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$190+ 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 4/3. Fares are subject to change and may not be available on all flights or dates of travel.
AZO — CHI
Mar 5 — Mar 121
Thu 3/5
Thu 3/12
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 February 3, 2026.

This United Airlines deal was found by Cheapflights users on 2/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:40 pm
AZO
-
ORD
Nonstop1h 14m
United Airlines
Sat 5/211:43 am
ORD
-
AZO
Nonstop1h 03m
United Airlines
Deal found 2/2$229
This United Airlines deal was found by Cheapflights users on 2/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/32:30 pm
AZO
-
ORD
Nonstop1h 12m
United Airlines
Thu 6/119:27 pm
ORD
-
AZO
Nonstop1h 03m
United Airlines
Deal found 2/2$259
This United Airlines deal was found by Cheapflights users on 2/1. 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 5/236:27 pm
AZO
-
ORD
Nonstop1h 14m
United Airlines
Thu 5/283:35 pm
ORD
-
AZO
Nonstop1h 06m
United Airlines
Deal found 2/1$273
This United Airlines deal was found by Cheapflights users on 2/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3010:49 am
AZO
-
ORD
Nonstop1h 14m
United Airlines
Sun 5/33:45 pm
ORD
-
AZO
Nonstop1h 06m
United Airlines
Deal found 2/2$284
This United Airlines deal was found by Cheapflights users on 2/1. 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.
Mon 5/112:30 pm
AZO
-
ORD
Nonstop1h 12m
United Airlines
Mon 5/189:15 pm
ORD
-
AZO
Nonstop1h 03m
United Airlines
Deal found 2/1$317
This Delta deal was found by Cheapflights users on 2/3. 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.
Wed 4/295:30 am
AZO
-
MDW
1 stop8h 13m
Delta
Sat 5/26:38 pm
MDW
-
AZO
1 stop2h 57m
Delta
Deal found 2/3$369
This Delta deal was found by Cheapflights users on 2/2. 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.
Wed 4/295:30 am
AZO
-
ORD
1 stop11h 48m
Delta
Sat 5/27:00 am
ORD
-
AZO
1 stop3h 50m
Delta
Deal found 2/2$369
This American Airlines deal was found by Cheapflights users on 2/1. 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 3/77:00 am
AZO
-
ORD
Nonstop1h 21m
American Airlines
Sun 3/84:40 pm
ORD
-
AZO
Nonstop0h 56m
American Airlines
Deal found 2/1$384
This Delta deal was found by Cheapflights users on 2/3. 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.
Thu 4/305:30 am
AZO
-
MDW
1 stop8h 13m
Delta
Sat 5/22:12 pm
MDW
-
AZO
2 stops7h 23m
Delta
Deal found 2/3$387
This American Airlines deal was found by Cheapflights users on 2/2. 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.
Thu 3/56:50 pm
AZO
-
ORD
Nonstop1h 18m
American Airlines
Wed 3/118:59 pm
ORD
-
AZO
Nonstop1h 04m
American Airlines
Deal found 2/2$387
This Delta deal was found by Cheapflights users on 2/3. 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.
Wed 4/2912:30 pm
AZO
-
MDW
1 stop6h 28m
Delta
Sun 5/31:23 pm
MDW
-
AZO
1 stop3h 07m
Delta
Deal found 2/3$405
This Delta deal was found by Cheapflights users on 2/1. 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 3/75:23 am
AZO
-
MDW
1 stop4h 31m
Delta
Sun 3/81:10 pm
MDW
-
AZO
1 stop3h 27m
Delta
Deal found 2/1$406

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 February 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$229
(United Airlines)

One-way from

$190
(Delta)

Good round-trip deal

$387 or less

Good one-way deal

$219 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 February 3, 2026.
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

Fri 5/1

6:40 pm-6:54 pm

Nonstop1h 14m

Chicago O'Hare Intl

Sat 5/2

11:43 am-1:46 pm

Nonstop1h 03m

$229

KalamazooChicago

AZO - ORD

AZOORD

Kalamazoo Intl

Wed 6/3

2:30 pm-2:42 pm

Nonstop1h 12m

Chicago O'Hare Intl

Thu 6/11

9:27 pm-11:30 pm

Nonstop1h 03m

$259

KalamazooChicago

AZO - ORD

AZOORD

Kalamazoo Intl

Thu 4/30

10:49 am-11:03 am

Nonstop1h 14m

Chicago O'Hare Intl

Sun 5/3

3:45 pm-5:51 pm

Nonstop1h 06m

$284

KalamazooChicago

AZO - ORD

AZOORD

Kalamazoo Intl

Mon 5/11

2:30 pm-2:42 pm

Nonstop1h 12m

Chicago O'Hare Intl

Mon 5/18

9:15 pm-11:18 pm

Nonstop1h 03m

$317

KalamazooChicago

AZO - MDW

AZOMDW

Kalamazoo Intl

Wed 4/29

12:30 pm-5:58 pm

1 stop6h 28m

Chicago Midway

Sat 5/2

6:38 pm-10:35 pm

1 stop2h 57m

$369

KalamazooChicago

AZO - ORD

AZOORD

Kalamazoo Intl

Wed 4/29

5:30 am-4:18 pm

1 stop11h 48m

Chicago O'Hare Intl

Sat 5/2

7:00 am-11:50 am

1 stop3h 50m

$369

KalamazooChicago

AZO - MDW

AZOMDW

Kalamazoo Intl

Thu 4/30

12:30 pm-5:58 pm

1 stop6h 28m

Chicago Midway

Sat 5/2

6:38 pm-10:35 pm

1 stop2h 57m

$381

KalamazooChicago

AZO - MDW

AZOMDW

Kalamazoo Intl

Fri 5/1

6:10 pm-8:47 am

1 stop15h 37m

Chicago Midway

Sat 5/2

6:38 pm-10:35 pm

1 stop2h 57m

$381

KalamazooChicago

AZO - ORD

AZOORD

Kalamazoo Intl

Sat 3/7

7:00 am-7:21 am

Nonstop1h 21m

Chicago O'Hare Intl

Sun 3/8

4:40 pm-6:36 pm

Nonstop0h 56m

$384

KalamazooChicago

AZO - ORD

AZOORD

Kalamazoo Intl

Thu 3/5

6:50 pm-7:08 pm

Nonstop1h 18m

Chicago O'Hare Intl

Wed 3/11

8:59 pm-11:03 pm

Nonstop1h 04m

$387

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/1

Showing 1-10 of 29 results
1
2
3
  • 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 month to book a flight from Kalamazoo to Chicago?

Currently, October is the cheapest month in which you can book a flight from Kalamazoo to Chicago (average of $83). 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 February 3, 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 at noon, which can drop the price by up to 33% 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 January 31, 2026.

Travelers seeking maximum savings on their Kalamazoo to Chicago flight should consider departing on Wednesday at noon 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.

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 February 3, 2026.

The most flights from AZO to CHI are scheduled on a Tuesday (7 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 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 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 14m. Your travel time can differ by up to 5h 14m. 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: American Airlines (68%), Envoy Air (68%), Japan Airlines (66%).

  • What are the cheapest flights from Kalamazoo to Chicago?

    Looking at all options, your cheapest flight can be booked for $133. While the most popular route (Kalamazoo Intl - Chicago O'Hare Intl) can be booked for $259 on average, our data indicates $383 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, October is the cheapest month in which you can book a flight from Kalamazoo to Chicago (average of $83). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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 February 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$318Average$386FlexibilityNo cancel feeOn-time71%

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