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$225+ 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 9/11. Fares are subject to change and may not be available on all flights or dates of travel.
AZO — CHI
Jul 21 — Jul 281
Tue 7/21
Tue 7/28
1 adult, Economy
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Cheap 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 June 21, 2026.

This United Airlines deal was found by Cheapflights users on 6/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/212:30 pm
AZO
-
ORD
Nonstop1h 12m
United Airlines
Sat 11/2811:40 am
ORD
-
AZO
Nonstop1h 03m
United Airlines
Deal found 6/18$229
This Delta deal was found by Cheapflights users on 6/16. 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 7/93:00 pm
AZO
-
MDW
1 stop4h 25m
Delta
Thu 7/169:19 am
MDW
-
AZO
1 stop4h 00m
Delta
Deal found 6/16$248
This Delta deal was found by Cheapflights users on 6/16. 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 8/116:00 pm
AZO
-
ORD
1 stop3h 30m
Delta
Tue 9/17:00 am
ORD
-
AZO
1 stop3h 01m
Delta
Deal found 6/16$248
This Delta deal was found by Cheapflights users on 6/19. 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 7/96:00 pm
AZO
-
ORD
1 stop3h 31m
Delta
Thu 7/168:52 am
ORD
-
AZO
1 stop4h 27m
Delta
Deal found 6/19$263
This Delta deal was found by Cheapflights users on 6/17. 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 7/13:04 pm
AZO
-
MDW
1 stop4h 27m
Delta
Sat 7/41:26 pm
MDW
-
AZO
1 stop2h 54m
Delta
Deal found 6/17$278
This Delta deal was found by Cheapflights users on 6/16. 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 7/16:00 pm
AZO
-
ORD
1 stop3h 31m
Delta
Sun 7/57:01 am
ORD
-
AZO
1 stop3h 01m
Delta
Deal found 6/16$278
This Delta deal was found by Cheapflights users on 6/18. 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 7/33:04 pm
AZO
-
ORD
2 stops7h 21m
Delta
Mon 7/65:22 pm
ORD
-
AZO
1 stop5h 34m
Delta
Deal found 6/18$284
This Delta deal was found by Cheapflights users on 6/19. 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 7/13:04 pm
AZO
-
MDW
1 stop4h 27m
Delta
Sun 7/56:58 pm
MDW
-
AZO
1 stop3h 58m
Delta
Deal found 6/19$293
This Delta deal was found by Cheapflights users on 6/17. 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.
Fri 7/173:00 pm
AZO
-
MDW
1 stop4h 25m
Delta
Tue 7/219:19 am
MDW
-
AZO
1 stop4h 00m
Delta
Deal found 6/17$308
This Delta deal was found by Cheapflights users on 6/17. 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.
Thu 6/253:04 pm
AZO
-
ORD
1 stop6h 27m
Delta
Mon 6/297:01 am
ORD
-
AZO
1 stop3h 01m
Delta
Deal found 6/17$308
This United Airlines deal was found by Cheapflights users on 6/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/94:38 pm
AZO
-
ORD
Nonstop1h 14m
United Airlines
Fri 12/1111:40 am
ORD
-
AZO
Nonstop1h 03m
United Airlines
Deal found 6/19$317
This Delta deal was found by Cheapflights users on 6/16. 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 6/206:50 am
AZO
-
MDW
1 stop3h 24m
Delta
Tue 7/219:19 am
MDW
-
AZO
1 stop4h 00m
Delta
Deal found 6/16$368

Find 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 June 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$229
(United Airlines)

One-way from

$225
(Delta)

Good round-trip deal

$347 or less

Good one-way deal

$294 or less
Provider with most accurate pricing for Kalamazoo Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Kalamazoo Intl-Chicago (CHI) flights.
Search Deals
From Kalamazoo Intl to Chicago (CHI)
Search Deals
One-way flight from Kalamazoo Intl to Chicago (CHI)
Search Deals
Price to beat on a round-trip flight from Kalamazoo Intl to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Kalamazoo Intl to Chicago (CHI).
Search Deals

