Cheap Flights from Orlando (ORLB) to Chicago (ORD)

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Compare Orlando to Chicago O'Hare International flight deals

Find the cheapest month or even day of the year to fly to Chicago O'Hare International

Book the best Chicago O'Hare International fare with no extra fees

Flight deals Cheapest month Find the best route Route info FAQs Tips and advice

Flight deals from Orlando to Chicago O'Hare International

Looking for a cheap last-minute deal or the best return flight from Orlando to Chicago O'Hare International Airport? If you want to travel next month, return fares start from $149. Find the lowest prices on one-way and return tickets right here.

Chicago.$148 per passenger.Departing Thu, 3 Dec, returning Tue, 8 Dec.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Orlando International on Thu, 3 Dec, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Tue, 8 Dec, arriving in Orlando International.Price includes taxes and charges.From $148, select.

Chicago.$148 per passenger.Departing Fri, 23 Oct, returning Tue, 27 Oct.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Orlando International on Fri, 23 Oct, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Tue, 27 Oct, arriving in Orlando International.Price includes taxes and charges.From $148, select.

Chicago.$189 per passenger.Departing Tue, 29 Sep, returning Mon, 5 Oct.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Orlando International on Tue, 29 Sep, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Mon, 5 Oct, arriving in Orlando International.Price includes taxes and charges.From $189, select.

Chicago.$205 per passenger.Departing Thu, 19 Nov, returning Thu, 26 Nov.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Orlando International on Thu, 19 Nov, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Thu, 26 Nov, arriving in Orlando International.Price includes taxes and charges.From $205, select.

Chicago.$225 per passenger.Departing Tue, 15 Sep, returning Tue, 29 Sep.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Orlando International on Tue, 15 Sep, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Tue, 29 Sep, arriving in Orlando International.Price includes taxes and charges.From $225, select.

Chicago.$233 per passenger.Departing Tue, 29 Sep, returning Sat, 3 Oct.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Orlando International on Tue, 29 Sep, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Sat, 3 Oct, arriving in Orlando International.Price includes taxes and charges.From $233, select.

Chicago.$256 per passenger.Departing Wed, 28 Oct, returning Sat, 7 Nov.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Orlando International on Wed, 28 Oct, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Sat, 7 Nov, arriving in Orlando International.Price includes taxes and charges.From $256, select.

Chicago.$279 per passenger.Departing Thu, 29 Oct, returning Tue, 1 Dec.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Orlando International on Thu, 29 Oct, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Tue, 1 Dec, arriving in Orlando International.Price includes taxes and charges.From $279, select.

Chicago.$281 per passenger.Departing Sat, 21 Nov, returning Tue, 8 Dec.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Orlando International on Sat, 21 Nov, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Tue, 8 Dec, arriving in Orlando International.Price includes taxes and charges.From $281, select.

Chicago.$308 per passenger.Departing Sat, 28 Nov, returning Wed, 2 Dec.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Orlando International on Sat, 28 Nov, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Wed, 2 Dec, arriving in Orlando International.Price includes taxes and charges.From $308, select.

Chicago.$332 per passenger.Departing Tue, 27 Oct, returning Tue, 3 Nov.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Orlando International on Tue, 27 Oct, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Tue, 3 Nov, arriving in Orlando International.Price includes taxes and charges.From $332, select.

Chicago.$335 per passenger.Departing Thu, 29 Oct, returning Tue, 1 Dec.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Orlando International on Thu, 29 Oct, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Tue, 1 Dec, arriving in Orlando International.Price includes taxes and charges.From $335, select.

Chicago.$354 per passenger.Departing Tue, 26 Jan, returning Tue, 26 Jan.Return flight with Delta.Outbound indirect flight with Delta, departs from Orlando International on Tue, 26 Jan, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Tue, 26 Jan, arriving in Orlando International.Price includes taxes and charges.From $354, select.

