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Cheap Flights from Cali to Chicago

Compare Cali to Chicago flight deals

Find the cheapest month or even day of the year to fly to Chicago

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Flight deals from Cali to Chicago

Looking for a cheap last-minute deal or the best return flight from Cali to Chicago? Find the lowest prices on one-way and return tickets right here.
Chicago.$393 per passenger.Departing Wed, 4 Mar, returning Sat, 7 Mar.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Cali on Wed, 4 Mar, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Sat, 7 Mar, arriving in Cali.Price includes taxes and charges.From $393, select.
Chicago.$429 per passenger.Departing Tue, 28 Apr, returning Mon, 4 May.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Cali on Tue, 28 Apr, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Mon, 4 May, arriving in Cali.Price includes taxes and charges.From $429, select.
Chicago.$482 per passenger.Departing Fri, 20 Feb, returning Sat, 7 Mar.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Cali on Fri, 20 Feb, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Sat, 7 Mar, arriving in Cali.Price includes taxes and charges.From $482, select.
Chicago.$498 per passenger.Departing Fri, 20 Feb, returning Thu, 26 Feb.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Cali on Fri, 20 Feb, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Thu, 26 Feb, arriving in Cali.Price includes taxes and charges.From $498, select.
Chicago.$503 per passenger.Departing Sat, 25 Apr, returning Tue, 28 Apr.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Cali on Sat, 25 Apr, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Tue, 28 Apr, arriving in Cali.Price includes taxes and charges.From $503, select.
Chicago.$528 per passenger.Departing Fri, 1 May, returning Mon, 4 May.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Cali on Fri, 1 May, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Mon, 4 May, arriving in Cali.Price includes taxes and charges.From $528, select.
Chicago.$533 per passenger.Departing Wed, 25 Mar, returning Sat, 11 Apr.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Cali on Wed, 25 Mar, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Sat, 11 Apr, arriving in Cali.Price includes taxes and charges.From $533, select.
Chicago.$719 per passenger.Departing Fri, 25 Sep, returning Mon, 28 Sep.Return flight with Copa.Outbound indirect flight with Copa, departs from Cali on Fri, 25 Sep, arriving in Chicago O'Hare International.Inbound indirect flight with Copa, departs from Chicago O'Hare International on Mon, 28 Sep, arriving in Cali.Price includes taxes and charges.From $719, select.

Find the cheapest month to fly from Cali to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Cali to Chicago flights are currently cheapest in March.
Feb
from $498
Mar
from $393
Apr
from $503
May
from $528
Jun
from $818
Jul
from $920
Aug
from $719
Sep
from $719
Oct
from $950
Nov
from $822
Dec
from $1,305
Jan
Find prices

Alternative Cali to Chicago routes

Looking for the cheapest, fastest or easiest route from Cali to Chicago? You could fly into the following airports instead.

Chicago Midway

14km from central Chicago
Closest
from $1,863
Search flights

Chicago O'Hare International

25km from central Chicago
Cheapest
from $393
Search flights

Chicago Dupage County

51km from central Chicago
Search flights

Chicago Rockford

126km from central Chicago
Search flights

Cali to Chicago: Flight information

The things to know before you go.
Cheapest flight found$393
Cheapest month to flyMarch

Check out these Chicago hotels

Ready to plan your stay? Other travellers rate these Chicago hotels for cleanliness, service and location.
The Robey, Chicago, a Member of Design Hotels
5.38 km from city centre
$554
Per night
Chicago Parthenon Hostel
1.46 km from city centre
$218
Per night
The Neighborhood Hotel Little Italy
2.91 km from city centre
$390
Per night
The Robey, Chicago, a Member of Design Hotels
5.38 km from city centre
$554
Per night
Chicago Parthenon Hostel
1.46 km from city centre
$218
Per night
The Neighborhood Hotel Little Italy
2.91 km from city centre
$390
Per night
Explore top-rated hotels

Finding cheap flights from Cali to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from Cali to Chicago is $393. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
Currently, there are no airlines that fly direct from Cali to Chicago. But we found flights with one or more stops from $393.
As of February 2026, there are no flights flying from Cali to Chicago.
The cheapest month to fly from Cali to Chicago is usually March.
If you're flying from Cali Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from $393.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Cali Airport to Chicago on Wednesday, 4 March 2026.
No airlines currently offer direct flights between Cali Airport and Chicago. Most routes have one or more stops.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In February, the average temperature is usually around -2°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, Spirit Airlines offers the cheapest flight tickets to Chicago.

Travelling from Alfonso B. Aragon Airport (CLO) to Chicago: what you need to know

  • Chicago and Cali (where Alfonso B. Aragon Airport is located) share the UTC-5 timezone. That means you won't have to change your watch on arrival.

  • Leave enough time to get on your CLO to Chicago flight. A good rule of thumb is to arrive two hours before international departures and an hour ahead for domestic flights.

  • Delays at check-in and security are likely if you're flying during high season, so give yourself a bit more breathing room. A good rule of thumb for peak times? Get there up to four hours ahead for international flights and at least two hours for domestic departures.

