Cheap Flights from Orlando to Chicago

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 return flight from Orlando to Chicago? If you want to travel next month, return fares start from $197. Find the lowest prices on one-way and return tickets right here.

Chicago.$145 per passenger.Departing Fri, 25 Sep, returning Mon, 28 Sep.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Orlando Sanford on Fri, 25 Sep, arriving in Chicago Rockford.Inbound direct flight with Allegiant Air departs from Chicago Rockford on Mon, 28 Sep, arriving in Orlando Sanford.Price includes taxes and charges.From $145, select.

Chicago.$150 per passenger.Departing Fri, 25 Sep, returning Wed, 14 Oct.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Orlando Sanford on Fri, 25 Sep, arriving in Chicago Rockford.Inbound direct flight with Allegiant Air departs from Chicago Rockford on Wed, 14 Oct, arriving in Orlando Sanford.Price includes taxes and charges.From $150, select.

Chicago.$174 per passenger.Departing Wed, 7 Oct, returning Wed, 14 Oct.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Orlando Sanford on Wed, 7 Oct, arriving in Chicago Rockford.Inbound direct flight with Allegiant Air departs from Chicago Rockford on Wed, 14 Oct, arriving in Orlando Sanford.Price includes taxes and charges.From $174, select.

Chicago.$187 per passenger.Departing Fri, 30 Oct, returning Wed, 11 Nov.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Orlando Sanford on Fri, 30 Oct, arriving in Chicago Rockford.Inbound direct flight with Allegiant Air departs from Chicago Rockford on Wed, 11 Nov, arriving in Orlando Sanford.Price includes taxes and charges.From $187, select.

Chicago.$197 per passenger.Departing Fri, 21 Aug, returning Mon, 24 Aug.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Orlando Sanford on Fri, 21 Aug, arriving in Chicago Rockford.Inbound direct flight with Allegiant Air departs from Chicago Rockford on Mon, 24 Aug, arriving in Orlando Sanford.Price includes taxes and charges.From $197, select.

Chicago.$207 per passenger.Departing Tue, 21 Jul, returning Tue, 11 Aug.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Orlando International on Tue, 21 Jul, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Tue, 11 Aug, arriving in Orlando International.Price includes taxes and charges.From $207, select.

Chicago.$214 per passenger.Departing Thu, 27 Aug, returning Tue, 1 Sep.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Orlando International on Thu, 27 Aug, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Tue, 1 Sep, arriving in Orlando International.Price includes taxes and charges.From $214, select.

Chicago.$225 per passenger.Departing Wed, 4 Nov, returning Wed, 11 Nov.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Orlando Sanford on Wed, 4 Nov, arriving in Chicago Rockford.Inbound direct flight with Allegiant Air departs from Chicago Rockford on Wed, 11 Nov, arriving in Orlando Sanford.Price includes taxes and charges.From $225, select.

Chicago.$225 per passenger.Departing Wed, 22 Jul, returning Wed, 29 Jul.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Orlando International on Wed, 22 Jul, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Wed, 29 Jul, arriving in Orlando International.Price includes taxes and charges.From $225, select.

Chicago.$240 per passenger.Departing Mon, 7 Dec, returning Fri, 11 Dec.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Orlando Sanford on Mon, 7 Dec, arriving in Chicago Rockford.Inbound direct flight with Allegiant Air departs from Chicago Rockford on Fri, 11 Dec, arriving in Orlando Sanford.Price includes taxes and charges.From $240, select.

Chicago.$253 per passenger.Departing Fri, 22 Jan, returning Mon, 25 Jan.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Orlando Sanford on Fri, 22 Jan, arriving in Chicago Rockford.Inbound direct flight with Allegiant Air departs from Chicago Rockford on Mon, 25 Jan, arriving in Orlando Sanford.Price includes taxes and charges.From $253, select.

Chicago.$285 per passenger.Departing Fri, 22 Jan, returning Mon, 8 Feb.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Orlando Sanford on Fri, 22 Jan, arriving in Chicago Rockford.Inbound direct flight with Allegiant Air departs from Chicago Rockford on Mon, 8 Feb, arriving in Orlando Sanford.Price includes taxes and charges.From $285, select.

