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Cheap flights from Kalamazoo to Chicago from $248

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Kalamazoo to Chicago departing on 6/6. 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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Find the cheapest flights from Kalamazoo to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
5:30 am - 8:43 am
AZO
-
MDW
4h 13m
1 stop
Delta Logo
6:58 pm - 11:56 pm
MDW
-
AZO
3h 58m
1 stop
$248Delta
Sa, Jun 6 - Mi, Jun 10
Delta Logo
5:30 am - 8:43 am
AZO
-
MDW
4h 13m
1 stop
Delta Logo
6:36 pm - 11:47 pm
MDW
-
AZO
4h 11m
1 stop
$263Delta
Di, Mai 19 - Di, Mai 26
Delta Logo
5:30 am - 8:47 am
AZO
-
MDW
4h 17m
1 stop
Delta Logo
1:22 pm - 5:35 pm
MDW
-
AZO
3h 13m
1 stop
$278Delta
Di, Mai 5 - Sa, Mai 9
Delta Logo
5:30 am - 8:43 am
AZO
-
MDW
4h 13m
1 stop
Delta Logo
6:36 pm - 11:47 pm
MDW
-
AZO
4h 11m
1 stop
$288Delta
Do, Mai 14 - So, Mai 17
Delta Logo
5:30 am - 8:47 am
AZO
-
MDW
4h 17m
1 stop
Delta Logo
6:36 pm - 10:36 pm
MDW
-
AZO
3h 00m
1 stop
$303Delta
So, Mai 3 - Sa, Mai 9
Delta Logo
5:30 am - 8:47 am
AZO
-
MDW
4h 17m
1 stop
Delta Logo
9:23 am - 5:35 pm
MDW
-
AZO
7h 12m
2 stops
$309Delta
So, Mai 3 - Sa, Mai 9
Delta Logo
5:30 am - 8:43 am
AZO
-
MDW
4h 13m
1 stop
Delta Logo
6:36 pm - 11:47 pm
MDW
-
AZO
4h 11m
1 stop
$393Delta
Do, Mai 7 - So, Mai 10
Delta Logo
5:30 am - 1:32 pm
AZO
-
MDW
9h 02m
2 stops
Delta Logo
6:36 pm - 11:47 pm
MDW
-
AZO
4h 11m
1 stop
$399Delta
So, Mai 3 - So, Mai 10
Delta Logo
3:04 pm - 6:31 pm
AZO
-
MDW
4h 27m
1 stop
Delta Logo
6:58 pm - 5:20 pm
MDW
-
AZO
21h 22m
1 stop
$400Delta
So, Jun 7 - Fr, Jun 12
Delta Logo
5:30 am - 1:32 pm
AZO
-
MDW
9h 02m
2 stops
Delta Logo
9:23 am - 5:35 pm
MDW
-
AZO
7h 12m
2 stops
$404Delta
So, Mai 3 - Sa, Mai 9

Delta flights from Kalamazoo to Chicago Midway Airport

Our best Delta deals on Kalamazoo to Chicago Midway Airport flight tickets
Delta
Jun 6
AZO5:30 amKalamazoo Intl
4h 13m
1 stop
MDW8:43 amChicago Midway
Jun 11
MDW6:58 pmChicago Midway
3h 58m
1 stop
AZO11:56 pmKalamazoo Intl
$248
Delta
May 19
AZO5:30 amKalamazoo Intl
4h 13m
1 stop
MDW8:43 amChicago Midway
May 26
MDW6:36 pmChicago Midway
4h 11m
1 stop
AZO11:47 pmKalamazoo Intl
$263
Delta
May 5
AZO5:30 amKalamazoo Intl
4h 17m
1 stop
MDW8:47 amChicago Midway
May 9
MDW1:22 pmChicago Midway
3h 13m
1 stop
AZO5:35 pmKalamazoo Intl
$278

momondo Fare Finder

 
Customize your flight search to find flights from Kalamazoo 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 April 23, 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

