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 round-trip flights from Orlando to Chicago?

The best price we found for a round-trip flight from Orlando to Chicago is $50. 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 51 minutes is the average flight time from Orlando to Chicago.

Which airlines fly direct from Orlando to Chicago?

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

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

There are 488 flights per week flying from Orlando to Chicago, as of May 2024.

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

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

What's the cheapest airport to fly to in Chicago?

If you're flying from Orlando, the cheapest airport near Chicago is Chicago O'Hare International – which is 15.8 miles away from the center of Chicago. We've found flights to this airport from $50 .

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 Wednesday, May 22, 2024 .

Can I get a direct flight from Orlando to Chicago?

Yes – the average flight time is 2 hours and 51 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 May, the average temperature is usually around 56°F. July is typically the warmest month in Chicago, when it usually averages around 80°F. You can expect the least rain in January. The coldest month is January, with temperatures averaging 18°F. The rainiest month is August.

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

The cheapest airline that flies to Chicago is Frontier Airlines.

Cheap Flights from Orlando (ORL) to Chicago (CHI) from $50

Compare Orlando 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 to Chicago

Looking for a cheap last-minute deal or the best round-trip flight from Orlando to Chicago? Find the lowest prices on one-way and round-trip tickets right here.

Chicago.$50 per passenger.Departing Wed, May 22, returning Wed, May 29.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from Orlando International on Wed, May 22, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departing from Chicago O'Hare International on Wed, May 29, arriving in Orlando International.Price includes taxes and charges.From $50, select.

Chicago.$53 per passenger.Departing Tue, Jul 2, returning Tue, Jul 30.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from Orlando International on Tue, Jul 2, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departing from Chicago O'Hare International on Tue, Jul 30, arriving in Orlando International.Price includes taxes and charges.From $53, select.

Chicago.$58 per passenger.Departing Tue, Jun 4, returning Wed, Jun 5.Round-trip flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departing from Orlando International on Tue, Jun 4, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departing from Chicago O'Hare International on Wed, Jun 5, arriving in Orlando International.Price includes taxes and charges.From $58, select.

Chicago.$61 per passenger.Departing Tue, Aug 6, returning Sun, Aug 11.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from Orlando International on Tue, Aug 6, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departing from Chicago O'Hare International on Sun, Aug 11, arriving in Orlando International.Price includes taxes and charges.From $61, select.

Chicago.$62 per passenger.Departing Tue, May 28, returning Tue, Jun 4.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from Orlando International on Tue, May 28, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departing from Chicago O'Hare International on Tue, Jun 4, arriving in Orlando International.Price includes taxes and charges.From $62, select.

Chicago.$62 per passenger.Departing Wed, Jul 31, returning Mon, Aug 5.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from Orlando International on Wed, Jul 31, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departing from Chicago Midway on Mon, Aug 5, arriving in Orlando International.Price includes taxes and charges.From $62, select.

Chicago.$63 per passenger.Departing Tue, Jun 4, returning Wed, Jun 5.Round-trip flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departing from Orlando International on Tue, Jun 4, arriving in Chicago O'Hare International.Inbound direct flight with Spirit Airlines departing from Chicago O'Hare International on Wed, Jun 5, arriving in Orlando International.Price includes taxes and charges.From $63, select.

Chicago.$81 per passenger.Departing Tue, Jun 25, returning Tue, Jul 2.Round-trip flight with Spirit Airlines and Frontier Airlines.Outbound direct flight with Spirit Airlines departing from Orlando International on Tue, Jun 25, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departing from Chicago O'Hare International on Tue, Jul 2, arriving in Orlando International.Price includes taxes and charges.From $81, select.

Stay one step ahead. Find the best value travel with the latest deals, tips and news.

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.

May

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Apr

Direct flights from Orlando to Chicago

Southwest Airlines

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	$50
Cheapest month to fly	May
Average flight time	2 hrs, 51 mins
Most popular airline	Southwest Airlines
Average flights per week	488

Finding cheap flights from Orlando 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 round-trip flight from Orlando to Chicago is $50. 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.
: 2 hours and 51 minutes is the average flight time from Orlando to Chicago.
: Southwest Airlines, American Airlines and Alaska Airlines fly direct from Orlando to Chicago.
: There are 488 flights per week flying from Orlando to Chicago, as of May 2024.
: The cheapest month to fly from Orlando to Chicago is usually May.
: If you're flying from Orlando, the cheapest airport near Chicago is Chicago O'Hare International – which is 15.8 miles away from the center of Chicago. We've found flights to this airport from $50.
: After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Orlando to Chicago on Wednesday, May 22, 2024.
: Yes – the average flight time is 2 hours and 51 minutes.
: 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 May, the average temperature is usually around 56°F. July is typically the warmest month in Chicago, when it usually averages around 80°F. You can expect the least rain in January. The coldest month is January, with temperatures averaging 18°F. The rainiest month is August.
: The cheapest airline that flies to Chicago is Frontier Airlines.

Orlando To Chicago

If you're traveling from Orlando to Chicago, there are up to 165 flights per week from which to choose on this route. Catch direct flights from Orlando International Airport to either Chicago O'Hare or Midway Airports.

Getting Around Orlando International Airport

Orlando Airport consists of a main terminal that is divided into two separate main terminals, A and B. Terminal A connects to Airside 1 and Airside 2. Terminal B connects to Airsides 3 and 4.

You can stay overnight at a large hotel that is situated right inside the airport's main terminal, before security access, and avoid the chances of missing an early morning flight. This airport also has a walk-in medical service facility should you experience any health problems prior to your flight.

Southwest Airlines runs frequent non-stop flights from Orlando to Chicago. A direct flight to Chicago takes close to three hours. Depart your flight from Orlando to Chicago on Southwest at Airside 2 at Terminal A, which also serves Virgin America and AirTran. United and American Airlines also have frequent non-stop flights to Chicago, departing from Airside 3 at Terminal B and Airside 1 at Terminal A, respectively.

Chicago Airport Tips

Whether you take a flight from Orlando to Chicago landing at O'Hare or Midway Airport, you will find yourself within less than 20 miles of the Loop, Chicago's downtown district. Once you have claimed any bags checked, you can opt to rent a car at the airport and drive on to your hotel or other destination. Of course, you can also take public transportation or a taxi into downtown Chicago from either airport. If you arrive at O'Hare Airport and are in a rush to take a cab, there is a taxi stand at Terminal 2 that is often overlooked. Beat the crowds and head there instead of waiting in what can often be very long lines. You can also save time and money by taking the 24-hour CTA Blue Line to Clark and Lake for about $5.00, then grab a taxi from there to your location at a less expensive price.

When traveling on a domestic flight to Chicago, such as flights from Orlando to Chicago, you may want to use Midway Airport as opposed to the much busier O'Hare, which often has delays, especially in bad weather. Travel early in the day to avoid crowds and congestion.

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