Chicago.$313 per passenger.Departing Fri, 5 Feb, returning Mon, 8 Feb.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Orlando Sanford on Fri, 5 Feb, arriving in Chicago Rockford.Inbound direct flight with Allegiant Air departs from Chicago Rockford on Mon, 8 Feb, arriving in Orlando Sanford.Price includes taxes and charges.From $313, select.

Chicago.$315 per passenger.Departing Wed, 25 Nov, returning Fri, 11 Dec.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Orlando Sanford on Wed, 25 Nov, arriving in Chicago Rockford.Inbound direct flight with Allegiant Air departs from Chicago Rockford on Fri, 11 Dec, arriving in Orlando Sanford.Price includes taxes and charges.From $315, select.

Chicago.$331 per passenger.Departing Fri, 25 Dec, returning Mon, 11 Jan.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Orlando Sanford on Fri, 25 Dec, arriving in Chicago Rockford.Inbound direct flight with Allegiant Air departs from Chicago Rockford on Mon, 11 Jan, arriving in Orlando Sanford.Price includes taxes and charges.From $331, select.

Chicago.$440 per passenger.Departing Sun, 30 Aug, returning Fri, 9 Oct.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Orlando International on Sun, 30 Aug, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Fri, 9 Oct, arriving in Orlando International.Price includes taxes and charges.From $440, 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 September.

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Direct flights 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	$145
Cheapest month to fly	September
Average flight time	2 hrs, 56 mins
Most popular airline	American Airlines
Average flights per week	600

Finding cheap flights from Orlando to Chicago: Frequently asked questions

How many airports are there in Chicago?

There are 3 airports in Chicago: Chicago Midway, Chicago O'Hare International 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 $145. 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 56 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 July 2026, there are 600 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 September.

Which is the cheapest airport to fly into in Chicago?

If you're flying from Orlando, the cheapest airport near Chicago is Chicago Rockford – which is 126.5 km away from the centre of Chicago. We've found flights into this airport from $145.

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 Friday, 25 September 2026.

Can I get a direct flight from Orlando to Chicago?

Yes – the average flight time is 2 hours and 56 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 July, the average temperature is usually around 22°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 Allegiant Air .

Flying from Orlando to Chicago: what you need to know

Begin your trip planning by checking out the ideal departure point for your flight from Orlando to Chicago. Explore your options for taking off from Orlando International Airport (MCO) or Orlando Sanford Airport (SFB), two of the city's main airports.
Chicago O'Hare International Airport (ORD) and Chicago Midway Airport (MDW) are the primary entry points to Chicago.
The average time for a direct Orlando to Chicago flight is 2 hours 55 minutes.
The timezone in Chicago is UTC-6, which is one hour behind Orlando.
The most popular route for flights from Orlando to Chicago is from Orlando International Airport (MCO) to Chicago O'Hare International Airport (ORD). Take your pick of 110 services every week between these two airports. If you'd like to get going as soon as possible, the earliest flight from MCO to ORD is the 05:40 Frontier Airlines option. If you prefer travelling later, the final scheduled service is at 22:17 with Frontier Airlines.
To ensure you make your Orlando to Chicago flight, leave plenty of time to check in and drop off your luggage. Turning up two hours ahead of international departures and an hour before domestic flights is the general rule.
During popular months like April, it's best to get to the airport well in advance. Plan to arrive two hours before a domestic departure and four hours ahead for an international flight whenever you're flying during high season in general.

How to find the cheapest flights from Orlando to Chicago

At the moment, $66 is the lowest price we've seen for a one-way ticket from Orlando to Chicago. The cheapest price for a return flight is $145. Keep in mind fares may change due to availability at the time of booking.
Book 11 months before you want to fly. Pricing trends suggest that this is the ideal window for finding cheap Orlando to Chicago flights.
The best month for finding cheap plane tickets from Orlando to Chicago is April. Use the 'Whole month' tool to compare flight prices, then choose the dates offering the lowest fares.
There's no need to check every day to find out if fares have dropped when you set up a Price Alert. We'll let you know as soon as a better deal comes up on cheap flights from Orlando to Chicago.
Choose your preferred departure and arrival times, airlines and number of stops with the filters. Alternatively, sort your Orlando to Chicago flight results by 'Best,' 'Fastest' or 'Cheapest.'

