Skyscanner home

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

Book the best Chicago fare with no extra fees

Flight deals from Orlando International to Chicago

Looking for a cheap last-minute deal or the best return flight from Orlando International to Chicago? Find the lowest prices on one-way and return tickets right here.
Chicago.P3,395 per passenger.Departing Sat, 17 Jan, returning Mon, 19 Jan.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Orlando International on Sat, 17 Jan, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Mon, 19 Jan, arriving in Orlando International.Price includes taxes and charges.From P3,395, select.
Chicago.P3,395 per passenger.Departing Fri, 27 Feb, returning Sun, 1 Mar.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Orlando International on Fri, 27 Feb, arriving in Chicago Midway.Inbound direct flight with Frontier Airlines departs from Chicago Midway on Sun, 1 Mar, arriving in Orlando International.Price includes taxes and charges.From P3,395, select.
Chicago.P3,395 per passenger.Departing Thu, 5 Feb, returning Mon, 9 Feb.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Orlando International on Thu, 5 Feb, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Mon, 9 Feb, arriving in Orlando International.Price includes taxes and charges.From P3,395, select.
Chicago.P3,408 per passenger.Departing Thu, 29 Jan, returning Mon, 2 Feb.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Orlando International on Thu, 29 Jan, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Mon, 2 Feb, arriving in Orlando International.Price includes taxes and charges.From P3,408, select.
Chicago.P3,688 per passenger.Departing Sat, 13 Dec, returning Thu, 8 Jan.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Orlando International on Sat, 13 Dec, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Thu, 8 Jan, arriving in Orlando International.Price includes taxes and charges.From P3,688, select.
Chicago.P4,525 per passenger.Departing Thu, 11 Dec, returning Mon, 15 Dec.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Orlando International on Thu, 11 Dec, arriving in Chicago Midway.Inbound direct flight with Frontier Airlines departs from Chicago Midway on Mon, 15 Dec, arriving in Orlando International.Price includes taxes and charges.From P4,525, select.
Chicago.P7,040 per passenger.Departing Wed, 18 Mar, returning Wed, 8 Apr.Return flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departs from Orlando International on Wed, 18 Mar, arriving in Chicago O'Hare International.Inbound direct flight with Spirit Airlines departs from Chicago O'Hare International on Wed, 8 Apr, arriving in Orlando International.Price includes taxes and charges.From P7,040, select.
Chicago.P7,040 per passenger.Departing Tue, 7 Apr, returning Wed, 8 Apr.Return flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departs from Orlando International on Tue, 7 Apr, arriving in Chicago O'Hare International.Inbound direct flight with Spirit Airlines departs from Chicago O'Hare International on Wed, 8 Apr, arriving in Orlando International.Price includes taxes and charges.From P7,040, 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 January.
Nov
from P9,314
Dec
from P4,525
Jan
from P3,395
Feb
from P3,395
Mar
from P7,047
Apr
from P7,040
May
from P23,064
Jun
from P24,424
Jul
from P24,331
Aug
from P24,513
Sep
Find prices
Oct
from P28,358

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 foundP3,395
Cheapest month to flyJanuary
Average flight time3 hrs, 2 mins
Most popular airlineAmerican Airlines
Average flights per week538

Finding cheap flights from Orlando International 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 return flight from Orlando International to Chicago is P3,395. 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.
3 hours and 2 minutes is the average flight time from Orlando International to Chicago.
American Airlines, Southwest Airlines and United fly direct from Orlando International to Chicago.
As of November 2025, there are 1,076 flights per week flying from Orlando International to Chicago.
The cheapest month to fly from Orlando International to Chicago is usually January.
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 P3,395.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Orlando International Airport to Chicago on Saturday, 17 January 2026.
Yes – the average flight time is 3 hours and 2 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 November, the average temperature is usually around 5°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.
Currently, Frontier Airlines offers the cheapest flight tickets to Chicago.

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

  • Around 2 hours 45 minutes is how long you can expect to be in the air on a direct flight from Orlando International Airport to Chicago.

  • Orlando International Airport is located in Orlando. Based in the UTC-5 timezone, Chicago is one hour behind Orlando.

  • Orlando International Airport (MCO) to O'Hare International Airport (ORD) is the most traveled route, with 94 weekly departures to pick from. If you have things to finalize before heading off, the last flight from MCO to ORD is with Frontier Airlines at 22:17. Choose the first departure with Frontier Airlines at 05:40 if you want to get on your way earlier.

  • To avoid rushing for your MCO to Chicago flight, leave plenty of time for things like check-in and baggage drop. Arriving two hours before international departures and one hour before domestic flights is the general rule.

  • If you're flying during a bank holiday or another peak period, allow extra time. A good rule is two hours before domestic flights and up to four hours before international departures. Lines at check-in and security will be longer.

  • Direct Orlando International Airport to Chicago tickets are available for booking. O'Hare International Airport (ORD) is where you'll be touching down.

