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$143+ Cheap flights from Kalamazoo (AZO) to Chicago (CHI)

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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
AZO — CHI
oct. 15 — oct. 221
mié. 10/15
mié. 10/22
1 adult, Economy
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Cheap flight deals from Kalamazoo to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Kalamazoo (AZO) to Chicago (CHI). 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 septiembre 15, 2025.

Round-trip from

$373
(American Airlines)

One-way from

$143
(Delta)

Good round-trip deal

$348 or less

Good one-way deal

$218 or less
From Kalamazoo Intl to Chicago (CHI)
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One-way flight from Kalamazoo Intl to Chicago (CHI)
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Price to beat on a round-trip flight from Kalamazoo Intl to Chicago (CHI).
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Price to beat on a one-way flight from Kalamazoo Intl to Chicago (CHI).
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Find flight deals from Kalamazoo to Chicago

Cheapest flights from Kalamazoo to Chicago
Explore the most affordable flight options available from Kalamazoo to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on septiembre 15, 2025.

This American Airlines deal was found by Cheapflights users on 9/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/56:00 amAZO - ORD
Nonstop1h 11mAmerican Airlines
lun. 12/88:20 amORD - AZO
Nonstop1h 00mAmerican Airlines
Deal found 9/13$373
This Delta deal was found by Cheapflights users on 9/13. 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.
vie. 12/55:25 amAZO - MDW
1 stop4h 29mDelta
lun. 12/86:40 pmMDW - AZO
1 stop4h 15mDelta
Deal found 9/13$392
This Delta deal was found by Cheapflights users on 9/13. 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.
vie. 12/511:46 amAZO - ORD
1 stop5h 32mDelta
lun. 12/86:45 amORD - AZO
1 stop3h 21mDelta
Deal found 9/13$392
This American Airlines deal was found by Cheapflights users on 9/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/205:44 pmAZO - ORD
Nonstop1h 12mAmerican Airlines
sáb. 9/278:10 amORD - AZO
Nonstop1h 00mAmerican Airlines
Deal found 9/13$419
This Delta deal was found by Cheapflights users on 9/15. 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.
sáb. 9/202:00 pmAZO - MDW
1 stop5h 35mDelta
sáb. 9/276:15 pmMDW - AZO
1 stop3h 53mDelta
Deal found 9/15$438
This Delta deal was found by Cheapflights users on 9/15. 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.
sáb. 9/202:00 pmAZO - ORD
1 stop3h 20mDelta
sáb. 9/277:10 amORD - AZO
1 stop5h 06mDelta
Deal found 9/15$438
This American Airlines deal was found by Cheapflights users on 9/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/1910:40 amAZO - ORD
Nonstop1h 13mAmerican Airlines
sáb. 9/278:10 amORD - AZO
Nonstop1h 00mAmerican Airlines
Deal found 9/14$458
This American Airlines deal was found by Cheapflights users on 9/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/25:00 amAZO - ORD
Nonstop1h 08mAmerican Airlines
jue. 11/610:00 pmORD - AZO
Nonstop0h 59mAmerican Airlines
Deal found 9/13$463
This Delta deal was found by Cheapflights users on 9/14. 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.
vie. 9/195:30 amAZO - ORD
1 stop3h 35mDelta
sáb. 9/277:10 amORD - AZO
1 stop5h 06mDelta
Deal found 9/14$465
This American Airlines deal was found by Cheapflights users on 9/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 9/145:44 pmAZO - ORD
Nonstop1h 12mAmerican Airlines
dom. 9/2110:00 pmORD - AZO
Nonstop0h 59mAmerican Airlines
Deal found 9/13$473
This Delta deal was found by Cheapflights users on 9/13. 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.
dom. 9/145:30 amAZO - MDW
1 stop4h 10mDelta
dom. 9/216:15 pmMDW - AZO
1 stop4h 31mDelta
Deal found 9/13$492
This Delta deal was found by Cheapflights users on 9/13. 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.
dom. 9/145:30 amAZO - ORD
1 stop5h 49mDelta
dom. 9/217:10 amORD - AZO
1 stop3h 00mDelta
Deal found 9/13$492

Cheapflights Fare Finder

 
Customize your flight search to find flights from Kalamazoo to Chicago 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 septiembre 15, 2025.
Use the filters below to find and compare flights from Kalamazoo to Chicago that are best for you.