Flying from Orlando

Orlando International Airport (MCO)

You can find a direct flight from Orlando to Chicago jetting out of Orlando International Airport (MCO). Start your trip at MCO and then touch down at Chicago O'Hare International Airport (ORD) or Chicago Midway Airport (MDW).
These are some of the major airlines offering direct Orlando to Chicago plane tickets out of MCO:
MCO is about 14 kilometres from central Orlando. If you're ride-sharing, catching a taxi or driving from the centre, it'll take you 25 minutes or so to get there, depending on traffic. If you're planning to take public transport, expect the travel time to be around 1 hour.
Planning to catch an early flight from Orlando to Chicago? Avoid the stress of rushing to the airport (and enjoy a little extra shut-eye) by choosing one of these hotels near Orlando International Airport:
When it comes to the on-time performance of Orlando International Airport, 77% of flights stick to their scheduled arrival time.
MCO is located at One Airport Boulevard.

Arriving in Chicago

Chicago O'Hare International Airport (ORD)

The distance from Chicago O'Hare International Airport (ORD) to central Chicago is roughly 26 kilometres. It'll take you about 30 minutes to reach the centre driving.
It usually takes 45 minutes to get there on public transport.
The last thing you need is a lengthy journey to your hotel if you're landing late on a flight from Orlando to Chicago. Book one of these accommodation options near ORD instead:
Pick up a Chicago O'Hare International Airport rental car and discover Chicago and beyond with your own set of wheels. Routes Car Rentals, Dollar and Budget are top outlets you can book with here.
Reserving your vehicle from Chicago O'Hare International Airport about four weeks ahead increases your chances of getting a good deal.
ORD is situated at 10000 West O'Hare.

Chicago Midway Airport (MDW)

Chicago Midway Airport (MDW) is around 14 kilometres from the centre of Chicago. Following your flight from Orlando to Chicago, it'll take you approximately 25 minutes to get to the heart of the city in a taxi or ride-share.
You can expect the journey to take approximately 30 minutes on public transport.
Hang the 'Do not disturb' sign on your door and rest at a hotel close to MDW. Here are a few options where you can settle in after your flight from Orlando to Chicago:
The quickest way to get to where you're going is with a Chicago Midway Airport rental car. Pick up your wheels from Dollar, Hertz or Budget and make a speedy getaway.
Secure your first choice, not your last resort. Securing your ride from MDW four weeks in advance often means better deals and a bigger choice of vehicles.
Chicago Midway Airport can be found at 5700 South Cicero.

Chicago Rockford Airport (RFD)

Hop off your flight from Orlando to Chicago and go directly to your hotel or start taking in the sights right away. Central Chicago is around 129 kilometres from Chicago Rockford Airport (RFD) and typically takes 1 hour 40 minutes to drive there.
Public transport can take you there in around 2 hours.
Stay in control of the next leg of your journey with a Chicago Rockford Airport rental car. Budget, Alamo and National make getting on the road effortless.
If you'd like a particular kind of vehicle, booking early increases your chances of finding what you want. Reserve your ride from RFD at least a few weeks ahead of your flight from Orlando to Chicago.
Chicago Rockford Airport's street address is 2 Airport Cir.

Best time to go to Chicago

March is the quietest month for flights from Orlando to Chicago, while July is the busiest. Choose the ideal time to go to Chicago based on whether you prefer a lively atmosphere or a more laid-back vibe.
When booking your Orlando to Chicago tickets, consider the type of weather you enjoy. July is the warmest month in Chicago, with temperatures ranging from 16ºC to 28ºC.
If you like cooler conditions, look for a cheap flight from Orlando to Chicago in January when temperatures average between -12ºC and 3ºC.

More about Chicago

When it comes to searching for somewhere to rest your head, you'll find the top stays in Chicago right here. Browse these options as soon as you've booked your flight from Orlando to Chicago:
Every great journey has to include some sightseeing. Millennium Park, The Art Institute of Chicago and Willis Tower are must-visits when exploring Chicago.

Explore more of the United States

Chicago is easy to fall in love with, but there are so many other corners of the United States just waiting to be discovered. Around 451 kilometres southeast of Chicago, a trip to Columbus will keep you busy. Start with attractions like Franklin Park Conservatory and Botanical Gardens, Columbus Park of Roses and Ohio Theatre.
If you're ready to explore another major destination in the United States, consider Indianapolis, roughly 257 kilometres southeast of Chicago. Lucas Oil Stadium, Eiteljorg Museum of American Indians and Western Art and The Children's Museum of Indianapolis are among the biggest draws.