  • Stopovers are the perfect opportunity to break up your journey and perhaps even explore a different city. When browsing for flight tickets from CLO to Chicago, deselect the 'Direct flights only' box to see where you can stop along the way. Here are some options to consider:

    • Miami International Airport (MIA)

    • Fort Lauderdale-Hollywood International Airport (FLL)

    • Tocumen International Airport (PTY)

  • To get to CLO from central Cali, it'll take about 35 minutes if you're going by car. It's roughly 19 kilometres from the airport to the city centre.

  • Have an early flight from Alfonso B. Aragon Airport to Chicago? Stay at a hotel close to CLO, like Hotel Royal Elim Internacional. Hotel Sin Escala will also put you moments from your departure gate.

  • 66.35% of flights that take off from Alfonso B. Aragon Airport reach their destination on time.

How to find the cheapest flights from Alfonso B. Aragon Airport (CLO) to Chicago

  • $236 is currently the best price for a one-way Alfonso B. Aragon Airport to Chicago flight. Return flight tickets start at $393. These fares may change depending on availability.

  • Booking early is often the key to scoring a cheap flight from CLO to Chicago. Prices tend to rise as demand increases, so the closer you get to departure, the more you'll likely spend on your ticket.

  • If you have flexibility with your travel plans, try using the 'Whole month' search tool. It'll give you the cheapest price across each month when looking for your Alfonso B. Aragon Airport to Chicago ticket.

  • Snapping up a cheap flight from CLO to Chicago couldn't be easier with Price Alerts. Simply set up one of these automatic notifications and we'll get in touch as soon as a deal gets even better.

  • Snag an affordable flight from Alfonso B. Aragon Airport to Chicago with the help of our filters. Choose your preferred departure time, duration and airlines, then sort the results by 'Cheapest' to see the best deals.

Airports in Chicago

O'Hare International Airport (ORD)

  • O'Hare International Airport (ORD) is around 40 kilometres from central Chicago. If you're opting for a ride-share or a cab, the drive will take roughly 35 minutes.

  • Travelling by public transport will take you around 55 minutes.

  • If you're arriving on a late flight from Alfonso B. Aragon Airport to Chicago, nothing beats the convenience of staying near the terminal. Pick up your bags from the carousel and then be showered and resting soon after at one of these accommodation options near ORD:

  • Fast-track your adventure by picking up an O'Hare International Airport rental car. Grab your wheels from Routes Car Rentals, Dollar or Budget to explore Chicago and beyond.

  • Secure the lowest price by reserving your vehicle from O'Hare International Airport around four weeks ahead of your flight from CLO to Chicago.

  • You'll find ORD at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Once your flight from Alfonso B. Aragon Airport to Chicago has hit the tarmac, you can make your way to the city centre in around 20 minutes by car. Central Chicago is roughly 19 kilometres from Chicago Midway International Airport (MDW).

  • If you travel by public transport, the ride to the centre will take you 45 minutes or so.

  • After stepping off your CLO to Chicago flight, rest your head at a hotel near MDW. These are some great options that'll help you get into relaxation mode:

  • No time to waste? The fastest way to get to where you're going is with a Chicago Midway International Airport rental car. Pick up your wheels from Dollar, Hertz or Budget and be off and running.

  • Avoid last-minute price surges. Reserving your ride four weeks before your arrival at MDW will help you stay within budget.

  • Chicago Midway International Airport can be found at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Chicago Rockford International Airport (RFD) is around 137 kilometres from the centre of Chicago. It'll take you about 1 hour 25 minutes to reach the city centre in a ride-share or cab once you've hopped off your flight from Alfonso B. Aragon Airport to Chicago.

  • If you're travelling on public transport, the journey will take you about 4 hours 15 minutes.

  • Check in to a hotel close to RFD and go from the runway to resting in a snap. Whether you're arriving on a late CLO to Chicago flight or just want to keep your travel plans simple, these stays are all about convenience:

  • Start your trip without stressing over how to get to where you're going with a Chicago Rockford International Airport rental car. Book your ideal wheels with trusted names here like Budget, Alamo and National.

  • Booking at least a few weeks in advance of your flight from Alfonso B. Aragon Airport to Chicago is always smart. Along with more affordable prices, you might find it easier to get the make and model you prefer at RFD.

  • Chicago Rockford International Airport's address is 2 Airport Cir.

Best time to go to Chicago

  • Travel to Chicago during peak season if you want a busy atmosphere, but remember that hotel prices may be higher. Alternatively, book your flights from Alfonso B. Aragon Airport to Chicago in the low season when prices are cheaper and it's not as busy.

  • Book an Alfonso B. Aragon Airport to Chicago flight ticket with a departure in July to explore the city during its warmest month. You can expect temperatures to range from 15ºC to 29ºC.

  • If you like cooler conditions, look for a cheap ticket from CLO to Chicago in January when temperatures average between -12ºC and 3ºC.

More about Chicago

Explore more of United States

  • Columbus is just one of the many places in United States waiting to be discovered after you've experienced Chicago. Around 451 kilometres away to the south-east, its top attractions include Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • Indianapolis is another standout destination in United States and is around 257 kilometres south-east of Chicago. No trip is complete without visiting The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

More travel options

Plan the rest of your trip from Cali to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.