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$248+ Cheap flights from Kalamazoo (AZO) 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 5/16. Fares are subject to change and may not be available on all flights or dates of travel.
AZO — MDW
May 18 — May 251
Mon 5/18
Mon 5/25
1 adult, Economy
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Cheap flight deals from Kalamazoo to Midway

Cheapest flights from Kalamazoo to Midway
Explore the most affordable flight options available from Kalamazoo to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 18, 2026.

This Delta deal was found by Cheapflights users on 4/16. 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 5/165:30 am
AZO
-
MDW
1 stop4h 13m
Delta
Sat 5/301:22 pm
MDW
-
AZO
1 stop3h 13m
Delta
Deal found 4/16$248
This Delta deal was found by Cheapflights users on 4/14. 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.
Wed 4/295:30 am
AZO
-
MDW
1 stop4h 17m
Delta
Sun 5/36:38 pm
MDW
-
AZO
1 stop2h 57m
Delta
Deal found 4/14$278
This Delta deal was found by Cheapflights users on 4/17. 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.
Wed 5/135:30 am
AZO
-
MDW
1 stop4h 13m
Delta
Sun 5/176:36 pm
MDW
-
AZO
1 stop4h 11m
Delta
Deal found 4/17$288
This Delta deal was found by Cheapflights users on 4/16. 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.
Fri 5/15:30 am
AZO
-
MDW
1 stop4h 17m
Delta
Tue 5/56:38 pm
MDW
-
AZO
1 stop2h 57m
Delta
Deal found 4/16$303
This Delta deal was found by Cheapflights users on 4/16. 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.
Thu 5/75:30 am
AZO
-
MDW
1 stop4h 13m
Delta
Sun 5/106:36 pm
MDW
-
AZO
1 stop4h 11m
Delta
Deal found 4/16$328
This Delta deal was found by Cheapflights users on 4/16. 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 4/225:30 am
AZO
-
MDW
1 stop4h 17m
Delta
Mon 11/239:30 am
MDW
-
AZO
1 stop3h 50m
Delta
Deal found 4/16$338
This Delta deal was found by Cheapflights users on 4/16. 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.
Tue 5/265:30 am
AZO
-
MDW
1 stop4h 13m
Delta
Sat 5/306:36 pm
MDW
-
AZO
1 stop3h 00m
Delta
Deal found 4/16$358
This Delta deal was found by Cheapflights users on 4/16. 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.
Fri 4/245:30 am
AZO
-
MDW
1 stop4h 17m
Delta
Sun 4/266:38 pm
MDW
-
AZO
1 stop2h 57m
Delta
Deal found 4/16$499
This Delta deal was found by Cheapflights users on 4/13. 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.
Mon 5/115:30 am
AZO
-
MDW
1 stop4h 13m
Delta
Mon 5/186:36 pm
MDW
-
AZO
1 stop4h 11m
Delta
Deal found 4/13$855
This Delta deal was found by Cheapflights users on 4/12. 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 4/265:30 am
AZO
-
MDW
1 stop4h 17m
Delta
Thu 4/301:24 pm
MDW
-
AZO
1 stop3h 05m
Delta
Deal found 4/12$856
This Delta deal was found by Cheapflights users on 4/16. 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.
Fri 4/175:30 am
AZO
-
MDW
1 stop4h 17m
Delta
Sun 4/191:24 pm
MDW
-
AZO
1 stop3h 05m
Delta
Deal found 4/16$893
This Delta deal was found by Cheapflights users on 4/14. 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 5/115:30 am
AZO
-
MDW
1 stop4h 13m
Delta
Fri 5/156:36 pm
MDW
-
AZO
1 stop4h 11m
Delta
Deal found 4/14$1,072

Find flight deals from Kalamazoo to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Kalamazoo (AZO) 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 April 18, 2026.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$248
(Delta)
Provider with most accurate pricing for Kalamazoo Intl-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Kalamazoo Intl-Chicago Midway flights.
Search Deals
From Kalamazoo Intl to Chicago Midway
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Kalamazoo 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 April 18, 2026.
Use the filters below to find and compare flights from Kalamazoo to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

