Cheap Flights from Orlando (MCO) to Chicago (CHIA)

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 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 $233. Find the lowest prices on one-way and return tickets right here.

Chicago.$147 per passenger.Departing Thu, 21 May, returning Sat, 30 May.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Orlando International on Thu, 21 May, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Sat, 30 May, arriving in Orlando International.Price includes taxes and charges.From $147, select.

Chicago.$170 per passenger.Departing Fri, 28 Aug, returning Wed, 2 Sep.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Orlando International on Fri, 28 Aug, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Wed, 2 Sep, arriving in Orlando International.Price includes taxes and charges.From $170, select.

Chicago.$183 per passenger.Departing Wed, 2 Sep, returning Sat, 5 Sep.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Orlando International on Wed, 2 Sep, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Sat, 5 Sep, arriving in Orlando International.Price includes taxes and charges.From $183, select.

Chicago.$184 per passenger.Departing Wed, 27 May, returning Wed, 10 Jun.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Orlando International on Wed, 27 May, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Wed, 10 Jun, arriving in Orlando International.Price includes taxes and charges.From $184, select.

Chicago.$191 per passenger.Departing Sat, 8 Aug, returning Tue, 25 Aug.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Orlando International on Sat, 8 Aug, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Tue, 25 Aug, arriving in Orlando International.Price includes taxes and charges.From $191, select.

Chicago.$200 per passenger.Departing Sat, 30 May, returning Mon, 1 Jun.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Orlando International on Sat, 30 May, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Mon, 1 Jun, arriving in Orlando International.Price includes taxes and charges.From $200, select.

Chicago.$204 per passenger.Departing Fri, 28 Aug, returning Mon, 31 Aug.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Orlando International on Fri, 28 Aug, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Mon, 31 Aug, arriving in Orlando International.Price includes taxes and charges.From $204, select.

Chicago.$207 per passenger.Departing Fri, 3 Jul, returning Tue, 7 Jul.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Orlando International on Fri, 3 Jul, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Tue, 7 Jul, arriving in Orlando International.Price includes taxes and charges.From $207, select.

Chicago.$213 per passenger.Departing Wed, 27 May, returning Tue, 7 Jul.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Orlando International on Wed, 27 May, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Tue, 7 Jul, arriving in Orlando International.Price includes taxes and charges.From $213, select.

Chicago.$233 per passenger.Departing Tue, 2 Jun, returning Tue, 9 Jun.Return flight with Spirit Airlines and Frontier Airlines.Outbound indirect flight with Spirit Airlines, departs from Orlando International on Tue, 2 Jun, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Tue, 9 Jun, arriving in Orlando International.Price includes taxes and charges.From $233, select.

Chicago.$234 per passenger.Departing Sat, 27 Jun, returning Sat, 4 Jul.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Orlando International on Sat, 27 Jun, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Sat, 4 Jul, arriving in Orlando International.Price includes taxes and charges.From $234, select.

Chicago.$234 per passenger.Departing Tue, 2 Jun, returning Tue, 2 Jun.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Orlando International on Tue, 2 Jun, arriving in Chicago O'Hare International.Inbound direct flight with Southwest Airlines departs from Chicago O'Hare International on Tue, 2 Jun, arriving in Orlando International.Price includes taxes and charges.From $234, select.

Chicago.$240 per passenger.Departing Fri, 3 Jul, returning Mon, 6 Jul.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Orlando International on Fri, 3 Jul, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Mon, 6 Jul, arriving in Orlando International.Price includes taxes and charges.From $240, select.

Chicago.$261 per passenger.Departing Wed, 24 Jun, returning Wed, 1 Jul.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Orlando International on Wed, 24 Jun, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Wed, 1 Jul, arriving in Orlando International.Price includes taxes and charges.From $261, select.

Chicago.$268 per passenger.Departing Wed, 29 Jul, returning Sun, 2 Aug.Return flight with Spirit Airlines and Allegiant Air.Outbound indirect flight with Spirit Airlines, departs from Orlando International on Wed, 29 Jul, arriving in Chicago Rockford.Inbound indirect flight with Allegiant Air, departs from Chicago Rockford on Sun, 2 Aug, arriving in Orlando International.Price includes taxes and charges.From $268, select.

Chicago.$275 per passenger.Departing Sat, 31 Oct, returning Mon, 2 Nov.Return flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departs from Orlando International on Sat, 31 Oct, arriving in Chicago O'Hare International.Inbound direct flight with Spirit Airlines departs from Chicago O'Hare International on Mon, 2 Nov, arriving in Orlando International.Price includes taxes and charges.From $275, 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 May.

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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	$147
Cheapest month to fly	May
Average flight time	3 hrs, 2 mins
Most popular airline	Southwest Airlines
Average flights per week	1,158

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 $147. 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 1 minute is the average flight time from Orlando International to Chicago.

Which airlines fly direct from Orlando International to Chicago?

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

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

As of May 2026, there are 1,737 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 May.

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 $147.

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, 21 May 2026.

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

Yes – the average flight time is 3 hours and 1 minute.

