C$36 Cheap Flights from Orlando (ORLB) to Chicago (CHIA)

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Flight deals from Orlando to Chicago

Looking for a cheap last-minute deal or the best return flight from Orlando to Chicago? If you want to travel next month, return fares start from C$94. Find the lowest prices on one-way and return tickets right here.

Chicago.C$36 per passenger.Departing Tue., May 19.One-way flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Orlando International on Tue., May 19, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$36, select.

Chicago.C$45 per passenger.Departing Thu., Apr. 30.One-way flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Orlando International on Thu., Apr. 30, arriving in Chicago Midway.Price includes taxes and charges.From C$45, select.

Chicago.C$65 per passenger.Departing Wed., Jul. 15.One-way flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Orlando Sanford on Wed., Jul. 15, arriving in Chicago Rockford.Price includes taxes and charges.From C$65, select.

Chicago.C$76 per passenger.Departing Wed., Oct. 7.One-way flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Orlando Sanford on Wed., Oct. 7, arriving in Chicago Rockford.Price includes taxes and charges.From C$76, select.

Chicago.C$82 per passenger.Departing Tue., Jun. 16.One-way flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Orlando International on Tue., Jun. 16, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$82, select.

Chicago.C$93 per passenger.Departing Fri., Sep. 4.One-way flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Orlando Sanford on Fri., Sep. 4, arriving in Chicago Rockford.Price includes taxes and charges.From C$93, select.

Chicago.C$111 per passenger.Departing Mon., Aug. 17.One-way flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Orlando Sanford on Mon., Aug. 17, arriving in Chicago Rockford.Price includes taxes and charges.From C$111, select.

Chicago.C$163 per passenger.Departing Mon., Nov. 2.One-way flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Orlando Sanford on Mon., Nov. 2, arriving in Chicago Rockford.Price includes taxes and charges.From C$163, select.

Chicago.C$305 per passenger.Departing Sat., Dec. 19.One-way flight with United.Outbound direct flight with United departs from Orlando International on Sat., Dec. 19, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$305, select.

Chicago.C$319 per passenger.Departing Fri., Feb. 12.One-way flight with Delta.Outbound indirect flight with Delta, departs from Orlando International on Fri., Feb. 12, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$319, select.

Chicago.C$319 per passenger.Departing Fri., Jan. 1.One-way flight with Delta.Outbound indirect flight with Delta, departs from Orlando International on Fri., Jan. 1, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$319, select.

Chicago.C$362 per passenger.Departing Fri., Feb. 12.One-way flight with United.Outbound direct flight with United departs from Orlando International on Fri., Feb. 12, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$362, select.

Chicago.C$512 per passenger.Departing Fri., Jan. 1.One-way flight with United.Outbound direct flight with United departs from Orlando International on Fri., Jan. 1, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$512, select.

Find the cheapest month to fly from Orlando to Chicago

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

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Which airlines fly from Orlando to Chicago?

Alternative Orlando to Chicago routes

Looking for the cheapest, fastest or easiest route from Orlando 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$36
Cheapest month to fly	May
Average flight time	2 hrs, 54 mins
Most popular airline	American Airlines
Average flights per week	606

Finding cheap flights from Orlando 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 to Chicago?

The best price we found for a return flight from Orlando to Chicago is C$94. 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 to Chicago?

2 hours and 54 minutes is the average flight time from Orlando to Chicago.

Which airlines fly direct from Orlando to Chicago?

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

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

As of April 2026, there are 606 flights per week flying from Orlando to Chicago.

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

The cheapest month to fly from Orlando to Chicago is usually May.

Which is the cheapest airport to fly into in Chicago?

If you're flying from Orlando, 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$94.

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

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Orlando to Chicago on Saturday, May 2, 2026.

Can I get a direct flight from Orlando to Chicago?

Yes – the average flight time is 2 hours and 54 minutes.

How can I get the best flight deal from Orlando 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 April, the average temperature is usually around 8°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 to Chicago with?

The cheapest airline that flies to Chicago is Frontier Airlines .