Sa 6/6

5:30 am-8:43 am

1 stop4h 13m

Chicago Midway

Mi 6/10

6:58 pm-11:56 pm

1 stop3h 58m

$248

KalamazooChicago

AZO - MDW

AZOMDW

Kalamazoo Intl

Di 5/19

5:30 am-8:43 am

1 stop4h 13m

Chicago Midway

Di 5/26

6:36 pm-11:47 pm

1 stop4h 11m

$263

KalamazooChicago

AZO - MDW

AZOMDW

Kalamazoo Intl

Di 5/5

5:30 am-8:47 am

1 stop4h 17m

Chicago Midway

Sa 5/9

1:22 pm-5:35 pm

1 stop3h 13m

$278

KalamazooChicago

AZO - MDW

AZOMDW

Kalamazoo Intl

Do 5/14

5:30 am-8:43 am

1 stop4h 13m

Chicago Midway

So 5/17

6:36 pm-11:47 pm

1 stop4h 11m

$288
Quickest round-trip

KalamazooChicago

AZO - MDW

AZOMDW

Kalamazoo Intl

So 5/3

5:30 am-8:47 am

1 stop4h 17m

Chicago Midway

Sa 5/9

6:36 pm-10:36 pm

1 stop3h 00m

$303

KalamazooChicago

AZO - MDW

AZOMDW

Kalamazoo Intl

So 5/3

5:30 am-8:47 am

1 stop4h 17m

Chicago Midway

Sa 5/9

9:23 am-5:35 pm

2 stops7h 12m

$309

KalamazooChicago

AZO - MDW

AZOMDW

Kalamazoo Intl

Do 5/7

5:30 am-8:43 am

1 stop4h 13m

Chicago Midway

So 5/10

6:36 pm-11:47 pm

1 stop4h 11m

$393

KalamazooChicago

AZO - MDW

AZOMDW

Kalamazoo Intl

So 5/3

5:30 am-1:32 pm

2 stops9h 02m

Chicago Midway

So 5/10

6:36 pm-11:47 pm

1 stop4h 11m

$399

KalamazooChicago

AZO - MDW

AZOMDW

Kalamazoo Intl

So 6/7

3:04 pm-6:31 pm

1 stop4h 27m

Chicago Midway

Fr 6/12

6:58 pm-5:20 pm

1 stop21h 22m

$400

KalamazooChicago

AZO - MDW

AZOMDW

Kalamazoo Intl

So 5/3

5:30 am-1:32 pm

2 stops9h 02m

Chicago Midway

Sa 5/9

9:23 am-5:35 pm

2 stops7h 12m

$404

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Kalamazoo 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 airline that flies from Kalamazoo Intl to Chicago Midway?

Delta is the most popular carrier operating from Kalamazoo Intl to Chicago Midway

When to book flights from Kalamazoo to Chicago Midway Airport

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

Cheap Kalamazoo to Chicago Midway Airport (AZO to MDW) flight deals and tips

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

Fastest flight time

4h 13m

Direct flights

None
The fastest flight from Kalamazoo to Chicago Midway Airport takes 4h 13m
There are no direct flights from Kalamazoo to Chicago Midway Airport. There are no popular flight routes from Kalamazoo to Chicago Midway Airport.
Search flight deals

Frequently asked questions about flying from Kalamazoo to Chicago Midway Airport

  • How far is Kalamazoo Intl to Chicago Midway by plane?

    The straight-line distance from Kalamazoo Intl to Chicago Midway is 116.0 mi. 4h 13m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Kalamazoo Intl Airport to Chicago Midway Airport?

    Prices for flights from Kalamazoo Intl Airport to Chicago Midway Airport are refreshed on a daily basis.

  • How old do you have to be to fly from Kalamazoo Intl Airport to Chicago Midway Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Kalamazoo Intl Airport to Chicago Midway Airport.

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

    The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
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Hammond
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
Porter
Griffith
Saint John

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Kalamazoo.

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

Yes. All flights to Chicago from Kalamazoo on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Kalamazoo.

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

If you are not ready to book a flight from Kalamazoo to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

An easier way to manage your Chicago Midway Airport trip

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