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$207+ 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 8/28. Fares are subject to change and may not be available on all flights or dates of travel.
AZO — CHI
Aug 6 — Aug 131
Thu 8/6
Thu 8/13
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 July 7, 2026.

This United Airlines deal was found by Cheapflights users on 7/4. 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.
Fri 12/186:27 pm
AZO
-
ORD
Nonstop1h 14m
United Airlines
Mon 12/217:45 am
ORD
-
AZO
Nonstop1h 05m
United Airlines
Deal found 7/4$244
This Delta deal was found by Cheapflights users on 7/6. 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 8/73:04 pm
AZO
-
MDW
1 stop4h 29m
Delta
Sat 8/86:42 pm
MDW
-
AZO
1 stop2h 51m
Delta
Deal found 7/6$248
This Delta deal was found by Cheapflights users on 7/3. 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 8/115:27 am
AZO
-
ORD
1 stop6h 15m
Delta
Tue 9/16:59 am
ORD
-
AZO
1 stop3h 02m
Delta
Deal found 7/3$248
This Delta deal was found by Cheapflights users on 7/3. 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 8/16:50 am
AZO
-
MDW
1 stop3h 23m
Delta
Sat 8/81:25 pm
MDW
-
AZO
1 stop2h 55m
Delta
Deal found 7/3$263
This Delta deal was found by Cheapflights users on 7/3. 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 7/175:30 am
AZO
-
ORD
1 stop3h 29m
Delta
Thu 1/147:35 pm
ORD
-
AZO
1 stop3h 11m
Delta
Deal found 7/3$263
This Delta deal was found by Cheapflights users on 7/6. 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 7/236:00 pm
AZO
-
ORD
1 stop3h 31m
Delta
Sat 7/255:18 pm
ORD
-
AZO
1 stop4h 14m
Delta
Deal found 7/6$278
This Delta deal was found by Cheapflights users on 7/2. 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 7/105:30 am
AZO
-
MDW
1 stop4h 43m
Delta
Mon 7/139:19 am
MDW
-
AZO
1 stop4h 00m
Delta
Deal found 7/2$308
This Delta deal was found by Cheapflights users on 7/2. 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 7/103:00 pm
AZO
-
ORD
1 stop6h 31m
Delta
Mon 7/137:17 pm
ORD
-
AZO
1 stop3h 34m
Delta
Deal found 7/2$308
This Delta deal was found by Cheapflights users on 7/4. 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 7/186:50 am
AZO
-
MDW
1 stop3h 23m
Delta
Tue 7/219:19 am
MDW
-
AZO
1 stop4h 00m
Delta
Deal found 7/4$323
This Delta deal was found by Cheapflights users on 7/6. 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 7/85:30 am
AZO
-
MDW
1 stop4h 43m
Delta
Thu 7/161:18 pm
MDW
-
AZO
1 stop2h 58m
Delta
Deal found 7/6$363
This Delta deal was found by Cheapflights users on 7/6. 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 7/83:00 pm
AZO
-
ORD
1 stop4h 29m
Delta
Tue 7/147:05 am
ORD
-
AZO
1 stop2h 55m
Delta
Deal found 7/6$363
This American Airlines deal was found by Cheapflights users on 7/2. 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 8/114:08 pm
AZO
-
ORD
Nonstop1h 22m
American Airlines
Tue 9/110:35 pm
ORD
-
AZO
Nonstop1h 06m
American Airlines
Deal found 7/2$411

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 July 7, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$244
(United Airlines)

One-way from

$207
(Delta)

Good round-trip deal

$349 or less

Good one-way deal

$328 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 July 7, 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

Fri 12/18

6:27 pm-6:41 pm

Nonstop1h 14m

Chicago O'Hare Intl

Mon 12/21

7:45 am-9:50 am

Nonstop1h 05m

$244

KalamazooChicago

AZO - MDW

AZOMDW

Kalamazoo Intl

Thu 8/13

3:04 pm-6:33 pm

1 stop4h 29m

Chicago Midway

Thu 8/20

9:24 am-2:24 pm

1 stop4h 00m

$248

KalamazooChicago

AZO - MDW

AZOMDW

Kalamazoo Intl

Sun 8/16

3:04 pm-6:33 pm

1 stop4h 29m

Chicago Midway

Sun 8/23

6:42 pm-11:52 pm

1 stop4h 10m

$248

KalamazooChicago

AZO - MDW

AZOMDW

Kalamazoo Intl

Fri 12/18

5:30 am-8:45 am

1 stop4h 15m

Chicago Midway

Mon 12/21

9:30 am-1:27 pm

1 stop2h 57m

$248

KalamazooChicago

AZO - MDW

AZOMDW

Kalamazoo Intl

Fri 8/28

5:27 am-9:17 am

1 stop4h 50m

Chicago Midway

Tue 9/1

5:45 pm-11:52 pm

1 stop5h 07m

$248

KalamazooChicago

AZO - MDW

AZOMDW

Kalamazoo Intl

Fri 8/7

3:04 pm-6:33 pm

1 stop4h 29m

Chicago Midway

Sat 8/8

6:42 pm-10:33 pm

1 stop2h 51m

$248

KalamazooChicago

AZO - ORD

AZOORD

Kalamazoo Intl

Sun 8/16

3:04 pm-8:30 pm

1 stop6h 26m

Chicago O'Hare Intl

Sun 8/23

7:30 pm-11:52 pm

1 stop3h 22m

$248

KalamazooChicago

AZO - ORD

AZOORD

Kalamazoo Intl

Tue 8/11

5:27 am-10:42 am

1 stop6h 15m

Chicago O'Hare Intl

Tue 9/1

6:59 am-11:01 am

1 stop3h 02m

$248

KalamazooChicago

AZO - ORD

AZOORD

Kalamazoo Intl

Fri 8/7

3:04 pm-6:29 pm

1 stop4h 25m

Chicago O'Hare Intl

Sat 8/8

6:59 am-11:01 am

1 stop3h 02m

$248

KalamazooChicago

AZO - ORD

AZOORD

Kalamazoo Intl

Sat 8/1

6:00 pm-8:31 pm

1 stop3h 31m

Chicago O'Hare Intl

Fri 8/7

7:30 pm-11:52 pm

1 stop3h 22m

$248

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

Showing 1-10 of 36 resultsSorted by cheapest first
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2
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4
  • 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 July 7, 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 afternoon, which can drop the price by up to 45% 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 July 7, 2026.

The most flights from AZO to CHI are scheduled on a Monday (5 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (4 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 July 4, 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 4 outbound flights 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 29m. 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 ($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: Envoy Air (87%), British Airways (85%), Japan Airlines (85%).

  • What are the cheapest flights from Kalamazoo to Chicago?

    Looking at all options, your cheapest flight can be booked for $248. While the most popular route (Kalamazoo Intl - Chicago O'Hare Intl) can be booked for $244 on average, our data indicates $433 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
Hammond
Lansing
Merrillville
Valparaiso
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 July 7, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$188Average$348FlexibilityNo cancel feeOn-time71%

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