Flying from Orlando to Chicago: what you need to know

Begin your trip planning by checking out the departure points for your flight from Orlando to Chicago. Explore your options for leaving from Orlando International Airport (MCO) or Orlando Sanford International Airport (SFB), two of the city's main airports.
O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW) are the key hubs in Chicago.
The average time for a direct flight from Orlando to Chicago is 2 hours 53 minutes. Chicago's timezone is UTC-5, making Chicago 1 hour behind Orlando.
Orlando International Airport (MCO) to O'Hare International Airport (ORD) is the most traveled route that connects these two cities. There are 220 departures a week to choose from. If you have things to finalize before heading off, the last flight from Orlando to Chicago is with Frontier Airlines at 23:07. Choose the first MCO to ORD departure with Frontier Airlines at 05:06 if you want to get going early.
To ensure you get on your flight from Orlando to Chicago, leave enough time to check in and find your gate. Turning up two hours before international departures and an hour before domestic flights is the standard rule.
Longer lines at check-in and security are more likely if you're heading away during high season, so give yourself a little extra breathing room. A good general rule for peak times? Get there up to four hours early for international flights and at least two hours for domestic departures.
You won't need a visa or passport to fly within United States. You will need a valid proof of identity though, such as a driver's licence or an ID card. Put them on your packing checklist once you've booked your cheap flights from Orlando to Chicago.

Flying from Orlando

Orlando International Airport (MCO)

Direct flights from Orlando to Chicago depart from Orlando International Airport (MCO). MCO offers nonstop services to two Chicago terminals, O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW).
Choose from a variety of airlines that offer direct flights from Orlando to Chicago departing from MCO. Get on board with any of these:
We make it a piece of cake to plan a flight from Orlando to Chicago with a stopover. To see the options leaving from Orlando International Airport, deselect 'Direct flights only.' Next, select a flight that has a stop long enough to see the sights of the city of your choice. Top stopovers include:
- Nashville International Airport (BNA)
- Los Angeles International Airport (LAX)
- Harry Reid Airport (formerly McCarran Airport) Airport (LAS)
To get to MCO from central Orlando, it'll take about 22 minutes by car. Of course, this depends on traffic. It's approximately 32 kilometres from the airport to the city centre.
Catching an early flight from Orlando to Chicago? Avoid rushing to the airport (and enjoy a little extra shut-eye) by picking one of these hotels near Orlando International Airport:

Arriving in Chicago

O'Hare International Airport (ORD)

O'Hare International Airport (ORD) to central Chicago is roughly 40 kilometres. It takes about 35 minutes to reach the centre driving.
It'll take around 54 minutes when travelling by public transport.
The last thing you need is a lengthy journey to your hotel if you're arriving on a late flight from Orlando to Chicago. Check in to one of these accommodation options near ORD instead:

Chicago Midway International Airport (MDW)

Central Chicago is approximately 19 kilometres from Chicago Midway International Airport (MDW). As soon as your flight from Orlando to Chicago has hit the runway and you've made your way out of the airport, expect a drive of about 21 minutes.
You can also opt for public transport, which will take roughly 46 minutes.
There are some cozy hotels where you can rest ahead of your adventure near MDW. Kick back after your flight from Orlando to Chicago at any of these perfectly located options:

How to find the cheapest flights from Orlando to Chicago

C$36 is the best price for a one-way ticket from Orlando to Chicago. Return flights start from C$94. These prices can change based on demand and availability.
Get cheap flights from Orlando to Chicago by booking at least 8 months ahead. Based on our research, that's the sweet spot for finding a bargain.
April is the cheapest month for tickets from Orlando to Chicago. If you need to travel during a different time of year, the 'Whole month' tool will show you the lowest prices across every month.
Log into your online account or use the app to create a Price Alert. You'll get notified straight away if there's a cheaper deal on this route. It's easy to do, and it'll save you time checking for cheap flights from Orlando to Chicago every day.
Tailor your travel plans using filters. Select your ideal arrival and departure times, airlines and total journey duration. You can also sort the results by 'Best,' 'Fastest' or 'Cheapest' flights from Orlando to Chicago.

Best time to go to Chicago

August is the most popular month for flights from Orlando to Chicago. To avoid the crowds, head to Chicago in February.
Lock in your flight from Orlando to Chicago for July if you want to visit the city during its warmest month. You can expect temperatures in Chicago to range from 15ºC to 29ºC.
Search for cheap flights from Orlando to Chicago in January if you like cooler conditions. Temperatures are at their lowest around then, ranging between -12ºC and 3ºC on average.

More about Chicago

When it comes to searching for somewhere to lay your head, you'll find the top stays in Chicago right here. Browse these hotels as soon as you've locked in your flight from Orlando to Chicago:
There are so many things to explore in this city it can be hard to figure out where to start. Millennium Park, Art Institute of Chicago and LandShark Beer Garden at Navy Pier are top attractions which should feature on any good Chicago itinerary.

Complete your Chicago trip with a car rental

We use the same magic that helped you find your cheap flight from Orlando to Chicago to track down amazing deals on car rentals. Search for your ride in seconds and compare your options in one place. Plus we give you all the info you need to drive in Chicago, from the most popular car type to the best time to book.