Fly from

Kalamazoo

Fly to

Chicago

Route

Depart

Return

Price

KalamazooChicago

AZO - ORD

AZOORD

Kalamazoo Intl

vie. 12/5

6:00 am-6:11 am

Nonstop1h 11m

Chicago O'Hare Intl

lun. 12/8

8:20 am-10:20 am

Nonstop1h 00m

$373

KalamazooChicago

AZO - MDW

AZOMDW

Kalamazoo Intl

vie. 12/5

5:25 am-8:54 am

1 stop4h 29m

Chicago Midway

lun. 12/8

6:40 pm-11:55 pm

1 stop4h 15m

$392

KalamazooChicago

AZO - ORD

AZOORD

Kalamazoo Intl

vie. 12/5

11:46 am-4:18 pm

1 stop5h 32m

Chicago O'Hare Intl

lun. 12/8

6:45 am-11:06 am

1 stop3h 21m

$392

KalamazooChicago

AZO - ORD

AZOORD

Kalamazoo Intl

mar. 9/30

5:44 pm-5:56 pm

Nonstop1h 12m

Chicago O'Hare Intl

sáb. 10/4

8:40 pm-10:51 pm

Nonstop1h 11m

$419

KalamazooChicago

AZO - ORD

AZOORD

Kalamazoo Intl

sáb. 9/20

5:44 pm-5:56 pm

Nonstop1h 12m

Chicago O'Hare Intl

sáb. 9/27

8:10 am-10:10 am

Nonstop1h 00m

$419

KalamazooChicago

AZO - ORD

AZOORD

Kalamazoo Intl

mar. 9/30

11:50 am-4:20 pm

1 stop5h 30m

Chicago O'Hare Intl

sáb. 10/4

5:00 pm-11:08 pm

1 stop5h 08m

$438

KalamazooChicago

AZO - ORD

AZOORD

Kalamazoo Intl

sáb. 9/20

5:30 am-9:10 am

1 stop4h 40m

Chicago O'Hare Intl

sáb. 9/27

7:10 am-1:16 pm

1 stop5h 06m

$438

KalamazooChicago

AZO - ORD

AZOORD

Kalamazoo Intl

dom. 11/2

5:00 am-5:08 am

Nonstop1h 08m

Chicago O'Hare Intl

jue. 11/6

10:00 pm-11:59 pm

Nonstop0h 59m

$463

KalamazooChicago

AZO - ORD

AZOORD

Kalamazoo Intl

vie. 9/19

5:30 am-8:05 am

1 stop3h 35m

Chicago O'Hare Intl

sáb. 9/27

7:10 am-1:16 pm

1 stop5h 06m

$465

KalamazooChicago

AZO - MDW

AZOMDW

Kalamazoo Intl

vie. 10/3

5:30 am-8:40 am

1 stop4h 10m

Chicago Midway

lun. 10/6

1:08 pm-5:16 pm

1 stop3h 08m

$492

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

Showing 1-10 of 22 results
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Best time to book a flight from Kalamazoo to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago 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.

Cheapflights Insights

Everything you need to know about your flight from Kalamazoo to Chicago

What is the cheapest month to book a flight from Kalamazoo to Chicago?

Currently, August is the cheapest month in which you can book a flight from Kalamazoo to Chicago (average of $245). Flying from Kalamazoo to Chicago in March is currently the most expensive (average of $321). 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.

What is the cheapest time of day to fly from AZO to CHI?

Find hourly flight availability from Kalamazoo to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated septiembre 15, 2025.

When flying from Kalamazoo to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 15% versus a flight in the evening.

What is the cheapest day to fly from Kalamazoo to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Kalamazoo to Chicago. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Kalamazoo to Chicago flight should consider departing on Friday afternoons when fares are most often at their lowest. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Kalamazoo to Chicago

Explore weekly flight availability from Kalamazoo to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated septiembre 15, 2025.

The most flights from AZO to CHI are scheduled on a Monday (6 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (6 on average).

Related info for your journey

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

    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. 1 airline have flights from Kalamazoo Intl to Chicago on a regular basis. Booking flights from Kalamazoo Intl to Chicago should not be difficult; the airport handles an average of 6 outbound flights to Chicago per day.

  • How long is the flight from Kalamazoo to Chicago?

    American Airlines and Delta can get you from Kalamazoo to Chicago in just under 1h 11m. Your travel time can differ by up to 3h 18m. Airlines will cover a distance of 122 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What is the cheapest airline to fly from Kalamazoo to Chicago round-trip?

    According to our current data, American Airlines ($318), offers the cheapest pricing from Kalamazoo to Chicago.

  • What are the most reliable airlines from Kalamazoo to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Kalamazoo to Chicago on time: Japan Airlines (89%), American Airlines (80%), Envoy Air (80%).

  • What are the cheapest flights from Kalamazoo to Chicago?

    Looking at all options, your cheapest flight can be booked for $159. While the most popular route (Kalamazoo Intl - Chicago O'Hare Intl) can be booked for $392 on average, our data indicates $521 when flying from Kalamazoo to Chicago.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Kalamazoo to Chicago 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 Kalamazoo to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Kalamazoo to Chicago (average of $245). Flying from Kalamazoo to Chicago in March is currently the most expensive (average of $321). 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?

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

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Alternative routes for Kalamazoo to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Kalamazoo to Chicago

Discover the top airline that operate flights from Kalamazoo to Chicago. 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 septiembre 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$318Average$373FlexibilityNo cancel feeOn-time71%

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