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$138+ 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 12/25. Fares are subject to change and may not be available on all flights or dates of travel.
AZO — CHI
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$367
(Delta)

One-way from

$138
(Delta)

Good round-trip deal

$370 or less

Good one-way deal

$234 or less
Provider with most accurate pricing for Kalamazoo Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Kalamazoo Intl-Chicago (CHI) flights.
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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 October 30, 2025.

This Delta deal was found by Cheapflights users on 10/30. 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 12/155:25 amAZO - ORD
1 stop5h 35mDelta
Mon 12/227:00 amORD - AZO
1 stop5h 26mDelta
Deal found 10/30$392
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Fri 10/3110:52 amAZO - ORD
Nonstop1h 10mAmerican Airlines
Mon 11/109:40 amORD - AZO
Nonstop1h 05mAmerican Airlines
Deal found 10/28$438
This American Airlines deal was found by Cheapflights users on 10/30. 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.
Tue 11/117:10 amAZO - ORD
Nonstop1h 09mAmerican Airlines
Sat 11/159:16 pmORD - AZO
Nonstop0h 59mAmerican Airlines
Deal found 10/30$449
This Delta deal was found by Cheapflights users on 10/28. 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 10/316:45 amAZO - ORD
1 stop3h 58mDelta
Mon 11/106:45 amORD - AZO
1 stop3h 21mDelta
Deal found 10/28$457
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Fri 11/214:14 pmAZO - ORD
Nonstop1h 15mAmerican Airlines
Fri 11/281:43 pmORD - AZO
Nonstop1h 00mAmerican Airlines
Deal found 10/28$458
This Delta deal was found by Cheapflights users on 10/29. 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 11/125:25 amAZO - MDW
1 stop4h 29mDelta
Wed 11/191:15 pmMDW - AZO
1 stop3h 08mDelta
Deal found 10/29$468
This Delta deal was found by Cheapflights users on 10/29. 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 11/126:04 pmAZO - ORD
1 stop3h 25mDelta
Wed 11/1910:46 amORD - AZO
1 stop5h 37mDelta
Deal found 10/29$468
This American Airlines deal was found by Cheapflights users on 10/29. 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.
Sat 11/84:51 pmAZO - ORD
Nonstop1h 20mAmerican Airlines
Sun 11/98:15 amORD - AZO
Nonstop0h 58mAmerican Airlines
Deal found 10/29$476
This Delta deal was found by Cheapflights users on 10/28. 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 11/215:25 amAZO - ORD
1 stop3h 41mDelta
Fri 11/286:45 amORD - AZO
1 stop3h 21mDelta
Deal found 10/28$477
This Delta deal was found by Cheapflights users on 10/28. 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 11/125:25 amAZO - ORD
1 stop3h 41mDelta
Sun 11/166:45 amORD - AZO
1 stop3h 21mDelta
Deal found 10/28$502
This American Airlines deal was found by Cheapflights users on 10/29. 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.
Fri 11/76:00 amAZO - ORD
Nonstop1h 08mAmerican Airlines
Mon 11/109:40 amORD - AZO
Nonstop1h 05mAmerican Airlines
Deal found 10/29$503
This Delta deal was found by Cheapflights users on 10/29. 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 11/75:56 pmAZO - ORD
1 stop3h 27mDelta
Mon 11/107:11 pmORD - AZO
1 stop3h 47mDelta
Deal found 10/29$522

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 October 30, 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 - MDW

AZOMDW

Kalamazoo Intl

Fri 4/17

5:30 am-8:42 am

1 stop4h 12m

Chicago Midway

Sat 4/18

5:59 pm-11:43 pm

1 stop4h 44m

$367

KalamazooChicago

AZO - ORD

AZOORD

Kalamazoo Intl

Sat 4/18

5:30 am-9:24 am

1 stop4h 54m

Chicago O'Hare Intl

Sun 4/19

7:00 am-11:00 am

1 stop3h 00m

$367

KalamazooChicago

AZO - ORD

AZOORD

Kalamazoo Intl

Mon 12/15

5:25 am-10:00 am

1 stop5h 35m

Chicago O'Hare Intl

Mon 12/22

7:00 am-1:26 pm

1 stop5h 26m

$392

KalamazooChicago

AZO - ORD

AZOORD

Kalamazoo Intl

Sat 4/18

7:33 pm-7:50 pm

Nonstop1h 17m

Chicago O'Hare Intl

Sun 4/19

10:00 pm-11:56 pm

Nonstop0h 56m

$428

KalamazooChicago

AZO - ORD

AZOORD

Kalamazoo Intl

Wed 11/12

7:10 am-7:19 am

Nonstop1h 09m

Chicago O'Hare Intl

Wed 11/19

1:40 pm-3:40 pm

Nonstop1h 00m

$449

KalamazooChicago

AZO - ORD

AZOORD

Kalamazoo Intl

Tue 11/11

7:10 am-7:19 am

Nonstop1h 09m

Chicago O'Hare Intl

Sat 11/15

9:16 pm-11:15 pm

Nonstop0h 59m

$449

KalamazooChicago

AZO - MDW

AZOMDW

Kalamazoo Intl

Wed 11/12

5:25 am-8:54 am

1 stop4h 29m

Chicago Midway

Wed 11/19

1:15 pm-5:23 pm

1 stop3h 08m

$468

KalamazooChicago

AZO - ORD

AZOORD

Kalamazoo Intl

Wed 11/12

6:04 pm-8:29 pm

1 stop3h 25m

Chicago O'Hare Intl

Wed 11/19

10:46 am-5:23 pm

1 stop5h 37m

$468

KalamazooChicago

AZO - ORD

AZOORD

Kalamazoo Intl

Thu 1/1

6:30 am-9:01 am

1 stop3h 31m

$138

KalamazooChicago

AZO - ORD

AZOORD

Kalamazoo Intl

Wed 12/31

2:10 pm-9:01 am

1 stop19h 51m

$143

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 19 results
1
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Compare providers for flights from Kalamazoo to Chicago

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 Kalamazoo to Chicago in October.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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 Kalamazoo-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Kalamazoo-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Kalamazoo-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Kalamazoo-Chicago flights, Cheapflights users trust eDreams the most. eDreams 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 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 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, January is the cheapest month in which you can book a flight from Kalamazoo to Chicago (average of $78). Flying from Kalamazoo to Chicago in July is currently the most expensive (average of $149). 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 October 30, 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 21% versus a flight at noon.

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. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 1 outbound flight to Chicago per day.

  • How long is the flight from Kalamazoo to Chicago?

    Delta can get you from Kalamazoo to Chicago in just under 4h 12m. Your travel time can differ by up to . Airlines will cover a distance of 117 mi.

  • 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: SkyWest Airlines (100%), Japan Airlines (92%), American Airlines (88%).

  • What are the cheapest flights from Kalamazoo to Chicago?

    Looking at all options, your cheapest flight can be booked for $179. While the most popular route (Kalamazoo Intl - Chicago O'Hare Intl) can be booked for $367 on average, our data indicates $543 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, January is the cheapest month in which you can book a flight from Kalamazoo to Chicago (average of $78). Flying from Kalamazoo to Chicago in July is currently the most expensive (average of $149). 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
Porter
Benton Harbor

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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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$318Average$386FlexibilityNo cancel feeOn-time71%

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