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Cheap flights from Akron to Chicago from $179

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Akron to Chicago departing on 9/21. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Akron to Chicago (CAK-MDW)

Cheap round-trip flights

Logo
11:37 am - 8:53 amCAK-MDW
22h 16m1 stop
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8:06 am - 7:20 pmMDW-CAK
10h 14m2 stops
$370
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Thu, Sep 18 - Sun, Sep 21
Logo
9:19 am - 11:46 pmCAK-MDW
15h 27m2 stops
Logo
11:07 am - 9:14 amMDW-CAK
21h 07m1 stop
$372
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Thu, Oct 16 - Sun, Oct 19
Logo
7:00 am - 6:43 pmCAK-MDW
12h 43m2 stops
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6:21 am - 8:17 amMDW-CAK
24h 56m1 stop
$397
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Fri, Oct 3 - Sun, Oct 5
Logo
6:00 am - 11:44 amCAK-MDW
6h 44m1 stop
Logo
5:56 pm - 7:17 pmMDW-CAK
48h 21m2 stops
$409
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Sun, Oct 12 - Tue, Oct 14
Logo
7:00 am - 6:43 pmCAK-MDW
12h 43m2 stops
Logo
6:21 am - 7:58 pmMDW-CAK
12h 37m1 stop
$430
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Fri, Sep 12 - Mon, Sep 15
Allegiant Air Logo
9:07 am - 4:33 pmCAK-MDW
8h 26m2 stops
Allegiant Air Logo
11:07 am - 9:14 amMDW-CAK
21h 07m1 stop
$443Allegiant Air
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Mon, Oct 20 - Thu, Oct 23
Logo
7:00 am - 9:51 amCAK-MDW
27h 51m1 stop
Logo
8:06 am - 7:20 pmMDW-CAK
10h 14m2 stops
$455
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Fri, Sep 26 - Sun, Sep 28
Logo
7:00 am - 9:51 amCAK-MDW
27h 51m1 stop
Logo
8:06 am - 7:20 pmMDW-CAK
10h 14m2 stops
$460
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Fri, Sep 26 - Sun, Sep 28
Logo
8:00 am - 9:18 amCAK-MDW
26h 18m1 stop
Logo
9:47 pm - 9:02 pmMDW-CAK
22h 15m2 stops
$519
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Sat, Sep 20 - Mon, Sep 22
Logo
7:00 am - 9:51 amCAK-MDW
27h 51m1 stop
Logo
8:06 am - 7:20 pmMDW-CAK
10h 14m2 stops
$535
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Fri, Sep 12 - Sun, Sep 14

momondo Fare Finder

 
Customize your flight search to find flights from Akron to Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated August 21, 2025.
Use the filters below to find and compare flights from Akron to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

AkronChicago

CAK - MDW

CAKMDW

Akron/Canton

Thu 9/18

11:37 am-8:53 am

1 stop22h 16m

Chicago Midway

Sun 9/21

8:06 am-7:20 pm

2 stops10h 14m

$370

AkronChicago

CAK - MDW

CAKMDW

Akron/Canton

Thu 10/16

9:19 am-11:46 pm

2 stops15h 27m

Chicago Midway

Sun 10/19

11:07 am-9:14 am

1 stop21h 07m

$372

AkronChicago

CAK - MDW

CAKMDW

Akron/Canton

Fri 10/3

7:00 am-6:43 pm

2 stops12h 43m

Chicago Midway

Sun 10/5

6:21 am-8:17 am

1 stop24h 56m

$397

AkronChicago

CAK - MDW

CAKMDW

Akron/Canton

Sun 10/12

6:00 am-11:44 am

1 stop6h 44m

Chicago Midway

Tue 10/14

5:56 pm-7:17 pm

2 stops48h 21m

$409

AkronChicago

CAK - MDW

CAKMDW

Akron/Canton

Fri 9/12

7:00 am-6:43 pm

2 stops12h 43m

Chicago Midway

Mon 9/15

6:21 am-7:58 pm

1 stop12h 37m

$430

AkronChicago

CAK - MDW

CAKMDW

Akron/Canton

Mon 10/20

9:07 am-4:33 pm

2 stops8h 26m

Chicago Midway

Thu 10/23

11:07 am-9:14 am

1 stop21h 07m

$443

AkronChicago

CAK - MDW

CAKMDW

Akron/Canton

Fri 9/26

7:00 am-9:51 am

1 stop27h 51m

Chicago Midway

Sun 9/28

8:06 am-7:20 pm

2 stops10h 14m

$455

AkronChicago

CAK - MDW

CAKMDW

Akron/Canton

Fri 9/26

7:00 am-9:51 am

1 stop27h 51m

Chicago Midway

Sun 9/28

8:06 am-7:20 pm

2 stops10h 14m

$460

AkronChicago

CAK - MDW

CAKMDW

Akron/Canton

Sat 9/20

8:00 am-9:18 am

1 stop26h 18m

Chicago Midway

Mon 9/22

9:47 pm-9:02 pm

2 stops22h 15m

$519

AkronChicago

CAK - MDW

CAKMDW

Akron/Canton

Fri 9/12

7:00 am-9:51 am

1 stop27h 51m

Chicago Midway

Sun 9/14

8:06 am-7:20 pm

2 stops10h 14m

$535

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Akron to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from Akron. The lowest ticket price found for a Tuesday departure recently was $370. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Akron because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $416.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Akron in the evening is the least expensive time of day to depart. momondo users have found prices as low as $357 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $400. Of course, these prices can vary depending on the time of year and what airport you fly to.

When to book flights from Akron to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Akron to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Akron to Chicago Midway Airport (CAK to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Akron to Chicago Midway Airport

Direct flights

None
There are no direct flights from Akron to Chicago Midway Airport. There are no popular flight routes from Akron to Chicago Midway Airport.
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  • How far is Akron/Canton to Chicago Midway by plane?

    Chicago Midway is 325.9 mi away from Akron/Canton. Flights usually cover this in 6h 44m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Akron/Canton Airport to Chicago Midway Airport?

    Prices for flights from Akron/Canton Airport to Chicago Midway Airport are updated daily.

  • How many operators does momondo search for flights from Akron/Canton Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Akron/Canton Airport to Chicago Midway Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Akron/Canton Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Akron to Chicago Midway Airport?

Best airlines flying from Akron to Chicago Midway Airport

Compare and see reviews for airlines that fly from Akron to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $217Free CancellationRating
7.4
8,930 reviews
Search United Airlines flights

Traveling to a place near Chicago?

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Why use momondo?

Why should I use momondo to find a flight deal from Akron to Chicago?

It is quick and easy to find Akron to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Akron to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Akron with this policy.

How can momondo help me find flights from Akron to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from Akron. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Akron to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Akron to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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