Chicago.$354 per passenger.Departing Tue, 2 Feb, returning Tue, 2 Feb.Return flight with Delta.Outbound indirect flight with Delta, departs from Orlando International on Tue, 2 Feb, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Tue, 2 Feb, arriving in Orlando International.Price includes taxes and charges.From $354, select.

Chicago.$355 per passenger.Departing Fri, 25 Dec, returning Fri, 1 Jan.Return flight with United.Outbound direct flight with United departs from Orlando International on Fri, 25 Dec, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Fri, 1 Jan, arriving in Orlando International.Price includes taxes and charges.From $355, select.

Chicago.$357 per passenger.Departing Tue, 27 Oct, returning Sat, 2 Jan.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Orlando International on Tue, 27 Oct, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Sat, 2 Jan, arriving in Orlando International.Price includes taxes and charges.From $357, select.

Find the cheapest month to fly from Orlando to Chicago O'Hare International

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

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Direct flights from Orlando to Chicago O'Hare International

Orlando to Chicago O'Hare International: Alternative routes

Compare routes from Orlando to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago O'Hare International.

Orlando to Chicago: Flight information

The things to know before you go.

Cheapest flight found	$149
Cheapest month to fly	October
Average flight time	3 hrs, 13 mins
Most popular airline	American Airlines
Average flights per week	585

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

How much are return flights from Orlando to Chicago O'Hare International?

The best price we found for a return flight from Orlando to Chicago O'Hare International is $149. 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 O'Hare International?

3 hours and 13 minutes is the average flight time from Orlando to Chicago O'Hare International.

Which airlines fly direct from Orlando to Chicago O'Hare International?

American Airlines, United and Emirates fly direct from Orlando to Chicago O'Hare International.

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

As of September 2026, there are 585 flights per week flying from Orlando to Chicago O'Hare International.

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

The cheapest month to fly from Orlando to Chicago O'Hare International is usually October.

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

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Orlando to Chicago O'Hare International Airport on Friday, 23 October 2026.

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

Yes – the average flight time is 3 hours and 13 minutes.

How can I find the best flight deal to Chicago O'Hare International?

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 O'Hare International 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.

Which is the cheapest airline to fly from Orlando to Chicago O'Hare International with?

The cheapest airline that flies to Chicago O'Hare International is Frontier Airlines .

Travelling from Orlando to Chicago O'Hare International Airport (ORD): What you need to know

Your journey comes together at Orlando's main airport, Orlando International Airport (MCO). Explore your options for catching a flight from Orlando to Chicago O'Hare International Airport (ORD) departing from this base.
The average time for a direct Orlando to Chicago O'Hare International Airport flight is 3 hours 5 minutes.
The timezone in Chicago is UTC-6, which is one hour behind Orlando. Chicago O'Hare International Airport is located in Chicago.
With 111 direct weekly flights between the two airports, Orlando International Airport (MCO) to Chicago O'Hare International Airport (ORD) is the busiest route. Frontier Airlines operates the earliest flight at 5:40am. If you prefer to get more out of your day before flying, the latest flight from MCO to ORD is with Frontier Airlines at 10:17pm.
For stress-free travel, arrive at the airport two hours ahead of international flights and an hour before domestic departures. This ensures you have enough time to board your flight from Orlando to ORD.
Flying during a peak time like March? Popular seasons (like Thanksgiving, Christmas and New Year) can add another hour at security. Play things extra safe and arrive up to four hours before an international flight and two hours before domestic departures.

Airports in Orlando

Orlando International Airport (MCO)

Get there in one go from Orlando International Airport (MCO). Direct flights from Orlando to Chicago O'Hare International Airport (ORD) are available from here.
A range of airlines at MCO offer direct flights from Orlando to Chicago O'Hare International Airport. The most popular include:
United is the airline most travellers choose for flights from MCO to ORD.
Among carriers on this route, United has the best record for on-time arrivals.
MCO is around 19 kilometres from central Orlando. If you're catching a taxi, ride-sharing or driving from the centre, it'll take 25 minutes or so to get there, depending on traffic conditions. If you're taking public transport, expect the journey time to be around 1 hour.
Planning to catch an early flight from Orlando to Chicago O'Hare International Airport? Avoid the hassle of rushing to the terminal (and enjoy a few extra z's) by staying at one of these hotels close to Orlando International Airport:
Of the flights that depart from Orlando International Airport, 77% arrive as scheduled at their destination.
You'll find MCO at One Airport Boulevard.

