C$71 Cheap Flights from Orlando International to Chicago

Compare Orlando International 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 Orlando International Airport to Chicago

Looking for a cheap last-minute deal or the best return flight from Orlando International Airport to Chicago? If you want to travel next month, return fares start from C$71. Find the lowest prices on one-way and return tickets right here.

Chicago.C$29 per passenger.Departing Thu., Apr. 23.One-way flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Orlando International on Thu., Apr. 23, arriving in Chicago Midway.Price includes taxes and charges.From C$29, select.

Chicago.C$31 per passenger.Departing Sat., May 2.One-way flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Orlando International on Sat., May 2, arriving in Chicago Midway.Price includes taxes and charges.From C$31, select.

Chicago.C$78 per passenger.Departing Tue., Mar. 24.One-way flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departs from Orlando International on Tue., Mar. 24, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$78, select.

Chicago.C$101 per passenger.Departing Fri., Aug. 28.One-way flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Orlando International on Fri., Aug. 28, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$101, select.

Chicago.C$105 per passenger.Departing Tue., Sep. 1.One-way flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Orlando International on Tue., Sep. 1, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$105, select.

Chicago.C$113 per passenger.Departing Tue., Jun. 2.One-way flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Orlando International on Tue., Jun. 2, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$113, select.

Chicago.C$140 per passenger.Departing Wed., Jul. 15.One-way flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Orlando International on Wed., Jul. 15, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$140, select.

Chicago.C$213 per passenger.Departing Sun., Nov. 15.One-way flight with Avelo Airlines.Outbound indirect flight with Avelo Airlines, departs from Orlando International on Sun., Nov. 15, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$213, select.

Chicago.C$281 per passenger.Departing Fri., Oct. 9.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Orlando International on Fri., Oct. 9, arriving in Chicago Midway.Price includes taxes and charges.From C$281, select.

Chicago.C$281 per passenger.Departing Sat., Nov. 7.One-way flight with United.Outbound direct flight with United departs from Orlando International on Sat., Nov. 7, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$281, select.

Chicago.C$297 per passenger.Departing Sun., Jan. 17.One-way flight with United.Outbound direct flight with United departs from Orlando International on Sun., Jan. 17, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$297, select.

Chicago.C$308 per passenger.Departing Tue., Dec. 15.One-way flight with Delta.Outbound indirect flight with Delta, departs from Orlando International on Tue., Dec. 15, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$308, select.

Chicago.C$328 per passenger.Departing Fri., Dec. 4.One-way flight with United.Outbound direct flight with United departs from Orlando International on Fri., Dec. 4, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$328, select.

Find the cheapest month to fly from Orlando International to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Orlando International to Chicago flights are currently cheapest in April.

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Direct flights from Orlando International to Chicago

Alternative Orlando International to Chicago routes

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

Orlando to Chicago: Flight information

The things to know before you go.

Cheapest flight found	C$29
Cheapest month to fly	April
Average flight time	3 hrs, 3 mins
Most popular airline	Southwest Airlines
Average flights per week	1,268

Finding cheap flights from Orlando International to Chicago: Frequently asked questions

How many airports are there in Chicago?

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.

How much are return flights from Orlando International to Chicago?

The best price we found for a return flight from Orlando International to Chicago is C$71. 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.

How long does it take to fly from Orlando International to Chicago?

3 hours and 3 minutes is the average flight time from Orlando International to Chicago.

Which airlines fly direct from Orlando International to Chicago?

Southwest Airlines, American Airlines and United fly direct from Orlando International to Chicago.

How many flights are there a week from Orlando International to Chicago?

As of March 2026, there are 634 flights per week flying from Orlando International to Chicago.

When is the cheapest time to fly from Orlando International to Chicago?

The cheapest month to fly from Orlando International to Chicago is usually April.

Which is the cheapest airport to fly into in Chicago?

If you're flying from Orlando International 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 C$71.

Which upcoming date is cheapest to fly from Orlando International Airport to Chicago on?

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Orlando International Airport to Chicago on Thursday, April 23, 2026.

Can I get a direct flight from Orlando International Airport to Chicago?

Yes – the average flight time is 3 hours and 3 minutes.

How can I get the best flight deal from Orlando International Airport to Chicago?

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.

When is the best time to book flights to Chicago?

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.

What’s the weather like in Chicago?

In March, the average temperature is usually around 3°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.

Which is the cheapest airline to fly from Orlando International Airport to Chicago with?

Currently, Frontier Airlines offers the cheapest flight tickets to Chicago.

