$282 Cheap Flights from Chicago (MDW) to Cali (CLO)

View $282 flight on Sat, Sep 27, 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 $282 for one-way flights and $335 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Fri, Sep 19 - Thu, Oct 2
MDW
Chicago
CLO
Cali
$335 Roundtrip, found 6 days ago
$335
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Sep 19 from Chicago to Cali, returning Thu, Oct 2, priced at $335 found 6 days ago
Delta
Fri, Sep 19 - Mon, Sep 22
MDW
Chicago
CLO
Cali
$343 Roundtrip, found 6 days ago
$343
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Sep 19 from Chicago to Cali, returning Mon, Sep 22, priced at $343 found 6 days ago
LATAM Airlines Group
Thu, Sep 18 - Tue, Sep 23
MDW
Chicago
CLO
Cali
$380 Roundtrip, found 6 days ago
$380
Roundtrip
found 6 days ago
Select LATAM Airlines Group flight, departing Thu, Sep 18 from Chicago to Cali, returning Tue, Sep 23, priced at $380 found 6 days ago
Delta
Tue, Oct 21 - Thu, Oct 23
MDW
Chicago
CLO
Cali
$410 Roundtrip, found 6 days ago
$410
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Oct 21 from Chicago to Cali, returning Thu, Oct 23, priced at $410 found 6 days ago
LATAM Airlines Group
Tue, Jul 29 - Wed, Aug 6
MDW
Chicago
CLO
Cali
$541 Roundtrip, found 2 days ago
$541
Roundtrip
found 2 days ago
Select LATAM Airlines Group flight, departing Tue, Jul 29 from Chicago to Cali, returning Wed, Aug 6, priced at $541 found 2 days ago
LATAM Airlines Group
Tue, Jul 29 - Fri, Aug 1
MDW
Chicago
CLO
Cali
$554 Roundtrip, found 2 days ago
$554
Roundtrip
found 2 days ago
Select LATAM Airlines Group flight, departing Tue, Jul 29 from Chicago to Cali, returning Fri, Aug 1, priced at $554 found 2 days ago
Delta
Fri, Sep 26 - Tue, Oct 7
MDW
Chicago
CLO
Cali
$577 Roundtrip, found 11 hours ago
$577
Roundtrip
found 11 hours ago
Select Delta flight, departing Fri, Sep 26 from Chicago to Cali, returning Tue, Oct 7, priced at $577 found 11 hours ago
LATAM Airlines Group
Tue, Jul 29 - Sun, Aug 3
MDW
Chicago
CLO
Cali
$695 Roundtrip, found 2 days ago
$695
Roundtrip
found 2 days ago
Select LATAM Airlines Group flight, departing Tue, Jul 29 from Chicago to Cali, returning Sun, Aug 3, priced at $695 found 2 days ago
LATAM Airlines Group
Tue, Jul 29 - Mon, Aug 4
MDW
Chicago
CLO
Cali
$706 Roundtrip, found 2 days ago
$706
Roundtrip
found 2 days ago
Select LATAM Airlines Group flight, departing Tue, Jul 29 from Chicago to Cali, returning Mon, Aug 4, priced at $706 found 2 days ago
Delta
Mon, Jul 28 - Wed, Aug 6
MDW
Chicago
CLO
Cali
$769 Roundtrip, found 2 days ago
$769
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Jul 28 from Chicago to Cali, returning Wed, Aug 6, priced at $769 found 2 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 $775
CLO
Alfonso Bonilla Aragon Intl.
CheapestClosest
Average driving time to city center27 min
Flights from $775
Flights from Chicago (MDW) to Cali (CLO)
Origin airport
Midway Intl.
Destination airport
Alfonso Bonilla Aragon Intl.
Airlines serving
Delta, LATAM Airlines Group
Roundtrip price
$335
Distance
2734 mi

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 September. 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 $282 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.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Alfonso Bonilla Aragon Intl. Airport (CLO) cost?
Discover the latest flight deals from MDW to CLO by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from MDW to CLO?
The cheapest flights from MDW to CLO are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from MDW to CLO?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from MDW to CLO. Sort your results by "Price (lowest to highest)" to snap up a great deal.
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.

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*Available to One Key members.