:35 am
CAK
-
MDW
2 stops16h 10m
Multiple Airlines
Wed 3/1811:19 am
MDW
-
CAK
1 stop8h 37m
Multiple Airlines
Deal found 1/22$390

Find 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 January 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$339
(Kiwi.com)

One-way from

$149
(Kiwi.com)

Popular in

June

Cheapest in

February

Average price

$219
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. 10% potential increase in price ($31 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 24, 2026.
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

Tue 2/3

8:00 am-12:05 pm

2 stops29h 05m

Chicago Midway

Fri 2/6

1:00 pm-10:24 pm

1 stop8h 24m

$339

AkronChicago

CAK - MDW

CAKMDW

Akron/Canton

Mon 3/9

6:00 am-8:53 pm

2 stops15h 53m

Chicago Midway

Mon 3/16

9:51 pm-9:13 pm

1 stop22h 22m

$339

AkronChicago

CAK - MDW

CAKMDW

Akron/Canton

Thu 3/12

9:05 pm-11:51 pm

1 stop27h 46m

Chicago Midway

Wed 3/18

11:19 am-8:56 pm

1 stop8h 37m

$344

AkronChicago

CAK - MDW

CAKMDW

Akron/Canton

Wed 3/11

8:00 am-6:13 pm

1 stop11h 13m

Chicago Midway

Sun 3/15

8:43 pm-3:25 pm

1 stop17h 42m

$355

AkronChicago

CAK - MDW

CAKMDW

Akron/Canton

Sun 3/8

7:05 am-10:19 pm

2 stops16h 14m

Chicago Midway

Sun 3/15

8:43 pm-3:25 pm

1 stop17h 42m

$357

AkronChicago

CAK - MDW

CAKMDW

Akron/Canton

Sun 3/15

9:05 pm-1:08 pm

1 stop17h 03m

Chicago Midway

Wed 3/18

11:19 am-9:46 am

2 stops21h 27m

$367

AkronChicago

CAK - MDW

CAKMDW

Akron/Canton

Wed 2/18

8:05 am-7:07 pm

2 stops12h 02m

Chicago Midway

Fri 2/20

7:30 am-10:24 pm

1 stop13h 54m

$371

AkronChicago

CAK - MDW

CAKMDW

Akron/Canton

Thu 3/12

9:05 pm-1:08 pm

1 stop17h 03m

Chicago Midway

Sun 3/15

8:43 pm-3:25 pm

1 stop17h 42m

$374

AkronChicago

CAK - MDW

CAKMDW

Akron/Canton

Fri 3/13

6:00 am-10:19 pm

2 stops17h 19m

Chicago Midway

Sun 3/15

8:43 pm-3:25 pm

1 stop17h 42m

$382

AkronChicago

CAK - MDW

CAKMDW

Akron/Canton

Sat 3/14

6:35 am-9:45 pm

2 stops16h 10m

Chicago Midway

Wed 3/18

11:19 am-8:56 pm

1 stop8h 37m

$390

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/22

Showing 1-10 of 14 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 January.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
ExpediaPrice Accuracy2 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Akron-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >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 Expedia the most. Expedia 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, November is the cheapest month in which you can book a flight from Akron to Chicago Midway Airport (average of $76). Flying from Akron to Chicago Midway Airport in February is currently the most expensive (average of $201). 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 January 24, 2026.
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
9,194 reviews

Boarding

7.7

Crew

8.1

Entertainment

7.1

Overall

7.4

Food

6.6

Comfort

7.3

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
9,194 reviews
United Airlines
7.4
Good
9,194 reviews

Boarding

7.7

Crew

8.1

Entertainment

7.1

Overall

7.4

Food

6.6

Comfort

7.3

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, November is the cheapest month in which you can book a flight from Akron to Chicago Midway Airport (average of $76). Flying from Akron to Chicago Midway Airport in February is currently the most expensive (average of $201). 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
Lansing
Merrillville
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 January 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$217Average$317FlexibilityNo cancel feeOn-time69%

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