  • A range of airlines operate direct flights from Orlando International Airport to Chicago. The most well-known include:

  • Central Orlando to MCO is around 14 kilometres. Depending on traffic conditions, it'll take about 20 minutes to reach there if you're driving, catching a cab or ride-sharing.

  • Searching for a hotel near MCO? If you're catching an early flight from Orlando International Airport to Chicago, these stays set you up for a seamless send-off:

  • Of the flights that depart from Orlando International Airport, 78.28% arrive as scheduled at their destination.

  • The address for MCO is One Airport Boulevard.

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

  • P1,698 is the cheapest price we've seen for a one-way Orlando International Airport to Chicago flight. A round-trip ticket right now is P3,395. Depending on when and how early you book, these fares may change.

  • Don't leave everything to the last moment. You're more likely to pick up cheap flights from MCO to Chicago if you book ahead. Airlines often have some amazing early bird discounts.

  • The 'Whole month' tool will show you the cheapest tickets from Orlando International Airport to Chicago across every month. It's a great way to find a bargain if your dates are flexible.

  • Finding a cheap flight from MCO to Chicago is a breeze with Price Alerts. Simply create one of these automatic notifications and we'll notify you as soon as there's a better deal.

  • Tailor your trip with filters. Pick your preferred 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

O'Hare International Airport (ORD)

  • O'Hare International Airport (ORD) is around 40 kilometres from the centre of Chicago. If you're opting for a ride-share or a cab, the drive takes roughly 35 minutes.

  • If you're travelling on public transport, expect a journey time of around 55 minutes.

  • The last thing you need is a long journey to your hotel if you're arriving on a late flight from Orlando International Airport to Chicago. Stay at one of these accommodation options near ORD instead:

  • Get on the fast track to adventure by picking up an O'Hare International Airport rental car. Grab your wheels from Routes Car Rentals, Dollar or Budget and explore beyond Chicago's main sights.

  • Reserving your ride from O'Hare International Airport around four weeks ahead of your flight from MCO to Chicago can help you get the lowest rate.

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Chicago Midway International Airport (MDW) is roughly 19 kilometres from central Chicago. After your flight from Orlando International Airport to Chicago, it'll take you around 20 minutes to reach the heart of the city in a ride-share or cab.

  • You can expect the journey to take roughly 45 minutes on public transport.

  • There are some great places to drop your things at near MDW. Unwind and get cosy after your MCO to Chicago flight at any of these well-located options:

  • Forget about inconvenient public transport schedules or cab lines. Pick up a Chicago Midway International Airport rental car and let your trip unfold on your terms. Check out the rates and availability from Dollar, Hertz and Budget.

  • Don't pay more than you need to. Securing your ride four weeks before your arrival at MDW can help you lock in a better rate.

  • The address for Chicago Midway International Airport is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Chicago Rockford International Airport (RFD) is about 137 kilometres from central Chicago. It'll take you about 1 hour 25 minutes to get to the city centre by ride-share or cab once you've hopped off your flight from Orlando International Airport to Chicago.

  • The journey will take you about 4 hours 15 minutes if you use public transport.

  • If you don't want to make your way into the centre, find a hotel near RFD. Get comfortable at one of these options after your MCO to Chicago flight:

  • Whether you'd like a mini for a solo getaway or a full-size SUV to fit the whole crew comfortably, you'll find the right Chicago Rockford International Airport rental car for your needs. Check out the types of wheels available here from suppliers such as Budget, Alamo and National.

  • Booking a couple of weeks in advance of your flight from Orlando International Airport to Chicago is a good move. As well as better prices, you'll likely have a better variety of makes and models to choose from at RFD.

  • The street address for Chicago Rockford International Airport is 2 Airport Cir.

Best time to go to Chicago

  • Carefully consider your dates before booking your flight from Orlando International Airport to Chicago. The city comes alive in peak season, but hotel prices are usually higher and top attractions can get busy. Visit Chicago in the low season if you want a more relaxed vibe.

  • Before booking a Orlando International Airport to Chicago plane ticket, think about the weather you're most comfortable in. July is the warmest month in Chicago, with temperatures ranging from 15ºC (59ºF) to 29ºC (84ºF).

  • January sees average temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Search for a cheap ticket from MCO to Chicago around that time if you like travelling in cooler conditions.

More about Chicago

  • When it comes to searching for somewhere to rest your head, you'll find the best places to stay in Chicago right here. Browse these options as soon as you've booked your flight from Orlando International Airport to Chicago:

  • There are so many things to see and do in this city it can be tricky to know where to begin. Art Institute of Chicago, Millennium Park and LandShark Beer Garden at Navy Pier are top attractions which should be on any good Chicago itinerary.

Explore more of United States

  • You've seen Chicago, now it's time to explore other parts of United States. Journey around 451 kilometres south-east to Columbus to check off its top attractions. From Franklin Park Conservatory and Botanical Gardens to Ohio Statehouse and German Village, you'll have a full itinerary ahead.

  • Around 257 kilometres south-east of Chicago, Indianapolis is another essential stop in United States. Start your sightseeing at The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

Plan the rest of your trip from Orlando to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.