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 May, the average temperature is usually around 13°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

The average duration of a direct flight from Orlando International Airport to Chicago is 2 hours 45 minutes.
The timezone in Chicago is UTC-6. The city is one hour behind Orlando, where Orlando International Airport is located.
Orlando International Airport (MCO) to Chicago O'Hare International Airport (ORD) is the most traveled route, with 111 weekly departures to choose from. If you prefer a later start to the day, the last flight from MCO to ORD is with Frontier Airlines at 22:17. Opt for the first departure with Frontier Airlines at 05:40 if you want to fly out earlier.
For a smooth journey, turn up at the airport two hours ahead of international flights and an hour before domestic departures. That way, you can comfortably board your MCO to Chicago flight.
Be prepared for longer queues during popular months such as March. Arriving up to four hours ahead of an international flight and two hours for a domestic departure is a smart move.
Start your trip at MCO and fly nonstop to Chicago O'Hare International Airport (ORD). That's where you can expect to land when searching for Orlando International Airport to Chicago tickets.
Numerous airlines offer direct flights from Orlando International Airport to Chicago. The most popular include:
The journey from central Orlando to MCO takes about 1 hour on public transport. If you drive, ride-share or grab a taxi, you'll cover the 14 kilometres in 25 minutes or so, depending on traffic.
Want a relaxed start to your trip? Stay near MCO. Whether you're boarding an early flight from Orlando International Airport to Chicago or don't want departure day to feel hectic, these hotels are a convenient choice:
When it comes to the on-time performance of Orlando International Airport, 77% of flights meet their scheduled arrival time.
You'll find MCO at One Airport Boulevard.

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

$46 is currently the best price for a one-way Orlando International Airport to Chicago flight. A return plane ticket starts at $147. These fares can change based on demand and availability.
To pick up cheap flights from MCO to Chicago, reserve your trip 11 months before your departure.
The best month for landing cheap Orlando International Airport to Chicago tickets is April. Use the 'Whole month' tool to compare prices, then choose the dates that offer the biggest savings.
There's no need to check every day to see if fares have dropped when you create a Price Alert. We'll notify you when there's an extra saving on cheap flights from MCO to Chicago.
Tailor your flights with filters. Select your arrival and departure times, total journey duration and airlines. You can also sort results by 'Cheapest,' 'Fastest' or 'Best' flights from Orlando International Airport to Chicago.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

Chicago O'Hare International Airport (ORD) is around 27 kilometres from central Chicago. If you're opting for a ride-share or a taxi, the drive will take roughly 30 minutes.
If you're taking public transport, expect a journey time of about 45 minutes.
Consider booking a hotel near ORD if you have a late flight from Orlando International Airport to Chicago. Check in to one of these options and avoid the hassle of a long transfer:
Reserving your vehicle from Chicago O'Hare International Airport about four weeks before your flight from MCO to Chicago can help you lock in the best possible rate.
You'll find ORD at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

After your flight from Orlando International Airport to Chicago has landed, you can reach the city centre in around 25 minutes by car. Central Chicago is roughly 16 kilometres from Chicago Midway International Airport (MDW).
The journey will take about 30 minutes on public transport.
Hang the 'Do not disturb' sign on your door and rest at a hotel near MDW. Here are a few options where you can settle in after your MCO to Chicago flight:
Avoid paying more than you need to. Booking your ride four weeks before your arrival at MDW can land you a better rate.
The address for Chicago Midway International Airport is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

Step off your flight from Orlando International Airport to Chicago and make your way to your hotel or jump right into exploring. Central Chicago is around 145 kilometres from Chicago Rockford International Airport (RFD) and usually takes 1 hour 40 minutes to drive there.
The journey will take you around 2 hours when travelling by public transport.
Find a hotel near RFD and get from baggage claim to your bed in a snap. Whether you have a late MCO to Chicago flight or just want a stress-free arrival, these accommodation options bring comfort closer to you:
If you're hoping for a specific make or model, booking early gives you a better shot at finding what you want. Reserve your ride from RFD a couple of weeks ahead of your flight from Orlando International Airport to Chicago.
The street address for Chicago Rockford International Airport is 2 Airport Cir.

Best time to go to Chicago

January is the quietest month for flights from Orlando International Airport to Chicago, while July is the busiest. Pick the best time to go to Chicago based on whether you want a lively atmosphere or a more laid-back vibe.
Lock in a Orlando International Airport to Chicago plane ticket with a departure in July if you're eager to visit the city during its warmest month. You can expect temperatures to range from 16ºC (61ºF) to 28ºC (82ºF).
Look for cheap tickets from MCO to Chicago in January if you want to travel in cooler conditions. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF) on average.

More about Chicago

After booking your flight from Orlando International Airport to Chicago, choose a hotel that puts you where you want to be. Make one of these accommodation options your base for exploring Chicago:
Art Institute of Chicago and Millennium Park are just a couple of the top-rated attractions to put on your Chicago travel itinerary. Continue your sightseeing adventures at Willis Tower.

Explore more of the United States

Chicago has plenty going for it, but there are so many other corners of the United States you'll want to see. Around 451 kilometres southeast of Chicago, a trip to Columbus will keep you busy. Start with leading attractions like Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.
Indianapolis is another essential stop in the United States and is around 257 kilometres southeast of Chicago. No trip is complete without seeing Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.