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 June 21, 2026.
Use the filters below to find and compare flights from Kalamazoo to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

KalamazooChicago

AZO - ORD

AZOORD

Kalamazoo Intl

Sat 11/21

2:03 pm-2:15 pm

Nonstop1h 12m

Chicago O'Hare Intl

Sat 11/28

11:40 am-1:43 pm

Nonstop1h 03m

$229

KalamazooChicago

AZO - MDW

AZOMDW

Kalamazoo Intl

Thu 7/9

3:00 pm-6:25 pm

1 stop4h 25m

Chicago Midway

Thu 7/16

9:19 am-2:19 pm

1 stop4h 00m

$248

KalamazooChicago

AZO - MDW

AZOMDW

Kalamazoo Intl

Wed 10/7

3:00 pm-6:37 pm

1 stop4h 37m

Chicago Midway

Wed 2/24

1:00 pm-5:11 pm

1 stop3h 11m

$248

KalamazooChicago

AZO - MDW

AZOMDW

Kalamazoo Intl

Sun 9/20

2:51 pm-6:33 pm

1 stop4h 42m

Chicago Midway

Tue 10/13

9:30 am-2:20 pm

1 stop3h 50m

$248

KalamazooChicago

AZO - MDW

AZOMDW

Kalamazoo Intl

Tue 8/4

5:27 am-9:17 am

1 stop4h 50m

Chicago Midway

Tue 8/11

6:42 pm-11:52 pm

1 stop4h 10m

$248

KalamazooChicago

AZO - MDW

AZOMDW

Kalamazoo Intl

Fri 8/21

3:04 pm-6:33 pm

1 stop4h 29m

Chicago Midway

Sun 8/23

9:24 am-2:24 pm

1 stop4h 00m

$248

KalamazooChicago

AZO - MDW

AZOMDW

Kalamazoo Intl

Fri 8/28

3:04 pm-6:33 pm

1 stop4h 29m

Chicago Midway

Fri 9/4

1:27 pm-5:20 pm

1 stop2h 53m

$248

KalamazooChicago

AZO - MDW

AZOMDW

Kalamazoo Intl

Sat 8/1

6:50 am-9:13 am

1 stop3h 23m

Chicago Midway

Sun 8/9

6:42 pm-11:52 pm

1 stop4h 10m

$248

KalamazooChicago

AZO - MDW

AZOMDW

Kalamazoo Intl

Sat 11/21

3:00 pm-6:37 pm

1 stop4h 37m

Chicago Midway

Sat 11/28

9:30 am-2:20 pm

1 stop3h 50m

$248

KalamazooChicago

AZO - ORD

AZOORD

Kalamazoo Intl

Fri 8/7

3:04 pm-8:30 pm

1 stop6h 26m

Chicago O'Hare Intl

Sun 8/9

7:00 am-2:24 pm

1 stop6h 24m

$248

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/17

Showing 1-10 of 34 resultsSorted by cheapest first
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  • Most accurate provider: When it comes to deals on Kalamazoo-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Kalamazoo-Chicago flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 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 June 21, 2026.

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 43% versus a flight at noon.

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 June 21, 2026.

The most flights from AZO to CHI are scheduled on a Monday (5 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (5 on average).

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 June 20, 2026.

Travelers seeking maximum savings on their Kalamazoo to Chicago flight should consider departing on Tuesday evenings when fares are most often at their lowest. Friday 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 5 outbound flights to Chicago per day.

  • How long is the flight from Kalamazoo to Chicago?

    United Airlines and Delta can get you from Kalamazoo to Chicago in just under 1h 12m. Your travel time can differ by up to 3h 13m. 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 ($188), 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: British Airways (86%), Japan Airlines (84%), Envoy Air (84%).

  • What are the cheapest flights from Kalamazoo to Chicago?

    Looking at all options, your cheapest flight can be booked for $163. While the most popular route (Kalamazoo Intl - Chicago O'Hare Intl) can be booked for $229 on average, our data indicates $417 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.

See more FAQs

Traveling to a place near Chicago?

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

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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 June 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$188Average$348FlexibilityNo cancel feeOn-time71%

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