KalamazooChicago

AZO - MDW

AZOMDW

Kalamazoo Intl

Sat 6/6

5:30 am-8:43 am

1 stop4h 13m

Chicago Midway

Tue 6/9

9:17 am-2:24 pm

1 stop4h 07m

$248

KalamazooChicago

AZO - MDW

AZOMDW

Kalamazoo Intl

Fri 6/12

3:04 pm-6:31 pm

1 stop4h 27m

Chicago Midway

Sun 6/14

9:17 am-2:24 pm

1 stop4h 07m

$248

KalamazooChicago

AZO - MDW

AZOMDW

Kalamazoo Intl

Mon 6/29

5:30 am-9:14 am

1 stop4h 44m

Chicago Midway

Fri 7/3

1:16 pm-5:20 pm

1 stop3h 04m

$248

KalamazooChicago

AZO - MDW

AZOMDW

Kalamazoo Intl

Sat 5/16

5:30 am-8:43 am

1 stop4h 13m

Chicago Midway

Sat 5/30

1:22 pm-5:35 pm

1 stop3h 13m

$248

KalamazooChicago

AZO - MDW

AZOMDW

Kalamazoo Intl

Wed 4/29

5:30 am-8:47 am

1 stop4h 17m

Chicago Midway

Sun 5/3

6:38 pm-10:35 pm

1 stop2h 57m

$278

KalamazooChicago

AZO - MDW

AZOMDW

Kalamazoo Intl

Wed 5/13

5:30 am-8:43 am

1 stop4h 13m

Chicago Midway

Sun 5/17

6:36 pm-11:47 pm

1 stop4h 11m

$288

KalamazooChicago

AZO - MDW

AZOMDW

Kalamazoo Intl

Fri 5/1

5:30 am-8:47 am

1 stop4h 17m

Chicago Midway

Tue 5/5

6:38 pm-10:35 pm

1 stop2h 57m

$303

KalamazooChicago

AZO - MDW

AZOMDW

Kalamazoo Intl

Thu 5/7

5:30 am-8:43 am

1 stop4h 13m

Chicago Midway

Sun 5/10

6:36 pm-11:47 pm

1 stop4h 11m

$328
Quickest round-trip

KalamazooChicago

AZO - MDW

AZOMDW

Kalamazoo Intl

Tue 5/26

5:30 am-8:43 am

1 stop4h 13m

Chicago Midway

Sat 5/30

6:36 pm-10:36 pm

1 stop3h 00m

$358

KalamazooChicago

AZO - MDW

AZOMDW

Kalamazoo Intl

Mon 5/11

5:30 am-8:43 am

1 stop4h 13m

Chicago Midway

Mon 5/18

6:36 pm-11:47 pm

1 stop4h 11m

$855

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/16

Showing 1-10 of 15 resultsSorted by cheapest first
1
2
  • Most accurate provider: When it comes to deals on Kalamazoo-Chicago Midway Airport flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on Kalamazoo-Chicago Midway Airport flight deals on Cheapflights vs. Expedia <90% of the time. Price accuracy is based on data collected from Kalamazoo-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Kalamazoo-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 Kalamazoo-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 Kalamazoo to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Kalamazoo 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.

Related info for your journey

Find useful and relevant information for your journey from Kalamazoo 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 Kalamazoo to Chicago Midway?

    Kalamazoo Intl (AZO), located 4.3 mi from the city center, is the airport you fly out of when you book flights from Kalamazoo to Chicago Midway. 0 airlines have flights from Kalamazoo Intl to Chicago Midway on a regular basis. Booking flights from Kalamazoo Intl to Chicago Midway should not be difficult; the airport handles an average of 0 outbound flights to Chicago Midway per day.

  • How long is the flight from Kalamazoo to Chicago Midway Airport?

    A quick flight from Kalamazoo to Chicago Midway Airport can take about 4h 13m. Delta provides one of the quickest options available for as low as $248. The distance between Kalamazoo and Chicago Midway Airport is about 117 mi.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Kalamazoo 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.

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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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