Orlando Sanford International Airport (SFB)

Using public transport, you can travel from central Orlando to SFB in about 1 hour. The terminal is roughly 40 kilometres away, and making the journey by car will take approximately 35 minutes.
Got an early start? Think about checking in to one of these accommodation options near Orlando Sanford International Airport the day before your Orlando to ORD flight:
69% of flights out of Orlando Sanford International Airport make it to their destination as expected.

About Chicago O'Hare International Airport (ORD)

If you're arriving on a late flight from Orlando to Chicago O'Hare International Airport, few things beat the convenience of staying near the terminal. Pick up your bags from the carousel and then be showered and sleeping not long after at one of these hotels near ORD:
Booking your vehicle around four weeks in advance of your Orlando to Chicago O'Hare International Airport flight can help you secure the lowest rate.
You'll find ORD at 10000 West O'Hare.

Getting from Chicago O'Hare International Airport (ORD) to central Chicago

Central Chicago is around 27 kilometres from Chicago O'Hare International Airport and takes about 30 minutes to reach by car. Explore your options for getting into the city, whether that's with a taxi, car hire or ride-share.
It takes around 45 minutes if you're travelling on public transport.

How to find the cheapest flights from Orlando to Chicago O'Hare International Airport (ORD)

The lowest price we've found for a one-way ticket from Orlando to Chicago O'Hare International Airport is $101. For a return flight on this route, the best price is $148. Depending on when you book and the availability, these fares may change.
To score cheap flights from Orlando to ORD, book your plane ticket 11 months ahead of your departure date.
April is when you're most likely to find a bargain on a Orlando to Chicago O'Hare International Airport ticket. If you want to travel at a different time of year, the 'Whole month' tool will give you the lowest prices for each month.
Locking in a cheap plane ticket from Orlando to ORD is a breeze with Price Alerts. Simply set up one of these automatic alerts and we'll notify you when there's a better deal.
Tailor your travel plans using filters. Choose your departure and arrival times, airlines and total journey duration. You can also sort the results by 'Cheapest,' 'Fastest' or 'Best' flights from Orlando to Chicago O'Hare International Airport.

The best time to fly from Orlando to Chicago O'Hare International Airport (ORD)

January is the quietest month for flights from Orlando to Chicago O'Hare International Airport (ORD), while July is the most popular. Find the best time to go to Chicago based on whether you prefer a laid-back vibe or a lively atmosphere.
The warmest month in Chicago is July, with temperatures ranging between 16ºC (61ºF) and 28ºC (82ºF). Book your Orlando to ORD plane ticket then if that's your ideal forecast.
If you want cooler conditions, look for a cheap ticket from Orlando to Chicago O'Hare International Airport in January when temperatures are between -12ºC (10ºF) and 3ºC (37ºF).

More about Chicago

When it comes to searching for somewhere to lay your head, you'll find the best places to stay in Chicago right here. Browse these options after locking in your flight from Orlando to Chicago O'Hare International Airport:
Millennium Park and Art Institute of Chicago are just two of the big attractions to put on your Chicago travel itinerary. Keep the sightseeing going at Willis Tower.

Explore more of the United States

You've visited Chicago, now it's time to discover other parts of the United States. Journey around 290 kilometres southeast to Indianapolis to check off its top attractions. From Lucas Oil Stadium to Eiteljorg Museum and The Children's Museum of Indianapolis, there's plenty to keep you on the go.
Milwaukee is another standout destination in the United States and is around 121 kilometres north of Chicago. No journey is complete without a visit to Richards Duplex Apartments by Frank Lloyd Wright, Miller Park and Milwaukee County Zoo.