Flying from Orlando International Airport (MCO) to Chicago: what you need to know

Jump on a direct flight from Orlando International Airport to Chicago and you'll be in the air for around 2 hours 49 minutes.
Chicago is 1 hour behind Orlando, where Orlando International Airport is located. Chicago operates on the UTC-5 timezone.
Orlando International Airport (MCO) to O'Hare International Airport (ORD) is the most popular route, with 220 departures a week to choose from. If you have things to do before leaving, the last flight from MCO to ORD is with Frontier Airlines at 23:07. Go for the first departure with Frontier Airlines at 05:06 if you want to get going early.
Give yourself plenty of time to make your flight from MCO to Chicago. As a general rule, arrive two hours before international departures and an hour ahead for domestic flights.
Peak months like July or vacation periods such as spring break and Christmas will mean longer queues at check-in and security. Travelling then? Play it safe and head to the terminal even earlier. Arriving two hours before domestic flights and up four hours ahead of an international flight is a smart move.
Nonstop flights from Orlando International Airport (MCO) to Chicago are available for booking. O'Hare International Airport (ORD) is where you'll be landing.
Direct flights from Orlando International Airport to Chicago are offered by a range of airlines. Book your seat with any of these:
After booking your flight tickets from Orlando International Airport to Chicago, get your travel documents in order. A visa or passport isn't necessary since you're flying within United States. As long as you have some other valid proof of identity, such as a driver's licence or an ID card, you're all set.
To reach MCO from central Orlando, it'll take around 22 minutes if you're travelling by car. Of course, this depends on traffic conditions. It's approximately 32 kilometres from the airport to the city centre.
Want a hassle-free start to your travels? Stay near MCO. Whether you're boarding an early flight from Orlando International Airport to Chicago or just don't want to be rushed, these hotels are ideal:

How to find the cheapest flights from Orlando International Airport (MCO) to Chicago

C$29 is the lowest price for a one-way ticket from Orlando International Airport to Chicago. A return flight starts at C$71. These prices may change depending on demand.
Lock in cheap tickets from MCO to Chicago by booking 8 months ahead. Based on our research, that's the sweet spot for landing a bargain.
Organize your trip for April. That's the cheapest month for tickets from Orlando International Airport to Chicago. If your travel dates are flexible, use the 'Whole month' tool to find the lowest price across each month.
Getting a cheap ticket from MCO to Chicago is a breeze with Price Alerts. All you need to do is create one of these automatic alerts and we'll let you know when the price has fallen.
Make the most of the filters to find your ideal journey. To see the 'Best,' 'Fastest' or 'Cheapest' flights from Orlando International Airport to Chicago, use the 'Sort by' function. You can also filter results by airline, departure and arrival times, and journey duration.

Airports in Chicago

O'Hare International Airport (ORD)

O'Hare International Airport (ORD) is around 40 kilometres from central Chicago. With a car rental or if you're catching a cab, the drive is about 35 minutes.
When travelling on public transport, expect a journey of about 54 minutes.
The last thing you want is a lengthy journey to your hotel if you're arriving on a late flight from Orlando International Airport to Chicago. Book one of these accommodation options near ORD instead:

Chicago Midway International Airport (MDW)

The centre of Chicago is approximately 19 kilometres from Chicago Midway International Airport (MDW). Once your flight from Orlando International Airport to Chicago has touched down and you've made your way through the terminal, the drive should take about 21 minutes.
You can also opt for public transport, which will take around 46 minutes.
After your flight from MCO to Chicago, tuck yourself in at a hotel close to MDW. These are some comfortable accommodation options that'll help you switch to relaxation mode:

Best time to go to Chicago

It's time to pick your dates for your flight from Orlando International Airport to Chicago. August is the most popular month for a trip to Chicago. If you prefer a quieter vibe, go in February.
Book your flight from Orlando International Airport to Chicago for July to experience the city during its warmest month. You can expect temperatures to range from 15ºC to 29ºC.
If you like travelling in cooler conditions, lock in a cheap flight from MCO to Chicago in January when temperatures average between -12ºC and 3ºC.

More about Chicago

When it comes to looking for somewhere to lay your head, you'll find the best stays in Chicago right here. Browse these hotels once you've booked your flight from Orlando International Airport to Chicago:
All great journeys should include a little sightseeing. Millennium Park, Art Institute of Chicago and LandShark Beer Garden at Navy Pier are must-visits when exploring Chicago.

Complete your Chicago trip with a car rental

Pick one of our car rentals in Chicago and see the sights on your own terms. Easily compare rates in one place to find the perfect set of wheels once you've locked in your hotel and cheap flights from Orlando International Airport to Chicago.