$210 Cheap Flights from Chicago (MDW) to Cali (CLO)

View $210 flight on Mon, Nov 10, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Alfonso Bonilla Aragon Intl. Airport (CLO)

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Cheap Flights from Chicago to Cali (MDW-CLO)

Prices were available within the past 7 days and start at $210 for one-way flights and $392 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, Jan 17 - Wed, Jan 28
MDW
Chicago
CLO
Cali
$392 Roundtrip, found 6 days ago
$392
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Jan 17 from Chicago to Cali, returning Wed, Jan 28, priced at $392 found 6 days ago
Delta
Mon, Jan 19 - Wed, Jan 28
MDW
Chicago
CLO
Cali
$408 Roundtrip, found 6 days ago
$408
Roundtrip
found 6 days ago
Select Delta flight, departing Mon, Jan 19 from Chicago to Cali, returning Wed, Jan 28, priced at $408 found 6 days ago
LATAM Airlines Group
Mon, Jan 26 - Wed, Feb 11
MDW
Chicago
CLO
Cali
$415 Roundtrip, found 6 days ago
$415
Roundtrip
found 6 days ago
Select LATAM Airlines Group flight, departing Mon, Jan 26 from Chicago to Cali, returning Wed, Feb 11, priced at $415 found 6 days ago
LATAM Airlines Group
Mon, Jan 26 - Mon, Feb 16
MDW
Chicago
CLO
Cali
$422 Roundtrip, found 6 days ago
$422
Roundtrip
found 6 days ago
Select LATAM Airlines Group flight, departing Mon, Jan 26 from Chicago to Cali, returning Mon, Feb 16, priced at $422 found 6 days ago
Delta
Mon, Jan 26 - Fri, Feb 13
MDW
Chicago
CLO
Cali
$426 Roundtrip, found 6 days ago
$426
Roundtrip
found 6 days ago
Select Delta flight, departing Mon, Jan 26 from Chicago to Cali, returning Fri, Feb 13, priced at $426 found 6 days ago
LATAM Airlines Group
Sat, Nov 29 - Wed, Dec 3
MDW
Chicago
CLO
Cali
$428 Roundtrip, found 1 day ago
$428
Roundtrip
found 1 day ago
Select LATAM Airlines Group flight, departing Sat, Nov 29 from Chicago to Cali, returning Wed, Dec 3, priced at $428 found 1 day ago
LATAM Airlines Group
Mon, Jan 19 - Sun, Feb 1
MDW
Chicago
CLO
Cali
$433 Roundtrip, found 6 days ago
$433
Roundtrip
found 6 days ago
Select LATAM Airlines Group flight, departing Mon, Jan 19 from Chicago to Cali, returning Sun, Feb 1, priced at $433 found 6 days ago
LATAM Airlines Group
Tue, Nov 25 - Thu, Feb 12
MDW
Chicago
CLO
Cali
$436 Roundtrip, found 6 days ago
$436
Roundtrip
found 6 days ago
Select LATAM Airlines Group flight, departing Tue, Nov 25 from Chicago to Cali, returning Thu, Feb 12, priced at $436 found 6 days ago
LATAM Airlines Group
Sat, Jan 17 - Tue, Jan 27
MDW
Chicago
CLO
Cali
$440 Roundtrip, found 6 days ago
$440
Roundtrip
found 6 days ago
Select LATAM Airlines Group flight, departing Sat, Jan 17 from Chicago to Cali, returning Tue, Jan 27, priced at $440 found 6 days ago
LATAM Airlines Group
Tue, Nov 25 - Mon, Feb 16
MDW
Chicago
CLO
Cali
$443 Roundtrip, found 6 days ago
$443
Roundtrip
found 6 days ago
Select LATAM Airlines Group flight, departing Tue, Nov 25 from Chicago to Cali, returning Mon, Feb 16, priced at $443 found 6 days ago

Alternative airports near Cali

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Alfonso Bonilla Aragon Intl. CLO. Cheapest and Closest option available. Average driving time to city center is 27 minutes. Flights from $1,277
CLO
Alfonso Bonilla Aragon Intl.
CheapestClosest
Average driving time to city center27 min
Flights from $1,277

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Alfonso Bonilla Aragon Intl. Airport (CLO) cost?
Grab a cheap one-way flight from $210 or cheap return flight from $392 from Midway Intl. Airport (MDW) to Alfonso Bonilla Aragon Intl. Airport (CLO) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Alfonso Bonilla Aragon Intl. Airport (CLO)?
Traveling in January is a great way to save, as it's the cheapest month for flights between MDW and CLO. You'll usually find the lowest fares during off-peak months.
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Alfonso Bonilla Aragon Intl. Airport (CLO)?
To find the cheapest airline flying from MDW to CLO, use Expedia's filter tool. Customize your search based on your travel style, such as preferred carriers and flight duration. You can then sort your results by "Price (lowest to highest)" to list the most affordable options first.
How many flights per day from Midway Intl. Airport (MDW) to Alfonso Bonilla Aragon Intl. Airport (CLO)?
Direct flights from Midway Intl. Airport (MDW) to Alfonso Bonilla Aragon Intl. Airport (CLO) aren't available daily, so you'll need to take a flight with a layover. Explore your options with Expedia's filters. Enter your dates and pick either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MDW to CLO?
Friday is generally the busiest day for flights, while Tuesday is often the quietest.* Remember that flight schedules can vary depending on a range of factors, including the time of year and carrier.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Alfonso Bonilla Aragon Intl. Airport (CLO)?
To avoid possible delays on the Midway Intl. Airport (MDW) to Alfonso Bonilla Aragon Intl. Airport (CLO) route, fly before 3 PM. Later departures have a 22% higher chance of being canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Alfonso Bonilla Aragon Intl. Airport (CLO) last-minute?
Waiting until just before your departure to book your flight from MDW to CLO often results in higher prices. Although you may find some last-minute deals, they're not always guaranteed. Allow some flexibility in your schedule for the best chance of getting a bargain.
Is it cheaper to book a MDW to CLO flight and hotel package?
Booking a MDW to CLO flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your travels all in one place. Select from our extensive range of stays and then add car rentals, flights and activities to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Alfonso Bonilla Aragon Intl. Airport (CLO)?
Typically, you're able to reschedule or cancel your MDW to CLO flight. However, there may be additional charges, especially if your booking was made over 24 hours ago. Double-check your itinerary for the airline's policies and fees on flight changes, or if you'd like more information, head to our Customer Service portal.

Travel information

Origin airport
Midway Intl.
Destination airport
Alfonso Bonilla Aragon Intl.
Airlines serving
Delta, LATAM Airlines Group
Roundtrip price
$392
Distance
2734 mi

Book with confidence

Chicago to Cali Flights

The cheapest times to fly from Chicago to Cali

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Cali are during the month of January. You can find some of the cheapest flights from Chicago to Cali with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Cali

Sunday is one of the best days to book for cheap flights from Chicago to Cali: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Cali

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Cali in 2025. You can also book with separate airlines for your outbound and return journeys, from $210 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Cali flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Cali airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to Cali Flights

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*Available to One Key members.